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

摘要: 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- two-photon absorption properties. Their fluorescence emission wavelength and quantum yields (Φ) are dependent solvent polarity, with a red-shift in more polar environment (λmax,em = 460–467 nm, Φ > 0.53 DMSO, λmax,em 475–491 < 0.17 Tris). show good binding affinity towards constitutive nNOS eNOS, confirming for first time that carboxymethyl group can be used as surrogate phosphate. Two-photon imaging nanotriggers living cells showed presence (especially 3′ position ribose) strongly favors addressing to eNOS cell context.