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Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs

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2008
Authors
Gomez-Ruiz, Santiago
Kaluđerović, Goran N.
Prashar, Sanjiv
Polo-Ceron, Dorian
Fajardo, Mariano
Žižak, Željko
Sabo, Tibor
Juranić, Zorica
Article (Published version)
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Abstract
A variety of substituted titanocene and ansa-titanocene complexes have been synthesized and characterized using traditional methods. The cytotoxic activity of the different titanocene complexes was tested against tumour cell lines human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal immunocompetent cells, peripheral blood mononuclear cells PBMC. Alkenyl substitution, either on the cyclopentadienyl ring or on the silicon-atom ansa-bridge of the titanocene compounds [Ti{Me2Si(g5-C5Me4)(g5-C5H3{CMe2CH2CH2CH@CH2})}Cl2] (8), [Ti{Me(CH2@CH)Si(g5-C5Me4)(g5-C5H4)}Cl2] (9) and [Ti(g5- C5H4{CMe2CH2CH2CH@CH2})2Cl2] (12) showed higher cytotoxic activities (IC50 values from 24 } 3 to 151 } 10 lM) relative to complexes bearing an additional alkenyl-substituted silyl substituent on the silicon bridge [Ti{Me{(CH2@CH)Me2SiCH2CH2}Si(g5- C5Me4)(g5-C5H4)}Cl2] (10) and [Ti{Me{(CH2@CH)3SiCH2CH2}Si(g5-C5Me4)(g5-C5H4)}Cl2] (11) which causes a dramatic ...decrease of the cytotoxicity (IC50 values from 155 } 9 to >200 lM). In addition, the synthesis of the analogous niobocene complex [Nb(g5- C5H4{CMe2CH2CH2CH=CH2})2Cl2] (13), is described. Structural studies based on DFT calculations of the most active complexes 8, 9 and 12 and the X-ray crystal structure of 13 are reported.

Keywords:
Anticancer drugs / Titanocene / Adenocarcinoma HeLa / Human myelogenous leukemia K562 / Human malignant melanoma Fem-x
Source:
Journal of Inorganic Biochemistry, 2008, 102, 8, 1558-1570
Publisher:
  • Elsevier
Projects:
  • Ministerio de Educacio´n y Ciencia, Spain (Grant no. CTQ2005-07918-C02-02/BQU),
  • Comunidad de Madrid (S-0505/PPQ-0328)
  • Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-142010)
  • Istraživanje dejstava modifikatora biološkog odgovora u fiziološkim i patološkim stanjima (RS-145006)

DOI: 10.1016/j.jinorgbio.2008.02.001

ISSN: 0162-0134; 1873-3344

PubMed: 18353439

WoS: 10.1016/j.jinorgbio.2008.02.001

Scopus: 2-s2.0-47049100123
[ Google Scholar ]
63
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4130
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