Synthesis 2022; 54(10): 2447-2456
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
,
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.
Key words
nitric oxide -
nitric oxide synthases -
nanotriggers -
photoactivation -
convergent synthesis
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737374.
Supporting Information
Publikationsverlauf
Eingereicht: 26. Dezember 2021
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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