21050-95-3Relevant articles and documents
Cationic lipophosphoramidates with two disulfide motifs: Synthesis, behaviour in reductive media and gene transfection activity
Fraix, Aurore,Le Gall, Tony,Berchel, Mathieu,Denis, Caroline,Lehn, Pierre,Montier, Tristan,Jaffrès, Paul-Alain
, p. 1650 - 1658 (2013)
Lipophosphoramidates have previously been identified as efficient vectors for gene delivery. The incorporation of functional groups that respond to a physiological stimulus is hypothesised to further improve the efficacy of this type of vector and eventually reduce its cytotoxicity. In the present work, we report the effects of the incorporation of two disulfide motifs into the hydrophobic domain, close to the phosphoramidate group. Three cationic vectors possessing such a red/ox sensitive function were synthesised. The capability of one of them (5b) to compact DNA is reported jointly with its ability to release that DNA in the presence of a reducing agent. Finally, compound 5b was tested as a vector for gene delivery into human cells in vitro and its cytotoxicity was also evaluated.
Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer
Roseblade, Ariane,Ung, Alison,Bebawy, Mary
, p. 1353 - 1368 (2017/10/10)
Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.
Caryophyllane Thiols, Vinyl Thioethers, Di- and Bis-Sulfides: Antioxidant and Membrane Protective Activities
Gyrdymova, Yulia V.,Sudarikov, Denis V.,Shevchenko, Oksana G.,Rubtsova, Svetlana A.,Slepukhin, Pavel A.,Kutchin, Aleksandr V.
, (2017/12/15)
Caryophyllane thioterpenoids were synthesized in 23 – 81% yields. The antioxidant properties of the obtained compounds in various model systems were found. It was revealed that 4,5-epoxycaryophyll-9-ylmethanethiol has the greatest antioxidant activity. The isomerism of sesquiterpenic fragments was shown to have a significant effect on the biological activity of the compounds.
The Effect of Oxidizing Agents in the Preparation of 2,3,5-triaryl-2H-tetrazolium Salts from 1,3,5-triarylformazans
Penev, Kalin I.,Mequanint, Kibret
, p. 1655 - 1660 (2016/09/23)
Tetrazolium salts are a group of versatile molecules with a relatively limited application due to synthesis difficulty and high cost of production. Here, we have comparatively examined several approaches for the preparation of 2-(4-nitrophenyl)-3,5-diphenyl-2H-tetrazolium chloride (NTC), as a model tetrazolium salt, through the oxidation of 1-(4-nitrophenyl)-3,5-diphenylformazan (NF), by means of interphase oxidation, dehydrogenation, and direct chlorination. Our findings indicate that chlorination of NF with 1-chlorobenztriazole to be the best choice to prepare NTC from small-scale and scaled-up considerations.
Symmetrization of cationic hydrogen bridges of protonated sponges induced by solvent and counteranion interactions as revealed by NMR spectroscopy
Pietrzak, Mariusz,Wehling, Jens P.,Kong, Shushu,Tolstoy, Peter M.,Shenderovich, Ilya G.,Lopez, Concepcion,Claramunt, Rosa Maria,Elguero, Jose,Denisov, Gleb S.,Limbach, Hans-Heinrich
supporting information; experimental part, p. 1679 - 1690 (2010/06/17)
The properties of the intramolecular hydrogen bonds of doubly 15N-labeled protonated sponges of the 1,8-bis(dimethylamino)naphthalene (DMANH+) type have been studied as a function of the solvent, counteranion, and temperature using low-temperature NMR spectroscopy. Information about the hydrogen-bond symmetries was obtained by the analysis of the chemical shifts δH and δN and the scalar coupling constants J(N,N), J(N,H), J(H,N) of the 15NH15N hydrogen bonds. Whereas the individual couplings J(N,H) and J(H,N) were averaged by a fast intramolecular proton tautomerism between two forms, it is shown that the sum | J(N,H)+J(H,N)| generally represents a measure of the hydrogen-bond strength in a similar way to δH and J(N,N). The NMR spectroscopic parameters of DMANH+ and of 4-nitro-DMANH+ are independent of the anion in the case of CD3CN, which indicates ion-pair dissociation in this solvent. By contrast, studies using CD2Cl2, [D8]toluene as well as the freon mixture CDF3/ CDF2Cl, which is liquid down to 100 K, revealed an influence of temperature and of the counteranions. Whereas a small counteranion such as trifluoroa-cetate perturbed the hydrogen bond, the large noncoordinating anion tetrakis[3,5-bis(trifluoromethyl)phenyl]borate B[{C6H3(CF3)2}4] - (BARF-), which exhibits a delocalized charge, made the hydrogen bond more symmetric. Lowering the temperature led to a similar symmetrization, an effect that is discussed in terms of solvent ordering at low temperature and differential solvent order/disorder at high temperatures. By contrast, toluene molecules that are ordered around the cation led to typical high-field shifts of the hydrogen-bonded proton as well as of those bound to carbon, an effect that is absent in the case of neutral NHN chelates.
An efficient method for the preparation of peptide alcohols
Katritzky, Alan Roy,Abo-Dya, Nader Elmaghwry,Tala, Srinivasa Rao,Gyanda, Kapil,Abdel-Samii, Zakaria Kamel
supporting information; experimental part, p. 4444 - 4447 (2009/12/25)
N-Protected ll-dipeptide alcohols 3a-p, diastereomeric mixture (3d + 3d′) and tripeptide alcohols 6a-c were synthesized by treatment of various amino alcohols with N-protected(α-aminoacyl)benzotriazoles 1a-c, 1f-m, (1a + 1a′) and N-protected(α-dipeptidoyl)benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.
Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate
Kim, Jeum-Jong,Kweon, Deok-Heon,Cho, Su-Dong,Kim, Ho-Kyun,Lee, Sang-Gyeong,Yoon, Yong-Jin
, p. 194 - 200 (2007/10/03)
AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.
