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, J. Xie

Research output: Contribution to journalArticle

2 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)9519-9532
Number of pages14
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number40
DOIs
StatePublished - 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Nguyen, N. H., Bogliotti, N., Chennoufi, R., Henry, E., Tauc, P., Salas, E., Roman, L. J., Slama-Schwok, A., Deprez, E., & Xie, J. (2016). Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases. Organic and Biomolecular Chemistry, 14(40), 9519-9532. https://doi.org/10.1039/c6ob01533f