New Detachable Poly(ethylene glycol) Conjugates: Cysteine-Cleavable Lipopolymers Regenerating Natural Phospholipid, Diacyl Phosphatidylethanolamine
| Autor: | Y P Quinn, Nasreen Mullah, Samuel Zalipsky, Shi Kun Huang, M Qazen, J A Walker nd |
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| Rok vydání: | 1999 |
| Předmět: |
Pharmacology
Phosphatidylethanolamine Liposome Phosphatidylethanolamines Organic Chemistry Biomedical Engineering Pharmaceutical Science Substrate (chemistry) Bioengineering Urethane Polyethylene Glycols chemistry.chemical_compound Drug Delivery Systems Thiolysis chemistry Liposomes Drug delivery Polymer chemistry Carbamates Cysteine Ethylene glycol Phospholipids Biotechnology Conjugate |
| Zdroj: | Bioconjugate Chemistry. 10:703-707 |
| ISSN: | 1520-4812 1043-1802 |
| DOI: | 10.1021/bc990031n |
| Popis: | A new strategy for the reversible attachment of methoxypoly(ethylene glycol) (mPEG) to an amino-containing substrate is described. The strategy is based on formation of a benzyl carbamate linkage substituted with a disulfide in the para or ortho position. While being stable under nonreducing conditions, the dithiobenzyl (DTB) urethane linkage is susceptible to cleavage by mild thiolysis with cysteine resulting in release of the parent amino component of the conjugate in its original form. The method is exemplified by preparation of mPEG-DTB-alcohol, its activation and attachment to distearoylphosphatidylethanolamine (DSPE). The resulting lipopolymer incorporates into liposomes, which are capable of losing their polymer coating under conditions approximating those existing in vivo. Implications for drug delivery are briefly discussed. |
| Databáze: | OpenAIRE |
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