Synthesis of a lipid/peptide/drug conjugate: N4-(acylpeptidyl)-ara-C

A lipid/peptide/drug conjugate, N4-(acylpeptidyl)-ara-C, is synthesized under mild conditions to give an ara-C prodrug protected against cytidine deaminase-catalyzed deactivation. The compounds can be bound, via their hydrocarbon tails, to phospholipid membranes and examined for chymotrypsin-induced...

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Bibliographic Details
Published in:Bioconjugate chemistry 1994-03, Vol.5 (2), p.162-166
Main Authors: Menger, F M, Guo, Y, Lee, A S
Format: Article
Language:English
Subjects:
Cytarabine - analogs & derivatives
Cytarabine - chemical synthesis
Cytarabine - chemistry
Cytidine Deaminase - metabolism
Indicators and Reagents
Oligopeptides - chemical synthesis
Prodrugs - chemical synthesis
Spectrometry, Mass, Fast Atom Bombardment
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Summary:A lipid/peptide/drug conjugate, N4-(acylpeptidyl)-ara-C, is synthesized under mild conditions to give an ara-C prodrug protected against cytidine deaminase-catalyzed deactivation. The compounds can be bound, via their hydrocarbon tails, to phospholipid membranes and examined for chymotrypsin-induced drug release. A tripeptide is too short to permit efficient enzyme/membrane contact and subsequent freeing of the drug. Faster rates can, presumably, be achieved by "fine tuning" the length and polarity of the peptide spacer attached to the drug.
ISSN:1043-1802