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Photoinduced Reduction of Pt IV within an Anti‐Proliferative Pt IV –Texaphyrin Conjugate
Author(s) -
Thiabaud Grégory,
Arambula Jonathan F.,
Siddik Zahid H.,
Sessler Jonathan L.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403094
Subject(s) - conjugate , platinum , chemistry , adduct , aqueous solution , stereochemistry , catalysis , biochemistry , organic chemistry , mathematical analysis , mathematics
In an effort to increase the stability and control the platinum reactivity of platinum–texaphyrin conjugates, two Pt IV conjugates were designed, synthesized, and studied for their ability to form DNA adducts. They were also tested for their anti‐proliferative effects using wild‐type and platinum‐resistant human ovarian cancer cell lines (A2780 and 2780CP, respectively). In comparison to an analogous first‐generation Pt II chimera, one of the new conjugates provided increased stability in aqueous environments. Using a combination of 1 H NMR spectroscopy and FAAS (flameless atomic‐absorption spectrometry), it was found that the Pt IV center within this conjugate undergoes photoinduced reduction to Pt II upon exposure to glass‐filtered daylight, resulting in an entity that binds DNA in a controlled manner. Under conditions in which the Pt IV complex is reduced to the corresponding Pt II species, these new conjugates demonstrated potent anti‐proliferative activity in both test ovarian cancer cell lines.