Sulforaphane is an isothiocyanate occurring in stored form as glucoraphanin in cruciferous vegetables such as cabbage, cauliflower, and kale, and at high levels in broccoli especially in broccoli sprouts. Glucoraphanin requires the plant enzyme myrosinase for converting it into sulforaphane. Sulforaphane is metabolized through mercapturic acid pathway, being conjugated with glutathione and undergoes further biotransformation, yielding metabolites. Sulforaphane is extensively investigated and is in the interest in medicine for its health benefits. It has been shown that sulforaphane may protect against various types of cancer, may also decrease the risk of cardiovascular disease, and help in autism and osteoporosis. Our review offers a short summary of interesting properties of sulforaphane. Both the in vitro and in vivo methods/models and clinical studies are mentioned.
- MeSH
- autistická porucha * farmakoterapie MeSH
- Brassica chemie MeSH
- fytogenní protinádorové látky terapeutické užití MeSH
- glukosinoláty metabolismus MeSH
- imidoestery metabolismus MeSH
- isothiokyanatany * chemie farmakologie terapeutické užití MeSH
- lidé MeSH
- nádory * prevence a kontrola MeSH
- osteoporóza farmakoterapie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- přehledy MeSH
BACKGROUND/AIM: Triple-negative breast cancer (TNBC) constitutes 15-20% of all breast carcinomas, affecting younger women more often and has a worse prognosis than other types of breast cancer, due to the combination of more aggressive clinical behavior and lack of molecular targets for therapy. This study assessed the effects of non-genotoxic concentrations of tributyltin isothiocyanate (TBT-ITC) and triphenyltin isothiocyanate (TPT-ITC) on MDA-MB-231 cells. MATERIALS AND METHODS: MTT assay, comet assay, kinetic imaging and flow cytometry were used for analysis of MDA-MB-231 cells. RESULTS: The results showed that 100 nM concentration of TBT-ITC and TPT-ITC, that did not affect viability or DNA integrity, slowed-down migration by CD44 down-regulation. Moreover, both compounds demonstrated immunomodulatory properties, attenuating PD-L1 expression in MDA-MB-231 cells. CONCLUSION: TPT-ITC was more effective in down-regulating CD44 expression and reducing migration than TBT-ITC, while TBT-ITC was more potent in lowering PD-L1 expression in comparison with TPT-ITC.
- MeSH
- apoptóza účinky léků MeSH
- imunofenotypizace MeSH
- isothiokyanatany chemie farmakologie MeSH
- lidé MeSH
- nádorové biomarkery * MeSH
- nádorové buněčné linie MeSH
- organocínové sloučeniny chemie MeSH
- pohyb buněk účinky léků MeSH
- poškození DNA účinky léků MeSH
- proliferace buněk účinky léků MeSH
- protinádorové látky chemie farmakologie MeSH
- triple-negativní karcinom prsu metabolismus MeSH
- viabilita buněk účinky léků MeSH
- Check Tag
- lidé MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
The cytotoxicity of two recently synthesized triorganotin isothiocyanate derivatives, nuclear retinoid X receptor ligands, was tested and compared in estrogen-receptor-positive MCF 7 and -negative MDA-MB-231 human breast carcinoma cell lines. A 48 h MTT assay indicated that tributyltin isothiocyanate (TBT-ITC) is more cytotoxic than triphenyltin isothiocyanate (TPT-ITC) in MCF 7 cells, and the same trend was observed in the MDA-MB-231 cell line. A comet assay revealed the presence of both crosslinks and increasing DNA damage levels after the 17 h treatment with both derivatives. Differences in cytotoxicity of TBT-ITC and TPT-ITC detected by FDA staining correspond to the MTT data, communicating more pronounced effects in MCF 7 than in the MDA-MB-231 cell line. Both derivatives were found to cause apoptosis, as shown by the mitochondrial membrane potential (MMP) depolarization and caspase-3/7 activation. The onset of caspase activation correlated with MMP dissipation and the total cytotoxicity more than with the amount of active caspases. In conclusion, our data suggest that the DNA damage induced by TBT-ITC and TPT-ITC treatment could underlie their cytotoxicity in the cell lines studied.
- MeSH
- apoptóza účinky léků MeSH
- isothiokyanatany chemie farmakologie MeSH
- lidé MeSH
- membránový potenciál mitochondrií účinky léků MeSH
- MFC-7 buňky MeSH
- nádorové buněčné linie MeSH
- nádory prsu farmakoterapie genetika metabolismus MeSH
- organocínové sloučeniny chemie farmakologie MeSH
- poškození DNA účinky léků MeSH
- protinádorové látky chemie farmakologie MeSH
- retinoidní X receptory metabolismus MeSH
- trialkylcínové sloučeniny chemie farmakologie MeSH
- Check Tag
- lidé MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
- srovnávací studie MeSH
Antimicrobial activity of crude seed extract of Moringa oleifera was investigated by thin layer chromatography bioassay against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Cladosporium cladosporioides, and Penicillium sclerotigenum; most of them were prominently inhibited by an isolate with R(F) 0.92-0.96. Characterization and identification of the extract revealed the occurrence of three bioactive compounds: 4-(?-L-rhamnopyranosyloxy)benzyl isothiocyanate, methyl N-4-(?-L-rhamnopyranosyloxy) benzyl carbamate (both known compounds), and 4-(ß-D-glucopyranosyl-1›4-?-L-rhamnopyranosyloxy)-benzyl thiocarboxamide, existence of which in any Moringa spp. or plant is reported for the first time. The UV spectrum of the novel compound showed maximum absorption at 273 and 225 nm in MeOH while the IR spectrum revealed several characteristic bands at 3100, 2900, 1700, 1500, 1300, 1100 and 1000 cm(-1). The (1)H-NMR showed signals at 1.2 and 3.77 ppm and the (13)C-NMR presented signals at 155, 122, 91.7 and 98.4 ppm. All the compounds at 5 mg/L had very high bactericidal activity against some of test pathogens even at contact period 1-2 h. 4-(ß-D-Glucopyranosyl-1›4-?-L-rhamnopyranosyloxy)benzyl thiocarboxamide was the most potent, with 99.2 % inhibition toward Shigella dysenteriae and 100 % toward Bacillus cereus, E. coli and Salmonella typhi within 4 h of contact.
- MeSH
- antiinfekční látky farmakologie MeSH
- Bacteria klasifikace účinky léků MeSH
- biotest MeSH
- chromatografie na tenké vrstvě metody MeSH
- glukosidy farmakologie MeSH
- glukosinoláty farmakologie chemie MeSH
- houby klasifikace účinky léků MeSH
- isothiokyanatany farmakologie chemie MeSH
- magnetická rezonanční spektroskopie MeSH
- mikrobiální testy citlivosti metody MeSH
- Moringa oleifera chemie MeSH
- počet mikrobiálních kolonií MeSH
- rostlinné extrakty farmakologie chemie MeSH
- semena rostlinná chemie MeSH
Contrary to a previous report, the sulfurisation of phosphorus(III) derivatives by 3-amino-1,2,4-dithiazole-5-thione (xanthane hydride) does not yield carbon disulfide and cyanamide as the additional reaction products. The reaction of xanthane hydride with triphenyl phosphine or trimethyl phosphite yields triphenyl phosphine sulfide or trimethyl thiophosphate, respectively, and thiocarbamoyl isothiocyanate which has been trapped with nucleophiles. The reaction pathway involves initial nucleophilic attack of the phosphorus at sulfur next to the thiocarbonyl group of xanthane hydride followed by decomposition of the phosphonium intermediate formed to products. The Hammett rho-values for the sulfurisation of substituted triphenyl phosphines and triphenyl phosphites in acetonitrile are approximately -1.0. The entropies of activation are very negative (-114+/-15 J mol-1 K-1) with little dependence on solvent which is consistent with a bimolecular association step leading to the transition state. The negative values of DeltaS(not equal) and rho values indicate that the rate limiting step of the sulfurisation reaction is formation of the phosphonium ion intermediate which has an early transition state with little covalent bond formation. The site of nucleophilic attack has been also confirmed using computational calculations. PMID: 17252130 [PubMed - indexed for MEDLINE]
- MeSH
- amitrol chemie MeSH
- chemické modely MeSH
- financování organizované MeSH
- fosfiny chemie MeSH
- fosfor chemie MeSH
- fosforitany chemie MeSH
- hydrolýza MeSH
- isothiokyanatany chemie MeSH
- kinetika MeSH
- kyanamid chemie MeSH
- síra chemie MeSH
- sirouhlík chemie MeSH
- termodynamika MeSH
- thiazoly chemie MeSH
- thioketony chemie MeSH
- triaziny chemie MeSH
- vodíková vazba MeSH
- MeSH
- antifungální látky chemická syntéza chemie terapeutické užití MeSH
- cyklizace MeSH
- imidazoly chemická syntéza chemie terapeutické užití MeSH
- indoly chemická syntéza chemie terapeutické užití MeSH
- isothiokyanatany chemická syntéza chemie terapeutické užití MeSH
- magnetická rezonanční spektroskopie metody MeSH
- rostlinné extrakty chemická syntéza chemie terapeutické užití MeSH
- MeSH
- isothiokyanatany farmakologie chemie MeSH
- lidé MeSH
- Check Tag
- lidé MeSH
