Abstract
A ruthenium polypyridine complex, [Ru(mptpy)(Mmptpy)Cl][PF6]2 (Ru1, mptpy = 4-(4-methylphenyl)-2,2′,6′,2″-mptpyridine, Mmptpy = 2-[4-(4-methylphenyl)-2,2′-bipyridin-6-yl]-1-methylpyridinum), was synthesised and characterised. The structure of the complex was determined by single-crystal X-ray crystallography. The ruthenium(II) core has an octahedral coordination environment. The interactions of the complex with DNA were analysed by UV–Vis and fluorescence spectroscopy, revealing a high binding affinity for double-stranded DNA. DNA photocleavage studies monitored by agarose gel electrophoresis showed that the complex cleaved DNA efficiently, whilst mechanistic studies showed that the complex produced reactive oxygen species including singlet oxygen, superoxide anions, and carbon-based radicals that cleave DNA. The complex also showed notable antiproliferation activity towards cancer cells in methyl thiazolyl tetrazolium assays.
Similar content being viewed by others
References
Sun RWY, Ma DL, Wong ELM, Che CM (2007) Dalton Trans 43:4884–4892
Suo JJ, Ma ZY, Xu JY, Tian JL, Liu X (2018) Appli Organomet Chem 32:3911–3923
Muthuraj V, Umadevi M (2018) J Mol Struct 1157:201–209
Cristina M, Huang HY, Riccardo R, Marcus S, Frank W, Chao H, Gilles G (2017) Eur J Org Chem 12:610–1745
Qiu K, Wang J, Song C, Wang L, Zhu H, Huang H, Huang J, Wang H, Ji L, Chao H (2017) ACS Appl Mater Inter 9:18482–18492
Heinemann F, Karges J, Gasser G (2017) Acc Chem Res 50:2727–2736
Ouyang M, Zeng LL, Qiu KQ, Chen Y, Ji LN, Chao H (2017) Eur J Org Chem 12:1589–1764
Zhang Y, Zhou Q, Tian N, Li C, Wang X (2017) Inorg Chem 4:1865–1873
Brunner J, Barton JK (2006) J Am Chem Soc 128:6772–6773
Reichardt C, Schneider KRA, Sainuddin T, Wachtler M, McFarland SA, Dietzek B (2017) J Phys Chem A 121:5635–5644
Zeglis BM, Pierre VC, Barton JK (2007) Chem Commun 44:4565–4579
Monro S, Colon KL, Yin H, Roque J, Konda P, Gujar S, Thummel RP, Lilge L, Cameron CG, McFarland SA (2018) Chem Rev 119:797–828
Benjamin JC, Madeleine H, James R, Sergio S, Martyn KP, Nigel SS (2015) Dalton Trans 44:20392–20405
Koizumi T, Tomon T, Tanaka K (2005) J Organomet Chem 690:1258–1264
Emmerling F, Bricks JL, Resch-Genger U, Kraus W, Schulz B, Li YQ, Reck G (2008) J Mol Struct 874:14–27
Guardigli M, Flamigni L, Barigelletti F, Richards CSW, Ward MD (1996) J Phys Chem 100:10620–10628
Cleary RL, Bardwell DA, Murray M, Jeffery JC, Ward MD (1997) J Chem Soc. Perkin Trans 2(11):2179–2184
Koizumi T, Tomon T, Tanaka K (2003) Organometallics 22:970–975
Jiang YH, Chai KK, Sun Y, Pang QW, Liu XL, Shi M, Wang J, Wei J, Liu D, Wang JT (2019) Heterocycles 98:387–394
Tarushi A, Kakoulidou C, Raptopoulou CP, Psycharis V, Kessissoglou DP, Zoi I, Papadopoulos AN, Psomas G (2017) J Inorg Biochem 170:85–97
Liu YX, Mo HW, Lv ZY, Shen F, Zhang CL, Qi YY, Mao ZW, Le XY (2018) Transit Metal Chem 43:259–271
LePecq JB, Paoletti C (1967) J Mol Biol 27:87–106
Chai KK, Jiang YH, Han TZ, Niu JL, Yao LS, Zhang HZ, Zeng M, Zhang L, Duan XM, Wang JT (2019) Polyhedron 157:124–130
Chai KK, Kuang WH, Lan Z, Zhang L, Jiang YH, Han TZ, Niu JN, Wang JT, Duan XM (2019) J Inorg Biochem 192:17–24
E-Batal H, Rocha JM, Méndez PF, GodÍnez LA, Guo K, Li XP, Lu XC, Wesdemiotis C, Moorefield CN, Newkome GR (2015) Heterocycles 90:502–514
Sheldrick GM (2015) Acta Crystallogr Sect C-Struct 71:3765–3768
Kumar C, Asuncion EH (1993) J Am Chem Soc 115:8547–8553
Rosu F, De Pauw E, Guittat L, Alberti P, Lacroix L, Mailliet P, Riou J-F, Mergny J-L (2003) Biochemistry 42:10361–10371
Dimiza F, Perdih F, Tangoulis V, Turel I, Kessissoglou DP, Psomas G (2011) J Inorg Biochem 105:476–489
Acknowledgements
We thank the Jiangxi Provincial Key Laboratory of Drug Design and Evaluation (20171BCD40015), Natural Science Foundation of Jiangxi Province (20181BAB213001), Graduate Students’ Science and Technology Innovation Project of Jiangxi Science & Technology Normal University (YC2017-X22), and College Students’ Science and Technology Innovation Project of Jiangxi Science & Technology Normal University (20181203021).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Jiang, Y., Chai, K., Han, T. et al. A ruthenium(II) complex with a methylated polypyridine ligand: synthesis, DNA binding, and antiproliferation activity. Transit Met Chem 44, 699–705 (2019). https://doi.org/10.1007/s11243-019-00336-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-019-00336-0