136025-56-4Relevant academic research and scientific papers
Phospholipid-induced aggregation and anthracene excimer formation
Chen, Kuan-Hung,Yang, Jye-Shane,Hwang, Chung-Yu,Fang, Jim-Min
supporting information; experimental part, p. 4401 - 4404 (2009/05/27)
(Chemical Equation) The zinc complex of anthryl bis(dipicolylamine) (1) aggregates upon binding with long-chain aliphatic phosphates and displays anthracene excimer fluorescence, which provides a new strategy toward detection of the biologically important lysophosphatidic acid in aqueous solution.
Fatty alcohol phosphates are subtype-selective agonists and antagonists of lysophosphatidic acid receptors
Virag, Tamas,Elrod, Don B.,Liliom, Karoly,Sardar, Vineet M.,Parrill, Abby L.,Yokoyama, Kazuaki,Durgam, Gangadhar,Deng, Wenlin,Miller, Duane D.,Tigyi, Gabor
, p. 1032 - 1042 (2007/10/03)
A more complete understanding of the physiological and pathological role of lysophosphatidic acid (LPA) requires receptor subtype-specific agonists and antagonists. Here, we report the synthesis and pharmacological characterization of fatty alcohol phosphates (FAP) containing saturated hydrocarbon chains from 4 to 22 carbons in length. Selection of FAP as the lead structure was based on computational modeling as a minimal structure that satisfies the two-point pharmacophore developed earlier for the interaction of LPA with its receptors. Decyl and dodecyl FAPs (FAP-10 and FAP-12) were specific agonists of LPA2 (EC50 = 3.7 ± 0.2 μM and 700 ± 22 nM, respectively), yet selective antagonists of LPA3 (Ki = 90 nM for FAP-12) and FAP-12 was a weak antagonist of LPA1. Neither LPA1 nor LPA3 receptors were activated by FAPs; in contrast, LPA2 was activated by FAPs with carbon chains between 10 and 14. Computational modeling was used to evaluate the interaction between individual FAPs (8 to 18) with LPA2 by docking each compound in the LPA binding site. FAP-12 displayed the lowest docked energy, consistent with its lower observed EC50. The inhibitory effect of FAP showed a strong hydrocarbon chain length dependence with C12 being optimum in the Xenopus laevis oocytes and in LPA3-expressing RH7777 cells. FAP-12 did not activate or interfere with several other G-protein-coupled receptors, including S1P-induced responses through S1P1.2,3.5 receptors. These data suggest that FAPs are ligands of LPA receptors and that FAP-10 and FAP-12 are the first receptor subtype-specific agonists for LPA2.
A new method for transforming primary amines into phosphoric acid monoesters
Luo,Ganem
, p. 3145 - 3146 (2007/10/02)
Nitrosation of dibenzylphosphoramidates enables the synthesis of phosphoric acid monoesters from primary n-alkylamines in good yield.
