Synthesis and Receptor Binding Analysis of Thirteen Oligomeric α-MSH Analogs
- 1 January 1999
- journal article
- research article
- Published by Taylor & Francis in Journal of Receptors and Signal Transduction
- Vol. 19 (1-4) , 467-480
- https://doi.org/10.3109/10799899909036665
Abstract
Thirteen oligomeric analogs from dimers up to a hexamer of alpha-melanocyte-stimulating hormone (alpha-MSH) were synthesized and tested on melanoma cells for their ability to bind to melanocortin type 1 (MC1) receptors and to stimulate melanin production in the cells. The peptidic oligomers were made by linking several copies of the alpha-MSH fragment analog Nle-Asp-His-[D-Phe]-Arg-Trp-Lys-NH2 to different templates through formation of oxime bonds. They were found to have binding affinities at 37 degrees C up to 8 times higher and melanogenesis-inducing activities up to 4 times higher than those of the native hormone. At 15 degrees C, one dimer showed a binding affinity 20 times higher than that of alpha-MSH. These results are discussed in terms of possible bridging of neighboring receptors which has been suggested to occur in some other systems.Keywords
This publication has 14 references indexed in Scilit:
- Natural Peptides as Building Blocks for the Synthesis of Large Protein-like Molecules with Hydrazone and Oxime LinkagesBioconjugate Chemistry, 1996
- Melanocortins and their implication in melanomaTrends in Endocrinology & Metabolism, 1995
- Facile synthesis of homogeneous artificial proteinsJournal of the American Chemical Society, 1994
- Optimum Cross-linking Spacer Length of Dimeric Neurokinin B Analogs for Interaction with NK-1 Tachykinin ReceptorsBulletin of the Chemical Society of Japan, 1993
- Construction of protein analogs by site-specific condensation of unprotected fragmentsBioconjugate Chemistry, 1992
- Biologically Active Monoiodinated α-MSH Derivatives for Receptor Binding Studies Using Human Melanoma CellsJournal of Receptor Research, 1991
- Radioreceptor Assay for α;-Msh Using Mouse B16 Melanoma CellsJournal of Receptor Research, 1988
- In situ melanin assay for MSH using mouse B16 melanoma cells in cultureAnalytical Biochemistry, 1986
- 4-Norleucine, 7-D-phenylalanine-alpha-melanocyte-stimulating hormone: a highly potent alpha-melanotropin with ultralong biological activity.Proceedings of the National Academy of Sciences, 1980
- LIGAND: A versatile computerized approach for characterization of ligand-binding systemsAnalytical Biochemistry, 1980