Abstract
Two indene-fused coumarin-based photoremovable protecting groups (PPGs) 3a and 3b were synthesized. Their respective efficiencies of releasing para-substituted benzoic acids upon irradiation at 365 nm wavelength were studied. Results showed that upon photoexcitation, PPG 3a caged acids favor photocleavage process rather than fluorescence decay, leading to higher uncaging yields but lower fluorescence quantum yields than 3b caged counterparts. In contrast, PPG 3b caged acids prefer fluorescence over photocleavage, resulting in low uncaging yields. Therefore, 3a was employed to prepare a photoactivable camptothecin prodrug 3aCPT. Cell viability assay showed a statistically significant cytotoxicity difference of 3aCPT against human MDA-MB-468 cells before and after excitation at 405 nm, suggesting that 3a has good potential for pharmaceutical applications.
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