New open-chain and water-soluble hypervalent iodine reagents were synthesized and used for the transfer of fluoroalkyl groups to sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a short cysteine-containing peptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained. The amount of side-products depended on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed - reaction with disulfides to form fluoroalkyl thiols.
- MeSH
- alkylace MeSH
- fluorované uhlovodíky chemická syntéza chemie MeSH
- indikátory a reagencie chemická syntéza chemie MeSH
- jod chemie MeSH
- molekulární struktura MeSH
- rozpustnost MeSH
- sulfhydrylové sloučeniny chemie MeSH
- voda chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The extraction and fractionation of naturally occurring iodine from environmental matrices followed by a spectrometric measurement is the most frequently used method for iodine determination. Nowadays, the inductively coupled plasma mass spectrometry (ICP-MS) represents the most common and reliable method of the total iodine content determination in environmental samples and foodstuff. Other methods such as liquid or gas chromatography which, besides iodine quantification, enable to distinguish individual iodine species are used as well. The aim of this paper is to summarize the most widely used analytical and sample preparation methods for the iodine determination in environmental matrices focused on soil and plant tissues.
The platinum(II) iodido complexes 1-5 of the general formula cis-[PtI2(Ln)2], where Ln stands for O-substituted 9-deazahypoxanthine derivatives, were prepared and thoroughly characterized by various techniques, including multinuclear 1D and 2D NMR spectroscopy. The complexes were screened for their anticancer potential in vitro on ten human cancer cell lines, concretely breast adenocarcinoma (MCF7), osteosarcoma (HOS), lung carcinoma (A549), cervix epithelioid carcinoma (HeLa), malignant melanoma (G-361), prostate carcinoma (22Rv1, PC-3), hepatocellular carcinoma (HepG2), ovarian carcinoma (A2780) and cisplatin-resistant ovarian carcinoma (A2780R). The complexes exhibited significant wide-spectrum anticancer activity in vitro against all the employed cell lines, with IC50≈0.5-24.0μM. Very good correlation between the lipophilicity parameter log P and IC50 values of anticancer activity in vitro were obtained by simple QSAR analysis. The most lipophilic complexes 2, 4 and 5 showed the best results, as they reached the sub-micromolar IC50 values against the A2780 and A2780R sub-lines, with the best result equal 0.5±0.1μM on A2780 for complex 5. The in vivo testing of the representative complexes 1, 4 and 5 (applied at the same dose of Pt as 2mg/kg dose of cisplatin) on a L1210 leukaemia model revealed their positive effect on the prolongation of the mean survival time, even if it was lower than that of cisplatin. The 1H NMR interaction study revealed the ability of complexes to interact with glutathione (GSH) and 5'-guanosine monophosphate (GMP) and overall higher stability of the complexes 1-5 as compared to cisplatin. The electrospray-ionization mass spectrometry experiments with complex 1 identified the formation of a rich collection of hydrolytic species in water-containing media after 24h and the interaction intermediates with sulfur-containing biomolecule l-cysteine, but not with the reduced glutathione at physiologically relevant concentration levels.
- MeSH
- antitumorózní látky chemie terapeutické užití toxicita MeSH
- apoptóza účinky léků MeSH
- buňky Hep G2 MeSH
- HeLa buňky MeSH
- hypoxanthiny chemie MeSH
- jod chemie MeSH
- Kaplanův-Meierův odhad MeSH
- komplexní sloučeniny chemie terapeutické užití toxicita MeSH
- léky antitumorózní - screeningové testy MeSH
- lidé MeSH
- MFC-7 buňky MeSH
- myši inbrední DBA MeSH
- myši MeSH
- nádorové buněčné linie MeSH
- nádory farmakoterapie mortalita patologie MeSH
- platina chemie MeSH
- transplantace heterologní MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
The alkynylation of various nitrogen- and/or sulphur-containing heterocyclic compounds using hypervalent iodine TMS-EBX by utilization of tertiary amines under mild conditions is described. The developed metal-free methodology furnishes the corresponding alkynylated heterocycles bearing quaternary carbon in high yields.
- MeSH
- acetylen chemie MeSH
- alkylační látky chemie MeSH
- biologické přípravky chemie MeSH
- chemické modely MeSH
- heterocyklické sloučeniny chemie MeSH
- indikátory a reagencie MeSH
- indoly chemie MeSH
- jod chemie MeSH
- jodidy chemie MeSH
- laktony chemie MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární konformace MeSH
- molekulární modely MeSH
- molekulární struktura MeSH
- organické látky chemie MeSH
- racionální návrh léčiv MeSH
- rhodanin chemie MeSH
- rozpouštědla chemie MeSH
- teplota MeSH
- uhlík chemie MeSH
- vodíková vazba MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Dietary supplements used by women during menopause are usually based on plant extracts containing isoflavonoids, daidzein and genistein. Genistein is a known inhibitor of many enzymes, including thyroid peroxidase (TPO). In the thyroid follicle, genistein acts as its alternate substrate for the formation of genistein iodinated derivatives. The aim of this study was to search for daidzein- and genistein-iodinated derivatives in urine of isoflavonoid-supplemented women. Additionally, selected phytoestrogens, steroid and thyroid hormones before and after three months of phytoestrogen supplementation were estimated. Urinary levels of free phytoestrogen increased significantly after therapy. They ranged between 0.3-1600, 0.6-670 and 0-206 nmol/L for daidzein, genistein and S-equol, respectively. Monoiodinated derivatives of genistein were observed (0-504 pmol/L) in 60% of the investigated samples. Steroid and thyroid hormone levels were within the normal range and were not significantly altered. The presence of monoiodinated derivates in human urine confirmed that genistein and daidzein may enter human thyroid follicles and influence TPO. Since the levels of the free thyroid hormones were not affected, we propose that the use of phytoestrogen dietary supplements is not associated with the development of thyroid-gland disorders in subjects with adequate iodine intake.
- MeSH
- genistein chemie moč MeSH
- isoflavony chemie moč MeSH
- jod aplikace a dávkování chemie MeSH
- lidé MeSH
- štítná žláza účinky léků fyziologie MeSH
- Check Tag
- lidé MeSH
- ženské pohlaví MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- MeSH
- bromidy farmakologie chemie toxicita MeSH
- experimenty na zvířatech MeSH
- finanční podpora výzkumu jako téma MeSH
- jod farmakologie chemie toxicita MeSH
- krysa rodu rattus metabolismus MeSH
- mateřské mléko metabolismus účinky léků MeSH
- zvířata MeSH
- Check Tag
- krysa rodu rattus metabolismus MeSH
- zvířata MeSH
- MeSH
- finanční podpora výzkumu jako téma MeSH
- jod chemie MeSH
- lidé MeSH
- molekulární modely MeSH
- proteiny chemie MeSH
- spektrometrie hmotnostní - ionizace laserem za účasti matrice MeSH
- tetranitromethan chemie MeSH
- tyrosin chemie MeSH
- vazebná místa MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- srovnávací studie MeSH
