Syntheses, Crystal Structures and Biological Activity of 2-Oxo-3-phenylpropionic Acid Aroyl Hydrazone Di-2,4-dichlorobenzyltin Complexes

被引:7
作者
Jiang Wu-Jiu [1 ]
Tan Yu-Xing [1 ]
Yu Jiang-Xi [1 ]
Zhu Xiao-Ming [1 ]
Zhang Fu-Xing [1 ]
Kuang Dai-Zhi [1 ]
机构
[1] Hengyang Normal Univ, Key Lab Funct Organometall Mat, Coll Chem & Mat Sci, Coll Hunan Prov, Hengyang 421008, Hunan, Peoples R China
关键词
organotin complex; hydrazone; synthesis; crystal structure; biological activity; DIORGANOTIN IV COMPLEXES; ORGANOTIN COMPOUNDS; ANTITUMOR-ACTIVITY; CANCER-CELLS; SCHIFF-BASE; THERMAL-STABILITY; DNA-BINDING; IN-VITRO; CHEMISTRY;
D O I
10.11862/CJIC.2016.179
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two substituted benzyltin complexes has been synthesized via the reaction of 2-oxo-3-phenylpropionic acid aroyl hydrazone with di-2,4-dichlorobenzyltin dichloride. The complexes Cl and C2 have been characterized by IR, UV-Vis, H-1 NMR, C-13 NMR Sn-119 NMR spectra, elemental analysis and the crystal structures have been determined by X-ray diffraction. In vitro antitumor activities of both complexes were evaluated by 3-(4,5-dimethylthiazoly-2-yl)- 2,5- diphenyltetrazolium bromide (MTT) assay against five human cancer cell lines (Hela, MCF7, HepG2, Colo205, NCI-H460) and two human cell lines (HEK293, HL7702). Two Complexes exhibited strong antitumor activity. Moreover, C2 less toxic than Cl. The interaction between complexes and calf thymus DNA were studied by EB fluorescent probe. The results show that the interaction of Cl with calf thymus DNA were intercalation and electrostatic attraction. However, the C2 were intercalation. CCDC: 1452066, Cl; 1452067, C2.
引用
收藏
页码:1383 / 1390
页数:8
相关论文
共 35 条
[1]  
[Anonymous], 2004, ORGANOTIN CHEM
[2]  
Armarego WLF, 2009, PURIFICATION OF LABORATORY CHEMICALS, 6TH EDITION, P1
[3]  
Baba H S, 2015, ORGANOMETALLICS, V34, P5555
[4]   Use of bis-aminoalcohol benzoquinones and dihydroxybenzoquinones in the formation of mono and polymeric structures of diorganotin(IV) derivatives [J].
Barba, Victor ;
Zaragoza, Jonathan ;
Hoepfl, Herbert ;
Farfan, Norberto ;
Beltran, Hiram I. ;
Zamudio-Rivera, Luis S. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (10) :1949-1956
[5]   SN-119, P-31, C-13 AND PROTON NUCLEAR MAGNETIC-RESONANCE AND MOSSBAUER STUDIES OF MONO-ORGANOTIN(IV), DI-ORGANOTIN(IV) AND TRI-ORGANOTIN(IV) DIALKYLDITHIOPHOSPHATES [J].
CLARK, HC ;
JAIN, VK ;
MEHROTRA, RC ;
SINGH, BP ;
SRIVASTAVA, G ;
BIRCHALL, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (03) :385-394
[6]   INVESTIGATIONS INTO THE ANTI-TUMOR ACTIVITY OF ORGANOTIN COMPOUNDS .1. DIORGANOTIN DIHALIDE AND DI-PSEUDOHALIDE COMPLEXES [J].
CROWE, AJ ;
SMITH, PJ ;
ATASSI, G .
CHEMICO-BIOLOGICAL INTERACTIONS, 1980, 32 (1-2) :171-178
[7]   Synthesis, characterization, molecular docking and cytotoxic activity of novel plumbagin hydrazones against breast cancer cells [J].
Dandawate, Prasad ;
Khan, Ejazuddin ;
Padhye, Subhash ;
Gaba, Himanshi ;
Sinha, Swati ;
Deshpande, Jyoti ;
Swamy, K. Venkateswara ;
Khetmalas, Madhukar ;
Ahmad, Aamir ;
Sarkar, Fazlul H. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (09) :3104-3108
[8]   Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones [J].
Effenberger, K. ;
Breyer, S. ;
Schobert, R. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) :1947-1954
[9]  
Feng YL, 2014, CHINESE J INORG CHEM, V30, P2767
[10]   NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist [J].
Fulmer, Gregory R. ;
Miller, Alexander J. M. ;
Sherden, Nathaniel H. ;
Gottlieb, Hugo E. ;
Nudelman, Abraham ;
Stoltz, Brian M. ;
Bercaw, John E. ;
Goldberg, Karen I. .
ORGANOMETALLICS, 2010, 29 (09) :2176-2179