Isothiocyanates(ITCs)are an important class of organic compounds characterized by the functional group R-N=C=S.These functional groups are widely found in multiple natural products and pharmaceutical important drugs.M...Isothiocyanates(ITCs)are an important class of organic compounds characterized by the functional group R-N=C=S.These functional groups are widely found in multiple natural products and pharmaceutical important drugs.Moreover,due to their high and versatile reactivity,they are widely used as an intermediate in organic synthesis.Keeping in view ITCs importance,this review summarizes their synthesis from nitrogen rich raw materials like amines,isocyanides,azides and some other compounds like oximes.Besides their synthesis,their application in organic compound synthesis as an intermediate will also be covered.Future research will likely focus on optimizing the synthesis of multifunctional isothiocyanates,understanding their complex biological mechanisms,exploring new applications,and highlighting the continued importance of isothiocyanates in modern chemistry and biotechnology.展开更多
Objectives:An allergy is an exaggerated immune response,and mast cells play central roles in allergic pathologies.Allyl isothiocyanate can suppress inflammatory responses;however,whether allyl isothiocyanate has a sup...Objectives:An allergy is an exaggerated immune response,and mast cells play central roles in allergic pathologies.Allyl isothiocyanate can suppress inflammatory responses;however,whether allyl isothiocyanate has a suppressive effect on allergic pathologies remains unclear.Methods:2,4-dinitrofluorobenzen or ovalbumin was used to establish a mouse model of allergic contact dermatitis or food allergy,respectively.The mRNA level of cytokines was determined using real-time polymerase chain reaction.To examine the effects of allyl isothiocyanate on mast cells,degranulation and intracellular calcium measurement,RNA sequencing,real-time polymerase chain reaction,and Western blotting were performed.Results:Allyl isothiocyanate ameliorated allergic contact dermatitis and food allergy.Allyl isothiocyanate decreased the mRNA levels of cytokines and degranulated mast cells in the allergic contact dermatitis model.Furthermore,allyl isothiocyanate decreased the mRNA levels of cytokines and the mast cell marker mMCP-1 in the food allergy model.Moreover,allyl isothiocyanate inhibited immunoglobulin E/antigeninduced β-hexosaminidase release in murine bone marrow-derived mast cells and RBL-2H3 cells.Allyl isothiocyanate also decreased the increase in intracellular calcium levels induced by immunoglobulin E/antigen in mast cells.In addition,allyl isothiocyanate suppressed calcium ionophore A23187-induced mast cell degranulation.Furthermore,allyl isothiocyanate reduced A23187 or compound 48/80-induced human mast cells degranulation.RNA-sequencing data revealed that immunoglobulin E/antigen induced the expression of activating transcription factor 3 in murine bone marrow-derived mast cells;however,allyl isothiocyanate downregulated activating transcription factor 3 levels.Additionally,allyl isothiocyanate inhibited endoplasmic reticulum stress-related proteins.Conclusions:The results of the present study showed that allyl isothiocyanate ameliorated allergic contactdermatitis and foodallergy via inhibition of mast cells.展开更多
Obesity has brought great challenges to global human health,and how to effectively prevent and control the occurrence and development of obesity has become an urgent problem.The role and mechanism of 4-[(α-Lrhamnosyl...Obesity has brought great challenges to global human health,and how to effectively prevent and control the occurrence and development of obesity has become an urgent problem.The role and mechanism of 4-[(α-Lrhamnosyloxy)benzyl]isothiocyanate(MITC),an active ingredient of Moringa oleifera Lam.,in the regulation of lipid metabolism have not been comprehensively investigated.In the present study,we investigated the mechanism of MITC in inhibiting lipid accumulation in mice fed with a high-fat diet(HFD)in terms of both lipolysis and central appetite regulation mediated by the gut microbe-gut-brain axis.MITC enhanced the characteristic indices associated with HFD mice and also promoted adipocytolysis and brown fat thermogenesis.Moreover,MITC was observed to improve leptin resistance,modulate the composition of gut microbiota such as Ruminococcaceae,Parasutterella,and Acetatifactor,promote 5-hydroxytryptamine secretion,further enhance the secretion of glucagon-like peptide-1(GLP-1)and peptide tyrosine-tyrosine(PYY)to activate peroxisome proliferator-activated receptor(PPAR)signaling in the hypothalamus,and modulate feeding behavior to inhibit lipid accumulation in HFD mice.These data suggest that MITC supplementation can help to alleviate obesity or obesity-related diseases.展开更多
In this editorial,we comment on a recent publication,which highlights the important findings from the study,including the antitumor and anti-inflammatory effects of isothiocyanates,their underlying mechanisms,and impl...In this editorial,we comment on a recent publication,which highlights the important findings from the study,including the antitumor and anti-inflammatory effects of isothiocyanates,their underlying mechanisms,and implications.Additionally,a related perspective is discussed.展开更多
BACKGROUND Allyl isothiocyanate(AITC),a classic anti-inflammatory and antitumorigenic agent,was recently identified as a potential treatment for obesity and insulin resistance.However,little is known about its direct ...BACKGROUND Allyl isothiocyanate(AITC),a classic anti-inflammatory and antitumorigenic agent,was recently identified as a potential treatment for obesity and insulin resistance.However,little is known about its direct impact on the liver.AIM To investigate the effect and underlying mechanism of AITC in nonalcoholic fatty liver disease(commonly referred to as NAFLD).METHODS To establish a mouse and cellular model of NAFLD,C57BL/6 mice were fed a high fat diet(HFD)for 8 wk,and AML-12 cells were treated with 200μM palmitate acid for 24 h.For AITC treatment,mice were administered AITC(100 mg/kg/d)orally and AML-12 cells were treated with AITC(20μmol/L).RESULTS AITC significantly ameliorated HFD-induced weight gain,hepatic lipid accumulation and inflammation in vivo.Furthermore,serum alanine aminotransferase and aspartate aminotransferase levels were markedly reduced in AITC-treated mice.Mechanistically,AITC significantly downregulated the protein levels of sterol regulatory elementbinding protein 1(SREBP1)and its lipogenesis target genes and upregulated the levels of proteins involved in fatty acidβ-oxidation,as well as the upstream mediators Sirtuin 1(Sirt1)and AMPactivated protein kinaseα(AMPKα),in the livers of HFD-fed mice.AITC also attenuated the nuclear factor kappa B(NF-κB)signaling pathway.Consistently,AITC relieved palmitate acid-induced lipid accumulation and inflammation in AML-12 cells in vitro through the Sirt1/AMPK and NF-κB signaling pathways.Importantly,further studies showed that the curative effect of AITC on lipid accumulation was abolished by siRNA-mediated knockdown of either Sirt1 or AMPKαin AML-12 cells.CONCLUSION AITC significantly ameliorates hepatic steatosis and inflammation by activating the Sirt1/AMPK pathway and inhibiting the NF-κB pathway.Therefore,AITC is a potential therapeutic agent for NAFLD.展开更多
Various amino acid esters were reacted with different isothiocyanates in alkaline Al2O3 at room temperature for 1 h affording thiohydantoins in moderate to excellent yields.
Isothiocyanates(ITCs) extracts were prepared from fresh broccoli.Their antioxidant properties were evaluated by using the in vitro bioassays,including superoxide anion radical( 2 O·-) ,hydroxyl radical(HO·-)...Isothiocyanates(ITCs) extracts were prepared from fresh broccoli.Their antioxidant properties were evaluated by using the in vitro bioassays,including superoxide anion radical( 2 O·-) ,hydroxyl radical(HO·-) and 2,2-diphenyl-1-picrylhydracyl(DPPH·) radical-scavenging methods,lipid peroxidation assay,and reducing power assay.The ITCs extracts exhibited significant dose-dependent antioxidant activities(P<0.01) .Its antioxidant-stability was affected by temperature and storage condition,although it was more stable than vitamin C(Vc) .GC-MS iden-tified sulforaphane in the ITCs extracts.The antioxidant activity of sulforaphane was approximately one tenth to one fifth of that of Vc.Sulforaphane was experimented to be one of dominating contributors to antioxidant capacity of ITCs extracts.However,there was no direct antioxidant activity found for benzyl isothiocyanate(BITC) in vitro. Therefore,it could be concluded that the general group(-N=C=S) was not the essential part for the antioxidant activity of sulforaphane.It is suggested that the ITCs extracts from broccoli can be developed into a promising food additive for healthy food.展开更多
In order to solve the problems of low accuracy and poor variety adaptability of the current measurement method of the permeability and coating property of sizing paste in textile industry, taking starch and polyvinyl ...In order to solve the problems of low accuracy and poor variety adaptability of the current measurement method of the permeability and coating property of sizing paste in textile industry, taking starch and polyvinyl alcohol(PVA) as the representatives of the most commonly used textile sizes, various concentrations of fluorescent molecules fluorescein isothiocyanate(FITC) were used to label starch and PVA to prepare fluorescein(F)-starch and F-PVA fluorescent sizes with different degrees of labeling(DLs) for the first time, respectively. Then the starch and PVA derivatives were employed to size pure cotton warp yarns. After preparing the sections of the sized yarns, the permeability and coating percentage of starch and PVA paste to the yarns were calculated by using a fluorescence microscope and the Photoshop software, respectively. The results demonstrate that F-starch and F-PVA with appropriate DL of 0.791% and 0.161%, respectively, exhibit good fluorescence property and similar sizing performance to the sizing performance of unlabeled starch and PVA. It is considered that fluorescence labeling of sizing agents with fluorescein units can provide an innovative way for the accurate determination of the permeability and coating property of sizing paste to warp yarns.展开更多
To date, in vivo investigations of polysaccharide’s pharmacokinetics are significantly restricted by the difficulty in their detection. This study was conducted to establish the quantitative determination of Lycium b...To date, in vivo investigations of polysaccharide’s pharmacokinetics are significantly restricted by the difficulty in their detection. This study was conducted to establish the quantitative determination of Lycium barbarum polysaccharides(LBPs) based on fluorescein isothiocyanate(FITC) pre-labeling and to investigate their tissue distribution in rat. We obtained the calibration curves linear over the range of 0.0–25 μg/m L in rat tissue samples with correlation coefficients greater than 0.99. The inter-day and intra-day precisions(RSD, %) were within 15%, and the relative recovery ranged 95.2%–102.4%, with RSD range 1.48%–9.58%, indicating that this experiment was suitable for the determination of LBPs. The fluorescence intensity was measured after 24 h storage at room temperature, 3 times of freeze-cycle and cryopreservation at –20 ℃ for 15 day, these results indicated that the stability of the samples was good. LBP-FITC was mainly absorbed by the small intestine and stomach, and mainly excreted in the urine through the kidney;this distinct difference in the tissue distribution of LBPs could be attributed to the size of these LBPs in relation to the pore sizes of the vascular beds in the kidney and liver. Results showed in this study enable us to comprehensively understand the biological effects of LBPs following its oral ingestion.展开更多
Liquid crystal（LC） compound with isothiocyanate and naphthyl group is an attractive high birefringence LC material,and can be used in optical devices. In this paper, the electro-optical properties of a series of thi...Liquid crystal（LC） compound with isothiocyanate and naphthyl group is an attractive high birefringence LC material,and can be used in optical devices. In this paper, the electro-optical properties of a series of this type of LC compounds were investigated. The melting points and enthalpy values of these LC compounds were higher than those of corresponding compounds with the phenyl group. These compounds exhibited high birefringence with a maximum value of 0.66. Fluorine substitution in the molecular almost does not affect the birefringence value. When these LC compounds with the naphthyl group were dissolved in a commercial LC mixture, the electro-optical properties depending on temperature were investigated. In the low-temperature region, LC mixtures with the naphthyl-group LC compounds exhibited higher viscosity than pure commercial LCs. In the high-temperature region, viscosity values very closely approached each other. When response performance was investigated, figure-of-merit（FoM） values were measured. The Fo M values of LC mixtures containing LC compounds with naphthyl group were lower than those of reference benzene LCs in the low-temperature region. However, in the high-temperature region, the results were reversed. These isothiocyanate LC compounds with naphthyl group can be applied in special fast-response LC device, particularly the ones used under high-temperature conditions.展开更多
BACKGROUND Using gas chromatography-mass spectrometry(GC/MS)analysis,we examined the composition of volatile components present in the yellow and green fruits,seeds,and jam of the scrambling shrub Capparis cartilagine...BACKGROUND Using gas chromatography-mass spectrometry(GC/MS)analysis,we examined the composition of volatile components present in the yellow and green fruits,seeds,and jam of the scrambling shrub Capparis cartilaginea(C.cartilaginea).These plant samples were collected from Kibbutz Yotvata in Israel.In all the tested samples,isothiocyanates were identified.Utilizing the PASS program,we ascertained the biological activity of these isothiocyanates present in the Capparis genus.The study results highlighted that all isothiocyanates could potentially act as apoptosis agonists,making them strong candidates for antitumor drugs.This information holds significant value for the fields of medicinal chemistry,pharmacology,and practical medicine.AIM To investigate the volatile components present in the yellow and green fruits,seeds,and jam of the C.cartilaginea shrub using GC/MS analysis,to detect isothiocyanates in all the analyzed plant samples,and to assess the biological activity of these isothiocyanates utilizing the PASS program.METHODS We utilized two primary methods to analyze the volatile compounds present in the yellow and green fruits,seeds,and jams of the C.cartilaginea,native to Israel.We identified biologically active isothiocyanates in these samples.Their anticipated biological activities were determined using the PASS program,with the most dominant activities being apoptosis agonist,anticarcinogenic,and antineoplastic specifically for genitourinary cancer.RESULTS Fruits,seeds,and jams containing isothiocyanates,which exhibit antineoplastic and anticarcinogenic activities,could be suggested for cancer prevention and management.Specific isothiocyanates,with therapeutic potential in this realm,could be recommended as potent anticancer agents in practical medicine following clinical trials.CONCLUSION The discovery that isothiocyanates exhibit potent antineoplastic and anticarcinogenic activities was unexpected.Additionally,certain isothiocyanates demonstrated antifungal,antiviral(specifically against arbovirus),and antiparasitic properties.展开更多
Four solid complexes of rare earth isothiocyanates with glycine were synthesized. They were characterized by chemical analysis, elemental analysis, Infrared spectra, X-ray powder diffraction and TO-DSC analysis. Their...Four solid complexes of rare earth isothiocyanates with glycine were synthesized. They were characterized by chemical analysis, elemental analysis, Infrared spectra, X-ray powder diffraction and TO-DSC analysis. Their chemical formulae were proved to be RE(NCS)2.Gly .H2O, where RE is La, Ce, Pr or Nd. The integral heats of solution of RE(NCS)3.3Gly. H2O in water, of RE(NCS)2. 7H2O in aqueous glycine solution and of glycine in water have been measured calorimetricaliy at 298. 15K. By means of a thermochemical cycle suggested in this paper, the standard molar enthalpies of formation for RE(NCS)2. 3Gly.H2O(c) were obtained and their lattice energies were calculated.展开更多
Using Schiff base as a phase transfer catalyst, ethoxycarbonyl isothiocyanate was synthesized by reacting ethyl chloroformate with sodium thiocyanate. In order to get the best synthetic technology, an orthogonal test ...Using Schiff base as a phase transfer catalyst, ethoxycarbonyl isothiocyanate was synthesized by reacting ethyl chloroformate with sodium thiocyanate. In order to get the best synthetic technology, an orthogonal test （L9（34）） was applied. The results show that reaction temperature, reaction time, content of catalyst and molar ratio of sodium thiocyanate to ethyl chloroformate are the main factors influencing the yield. The four factors chosen for the present investigation are based on the results of a single-factor test. The optimum synthetic technology is determined as follows： reaction temperature 35 ℃, reaction time 3 h, the content of catalyst （molar fraction based on ethyl chloroformate） 1.5% and molar ratio of sodium thiocyanate to ethyl chloroformate 1.1. Under the optimized synthetic technology, the experimental yield reaches 96.8%.展开更多
Reaction of α-(1H-1,2,4-triazol-1-yl)acetophenone with phenyl isothiocyanate in the presence of a base and subse- quent alkylation leads to the ketene S,N-acetal(2),(4),(7), (8);thiazolidone(3),thiazolidine(5)and 1,3...Reaction of α-(1H-1,2,4-triazol-1-yl)acetophenone with phenyl isothiocyanate in the presence of a base and subse- quent alkylation leads to the ketene S,N-acetal(2),(4),(7), (8);thiazolidone(3),thiazolidine(5)and 1,3-thiazine(6),展开更多
Introduction The study of metal complexes with the crown ether is a quite interesting research field, but the research has mainly focused on the metal complexes with some crown ethers with a relatively small cavity su...Introduction The study of metal complexes with the crown ether is a quite interesting research field, but the research has mainly focused on the metal complexes with some crown ethers with a relatively small cavity such as 12-crown-4, 15-crown-5 and 18- crown-6 as well as their derivatives. Crown ethers with a larger cavity contain more oxygen atoms, so they have the ability to form the complexes of a higher co-展开更多
Metam sodium （MS; sodium N-methyl dithiocarbamate） has emerged as a promising soil fumigant in the US to replace methyl bromide （MeBr）. Metam potassium （MK; potassium N-methyl dithiocarbamate） and MS break down ...Metam sodium （MS; sodium N-methyl dithiocarbamate） has emerged as a promising soil fumigant in the US to replace methyl bromide （MeBr）. Metam potassium （MK; potassium N-methyl dithiocarbamate） and MS break down into the volatile gas methyl isothiocyanate （MITC） to control soil borne pests. Many studies have focused on MS, but MK has not been studied as thoroughly. The objective of this research was to determine the effect of increasing organic matter （OM） treatments and soil texture to minimize the off-gassing of MS and MK. Bench-scale soil column studies were performed to simulate organic matter treatments that may decrease the volatilization loss of MITC. Incorporation depth of OM simulated surface tillage （0-15 cm） practices. Soil was packed in steel columns and MS or MK was applied at a depth of 15 cm and MITC volatilization was measured using gas chromatography/mass spectroscopy. Volatilization of MITC behaved similarly for MS and MK with MITC movement impacted by soil texture. MITC volatilization was lower from a sandy clay loam than a sandy soil. Surface incorporation of OM did not significantly decrease MITC volatilization. These results suggest that soil texture is the dominant factor reducing MITC off-gassing and prolonging the time needed to control soil borne pests.展开更多
The mechanism of the nonlinear concentration dependence of the intestinal absorption of fluorescein isothiocyanate dextran 4,000 (FD-4) was studied using in situ rat intestinal loops and the in vitro Ussing-type chamb...The mechanism of the nonlinear concentration dependence of the intestinal absorption of fluorescein isothiocyanate dextran 4,000 (FD-4) was studied using in situ rat intestinal loops and the in vitro Ussing-type chamber method. The intestinal absorption rate constant of FD-4, as evaluated by the intestinal loop method, increased significantly in a nonlinear fashion as the FD-4 concentration increased up to 0.2 mM and tended to decrease at concentrations higher than 0.2 mM. The mucosal-to-serosal permeation of FD-4 across rat ileal sheets, as evaluated by the in vitro Ussing-type chamber method, also increased in a nonlinear fashion in the low concentration range (0.01 - 0.02 mM), before decreasing as the concentration increased further, whereas serosal-to-mucosal permeation decreased in a concentration-dependent manner. In addition, mucosal-to-serosal flux and serosal-to-mucosal flux were increased and reduced in the presence of the metabolic inhibitor 2, 4-dinitrophenol, respectively. These results suggest that FD-4 is predominantly secreted into the intestinal lumen by an efflux transport system.展开更多
Objective To investigate the mechanism of benzyl isothiocyanate(BITC)in the treatment of anaplastic thyroid cancer(ATC).Methods Using network pharmacological analysis,key targets of BITC and ATC were screened,followed...Objective To investigate the mechanism of benzyl isothiocyanate(BITC)in the treatment of anaplastic thyroid cancer(ATC).Methods Using network pharmacological analysis,key targets of BITC and ATC were screened,followed by CO and KEGG enrichment analysis.In order to validate the findings,AutoDock software was used to dock BITC and ATC key targets.BITC was applied to two ATC cell lines(8505C and CAL-62).Flow cytometry was used to analyze cell apoptosis.Autophagy inhibitors hydroxychloroquine sulfate(HCQ)and 3-methyladenine(3MA)were used in combination with BITC.Real-time quantitative PCR was conducted to detect the gene level of LC3B,while Western blotting was utilized to examine the expression of NF-kB,LC3B I,Beclin-1,and Bcl-2.In animal experiments,a mouse tumor model was constructed using CAL-62 cells,treated with intraperitoneal injections of BITC(100 mg/kg)and normal saline respectively,administered every other day for a total of 21 days.Immunoblotting of tumor tissue was performed to detect the expression of LC3B II,Bcl-2,Beclin-1,and NFkB.Results A total of 10 key targets with binding energies≤-4.0 kcal/mol were identified.KECG analysis showed that these genes are mainly involved in NF-kB signaling pathway and apoptosis.BITC inhibited ATC cells with IC50 values of 27.56μmol/L for 8505C and 28.30μmol/L for CAL-62.The expression levels of NF-kB,Beclin-1,and Bcl-2 decreased,while LC3B I and LC3B gene expression increased.Combining 3MA with BITC enhanced cell inhibition LC3B II expression.HCQ increased LC3B II expression without enhancing cell and viability inhibition.In the mouse tumor model,compared to the control group,the treatment group had higher LC3B II and lower Bcl-2,Beclin-1,and NF-kB levels.Conclusion BITC could inhibit the growth of ATC cells in vitro and in vivo,disrupt the autophagy degradation,and inhibit the NF-kB pathway.展开更多
A metal-free,efficient and easy-to-hand protocol for the synthesis of 2-perfluoroalkylquinazolins has been achieved by Eosin B catalyzed radical cascade arylation/cyclization reaction of fluorinated imidoyl isothiocya...A metal-free,efficient and easy-to-hand protocol for the synthesis of 2-perfluoroalkylquinazolins has been achieved by Eosin B catalyzed radical cascade arylation/cyclization reaction of fluorinated imidoyl isothiocyanates with aryldiazonium Salts.A variety of highly functionalized quinozaline derivatives bearing pharmaceutically important thiol and fluoroalkyl groups were efficiently assembled with broad substrate scope and good functional group tolerance.A series of mechanism experiments indicate that this reaction undergoes a radical cascade arylation/cyclization pathway.展开更多
A novel photocatalytic energy transfer-driven radical relay strategy has been introduced for the chemoand regioselective 1,4-difunctionalization of carbon-sulfur double bonds.This represents the first instance of radi...A novel photocatalytic energy transfer-driven radical relay strategy has been introduced for the chemoand regioselective 1,4-difunctionalization of carbon-sulfur double bonds.This represents the first instance of radical-mediated dual-functionalization of X-Y type unsaturated bonds,enabling the synthesis of complex linear molecules with C–O,C–N,and C-S bonds in a single operation.The method surpasses traditional approaches by avoiding the need for thiourea intermediates and the harsh conditions typically associated with them.The developed strategy exemplifies versatility,being applicable to 1,4-oxyamination,1,4-diamination,and 1,4-sulfonamination reactions,and has demonstrated compatibility with over 60 different substrates.The research also elucidates the role of electronic complementarity between radicals and receptors in achieving high selectivity in 1,4-difunctionalization reactions.This study significantly advances the field of bifunctionalization and remote difunctionalization reactions,with profound implications for the development of pharmaceuticals and materials science.展开更多
文摘Isothiocyanates(ITCs)are an important class of organic compounds characterized by the functional group R-N=C=S.These functional groups are widely found in multiple natural products and pharmaceutical important drugs.Moreover,due to their high and versatile reactivity,they are widely used as an intermediate in organic synthesis.Keeping in view ITCs importance,this review summarizes their synthesis from nitrogen rich raw materials like amines,isocyanides,azides and some other compounds like oximes.Besides their synthesis,their application in organic compound synthesis as an intermediate will also be covered.Future research will likely focus on optimizing the synthesis of multifunctional isothiocyanates,understanding their complex biological mechanisms,exploring new applications,and highlighting the continued importance of isothiocyanates in modern chemistry and biotechnology.
基金funded by the“Xinlin Young Talent Program”from Shanghai University of Traditional Chinese Medicine,and the Skate Key Laboratory of Drug Research(No.SIMMI1803KF-11).
文摘Objectives:An allergy is an exaggerated immune response,and mast cells play central roles in allergic pathologies.Allyl isothiocyanate can suppress inflammatory responses;however,whether allyl isothiocyanate has a suppressive effect on allergic pathologies remains unclear.Methods:2,4-dinitrofluorobenzen or ovalbumin was used to establish a mouse model of allergic contact dermatitis or food allergy,respectively.The mRNA level of cytokines was determined using real-time polymerase chain reaction.To examine the effects of allyl isothiocyanate on mast cells,degranulation and intracellular calcium measurement,RNA sequencing,real-time polymerase chain reaction,and Western blotting were performed.Results:Allyl isothiocyanate ameliorated allergic contact dermatitis and food allergy.Allyl isothiocyanate decreased the mRNA levels of cytokines and degranulated mast cells in the allergic contact dermatitis model.Furthermore,allyl isothiocyanate decreased the mRNA levels of cytokines and the mast cell marker mMCP-1 in the food allergy model.Moreover,allyl isothiocyanate inhibited immunoglobulin E/antigeninduced β-hexosaminidase release in murine bone marrow-derived mast cells and RBL-2H3 cells.Allyl isothiocyanate also decreased the increase in intracellular calcium levels induced by immunoglobulin E/antigen in mast cells.In addition,allyl isothiocyanate suppressed calcium ionophore A23187-induced mast cell degranulation.Furthermore,allyl isothiocyanate reduced A23187 or compound 48/80-induced human mast cells degranulation.RNA-sequencing data revealed that immunoglobulin E/antigen induced the expression of activating transcription factor 3 in murine bone marrow-derived mast cells;however,allyl isothiocyanate downregulated activating transcription factor 3 levels.Additionally,allyl isothiocyanate inhibited endoplasmic reticulum stress-related proteins.Conclusions:The results of the present study showed that allyl isothiocyanate ameliorated allergic contactdermatitis and foodallergy via inhibition of mast cells.
基金supported by the Basic Research Project of Yunnan Provincial Science and Technology Department(202201AT070262)the Project of Yunnan Province Food and Drug Homologous Resources Functional Food Innovation Team(A3032023057)+1 种基金the Yunnan Province Ten Thousand Plan Industrial Technology Talents Project(YNWR-CYJS-2020-010)the Yunnan Province-City Integration Project(202302 AN360002).
文摘Obesity has brought great challenges to global human health,and how to effectively prevent and control the occurrence and development of obesity has become an urgent problem.The role and mechanism of 4-[(α-Lrhamnosyloxy)benzyl]isothiocyanate(MITC),an active ingredient of Moringa oleifera Lam.,in the regulation of lipid metabolism have not been comprehensively investigated.In the present study,we investigated the mechanism of MITC in inhibiting lipid accumulation in mice fed with a high-fat diet(HFD)in terms of both lipolysis and central appetite regulation mediated by the gut microbe-gut-brain axis.MITC enhanced the characteristic indices associated with HFD mice and also promoted adipocytolysis and brown fat thermogenesis.Moreover,MITC was observed to improve leptin resistance,modulate the composition of gut microbiota such as Ruminococcaceae,Parasutterella,and Acetatifactor,promote 5-hydroxytryptamine secretion,further enhance the secretion of glucagon-like peptide-1(GLP-1)and peptide tyrosine-tyrosine(PYY)to activate peroxisome proliferator-activated receptor(PPAR)signaling in the hypothalamus,and modulate feeding behavior to inhibit lipid accumulation in HFD mice.These data suggest that MITC supplementation can help to alleviate obesity or obesity-related diseases.
文摘In this editorial,we comment on a recent publication,which highlights the important findings from the study,including the antitumor and anti-inflammatory effects of isothiocyanates,their underlying mechanisms,and implications.Additionally,a related perspective is discussed.
基金Supported by Natural Science Foundation of China,No.81700504 and No.81700511Science Foundation of Health Bureau of Zhejiang Province,No.2017183691+1 种基金Natural Science Foundation of Zhejiang Province,No.LY17H030006 and No.LQ15H030002Zhejiang Medical Science and Technology Project,No.2017193668
文摘BACKGROUND Allyl isothiocyanate(AITC),a classic anti-inflammatory and antitumorigenic agent,was recently identified as a potential treatment for obesity and insulin resistance.However,little is known about its direct impact on the liver.AIM To investigate the effect and underlying mechanism of AITC in nonalcoholic fatty liver disease(commonly referred to as NAFLD).METHODS To establish a mouse and cellular model of NAFLD,C57BL/6 mice were fed a high fat diet(HFD)for 8 wk,and AML-12 cells were treated with 200μM palmitate acid for 24 h.For AITC treatment,mice were administered AITC(100 mg/kg/d)orally and AML-12 cells were treated with AITC(20μmol/L).RESULTS AITC significantly ameliorated HFD-induced weight gain,hepatic lipid accumulation and inflammation in vivo.Furthermore,serum alanine aminotransferase and aspartate aminotransferase levels were markedly reduced in AITC-treated mice.Mechanistically,AITC significantly downregulated the protein levels of sterol regulatory elementbinding protein 1(SREBP1)and its lipogenesis target genes and upregulated the levels of proteins involved in fatty acidβ-oxidation,as well as the upstream mediators Sirtuin 1(Sirt1)and AMPactivated protein kinaseα(AMPKα),in the livers of HFD-fed mice.AITC also attenuated the nuclear factor kappa B(NF-κB)signaling pathway.Consistently,AITC relieved palmitate acid-induced lipid accumulation and inflammation in AML-12 cells in vitro through the Sirt1/AMPK and NF-κB signaling pathways.Importantly,further studies showed that the curative effect of AITC on lipid accumulation was abolished by siRNA-mediated knockdown of either Sirt1 or AMPKαin AML-12 cells.CONCLUSION AITC significantly ameliorates hepatic steatosis and inflammation by activating the Sirt1/AMPK pathway and inhibiting the NF-κB pathway.Therefore,AITC is a potential therapeutic agent for NAFLD.
基金National Natural Science Foundation of China(Grant No.20972005)
文摘Various amino acid esters were reacted with different isothiocyanates in alkaline Al2O3 at room temperature for 1 h affording thiohydantoins in moderate to excellent yields.
基金Supported by the Natural Science Foundation of Zhejiang Province(Y3090135)
文摘Isothiocyanates(ITCs) extracts were prepared from fresh broccoli.Their antioxidant properties were evaluated by using the in vitro bioassays,including superoxide anion radical( 2 O·-) ,hydroxyl radical(HO·-) and 2,2-diphenyl-1-picrylhydracyl(DPPH·) radical-scavenging methods,lipid peroxidation assay,and reducing power assay.The ITCs extracts exhibited significant dose-dependent antioxidant activities(P<0.01) .Its antioxidant-stability was affected by temperature and storage condition,although it was more stable than vitamin C(Vc) .GC-MS iden-tified sulforaphane in the ITCs extracts.The antioxidant activity of sulforaphane was approximately one tenth to one fifth of that of Vc.Sulforaphane was experimented to be one of dominating contributors to antioxidant capacity of ITCs extracts.However,there was no direct antioxidant activity found for benzyl isothiocyanate(BITC) in vitro. Therefore,it could be concluded that the general group(-N=C=S) was not the essential part for the antioxidant activity of sulforaphane.It is suggested that the ITCs extracts from broccoli can be developed into a promising food additive for healthy food.
基金National Natural Science Foundation of China(Nos.51573095 and 51873187)Project of Key Laboratory of Clean Dyeing and Finishing Technology of Zhejiang Province,China(No.QJRZ1902)+1 种基金Technological Research Project for Public Welfare of Zhejiang Province,China(No.LGG21E030005)Postdoctoral Research Program of Zhejiang Province in 2021,China。
文摘In order to solve the problems of low accuracy and poor variety adaptability of the current measurement method of the permeability and coating property of sizing paste in textile industry, taking starch and polyvinyl alcohol(PVA) as the representatives of the most commonly used textile sizes, various concentrations of fluorescent molecules fluorescein isothiocyanate(FITC) were used to label starch and PVA to prepare fluorescein(F)-starch and F-PVA fluorescent sizes with different degrees of labeling(DLs) for the first time, respectively. Then the starch and PVA derivatives were employed to size pure cotton warp yarns. After preparing the sections of the sized yarns, the permeability and coating percentage of starch and PVA paste to the yarns were calculated by using a fluorescence microscope and the Photoshop software, respectively. The results demonstrate that F-starch and F-PVA with appropriate DL of 0.791% and 0.161%, respectively, exhibit good fluorescence property and similar sizing performance to the sizing performance of unlabeled starch and PVA. It is considered that fluorescence labeling of sizing agents with fluorescein units can provide an innovative way for the accurate determination of the permeability and coating property of sizing paste to warp yarns.
基金the support from the National Key Research and Development Program of China(No.2016YFD400604-02)the National Natural Science Foundation of China(No.82073551,82003457,81273069)+3 种基金the Postgraduate Research&Practice Innovation Program of Jiangsu Province(No.KYCX19_0121)the Scientific Research Foundation of Graduate School of Southeast University(No.YBPY1944)the Fundamental Research Funds for the Central Universities(No.2242020R10006)CNS Research Fund for DRI。
文摘To date, in vivo investigations of polysaccharide’s pharmacokinetics are significantly restricted by the difficulty in their detection. This study was conducted to establish the quantitative determination of Lycium barbarum polysaccharides(LBPs) based on fluorescein isothiocyanate(FITC) pre-labeling and to investigate their tissue distribution in rat. We obtained the calibration curves linear over the range of 0.0–25 μg/m L in rat tissue samples with correlation coefficients greater than 0.99. The inter-day and intra-day precisions(RSD, %) were within 15%, and the relative recovery ranged 95.2%–102.4%, with RSD range 1.48%–9.58%, indicating that this experiment was suitable for the determination of LBPs. The fluorescence intensity was measured after 24 h storage at room temperature, 3 times of freeze-cycle and cryopreservation at –20 ℃ for 15 day, these results indicated that the stability of the samples was good. LBP-FITC was mainly absorbed by the small intestine and stomach, and mainly excreted in the urine through the kidney;this distinct difference in the tissue distribution of LBPs could be attributed to the size of these LBPs in relation to the pore sizes of the vascular beds in the kidney and liver. Results showed in this study enable us to comprehensively understand the biological effects of LBPs following its oral ingestion.
基金Project supported by the National Natural Science Foundation of China(Grant Nos.61378075,61377032,11604327,and 61475152)the Science Foundation of State Key Laboratory of Applied Optics,China
文摘Liquid crystal（LC） compound with isothiocyanate and naphthyl group is an attractive high birefringence LC material,and can be used in optical devices. In this paper, the electro-optical properties of a series of this type of LC compounds were investigated. The melting points and enthalpy values of these LC compounds were higher than those of corresponding compounds with the phenyl group. These compounds exhibited high birefringence with a maximum value of 0.66. Fluorine substitution in the molecular almost does not affect the birefringence value. When these LC compounds with the naphthyl group were dissolved in a commercial LC mixture, the electro-optical properties depending on temperature were investigated. In the low-temperature region, LC mixtures with the naphthyl-group LC compounds exhibited higher viscosity than pure commercial LCs. In the high-temperature region, viscosity values very closely approached each other. When response performance was investigated, figure-of-merit（FoM） values were measured. The Fo M values of LC mixtures containing LC compounds with naphthyl group were lower than those of reference benzene LCs in the low-temperature region. However, in the high-temperature region, the results were reversed. These isothiocyanate LC compounds with naphthyl group can be applied in special fast-response LC device, particularly the ones used under high-temperature conditions.
文摘BACKGROUND Using gas chromatography-mass spectrometry(GC/MS)analysis,we examined the composition of volatile components present in the yellow and green fruits,seeds,and jam of the scrambling shrub Capparis cartilaginea(C.cartilaginea).These plant samples were collected from Kibbutz Yotvata in Israel.In all the tested samples,isothiocyanates were identified.Utilizing the PASS program,we ascertained the biological activity of these isothiocyanates present in the Capparis genus.The study results highlighted that all isothiocyanates could potentially act as apoptosis agonists,making them strong candidates for antitumor drugs.This information holds significant value for the fields of medicinal chemistry,pharmacology,and practical medicine.AIM To investigate the volatile components present in the yellow and green fruits,seeds,and jam of the C.cartilaginea shrub using GC/MS analysis,to detect isothiocyanates in all the analyzed plant samples,and to assess the biological activity of these isothiocyanates utilizing the PASS program.METHODS We utilized two primary methods to analyze the volatile compounds present in the yellow and green fruits,seeds,and jams of the C.cartilaginea,native to Israel.We identified biologically active isothiocyanates in these samples.Their anticipated biological activities were determined using the PASS program,with the most dominant activities being apoptosis agonist,anticarcinogenic,and antineoplastic specifically for genitourinary cancer.RESULTS Fruits,seeds,and jams containing isothiocyanates,which exhibit antineoplastic and anticarcinogenic activities,could be suggested for cancer prevention and management.Specific isothiocyanates,with therapeutic potential in this realm,could be recommended as potent anticancer agents in practical medicine following clinical trials.CONCLUSION The discovery that isothiocyanates exhibit potent antineoplastic and anticarcinogenic activities was unexpected.Additionally,certain isothiocyanates demonstrated antifungal,antiviral(specifically against arbovirus),and antiparasitic properties.
基金Projects supported by the National Natural Science Foundation of China.
文摘Four solid complexes of rare earth isothiocyanates with glycine were synthesized. They were characterized by chemical analysis, elemental analysis, Infrared spectra, X-ray powder diffraction and TO-DSC analysis. Their chemical formulae were proved to be RE(NCS)2.Gly .H2O, where RE is La, Ce, Pr or Nd. The integral heats of solution of RE(NCS)3.3Gly. H2O in water, of RE(NCS)2. 7H2O in aqueous glycine solution and of glycine in water have been measured calorimetricaliy at 298. 15K. By means of a thermochemical cycle suggested in this paper, the standard molar enthalpies of formation for RE(NCS)2. 3Gly.H2O(c) were obtained and their lattice energies were calculated.
基金Project(2007AA06Z122) supported by the National High Technology Research and Development Program of ChinaProject(20110491267) supported by the Postdoctoral Science Foundation of ChinaProject(74341015502) supported by Postdoctoral Fund of Central South University,China
文摘Using Schiff base as a phase transfer catalyst, ethoxycarbonyl isothiocyanate was synthesized by reacting ethyl chloroformate with sodium thiocyanate. In order to get the best synthetic technology, an orthogonal test （L9（34）） was applied. The results show that reaction temperature, reaction time, content of catalyst and molar ratio of sodium thiocyanate to ethyl chloroformate are the main factors influencing the yield. The four factors chosen for the present investigation are based on the results of a single-factor test. The optimum synthetic technology is determined as follows： reaction temperature 35 ℃, reaction time 3 h, the content of catalyst （molar fraction based on ethyl chloroformate） 1.5% and molar ratio of sodium thiocyanate to ethyl chloroformate 1.1. Under the optimized synthetic technology, the experimental yield reaches 96.8%.
文摘Reaction of α-(1H-1,2,4-triazol-1-yl)acetophenone with phenyl isothiocyanate in the presence of a base and subse- quent alkylation leads to the ketene S,N-acetal(2),(4),(7), (8);thiazolidone(3),thiazolidine(5)and 1,3-thiazine(6),
文摘Introduction The study of metal complexes with the crown ether is a quite interesting research field, but the research has mainly focused on the metal complexes with some crown ethers with a relatively small cavity such as 12-crown-4, 15-crown-5 and 18- crown-6 as well as their derivatives. Crown ethers with a larger cavity contain more oxygen atoms, so they have the ability to form the complexes of a higher co-
文摘Metam sodium （MS; sodium N-methyl dithiocarbamate） has emerged as a promising soil fumigant in the US to replace methyl bromide （MeBr）. Metam potassium （MK; potassium N-methyl dithiocarbamate） and MS break down into the volatile gas methyl isothiocyanate （MITC） to control soil borne pests. Many studies have focused on MS, but MK has not been studied as thoroughly. The objective of this research was to determine the effect of increasing organic matter （OM） treatments and soil texture to minimize the off-gassing of MS and MK. Bench-scale soil column studies were performed to simulate organic matter treatments that may decrease the volatilization loss of MITC. Incorporation depth of OM simulated surface tillage （0-15 cm） practices. Soil was packed in steel columns and MS or MK was applied at a depth of 15 cm and MITC volatilization was measured using gas chromatography/mass spectroscopy. Volatilization of MITC behaved similarly for MS and MK with MITC movement impacted by soil texture. MITC volatilization was lower from a sandy clay loam than a sandy soil. Surface incorporation of OM did not significantly decrease MITC volatilization. These results suggest that soil texture is the dominant factor reducing MITC off-gassing and prolonging the time needed to control soil borne pests.
文摘The mechanism of the nonlinear concentration dependence of the intestinal absorption of fluorescein isothiocyanate dextran 4,000 (FD-4) was studied using in situ rat intestinal loops and the in vitro Ussing-type chamber method. The intestinal absorption rate constant of FD-4, as evaluated by the intestinal loop method, increased significantly in a nonlinear fashion as the FD-4 concentration increased up to 0.2 mM and tended to decrease at concentrations higher than 0.2 mM. The mucosal-to-serosal permeation of FD-4 across rat ileal sheets, as evaluated by the in vitro Ussing-type chamber method, also increased in a nonlinear fashion in the low concentration range (0.01 - 0.02 mM), before decreasing as the concentration increased further, whereas serosal-to-mucosal permeation decreased in a concentration-dependent manner. In addition, mucosal-to-serosal flux and serosal-to-mucosal flux were increased and reduced in the presence of the metabolic inhibitor 2, 4-dinitrophenol, respectively. These results suggest that FD-4 is predominantly secreted into the intestinal lumen by an efflux transport system.
文摘Objective To investigate the mechanism of benzyl isothiocyanate(BITC)in the treatment of anaplastic thyroid cancer(ATC).Methods Using network pharmacological analysis,key targets of BITC and ATC were screened,followed by CO and KEGG enrichment analysis.In order to validate the findings,AutoDock software was used to dock BITC and ATC key targets.BITC was applied to two ATC cell lines(8505C and CAL-62).Flow cytometry was used to analyze cell apoptosis.Autophagy inhibitors hydroxychloroquine sulfate(HCQ)and 3-methyladenine(3MA)were used in combination with BITC.Real-time quantitative PCR was conducted to detect the gene level of LC3B,while Western blotting was utilized to examine the expression of NF-kB,LC3B I,Beclin-1,and Bcl-2.In animal experiments,a mouse tumor model was constructed using CAL-62 cells,treated with intraperitoneal injections of BITC(100 mg/kg)and normal saline respectively,administered every other day for a total of 21 days.Immunoblotting of tumor tissue was performed to detect the expression of LC3B II,Bcl-2,Beclin-1,and NFkB.Results A total of 10 key targets with binding energies≤-4.0 kcal/mol were identified.KECG analysis showed that these genes are mainly involved in NF-kB signaling pathway and apoptosis.BITC inhibited ATC cells with IC50 values of 27.56μmol/L for 8505C and 28.30μmol/L for CAL-62.The expression levels of NF-kB,Beclin-1,and Bcl-2 decreased,while LC3B I and LC3B gene expression increased.Combining 3MA with BITC enhanced cell inhibition LC3B II expression.HCQ increased LC3B II expression without enhancing cell and viability inhibition.In the mouse tumor model,compared to the control group,the treatment group had higher LC3B II and lower Bcl-2,Beclin-1,and NF-kB levels.Conclusion BITC could inhibit the growth of ATC cells in vitro and in vivo,disrupt the autophagy degradation,and inhibit the NF-kB pathway.
基金grateful to the National Natural Science Foundation of China,China(No.22161024)for the financial support.
文摘A metal-free,efficient and easy-to-hand protocol for the synthesis of 2-perfluoroalkylquinazolins has been achieved by Eosin B catalyzed radical cascade arylation/cyclization reaction of fluorinated imidoyl isothiocyanates with aryldiazonium Salts.A variety of highly functionalized quinozaline derivatives bearing pharmaceutically important thiol and fluoroalkyl groups were efficiently assembled with broad substrate scope and good functional group tolerance.A series of mechanism experiments indicate that this reaction undergoes a radical cascade arylation/cyclization pathway.
基金the National Natural Science Foundation of China(No.22101059)the financial support from Guangxi Science and Technology Program of China(No.2023GXNSFBA026275)Guangxi Normal University。
文摘A novel photocatalytic energy transfer-driven radical relay strategy has been introduced for the chemoand regioselective 1,4-difunctionalization of carbon-sulfur double bonds.This represents the first instance of radical-mediated dual-functionalization of X-Y type unsaturated bonds,enabling the synthesis of complex linear molecules with C–O,C–N,and C-S bonds in a single operation.The method surpasses traditional approaches by avoiding the need for thiourea intermediates and the harsh conditions typically associated with them.The developed strategy exemplifies versatility,being applicable to 1,4-oxyamination,1,4-diamination,and 1,4-sulfonamination reactions,and has demonstrated compatibility with over 60 different substrates.The research also elucidates the role of electronic complementarity between radicals and receptors in achieving high selectivity in 1,4-difunctionalization reactions.This study significantly advances the field of bifunctionalization and remote difunctionalization reactions,with profound implications for the development of pharmaceuticals and materials science.
