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A Twist‐Assisted Biphenyl Photosensitizer Passable Through Glucose Channel
Author(s) -
Tsuga Yuki,
Katou Masataka,
Kuwabara Satoshi,
Kanamori Takashi,
Ogura Shunichiro,
Okazaki Shigetoshi,
Ohtani Hiroyuki,
Yuasa Hideya
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201900378
Subject(s) - photosensitizer , biphenyl , twist , medicine , chemistry , photochemistry , mathematics , organic chemistry , geometry
While the development of low‐molecular‐weight drugs is saturating, agents for photodynamic therapies (PDTs) may become alternative seeds in pharmaceutical industry. Among them, orally administrative, cancer‐selective, and side effect‐free photosensitizers (PSs) that can be activated by tissue‐penetrative near‐infrared (NIR) lights are strongly demanded. We discovered such a PS from scratch by focusing on a twist‐assisted spin‐orbit charge transfer intersystem crossing (ISC) mechanism in a biphenyl derivative, which was demonstrated by thorough photophysical studies. The unique ISC mechanism enables the PS to be small and slim so as to pass through glucose transporters and exert a PDT effect selectively on a cancer cell line. The smallness will allow for oral administration and fast clearance, which have been agenda of approved PSs with larger molecular weights. We also demonstrated that our PS was able to be activated with an NIR pulse laser through two‐photon excitation.