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.
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.
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.
