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Rong Zeng,Renzhong Qiao,Zehu Wang,Hongran Wang,Liqiang Chen,Lin Yang,Liming Hu,Zelin Li 한국고분자학회 2012 Macromolecular Research Vol.20 No.4
Two kinds of chitosan-stavudine (d4T) conjugates, chitosan-O-isopropyl-5'-O-d4T monophosphate conjugate (Cs-P-d4T) with a phosphoramide linkage and chitosan-5'-O-succinyl-d4T conjugate (Cs-S-d4T) with a succinic spacer, were synthesized using an Atherton-Todd reaction and carbodiimide coupling reaction, respectively, and then structurally characterized. Their in vitro drug release behaviors and anti-human immunodeficiency virus (HIV) activity were investigated and compared. Both of the chitosan-d4T conjugates more strongly prefer to release corresponding d4T derivatives rather than free d4T in a prolonged manner but have different hydrolysis routes. The anti-HIV activity and cytotoxicity evaluated in the MT4 cell line revealed that the anti-HIV selectivity index was in the following order: Cs-P-d4T > d4T >> Cs-S-d4T since the released d4T-5'-(O-isopropyl) monophosphate from Cs-P-d4T can bypass the rate-limiting bottleneck of nucleoside phosphorylation, while the released 5'-O-succinyl-d4T from Cs-Sd4T has to be hydrolyzed to d4T and then successively phosphorylated to its active form to exert antiviral activity. The results suggested that constructing a chitosan-nucleoside reverse transcriptase inhibitor (NRTI) conjugate with a phosphoramide linkage may be an efficient approach for improving NRTI therapy efficacy in antiretroviral treatment.
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