43016-78-0Relevant articles and documents
Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
Agafonova, Mariya N.,Chirkova, Milana N.,Druk, Anastasia Y.,Grishaev, Denis Y.,Kayumov, Airat R.,Kazakova, Renata R.,Krylova, Elena S.,Nikishova, Tatyana V.,Nikitina, Elena V.,Sabirova, Alina E.,Sapozhnikov, Sergey V.,Shtyrlin, Nikita V.,Shtyrlin, Yurii G.
, (2021/01/06)
A diverse series of 43 novel “soft antimicrobials” based on quaternary ammonium pyridoxine derivatives which include six-membered acetals and ketals of pyridoxine bound via cleavable linker moieties (amide, ester) with a fragment of fatty carboxylic acid was designed. Nine compounds exhibited in vitro promising antibacterial activity against Gram-positive and Gram-negative bacterial strains with MIC values comparable with reference antiseptics miramistin, benzalkonium chloride and chlorohexidine. On various clinical isolates, the lead compounds 6i and 12a exhibited antibacterial activity comparable with that of benzalkonium chloride while higher than that of miramistin. Moreover, 6i and 12a were able to kill bacteria embedded into the matrix of mono- and dual species biofilms. The treatment of bacterial cells by either 6i and 12a lead to fast depolarization of the membrane suggesting that the membrane is an apparent molecular target of compounds. 6i and 12a were non mutagenic neither in SOS-chromotest nor in Ames test and non-toxic in vivo at acute oral (LD50 > 2000 mg/kg) and cutaneous administration (LD50 > 2500 mg/kg) on mice. Taken together, our data allow suggesting described active compounds as promising starting point for the new antibacterial agents development.
Thermal behavior of long-chain alkanoylcholine soaps
Tolentino, Ainhoa,Alla, Abdelilah,Martinez De Ilarduya, Antxon,Font-Bardia, Merce,Leon, Salvador,Munoz-Guerra, Sebastian
, p. 10738 - 10750 (2014/03/21)
Long-chain alkanoylcholines prepared from fatty acids (nACh) are fully sustainable cationic surfactants that are known for their biological and medicinal properties. In the present work the thermal behavior of the homologous series of alkanoylcholine iodides with n = 12, 14, 16 and 18, has been examined within the 25-200 °C range of temperatures. Up to three thermotropic phases have been identified, and the thermal transitions implied in their interconversion have been characterized by DSC and simultaneous WAXS and SAXS analysis carried out in real-time. All three phases consist of a bilayered structure with alkanoyl chains confined in the space between the head group layers and interdigitated to a greater or lesser extent. Melting-crystallization of either the polymethylene segments or the choline iodide groups is involved in such transitions. Additionally, a crystal phase consisting also of a bilayered structure but excluding side chain interdigitation was observed upon crystallization from solution and its structure was elucidated by single-crystal X-ray diffraction direct methods. The close correlation existing between thermal properties, phase structure and n has been brought into evidence.
Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS
Li, Xingnan,Franke, Adrian A.
, p. 3192 - 3198 (2011/11/04)
We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC-MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2-10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.
