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http://hdl.handle.net/2445/106871
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DC Field | Value | Language |
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dc.contributor.author | Gandioso, Albert | - |
dc.contributor.author | Cano, Marc | - |
dc.contributor.author | Massaguer i Vall-llovera, Anna | - |
dc.contributor.author | Marchán Sancho, Vicente | - |
dc.date.accessioned | 2017-02-13T14:42:08Z | - |
dc.date.available | 2017-11-09T23:01:20Z | - |
dc.date.issued | 2016-11-09 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/106871 | - |
dc.description.abstract | We describe for the first time the synthesis and photochemical properties of a coumarin-caged cyclic RGD peptide and demonstrate that uncaging can be efficiently performed with biologically compatible green light. This was accomplished by using a new dicyanocoumarin derivative (DEAdcCE) for the protection of the carboxyl function at the side chain of the aspartic acid residue, which was selected on the basis of Fmoc-tBu SPPS compatibility and photolysis efficiency. The shielding effect of a methyl group incorporated in the coumarin derivative near the ester bond linking both moieties in combination with the use of acidic additives such as HOBt or Oxyma during the basic Fmoc-removal treatment were found to be very effective for minimizing aspartimide-related side reactions. In addition, a conjugate between the dicyanocoumarin-caged cyclic RGD peptide and ruthenocene, which was selected as a metallodrug model cargo, has been synthesized and characterized. The fact that green-light triggered photoactivation can be efficiently performed both with the caged peptide and with its ruthenocenoyl bioconjugate reveals great potential for DEAdcCE-caged peptide sequences as selective drug carriers in the context of photocontrolled targeted anticancer strategies. | - |
dc.format.extent | 9 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.6b02415 | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2016, vol. 81, num. 23, p. 11556-11564 | - |
dc.relation.uri | https://doi.org/10.1021/acs.joc.6b02415 | - |
dc.rights | (c) American Chemical Society , 2016 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Síntesi de pèptids | - |
dc.subject.classification | Cèl·lules canceroses | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.classification | Llum | - |
dc.subject.other | Peptide synthesis | - |
dc.subject.other | Cancer cells | - |
dc.subject.other | Organic synthesis | - |
dc.subject.other | Light | - |
dc.title | A green light-triggerable RGD peptide for photocontrolled targeted drug delivery: synthesis and photolysis studies | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 667553 | - |
dc.date.updated | 2017-02-13T14:42:08Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 27934458 | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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667553.pdf | 798.8 kB | Adobe PDF | View/Open |
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