Citation: Yu-Xing TAN, Xu-Jian ZHANG, Le CHEN, Fang-Fang MAO, Wu-Jiu JIANG. Syntheses, Antitumor Activity and DNA Interaction of Diphenyltin Complexes Based on Salen-like Ligand[J]. Chinese Journal of Inorganic Chemistry, ;2021, 37(10): 1801-1808. doi: 10.11862/CJIC.2021.209 shu

Syntheses, Antitumor Activity and DNA Interaction of Diphenyltin Complexes Based on Salen-like Ligand

Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Functional Organometallic Materials, University of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Wu-Jiu JIANG, jwj_china@163.com
Received Date: 9 May 2021
Revised Date: 15 July 2021

Figures(7)

Two diphenyltin complexes, [(C₆H₅(O)C＝N—N＝C(Ph)—(Ph)C＝N—N＝C(O)—C₆H₅)₂SnPh₂(CH₃OH)]· 3CH₃OH (1) and[(o-OH—C₆H₄(O)C＝N—N＝C(Ph)— (Ph)C＝N—N＝C(O)— (o-OH—C₆H₄))₂SnPh₂(CH₃OH)] · CH₃OH (2), have been synthesized via the reaction of diphenyl ethylenedione benzoyl hydrazone or diphenylethylenedione salicylhydrazone with diphenyltin dichloride. Complexes 1 and 2 have been characterized by IR, ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR spectra, elemental analysis, HRMS and the crystal structures have been determined by X-ray diffraction. The thermostability of complexes 1 and 2 were analyzed, and in vitro antitumor activities of both the complexes were evaluated by MTT against three human cancer cell lines. It was found that complex 2 showed a slightly better inhibitory effect on cancer cells NCI-H460, HepG2, MCF7. The interaction of complex 2 with DNA was investigated using UV-Vis absorption spectroscopy and fluorescence quench spectra. It was found that complex 2 could bind to DNA through an intercalation mode.
- organotin complex,
- salen-like ligand,
- antitumor activity,
- DNA
1. [1]
  Rosenberg B, Vancamp L, Trosko J E, Mansour V H. Nature, 1969, 222(5191): 385-386 doi: 10.1038/222385a0
2. [2]
  Basu Baul T S, Addepalli M R, Duthie A, Singh P, Koch B, Gildenast H, Englert U, Rojas-León I, Höpfl H. Appl. Organomet. Chem. , 2021, 35(2): e6080
3. [3]
  Uddin N, Rashid F, Haider A, Tirmizi S A, Raheel A, Imran M, Zaib S, Diaconescu P L, Iqbal J, Ali S. Appl. Organomet. Chem. , 2021, 35(4): e6165
4. [4]
  Hong M, Geng H L, Niu M J, Wang F, Li D C, Liu J F, Yin H D. Eur. J. Med. Chem. , 2014, 86: 550-561 doi: 10.1016/j.ejmech.2014.08.070
5. [5]
  Wang H, Hu L, Du W, Tian X H, Zhang Q, Hu Z J, Luo L, Zhou H P, Wu J Y, Tian Y P. ACS Biomater. Sci. Eng. , 2017, 3(5): 836-842 doi: 10.1021/acsbiomaterials.6b00786
6. [6]
  Banti C N, Hadjikakou S K, Sismanoglu T, Hadjiliadis N. J. Inorg. Biochem. , 2019, 194: 114-152 doi: 10.1016/j.jinorgbio.2019.02.003
7. [7]
  Amir M K, Khan S, Zia ur R, Shah A, Butler I S. Inorg. Chim. Acta, 2014, 423: 14-25 doi: 10.1016/j.ica.2014.07.053
8. [8]
  Carraher C E, Roner M R. J. Organomet. Chem. , 2014, 751: 67-82 doi: 10.1016/j.jorganchem.2013.05.033
9. [9]
  Ay B, Şahin O, Demir B S, Saygideger Y, López-de-Luzuriaga J M, Mahmoudi G, Safin D A. New J. Chem. , 2020, 44(21): 9064-9072 doi: 10.1039/D0NJ00921K
10. [10]
  Srivastava A K, Ghosh S, Jana S, Pal S. Inorg. Chim. Acta, 2018, 483: 329-336 doi: 10.1016/j.ica.2018.08.036
11. [11]
  Ramírez-Jiménez A, Luna-García R, Cortés-Lozada A, Hernández S, Ramírez-Apan T, Nieto-Camacho A, Gómez E. J. Organomet. Chem. , 2013, 738: 10-19 doi: 10.1016/j.jorganchem.2013.03.038
12. [12]
  Baul T S B, Dutta D, Duthie A, Guchhait N, Rocha B G M, Guedes da Silva M F C, Mokhamatam R B, Raviprakash N, Manna S K. J. Inorg. Biochem. , 2017, 166: 34-48 doi: 10.1016/j.jinorgbio.2016.10.008
13. [13]
  Baul T S B, Paul A, Pellerito L, Scopelliti M, Singh P, Verma P, Duthie A, de Vos D, Tiekink E R T. Invest. New Drugs, 2011, 29(2): 285-299 doi: 10.1007/s10637-009-9360-3
14. [14]
  Shang X M, Meng X G, Alegria E C B A, Li Q S, da Silva M F C G, Kuznetsov M L, Pombeiro A J L. Inorg. Chem. , 2011, 50(17): 8158-8167 doi: 10.1021/ic200635g
15. [15]
  Attanzio A, Ippolito M, Girasolo M A, Saiano F, Rotondo A, Rubino S, Mondello L, Capobianco M L, Sabatino P, Tesoriere L, Casella G. J. Inorg. Biochem. , 2018, 188: 102-112 doi: 10.1016/j.jinorgbio.2018.04.006
16. [16]
  Jiang W J, Fan J S, Zhou Q, Zhang F X, Kuang D Z, Tan Y X. Bioorg. Chem. , 2020, 94: 103402 doi: 10.1016/j.bioorg.2019.103402
17. [17]
  Sheldrick G M. SHELXL-97, Program for Crystal Structure Refinement, University of Geöttingen, Germany, 1997.
18. [18]
  LUO B, YU H T, LIU M Q, ZHANG F X, KUANG D Z, TAN Y X, JIANG W J. Chinese J. Inorg. Chem. , 2019, 35(7): 1212-1220
19. [19]
  LIU J, LI Z Q, YI Y Y, ZHONG Y X, YU H T, TAN Y X, JIANG W J. Chinese J. Inorg. Chem. , 2019, 35(12): 2200-2208 doi: 10.11862/CJIC.2019.269
20. [20]
  JIANG W J, TAN Y X, KUANG D Z, ZHANG F X, LIU M Q. Scientia Sinica: Chimica, 2019, 49(8): 1083-1093
21. [21]
  Deacon G B, Phillips R J. Coord. Chem. Rev. , 1980, 33(3): 227-250 doi: 10.1016/S0010-8545(00)80455-5
22. [22]
  Hong M, Yin H D, Zhang X Y, Li C, Yue C H, Cheng S. J. Organomet. Chem. , 2013, 724: 23-31 doi: 10.1016/j.jorganchem.2012.10.031
23. [23]
  Salam M A, Hussein M A, Ramli I, Islam M S. J. Organomet. Chem. , 2016, 813: 71-77 doi: 10.1016/j.jorganchem.2016.04.007
24. [24]
  Davies A G. Organotin Chemistry. 2nd ed. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, 2004.
25. [25]
  Pretsch E, Bühlmann P, Badertscher M. Structure Determination of OrganicCompounds. 4th ed. Berlin Heidelberg: Springer-Verlag, 2009.
26. [26]
  López-Torres E, Zani F, Mendiola M A. J. Inorg. Biochem. , 2011, 105(5): 600-608 doi: 10.1016/j.jinorgbio.2011.01.014
27. [27]
  Pyle A M, Rehmann J P, Meshoyrer R, Kumar C V, Turro N J, Barton J K. J. Am. Chem. Soc. , 1989, 111(8): 3051-3058 doi: 10.1021/ja00190a046
28. [28]
  Wang M, Yu F, Jiang W J, Tan Y X, Zhang F X, Kuang D Z. Chin. J. Struct. Chem. , 2020, 39(11): 1965-1972
29. [29]
  Zhang Z J, Zeng H T, Liu Y, Kuang D Z, Zhang F X, Tan Y X, Jiang W J. Inorg. Nano-Metal Chem. , 2018, 48(10): 486-494 doi: 10.1080/24701556.2019.1571513
30. [30]
  Yan C Q, Zhang J L, Liang T G, Li Q S. Biomed. Pharmacother. , 2015, 71: 119-127 doi: 10.1016/j.biopha.2015.02.027
31. [31]
  Zhao Y, Li Z, Li H H, Wang S N, Niu M J. Inorg. Chim. Acta, 2018, 482: 136-143 doi: 10.1016/j.ica.2018.06.008
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