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Development of photolabile caged analogs of endothelin-1.

Abstract : Photoactivable caged analogs of endothelin-1 (ET-1) were obtained after derivatization with the photolabile 4,5-dimethoxynitrobenzyl (DMNB) group. This was achieved by the incorporation of N-alpha-Fmoc caged building blocks of Lys, Asp, Glu and Tyr during the solid phase peptide synthesis step. The C-terminal carboxylic function was also derivatized. However, difficulties were encountered with the introduction of the Asp and Glu photoactivable building blocks. As a matter of fact, formation of an aminosuccinyl derivative, through cyclization of the Asp(ODMNB) residue, and the formation of a pyrrolidone ring from the Glu(ODMNB) residue were highly favored by the electronic properties of the photocleavable function. ET-1 analogs were also tested in the ET(A) and ET(B) paradigms and specific pharmacological profiles were obtained for each peptide.
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https://hal-riip.archives-ouvertes.fr/pasteur-00819999
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Submitted on : Thursday, May 2, 2013 - 10:26:25 PM
Last modification on : Monday, October 8, 2018 - 5:44:04 PM

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S. Bourgault, M. Létourneau, A. Fournier. Development of photolabile caged analogs of endothelin-1.. Peptides, Elsevier, 2007, 28 (5), pp.1074-82. ⟨10.1016/j.peptides.2007.02.013⟩. ⟨pasteur-00819999⟩

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