Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 40, Pages 9519-9532Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01533f
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Funding
- Agence Nationale de la Recherche [ANR-14-CE06-0031]
- National Science Foundation [NSF-CHE 1415895]
- Institut d'Alembert [FR3242]
- government of Vietnam
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1415895] Funding Source: National Science Foundation
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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 (Phi) are dependent on the solvent polarity, with a red-shift in a more polar environment (lambda(max,em) = 460-467 nm, Phi > 0.53 in DMSO, and lambda(max,em) = 475-491 nm, Phi < 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.
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