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• W2070058422 abstract "The hydrolysis kinetics of five 4-imidazolidinones derived from acetone and the dipeptides Ala-Gly, Ala-Ala, Phe-Leu, Leu-Gly and Asp-Phe methyl ester were studied to assess their suitability as prodrug forms for the α-aminoamtde moiety occurring in peptides. The imidazolidinyl peptides were found to undergo a complete hydrolysis in the pH range 1–10 at 37°C and most of them showed a sigmoidal pH-rale profile with maximum rates at pH > 4. The stability of the derivatives varied widely, the following half-lives being obtained at pH 7.40 and 37°C: 0.9 h (Asp-Phe methyl ester), 3.4 h (Phe-Leu), 24.6 h (Ala-Ala). 410 h (Ala-Gly) and 530 h (Leu-Gly). The major structural factor influencing the stability appeared to be the stcric properties within the C-terminal amino acid residue. The 4-imidazolidinones are much weaker bases (pKa about 3.1) than the parent dipeptides and, as determined by partition experiments in octanol-aqueous buffer systems with the Phe-Leu derivative, they are more Hpophilic than the parent compounds. It is suggested that 4-imidazolidinone formation in principle may Become a useful approach to bioreversible dehvatization of dipeptides or other peptides containing an α aminoamide function with the aim of solving delivery problems fur peptide drugs." @default.
• W2070058422 created "2016-06-24" @default.
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• W2070058422 date "1984-07-01" @default.
• W2070058422 modified "2023-10-12" @default.
• W2070058422 title "Prodrugs as drug delivery systems. XXX. 4-Imidazolidinones as potential bioreversible derivatives for the α-aminoamide moiety in peptides" @default.
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• W2070058422 doi "https://doi.org/10.1016/0378-5173(84)90174-1" @default.
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