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Highly Efficient and Biologically Compatible Photoremovable Protecting Group for Releasing Tertiary Amines through Two‐Photon Excitation

Von Wiley-VCH zur Verfügung gestellt

Photoremovable protecting groups (PPGs) releasable by two-photon excitation (2PE) provide spatio-temporal control over the photoactivation of biological effectors to study biological systems. We synthesized four derivatives of the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) chromophore by functionalization of position C4 to generate four different derivatives (MeO-CyHQ, Mor-CyHQ, pTol-CyHQ, and TMP-CyHQ) for studying the release of tertiary amines via 2PE. Sulpiride, an anti-dopaminergic drug, was selected as a model substrate. All probes had excellent properties for use in biological settings, including high quantum yield (Φ u ), hydrolytic stability, and good aqueous solubility in simulated physiological buffer. The TMP-CyHQ probe enhanced the two-photon uncaging action cross-section (δ u ) 8-fold (2.64 GM) compared to the parent CyHQ-sulpiride. The optimized PPG was used to mediate the photoactivation of various biological effectors containing the tertiary amine functionality (tamoxifen, 4-hydroxytamoxifen, yohimbine) using 2PE. All constructs showed excellent efficiency with δ u ranging from 1.21 to 2.42 GM and moderate to excellent yields of tertiary amines released.

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