Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases. Issue 40 (19th September 2016)

• Record Type: Journal Article
• Authors: Nguyen, N.-H.; Bogliotti, N.; Chennoufi, R.; Henry, E.; Tauc, P.; Salas, E.; Roman, L. J.; Slama-Schwok, A.; Deprez, E.; Xie, J.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 40(2016)
• Page Start: 9519
• Page End: 9532
• Publication Date: 2016-09-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01533f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthesis, photophysical properties, binding affinity and two-photon fluorescence imaging in living cells of photoactivable NADPH mimics targeting the nitric oxide synthases NADPH binding site are reported. 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 ( λ max, em = 460–467 nm, Φ > 0.53 in DMSO, and λ max, 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.