Citation: Hui GUO, Tao WANG, Wen-Qing SU, Dan LI, Xing-Xing CHEN, Jie-Ying WU, Qiong ZHANG, Yu-Peng TIAN. Synthesis, Structure, and Interaction with DNA of Alkoxy Tribipyridine Ruthenium Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(10): 2019-2027. doi: 10.11862/CJIC.2022.202 shu

Synthesis, Structure, and Interaction with DNA of Alkoxy Tribipyridine Ruthenium Complexes

Hui GUO ¹ ,
Tao WANG ² ,
Wen-Qing SU ¹ ,
Dan LI ¹ ,
Xing-Xing CHEN ¹ ,
Jie-Ying WU ¹ ,
Qiong ZHANG ^{1, 3,,} ,
Yu-Peng TIAN ^{1, 3,,}

1.
Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province, Department of Chemistry, Anhui University, Hefei 230601, China
2.
School of Life Science, Anhui University, Hefei 230601, China
3.
State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China

Corresponding author: Qiong ZHANG, zhangqiong.314@163.com Yu-Peng TIAN, yptian@ahu.edu.com
Received Date: 9 April 2022
Revised Date: 16 August 2022

Figures(10)

Two ruthenium complexes (Ru-Cl, Ru-NCMe) containing long alkoxy tribipyridine and 2, 2′-bipyridine were synthesized and characterized by mass spectrometry, NMR, single crystal X-ray diffraction analysis, etc. Based on their crystal structural information, it can be found that the sixth coordination position in complex Ru-Cl is Cl^- ion, and the sixth coordination position in complex Ru-NCME is N atom in acetonitrile molecule. The interaction of the two complexes with various amino acids and DNA was studied by UV-Vis absorption and fluorescence spectros-copy. It was found that the complexes with long alkyl chains and rigid coordination planes had an obvious specific recognition effect on DNA. Further study found that they could bind DNA in the way of insertion and electrostatic. Both results of the experiments and the theoretical calculation were consistent.
- Ru(Ⅱ) complexes,
- tribipyridine,
- crystal structures,
- DNA response
1. [1]
  Wang W J, Mu X, Tan C P, Wang Y J, Zhang Y B, Li G H, Mao Z W. Induction and Monitoring of DNA Phase Separation in Living Cells by a Light-Switching Ruthenium Complex[J]. J. Am. Chem. Soc., 2021,143(30):11370-11381. doi: 10.1021/jacs.1c01424
2. [2]
  Zhang H W, Tian L, Xiao R X, Zhou Y, Zhang Y Y, Hao J, Liu Y J, Wang J P. Anticancer Effect Evaluation In Vitro and In Vivo of Iridium (Ⅲ) Polypyridyl Complexes Targeting DNA and Mitochondria[J]. Bioorgan. Chem., 2021,115105290. doi: 10.1016/j.bioorg.2021.105290
3. [3]
  Zamora A, Wachter E, Vera M, Heidary D, Rodríguez V, Ortega E, Fernández-Espín V, Janiak C, Glazer E C, Barone G, Ruiz J. Organoplatinum(Ⅱ) Complexes Self-Assemble and Recognize AT-Rich Duplex DNA Sequences[J]. Inorg. Chem., 2021,60(4):2178-2187. doi: 10.1021/acs.inorgchem.0c02648
4. [4]
  Hoque M A, Chowdhury A D, Maji S, Benet-Buchholz J, Ertem M Z, Gimbert-Suriñach C, Lahiri G K, Llobet A. Synthesis, Characterization, and Water Oxidation Activity of Isomeric Ru Complexes[J]. Inorg. Chem., 2021,60(8):5791-5803. doi: 10.1021/acs.inorgchem.1c00112
5. [5]
  Arora K, Herroon M, Al-Afyouni M H, Toupin N P, Rohrabaugh T N, Loftus L M, Podgorski I, Turro C, Kodanko J J. Catch and Release Photosensitizers: Combining Dual-Action Ruthenium Complexes with Protease Inactivation for Targeting Invasive Cancers[J]. J. Am. Chem. Soc., 2018,140(43):14367-14380. doi: 10.1021/jacs.8b08853
6. [6]
  Li B F, Zhou X M, Liu H X, Deng H P, Huang R, Xing D. Simultaneous Detection of Antibiotic Resistance Genes on Paper - Based Chip Using[Ru(phen)₂dppz]²⁺ Turn - On Fluorescence Probe[J]. ACS Appl. Mater. Interfaces, 2018,10(5):4494-4501. doi: 10.1021/acsami.7b17653
7. [7]
  Toupin N, Steinke S J, Nadella S, Li A, Rohrabaugh T N, Samuels E R, Turro C, Sevrioukova I F, Kodanko J J. Photosensitive Ru(Ⅱ) Complexes as Inhibitors of the Major Human Drug Metabolizing Enzyme CYP3A4[J]. J. Am. Chem. Soc., 2021,143(24):9191-9205. doi: 10.1021/jacs.1c04155
8. [8]
  Conti L, Mengoni A, Giacomazzo G E, Mari L, Perfetti M, Fagorzi C, Sorace L, Valtancoli B, Giorgi C. Exploring the Potential of Highly Charged Ru(Ⅱ)- and Heteronuclear Ru(Ⅱ)/Cu(Ⅱ)-Polypyridyl Complexes as Antimicrobial Agents[J]. J. Inorg. Biochem., 2021,220111467. doi: 10.1016/j.jinorgbio.2021.111467
9. [9]
  Scoditti S, Dabbish E, Russo N, Mazzone G, Sicilia E. Anticancer Activity, DNA Binding, and Photodynamic Properties of a N∧C∧N-Coordinated Pt(Ⅱ) Complex[J]. Inorg. Chem., 2021,60(14):10350-10360. doi: 10.1021/acs.inorgchem.1c00822
10. [10]
  Fairbanks S D, Robertson C C, Keene F R, Thomas J A, Williamson M P. trans-Hydrogenation, gem-Hydrogenation, and trans-Hydrometalation of Alkynes: An Interim Report on an Unorthodox Reactivity Paradigm[J]. J. Am. Chem. Soc., 2018,141(1):11-24.
11. [11]
  Almaqwashi A A, Zhou W, Naufer M N, Riddell I A, Yilmaz Ö H, Lippard S J, Williams M C. DNA Intercalation Facilitates Efficient DNA-Targeted Covalent Binding of Phenanthriplatin[J]. J. Am. Chem. Soc., 2019,141(4):537-1545.
12. [12]
  Tan C P, Liu J, Chen L M, Shi S, Ji L N. Synthesis, Structural Characteristics, DNA Binding Properties and Cytotoxicity Studies of a Series of Ru (Ⅲ) Complexes[J]. J. Inorg. Biochem., 2008,102(8):1644-1653. doi: 10.1016/j.jinorgbio.2008.03.005
13. [13]
  Qian C, Wu J H, Ji L N, Chao H. Topoisomerase Ⅱα Poisoning and DNA Double - Strand Breaking by Chiral Ruthenium (Ⅱ) Complexes Containing 2 - Furanyl - imidazo[4,5-f][1,10]phenanthroline Derivatives[J]. Dalton Trans., 2016,45(26):10546-10555. doi: 10.1039/C6DT01422D
14. [14]
  Zhang C, Guan R L, Liao X X, Cheng O Y, Liu J P, Ji L N, Chao H. Mitochondrial DNA Targeting and Impairment by a Dinuclear Ir-Pt Complex that Overcomes Cisplatin Resistance[J]. Inorg. Chem. Front., 2020,7(9):1864-1871. doi: 10.1039/D0QI00224K
15. [15]
  Huang H Y, Zhang P Y, Chen Y, Qiu K Q, Jin C Z, Ji L N, Chao H. Synthesis, Characterization and Biological Evaluation of Labile Intercalative Ruthenium (Ⅱ) Complexes for Anticancer Drug Screening[J]. Dalton Trans., 2016,45(33):13135-13145. doi: 10.1039/C6DT01270A
16. [16]
  Shen J C, Rees T W, Ji L N, Chao H. Recent Advances in Ruthenium(Ⅱ) and Iridium(Ⅲ) Complexes Containing Nanosystems for Cancer Treatment and Bioimaging[J]. Coord. Chem. Rev., 2021,443214016. doi: 10.1016/j.ccr.2021.214016
17. [17]
  Yu B L, Rees T W, Liang J W, Jin C Z, Chen Y, Ji L N, Chao H. DNA Interaction of Ruthenium(Ⅱ) Complexes with Imidazo[4, 5-f][1, 10]phenanthroline Derivatives[J]. Dalton Trans., 2019,48(12):3914-3921. doi: 10.1039/C9DT00454H
18. [18]
  Liu J G, Lai H Q, Xiong Z S, Chen B L, Chen T F. Functionalization and Cancer-Targeting Design of Ruthenium Complexes for Precise Cancer Therapy[J]. Chem. Commun., 2019,55(67):9904-9914. doi: 10.1039/C9CC04098F
19. [19]
  Monro S, Colon K L, Yin H M, Roque J, Konda P, Gujar S, Thummel R P, Lilge L, Cameron C G, McFarland S A. Transition Metal Complexes and Photodynamic Therapy from a Tumor-Centered Approach: Challenges, Opportunities, and Highlights from the Development of TLD1433[J]. Chem. Rev., 2018,119(2):797-828.
20. [20]
  WANG S C. Design, Synthesis, Properties of Mono-, Di-/Trinuclear Pt (Ⅱ), Ru (Ⅱ) Complexes Containing Polypyridine Ligand. Hefei: Anhui University, 2015.
21. [21]
  Zhang H M, Wang Y, Wang Y Q, Han Q Q, Yan H H, Yang T, Guo Z J, Wang X Y. Platinum Complexes as Inhibitors of DNA Repair Protein Ku70 and Topoisomerase Ⅱα in Cancer Cells[J]. Dalton Trans., 2022,51(8):3188-3197. doi: 10.1039/D1DT03700E
22. [22]
  Sangeetha S, Murali M. Cytotoxic Ruthenium(Ⅱ) Complexes Containing a Dangling Pyridine: Selectivity for Diseased Cells Mediated by pH-Dependent DNA Binding[J]. Inorg. Chem., 2022,61(6):2864-2882. doi: 10.1021/acs.inorgchem.1c03399
23. [23]
  Yao Q C, Li H D, Xian L M, Xu F, Xia J, Fan J L, Du J J, Wang J Y, Peng X J. Differentiating RNA from DNA by a Molecular Fluorescent Probe Based on the "Door-Bolt" Mechanism Biomaterials[J]. Biomaterials, 2018,177:78-87. doi: 10.1016/j.biomaterials.2018.05.050
24. [24]
  Fairbanks S D, Robertson C C, Keene F R, Thomas J A, Williamson M P. Structural Investigation into the Threading Intercalation of a Chiral Dinuclear Ruthenium (Ⅱ) Polypyridyl Complex through a B-DNA Oligonucleotide[J]. J. Am. Chem. Soc., 2019,141(11):4644-4652. doi: 10.1021/jacs.8b12280
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