Synthesis 2022; 54(10): 2447-2456
DOI: 10.1055/s-0041-1737374
paper

Synthesis and Spectroscopic Characterization of Novel Thiourea-Bearing Photoactivatable NADPH Mimics Targeting NO Synthases

Clément L. Polese
a   PPSM, ENS Paris-Saclay, CNRS, Université Paris-Saclay, Gif-sur-Yvette, 91190, France
,
Eric Deprez
b   LBPA, ENS Paris-Saclay, CNRS, Université Paris-Saclay, Gif-sur-Yvette, 91190, France
,
Patrick Tauc
b   LBPA, ENS Paris-Saclay, CNRS, Université Paris-Saclay, Gif-sur-Yvette, 91190, France
,
Nicolas Bogliotti
a   PPSM, ENS Paris-Saclay, CNRS, Université Paris-Saclay, Gif-sur-Yvette, 91190, France
,
Juan Xie
a   PPSM, ENS Paris-Saclay, CNRS, Université Paris-Saclay, Gif-sur-Yvette, 91190, France
› Institutsangaben
This work is supported by the Agence Nationale de la Recherche (ANR-14-CE06-0031 to E.D. and J.X.).


Abstract

A new set of photoactivatable NADPH mimics bearing a thiourea linkage between a diarylbutadiene and an adenosine moiety functionalized by O-carboxymethyl groups has been designed and synthesized in a convergent strategy. These compounds display absorption and fluorescence emission maxima in DMSO (λmax,abs = 390 nm and λmax,em = 460 nm, respectively) consistent with the previously described analogues, with good fluorescence quantum yields (ΦF = 0.35–0.36), as well as two-photon absorption (σ2 = 10.1 GM at λmax,exc = 780 nm). These molecules could be useful photosensitive tools for biological studies, especially for cellular studies of nitric oxide synthases.

Supporting Information



Publikationsverlauf

Eingereicht: 26. Dezember 2021

Angenommen nach Revision: 28. Januar 2022

Artikel online veröffentlicht:
08. März 2022

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