2002
DOI: 10.1081/jlc-120004751
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Lipophilic Character of Novel Amino Acid Derivatives of Zidovudine With Anti Hiv Activity

Abstract: The lipophilic properties of a novel series of zidovudine amino acid derivatives were measured using chromatographic techniques, reversed-phase thin layer chromatography (RP-TLC) and reversed-phase high performance liquid chromatography (RP-HPLC), as well as the classic shake flask (log P o=w ) and theoretical CLOGP methods. These novel derivatives, obtained by association of zidovudine (AZT) with the essential amino acids leucine (AZT-Leu), isoleucine (AZT-iLeu), phenylalanine (AZT-Phe), valine (AZT-Val), pro… Show more

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Cited by 10 publications
(6 citation statements)
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“…Although some of these prodrugs showed promising biological activities as measured in anti HIV in vitro assays, [19] they had a poor resistance to chemical and enzymatic hydrolysis, which was also accompanied by a limited bound fraction to HSA. [6,[22][23][24][25] Recently, we reported the synthesis and chemical stability evaluation of three novel prodrugs of AZT obtained by derivatization with different dicarboxylic acids (1-3, Figure 1.c): succinic (1), glutaric (2) and adipic (3) acids. [18] These single prodrugs exhibited adequate chemical stabilities at different pH values (2 -7.4).…”
Section: Methodsmentioning
confidence: 99%
“…Although some of these prodrugs showed promising biological activities as measured in anti HIV in vitro assays, [19] they had a poor resistance to chemical and enzymatic hydrolysis, which was also accompanied by a limited bound fraction to HSA. [6,[22][23][24][25] Recently, we reported the synthesis and chemical stability evaluation of three novel prodrugs of AZT obtained by derivatization with different dicarboxylic acids (1-3, Figure 1.c): succinic (1), glutaric (2) and adipic (3) acids. [18] These single prodrugs exhibited adequate chemical stabilities at different pH values (2 -7.4).…”
Section: Methodsmentioning
confidence: 99%
“…[4,6] A 50 mL aliquot of the test solutions of each compound was applied to the plates in random positions. Compounds 1, 2, and 8 were dissolved in acetone, 3, 4, and 7 in methanol, and 5 and 6 in chloroform, reaching a final concentration in the corresponding solvent of 1 mg/mL.…”
Section: R M Assaymentioning
confidence: 99%
“…[4,6,7] Conventional Shake-Flask Methods (Log P oct ) Data were acquired by means of a Peak Simple Chromatography Data System.…”
Section: Log K 0 Assaymentioning
confidence: 99%
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“…21 Many nucleoside analogues with interesting biological properties have been developed by substitution at the 5 0 -O position of the NRTI with lipophilic chemical moieties linked by enzymatically hydrolysable functions such as ester and carbonate bonds. [19][20][21][22][23][24][25][26][27] The lipophilic character of the side chains at the 5 0 -O position should inuence their ability to cross the cell membrane by passive diffusion, which is a key feature in the absence of an active nucleoside transport system. [22][23][24]28,29 As stated by Parang et al, 20 more selective compounds can be designed by using the strategy of 5 0 -O-carbonates substitution.…”
Section: Introductionmentioning
confidence: 99%