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

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 (λ_max,abs = 390 nm and λ_max,em = 460 nm, respectively) consistent with the previously described analogues, with good fluorescence quantum yields (Φ_F = 0.35–0.36), as well as two-photon absorption (σ² = 10.1 GM at λ_max,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

Publication History

Received: 26 December 2021

Accepted after revision: 28 January 2022

Article published online:
08 March 2022

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