Synthesis and radioprotective properties of certain diol lipids

Chechulina, L. A.; Puchkova, S. M.; Novikova, A. P.; Baskakova, Z. M.; Vysokov, V. I.; Afanas'eva, G. B.

doi:10.1007/bf00770450

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“…Thereby we took advantage of the possibility to alkylate using an alcohol instead of an alkyl halide. 4-(Decyloxy)butan-1-ol(11) 39 was synthesized from butane-1,4-diol and 1-bromodecane using a procedure by Tanaka et al 40 and reacted with 2-N-acetyl-6-O-DPC-protected guanine (7) under Mitsunobu conditions to give 12 in moderate yields (Scheme 2). The final deprotecting step with NH 4 OH and MeOH afforded the target molecule 3 in a 32% yield (9% over three steps).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of Lipophilic Guanine N-9 Derivatives: Membrane Anchoring of Nucleobases Tailored to Fatty Acid Vesicles

et al. 2017

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Covalent or noncovalent surface functionalization of soft-matter structures is an important tool for tailoring their function and stability. Functionalized surfaces and nanoparticles have found numerous applications in drug delivery and diagnostics, and new functionalization chemistry is continuously being developed in the discipline of bottom-up systems chemistry. The association of polar functional molecules, e.g., molecular recognition agents, with soft-matter structures can be achieved by derivatization with alkyl chains, allowing noncovalent anchoring into amphiphilic membranes. We report the synthesis of five new guanine-N9 derivatives bearing alkyl chains with different attachment chemistries, exploiting a synthesis pathway that allows a flexible choice of hydrophobic anchor moiety. In this study, these guanine derivatives were functionalized with C chains for insertion into decanoic acid bilayer structures, in which both alkyl chain length and attachment chemistry determined their interaction with the membrane. Incubation of these guanine conjugates, as solids, with a decanoic acid vesicle suspension, showed that ether- and triazole-linked C anchors yielded an increased partitioning of the guanine derivative into the membranous phase compared to directly N-9-linked saturated alkyl anchors. Decanoic acid vesicle membranes could be loaded with up to 5.5 mol % guanine derivative, a 6-fold increase over previous limits. Thus, anchor chemistries exhibiting favorable interactions with a bilayer's hydrophilic surface can significantly increase the degree of structure functionalization.

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Section: ■ Results and Discussionmentioning

confidence: 99%