Synthesis and characterization of monodisperse poly(ethylene glycol)-conjugated collagen pentapeptides with collagen biosynthesis-stimulating activity
Bioorganic & Medicinal Chemistry Letters, ISSN: 0960-894X, Vol: 25, Issue: 1, Page: 38-42
2015
- 17Citations
- 17Captures
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Metrics Details
- Citations17
- Citation Indexes17
- 17
- CrossRef9
- Captures17
- Readers17
- 17
Article Description
Although collagen pentapeptide (Lys-Thr-Thr-Lys-Ser, KTTKS) has received a great deal of attention owing to its collagen biosynthesis-stimulating effects, its enzymatic instability in the skin is an obstacle to effective topical application. PEGylation is a useful approach for improving the chemical and biological stability of peptides. However, the polydispersity of poly(ethylene glycol) (PEG) produces conjugates with different molecular sizes, which may create difficulties in chemical characterization and purity control, and in variability of biological properties. To overcome these difficulties, monodisperse PEG was site-specifically conjugated to the N-terminal amine of KTTKS to produce a single molecular conjugate, enabling more complete chemical characterization and more exact product specifications. PEG–KTTKS conjugates prepared using monodisperse PEG with two different molecular weights, monodisperse PEG 220 and PEG 572, were characterized by mass spectrometry. These monodisperse PEG–KTTKS conjugates showed no cytotoxicity (1–100 μM) and stimulated collagen biosynthesis in human skin fibroblasts. They also had high stability against proteolytic enzymes in rat skin. This study demonstrates the usefulness of monodisperse PEG for preparing chemically defined conjugates and suggests that monodisperse PEG-KTTKS would be a good candidate for use as a collagen biosynthesis-stimulating agent.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0960894X14012050; http://dx.doi.org/10.1016/j.bmcl.2014.11.021; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84913582485&origin=inward; http://www.ncbi.nlm.nih.gov/pubmed/25433999; https://linkinghub.elsevier.com/retrieve/pii/S0960894X14012050; https://dx.doi.org/10.1016/j.bmcl.2014.11.021
Elsevier BV
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