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Theoretical investigation and design of two-photon fluorescent probes for visualizing β-galactosidase activity in living cells

机译：双光子荧光探针对活细胞β-半乳糖苷酶活性的理论研究和设计

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As a marker enzyme, the underlying biological mechanisms of β-galactosidase (β-gal) and its role in senescence and aging still remain unknown. Two-photon (TP) fluorescence microscopy (TPFM) is a promising approach for detecting β-gal enzyme activity in living specimens. In the present study, we have firstly designed a series of novel naphthalene-based β-gal ratiometric TP fluorescent chromophores, and carried out quantum-chemical calculations on their structural and linear/nonlinear optical properties. We have thoroughly studied the effects of different biological bridge groups (quinoline, benzo[ d ]thiophene, thiophene, diazine) and cyano groups on the one-photon absorption (OPA), fluorescence, as well as two-photon absorption (TPA) properties of β-gal probes and the corresponding reaction products. The calculated results show that the product molecules always exhibit longer absorption and emission wavelengths, and possess both stronger TP transition probability and a larger net charge change relative to that of corresponding β-gal probes, due to their better planarity and larger transition dipole moment. Our analysis suggests that the net charge change dominates the TPA cross section ( δ _(max) ). There is an optimal match for δ _(max) and radiation rate ( k _(r) ) following the increase of the net charge change to improve nonlinear optical activity in the studied molecules. The substitution of benzo[ d ]thiazole with benzo[ d ]thiophene is an optimal approach for β-gal probe design with the largest fluorescence efficiency and δ _(max) . We hope this contribution can provide detailed theoretical analysis of OPA and TPA properties of β-gal probes and relevant products, and provide insight into the structure–property relationships for guiding experimental design.
机译：作为标记酶，β-半乳糖苷酶（β-加仑）的潜在生物机制及其在衰老和衰老中的作用仍然是未知的。双光子（TP）荧光显微镜（TPFM）是检测活样本中β-加仑酶活性的有希望的方法。在本研究中，我们首先设计了一系列新的萘基β-加仑比率TP荧光发色团，并对它们的结构和线性/非线性光学性能进行量子化学计算。我们已经彻底研究了不同生物桥组（喹啉，苯并[D]噻吩，噻吩，二胶液）和氰基对单光子吸收（OPA），荧光以及双光子吸收（TPA）性质的影响β-加仑探针和相应的反应产物。计算结果表明，由于其更好的平面性和更大的平面性，具有更好的平面性和较大的过渡偶极探针，产品分子总是表现出较长的吸收和发射波长，并且具有相对于相应的β-加探针的净电荷变化。我们的分析表明，净电荷变化占主导地位TPA横截面（Δ_（最大））。在净电荷变化的增加之后，在净电荷变化的增加之后，存在最佳匹配（k _（k _（r）），以改善所研究的分子中的非线性光学活性。苯并[D]噻唑与苯并[d]噻吩的取代是β-加仑探针设计具有最大荧光效率的最佳方法和Δ_（最大值）。我们希望这一贡献能够提供β-GAL探针和相关产品的OPA和TPA性质的详细的理论分析，并提供对指导实验设计的结构性质关系的洞察。

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