dc.contributor.author | Testa, Chiara | en_US |
dc.contributor.author | Scrima, Mario | en_US |
dc.contributor.author | Grimaldi, Manuela | en_US |
dc.contributor.author | D’Ursi, Anna M. | en_US |
dc.contributor.author | Dirain, Marvin L. | en_US |
dc.contributor.author | Lubin-Germain, Nadège | en_US |
dc.contributor.author | Singh, Anamika | en_US |
dc.contributor.author | Haskell-Luevano, Carrie | en_US |
dc.contributor.author | Chorev, Michael | en_US |
dc.contributor.author | Rovero, Paolo | en_US |
dc.contributor.author | Papini, Anna M. | en_US |
dc.date.accessioned | 2015-11-03T15:58:19Z | |
dc.date.issued | 2014 | en_US |
dc.identifier.citation | Testa, C., M. Scrima, M. Grimaldi, A. M. D’Ursi, M. L. Dirain, N. Lubin-Germain, A. Singh, et al. 2014. “1,4-Disubstituted-[1,2,3]triazolyl-Containing Analogues of MT-II: Design, Synthesis, Conformational Analysis, and Biological Activity.” Journal of Medicinal Chemistry 57 (22): 9424-9434. doi:10.1021/jm501027w. http://dx.doi.org/10.1021/jm501027w. | en |
dc.identifier.issn | 0022-2623 | en |
dc.identifier.uri | http://nrs.harvard.edu/urn-3:HUL.InstRepos:23474014 | |
dc.description.abstract | Side chain-to-side chain cyclizations represent a strategy to select a family of bioactive conformations by reducing the entropy and enhancing the stabilization of functional ligand-induced receptor conformations. This structural manipulation contributes to increased target specificity, enhanced biological potency, improved pharmacokinetic properties, increased functional potency, and lowered metabolic susceptibility. The CuI-catalyzed azide–alkyne 1,3-dipolar Huisgen’s cycloaddition, the prototypic click reaction, presents a promising opportunity to develop a new paradigm for an orthogonal bioorganic and intramolecular side chain-to-side chain cyclization. In fact, the proteolytic stable 1,4- or 4,1-disubstituted [1,2,3]triazolyl moiety is isosteric with the peptide bond and can function as a surrogate of the classical side chain-to-side chain lactam forming bridge. Herein we report the design, synthesis, conformational analysis, and functional biological activity of a series of i-to-i+5 1,4- and 4,1-disubstituted [1,2,3]triazole-bridged cyclopeptides derived from MT-II, the homodetic Asp5 to Lys10 side chain-to-side chain bridged heptapeptide, an extensively studied agonist of melanocortin receptors. | en |
dc.language.iso | en_US | en |
dc.publisher | American Chemical
Society | en |
dc.relation.isversionof | doi:10.1021/jm501027w | en |
dc.relation.hasversion | http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4255721/pdf/ | en |
dash.license | LAA | en_US |
dc.subject | Article | en |
dc.title | 1,4-Disubstituted-[1,2,3]triazolyl-Containing Analogues of MT-II: Design, Synthesis, Conformational Analysis, and Biological Activity | en |
dc.type | Journal Article | en_US |
dc.description.version | Version of Record | en |
dc.relation.journal | Journal of Medicinal Chemistry | en |
dash.depositing.author | Chorev, Michael | en_US |
dc.date.available | 2015-11-03T15:58:19Z | |
dc.identifier.doi | 10.1021/jm501027w | * |
dash.authorsordered | false | |
dash.contributor.affiliated | Chorev, Michael | |