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Cyclic azapeptide integrin ligand synthesis and biological activity
dc.contributor.author | Spiegel, J. |
dc.contributor.author | Mas Moruno, Carlos |
dc.contributor.author | Kessler, H. |
dc.contributor.author | Lubell, W.D. |
dc.contributor.other | Universitat Politècnica de Catalunya. Departament de Ciència dels Materials i Enginyeria Metal·lúrgica |
dc.date.accessioned | 2014-04-30T10:59:18Z |
dc.date.created | 2012 |
dc.date.issued | 2012 |
dc.identifier.citation | Spiegel, J. [et al.]. Cyclic azapeptide integrin ligand synthesis and biological activity. "Journal of organic chemistry", 2012, vol. 77, núm. 12, p. 5271-5278. |
dc.identifier.issn | 0022-3263 |
dc.identifier.uri | http://hdl.handle.net/2117/22781 |
dc.description.abstract | Aza-peptides are obtained by replacement of the α-C-atom of one or more amino acids by a nitrogen atom in a peptide sequence. Introduction of aza-residues into peptide sequences may result in unique structural and pharmacological properties, such that aza-scanning may be used to probe structure–activity relationships. In this study, a general approach for the synthesis of cyclic aza-peptides was developed by modification of strategies for linear aza-peptide synthesis and applied in the preparation of cyclic aza-pentapeptides containing the RGD (Arg-Gly-Asp) sequence. Aza-amino acid scanning was performed on the cyclic RGD-peptide Cilengitide, cyclo[R-G-D-f-N(Me)V] 1, and its parent peptide cyclo(R-G-D-f-V) 2, potent antagonists of the αvβ3, αvβ5, and α5β1 integrin receptors, which play important roles in human tumor metastasis and tumor-induced angiogenesis. Although incorporation of the aza-residues resulted generally in a loss of binding affinity, cyclic aza-peptides containing aza-glycine retained nanomolar activity toward the αvβ3 receptor. |
dc.format.extent | 8 p. |
dc.language.iso | eng |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Spain |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ |
dc.subject | Àrees temàtiques de la UPC::Enginyeria dels materials |
dc.subject.lcsh | Peptides |
dc.title | Cyclic azapeptide integrin ligand synthesis and biological activity |
dc.type | Article |
dc.subject.lemac | Pèptids |
dc.identifier.doi | 10.1021/jo300311q |
dc.description.peerreviewed | Peer Reviewed |
dc.relation.publisherversion | http://pubs.acs.org/doi/abs/10.1021/jo300311q |
dc.rights.access | Restricted access - publisher's policy |
local.identifier.drac | 13618374 |
dc.description.version | Postprint (published version) |
dc.date.lift | 10000-01-01 |
local.citation.author | Spiegel, J.; Mas-Moruno, C.; Kessler, H.; Lubell, W.D. |
local.citation.publicationName | Journal of organic chemistry |
local.citation.volume | 77 |
local.citation.number | 12 |
local.citation.startingPage | 5271 |
local.citation.endingPage | 5278 |
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