Optimizing the Electronic Properties of Photoactive Anticancer Oxypyridine-Bridged Dirhodium(II,II) Complexes

Li, Zhanyong; David, Amanda; Albani, Bryan A.; Pellois, Jean-Philippe; Turro, Claudia; Dunbar, Kim R.

doi:10.1021/ja5078359

Title: Optimizing the Electronic Properties of Photoactive Anticancer Oxypyridine-Bridged Dirhodium(II,II) Complexes

Journal Article · Sun Nov 30 23:00:00 EST 2014 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/ja5078359 · OSTI ID:1430198

Li, Zhanyong ^[1]; David, Amanda ^[2]; Albani, Bryan A. ^[3]; Pellois, Jean-Philippe ^[4]; Turro, Claudia ^[3]; Dunbar, Kim R. ^[2]

Texas A & M Univ., College Station, TX (United States). Dept. of Chemistry; The Ohio State University
Texas A & M Univ., College Station, TX (United States). Dept. of Chemistry
The Ohio State Univ., Columbus, OH (United States). Dept. of Chemistry and Biochemistry
Texas A & M Univ., College Station, TX (United States). Dept. of Biochemistry and Biophysics

A series of partial paddlewheel dirhodium compounds of general formula cis-[Rh₂(xhp)₂(CH₃CN)_n][BF₄]₂ (n = 5 or 6) were synthesized {xhp = 6-R-2-oxypyridine ligands, R = -CH₃ (mhp), -F (fhp), -Cl (chp)}. X-ray crystallographic studies indicate the aforementioned compounds contain two cis-oriented bridging xhp ligands, with the remaining sites being coordinated by CH₃CN ligands. The lability of the equatorial (eq) CH₃CN groups in these complexes in solution is in the order -CH₃ > -Cl > -F, in accord with the more electron rich bridging ligands exerting a stronger trans effect. In the case of cis-[Rh₂(chp)₂(CH₃CN)₆][BF₄]₂ (5), light irradiation enhances the production of the aqua adducts in which eq CH₃CN is replaced by H₂O molecules, whereas the formation of the aqua species for cis-[Rh₂(fhp)₂(CH₃CN)₆][BF₄]₂ (7) is only slightly increased by irradiation. The potential of both compounds to act as photochemotherapy agents was evaluated. A 16.4-fold increase in cytotoxicity against the HeLa cell line was observed for 5 upon 30 min irradiation (λ > 400 nm), in contrast to the nontoxic compound 7, which is in accord with the results from the photochemistry. Furthermore, the cell death mechanism induced by 5 was determined to be apoptosis. In conclusion, these results clearly demonstrate the importance of tuning the ligand field around the dimetal center to maximize the photoreactivity and achieve the best photodynamic action.

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Research Organization:: The Ohio State Univ., Columbus, OH (United States); Texas A & M Univ., College Station, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); Welch Foundation, Houston, TX (United States); National Science Foundation (NSF)

Grant/Contract Number:: SC0010542

OSTI ID:: 1430198

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 49 Vol. 136; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Photochemistry and DNA photocleavage by a new unsupported dirhodium(II,II) complex Li, Zhanyong; Burya, Scott J.; Turro, Claudia Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 371, Issue 1995 https://doi.org/10.1098/rsta.2012.0128	journal	July 2013
Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation Perdew, John P.; Chevary, J. A.; Vosko, S. H. Physical Review B, Vol. 46, Issue 11 https://doi.org/10.1103/PhysRevB.46.6671	journal	September 1992
Generalized gradient approximation for the exchange-correlation hole of a many-electron system Perdew, John P.; Burke, Kieron; Wang, Yue Physical Review B, Vol. 54, Issue 23 https://doi.org/10.1103/PhysRevB.54.16533	journal	December 1996
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