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Novel lipidic-amino acid based drug and peptide delivery system

Christodoulou, Marika; (1994) Novel lipidic-amino acid based drug and peptide delivery system. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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The lipidic amino acids are synthetic α-amino acids with long alkyl side chains. The lipidic amino acids and their homo oligomers represent compounds combining the structural properties of proteins and peptides and the physical characteristics of lipids and membranes. The lipidic amino acids were synthesized from the appropriate alkyl bromide and diethyl-acetamido malonate. Resolution was achieved enzymatically using Acylase I or chemically by forming diastereomers of the amino acids with an optically pure α-pinene derivative. The aim of the project was the synthesis of the lipidic amino acids and peptides and their conjugation with natural peptides including elastase inhibitors and enkephalins. The lipidic amino acids and their oligomers were envisaged to increase the membrane permeability of peptides. In addition, it is envisaged that the long alkyl side chains of the lipidic amino acids will physically protect against the metabolic breakdown of the enzyme labile elastase and enkephalin peptides. The use of the lipidic amino acids as a polymeric drug delivery system was investigated. Random polymerisation of homo- and hetero-trimers by the active ester method yielded as series of products to be tested for drug encapsulation capacity and metabolic stability. Low solubility of these products limited their use in drug encapsulation and stability studies.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Novel lipidic-amino acid based drug and peptide delivery system
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Health and environmental sciences
URI: https://discovery.ucl.ac.uk/id/eprint/10104800
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