123253-22-5Relevant academic research and scientific papers
Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities
Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto
supporting information, p. 2544 - 2550 (2019/11/13)
Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2S. Three AKGs (5l–5n) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (5a–5k, 5o). Their structures were established using 1H and 13C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs 5a–5m and 5o showed activity against five clinical isolates and P. aeruginosa ATCC 15442, with MIC values in the range of 15–125 μg/mL. In addition, at half of the MIC, most of the AKGs reduced S. aureus biofilm formation in the range of 23%–99% and P. aeruginosa ATCC 15442 biofilm formation in the range of 14%–64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.
Self-assembling ligands for multivalent nanoscale heparin binding
Rodrigo, Ana C.,Barnard, Anna,Cooper, James,Smith, David K.
scheme or table, p. 4675 - 4679 (2011/06/27)
Supramolecular string of pearls: Polycationic ligands are designed to self-assemble into spherical pseudo-dendrimers that are capable of binding polyanionic heparin with affinities and binding modes similar to covalent nanostructures such as dendrimers an
Synthesis, critical micelle concentrations, and antimycobacterial properties of homologous, dendritic amphiphiles. Probing intrinsic activity and the "cutoff" effect
Sugandhi, Eko W.,Macri, Richard V.,Williams, André A.,Kite, Brett L.,Slebodnick, Carla,Falkinham III, Joseph O.,Esker, Alan R.,Gandour, Richard D.
, p. 1645 - 1650 (2008/02/01)
Newkome-type, 1→3 C-branched dendrons make an excellent headgroup for amphiphiles with ultralong, saturated, linear alkyl chains. Synthesis of a homologous series of five such amphiphiles from 14 to 22 carbons- RNHCONHC(CH2CH2CO2H)3, R = n-C nH2n+1, n = 14, 16, 18, 20, 22-proceeds readily. These amphiphiles are soluble in aqueous solutions of triethanolamine. Surface-tension measurements on this homologous series reveal an unusually gradual decrease in log critical micelle concentration (CMC) as the chain length increases. In fact, the tetradecyl homologue does not appear to form micelles. Further, measurements of minimal inhibitory concentration (MIC) by broth microdilution against Mycobacterium smegmatis as a function of the initial cell density provide a direct measure of the intrinsic activity (MIC0) of each homologue. The hexadecyl homologue is the most active at inhibiting growth with an MIC0 equal to 3.5 × 10-5 M, which is 100-fold below the CMC.
