title: Convergent synthesis and properties of photoactivable NADPH mimics targeting nitric oxide synthases.
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.
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France. joanne.xie@ens-cachan.fr.
authors.forename: N-H
authors.initials: NH
authors.lastname: Nguyen
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France. joanne.xie@ens-cachan.fr.
authors.forename: N
authors.initials: N
authors.lastname: Bogliotti
authors.affiliation: LBPA, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France.
authors.forename: R
authors.initials: R
authors.lastname: Chennoufi
authors.affiliation: LBPA, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France.
authors.forename: E
authors.identifier: http://orcid.org/0000-0002-2547-3467
authors.initials: E
authors.lastname: Henry
authors.affiliation: LBPA, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France.
authors.forename: P
authors.initials: P
authors.lastname: Tauc
authors.affiliation: Department of Biochemistry, University of Texas Health Science Center, San Antonio, Texas 78384-7760, USA.
authors.forename: E
authors.initials: E
authors.lastname: Salas
authors.affiliation: Department of Biochemistry, University of Texas Health Science Center, San Antonio, Texas 78384-7760, USA.
authors.forename: L J
authors.initials: LJ
authors.lastname: Roman
authors.affiliation: Université Paris Saclay, INRA UR 892, Jouy en Josas, 78350, France.
authors.forename: A
authors.initials: A
authors.lastname: Slama-Schwok
authors.affiliation: LBPA, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France.
authors.forename: E
authors.initials: E
authors.lastname: Deprez
authors.affiliation: PPSM, ENS Cachan, CNRS, Université Paris-Saclay, Cachan, 94235 France. joanne.xie@ens-cachan.fr.
authors.forename: J
authors.initials: J
authors.lastname: Xie
mesh_terms: D000225:Adenine / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D057930:Click Chemistry; D006367:HeLa Cells; D006801:Humans; D008027:Light; D057054:Molecular Imaging; D009249:NADP / Q000378:metabolism*; D019001:Nitric Oxide Synthase / Q000378:metabolism*
chemical_list: D009249:NADP; D019001:Nitric Oxide Synthase; D000225:Adenine