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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Structural Features and Photophysical and Antiproliferative Properties of Me2N-pbt-Cycloplatinated Complexes with
David Gómez de Segura1, Michèle Salmain2, Benoît Bertrand2
1Departamento de Química-Instituto de Investigación en Química (IQUR), Universidad de La Rioja, 26006 Logroño, Spain.
Abstract:
2-(4-dimethylaminophenyl)benzothiazolate (Me2N-pbt)-cyclometalated platinum complexes containing four different picolinate ligands, [Pt(Me2N-pbt)(R-pic-κN∧O)] (R = 3-H 1, 3-NH2 2, 3-OH 3, 4-COOH 4) were prepared and examined for their photophysical properties, singlet oxygen production, and bioactivity. X-ray studies of 1 and 3·CHCl3 revealed aggregation to give 1D infinite chains. They showed phosphorescent emissions essentially associated with metal-perturbed 3ILCT excited states in 1-3 and mixed 3LL'CT/3ILCT (L = Me2N-pbt, L' = pic) in 4, in agreement with theoretical calculations. Their tendency to self-assemble was demonstrated in films (1, 3) and DMSO/H2O (3). Complexes 1-3 showed singlet oxygen photosensitization quantum yields (ϕΔ 1O2) in the range of 13-17%. The in vitro biological activity toward selected cell lines in dark conditions and under 5 min irradiation at 450 nm was tested. Complex 3 showed the highest phototoxicity with up to 10 times improvement of the antiproliferative activity upon irradiation, with EC50 values in the nanomolar range, related to overproduction of ROS in dark conditions, further enhanced upon irradiation. Complexes 1-4 did not bind to DNA, while the most potent complex 3 demonstrated interaction with BSA and photooxidation of NADH. Finally, intracellular dose-dependent ROS production in MDA-MB-231 cells treated with 3 was observed in the dark and further stimulated upon blue light irradiation.
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