Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs
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2008
Authors
Gomez-Ruiz, SantiagoKaluđerović, Goran N.
Prashar, Sanjiv
Polo-Ceron, Dorian
Fajardo, Mariano
Žižak, Željko S.
Sabo, Tibor
Juranić, Zorica D.
Article (Published version)
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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(eta(5)-C5Me4) (eta(5)-C5H3{CMe2CH2CH2CH=CH2})}Cl-2] (8), [Ti{Me(CH2=CH)Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (9) and [Ti(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (12) showed higher cytotoxic activities (IC50 values from 24 +/- 3 to 151 +/- 10 mu M) relative to complexes bearing an additional alkenyl-substituted silyl substituent on the silicon bridge [Ti{Me{(CH2=CH)Me2SiCH2CH2}Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (10) and [Ti{Me{(CH2=CH)(3)SiCH2CH2} Si(eta(5)-C5Me4)(eta(5...) -C5H4)}Cl-2] (11) which causes a dramatic decrease of the cytotoxicity (IC50 values from 155 +/- 9 to gt 200 mu M). In addition, the synthesis of the analogous niobocene complex [Nb(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (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. (c) 2008 Elsevier Inc. All rights reserved.
Keywords:
anticancer drugs / titanocene / adenocarcinoma HeLa / human myelogenous leukemia K562 / human malignant melanoma Fem-xSource:
Journal of Inorganic Biochemistry, 2008, 102, 8, 1558-1570Publisher:
- Elsevier Science Inc, New York
Funding / projects:
- Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology (RS-MESTD-MPN2006-2010-142010)
- Istraživanje dejstava modifikatora biološkog odgovora u fiziološkim i patološkim stanjima (RS-MESTD-MPN2006-2010-145006)
DOI: 10.1016/j.jinorgbio.2008.02.001
ISSN: 0162-0134
PubMed: 18353439
WoS: 000258012000002
Scopus: 2-s2.0-47049100123
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Gomez-Ruiz, Santiago AU - Kaluđerović, Goran N. AU - Prashar, Sanjiv AU - Polo-Ceron, Dorian AU - Fajardo, Mariano AU - Žižak, Željko S. AU - Sabo, Tibor AU - Juranić, Zorica D. PY - 2008 UR - https://cherry.chem.bg.ac.rs/handle/123456789/959 AB - 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(eta(5)-C5Me4) (eta(5)-C5H3{CMe2CH2CH2CH=CH2})}Cl-2] (8), [Ti{Me(CH2=CH)Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (9) and [Ti(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (12) showed higher cytotoxic activities (IC50 values from 24 +/- 3 to 151 +/- 10 mu M) relative to complexes bearing an additional alkenyl-substituted silyl substituent on the silicon bridge [Ti{Me{(CH2=CH)Me2SiCH2CH2}Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (10) and [Ti{Me{(CH2=CH)(3)SiCH2CH2} Si(eta(5)-C5Me4)(eta(5) -C5H4)}Cl-2] (11) which causes a dramatic decrease of the cytotoxicity (IC50 values from 155 +/- 9 to gt 200 mu M). In addition, the synthesis of the analogous niobocene complex [Nb(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (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. (c) 2008 Elsevier Inc. All rights reserved. PB - Elsevier Science Inc, New York T2 - Journal of Inorganic Biochemistry T1 - Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs VL - 102 IS - 8 SP - 1558 EP - 1570 DO - 10.1016/j.jinorgbio.2008.02.001 ER -
@article{ author = "Gomez-Ruiz, Santiago and Kaluđerović, Goran N. and Prashar, Sanjiv and Polo-Ceron, Dorian and Fajardo, Mariano and Žižak, Željko S. and Sabo, Tibor and Juranić, Zorica D.", year = "2008", 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(eta(5)-C5Me4) (eta(5)-C5H3{CMe2CH2CH2CH=CH2})}Cl-2] (8), [Ti{Me(CH2=CH)Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (9) and [Ti(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (12) showed higher cytotoxic activities (IC50 values from 24 +/- 3 to 151 +/- 10 mu M) relative to complexes bearing an additional alkenyl-substituted silyl substituent on the silicon bridge [Ti{Me{(CH2=CH)Me2SiCH2CH2}Si(eta(5)-C5Me4)(eta(5)-C5H4)}Cl-2] (10) and [Ti{Me{(CH2=CH)(3)SiCH2CH2} Si(eta(5)-C5Me4)(eta(5) -C5H4)}Cl-2] (11) which causes a dramatic decrease of the cytotoxicity (IC50 values from 155 +/- 9 to gt 200 mu M). In addition, the synthesis of the analogous niobocene complex [Nb(eta(5)- C5H4{CMe2CH2CH2CH=CH2})(2)Cl-2] (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. (c) 2008 Elsevier Inc. All rights reserved.", publisher = "Elsevier Science Inc, New York", journal = "Journal of Inorganic Biochemistry", title = "Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs", volume = "102", number = "8", pages = "1558-1570", doi = "10.1016/j.jinorgbio.2008.02.001" }
Gomez-Ruiz, S., Kaluđerović, G. N., Prashar, S., Polo-Ceron, D., Fajardo, M., Žižak, Ž. S., Sabo, T.,& Juranić, Z. D.. (2008). Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs. in Journal of Inorganic Biochemistry Elsevier Science Inc, New York., 102(8), 1558-1570. https://doi.org/10.1016/j.jinorgbio.2008.02.001
Gomez-Ruiz S, Kaluđerović GN, Prashar S, Polo-Ceron D, Fajardo M, Žižak ŽS, Sabo T, Juranić ZD. Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs. in Journal of Inorganic Biochemistry. 2008;102(8):1558-1570. doi:10.1016/j.jinorgbio.2008.02.001 .
Gomez-Ruiz, Santiago, Kaluđerović, Goran N., Prashar, Sanjiv, Polo-Ceron, Dorian, Fajardo, Mariano, Žižak, Željko S., Sabo, Tibor, Juranić, Zorica D., "Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs" in Journal of Inorganic Biochemistry, 102, no. 8 (2008):1558-1570, https://doi.org/10.1016/j.jinorgbio.2008.02.001 . .