Substitution Effect on the One- and Two-photon Sensitivity of DMAQ “Caging” Groups

Morgane Petit (1) , Christine Tran (1) , Thomas Roger (1) , Thibault Gallavardin (1) , Hamid Dhimane (1) , Francisco Palma-Cerda (2) , Mireille Blanchard-Desce (3) , Francine C. Acher (1) , David Ogden (2) , Peter Dalko (1)

1 LCBPT - UMR 8601 - Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques
2 LPC - UMR 8118 - Laboratoire de physiologie cérébrale
3 CPM - Chimie et Photonique Moléculaires

The systematic SAR study of a "caging" group showed a strong influence of the position of the donor dimethylamino group on the efficiency of photolysis of the DMAQ (2-hydroxymethylene-(N,N-dimethylamino)quinoline) caged acetate under one-photon near-UV or two-photon near-IR excitation. Photorelease of l-glutamate by the most efficient 8-DMAQ derivative strongly and efficiently activated glutamate receptors, generating large, fast rising responses similar to those elicited by glutamate photoreleased from the widely used MNI-caged glutamate.

Keywords: Glutamates/chemistry*; Molecular Structure; Photolysis; Photons*; Quinolines/chemistry*; Structure-Activity Relationship; Glutamates; Quinolines

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

Morgane Petit, Christine Tran, Thomas Roger, Thibault Gallavardin, Hamid Dhimane, et al.. Substitution Effect on the One- and Two-photon Sensitivity of DMAQ “Caging” Groups. Organic Letters, 2012, 14 (24), pp.6366-6369. ⟨10.1021/ol3031704⟩. ⟨hal-02383436⟩