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Issue 40, 2016
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Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases

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Abstract

A new series of photoactivable NADPH mimics bearing one or two O-carboxymethyl groups on the adenosine moiety have been readily synthesized using click chemistry. These compounds display interesting one- or two-photon absorption properties. Their fluorescence emission wavelength and quantum yields (Φ) are dependent on the solvent polarity, with a red-shift in a more polar environment (λmax,em = 460–467 nm, Φ > 0.53 in DMSO, and λmax,em = 475–491 nm, Φ < 0.17 in Tris). These compounds show good binding affinity towards the constitutive nNOS and eNOS, confirming for the first time that the carboxymethyl group can be used as a surrogate of phosphate. Two-photon fluorescence imaging of nanotriggers in living cells showed that the presence of one carboxymethyl group (especially on the 3′ position of the ribose) strongly favors the addressing of nanotriggers to eNOS in the cell context.

Graphical abstract: Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases

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Supplementary files

Article information


Submitted
18 Jul 2016
Accepted
09 Sep 2016
First published
12 Sep 2016

Org. Biomol. Chem., 2016,14, 9519-9532
Article type
Paper

Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases

N.-H. Nguyen, N. Bogliotti, R. Chennoufi, E. Henry, P. Tauc, E. Salas, L. J. Roman, A. Slama-Schwok, E. Deprez and J. Xie, Org. Biomol. Chem., 2016, 14, 9519
DOI: 10.1039/C6OB01533F

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