Photophysics of glycosylated derivatives of a chlorin, isobacteriochlorin and bacteriochlorin for photodynamic theragnostics: discovery of a two-photon-absorbing photosensitizer.

Photophysics of glycosylated derivatives of a chlorin, isobacteriochlorin and bacteriochlorin for photodynamic theragnostics: discovery of a two-photon-absorbing photosensitizer.
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DOI:
10.1111/php.12179
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发表时间:
2014-03
影响因子:
3.3
通讯作者:
Drain CM
Drain CM
中科院分区:
生物学3区
文献类型:
--
作者:
Aggarwal A;Thompson S;Singh S;Newton B;Moore A;Gao R;Gu X;Mukherjee S;Drain CM

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The photophysical properties of a chlorin, isobacteriochlorin, and bacteriochlorin built on a core tetrapentafluorophenylporphyrin (TPPF20) and the non-hydrolysable para thioglycosylated conjugates of these chromophores are presented. The photophysical characterization of these compounds was done in three different solvents to correlate to different environments in cells and tissues. Compared to TPPF20 these conjugates have greater absorption in the red region of the visible spectrum and greater fluorescence quantum yields. The excited state lifetimes are from 3-11 nsec. The radiative and non-radiative rate constants for deactivation of the excited state were estimated from the fluorescence quantum yield and excited state lifetime. The data indicates that the bacteriochlorin has strong absorption bands near 730 nm and efficiently enters the triplet manifold. The isobacteriochlorin has a 40-70% fluorescence quantum yield depending on solvent, so it may be a good fluorescent tag. The isobacteriochlorins also display enhanced 2-photon absorption, thereby allowing the use of 860 nm light to excite the compound. While the 2-photon cross section of 25 GM units is not large, low light and low chromophore concentrations can induce apoptosis. The glycosylated compounds accumulate in cells and a head and neck squamous carcinoma xenograft tumor model in mice. These compounds are robust to photobleaching.
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