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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Show full item recordAbstract
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-xSource:
Journal of Inorganic Biochemistry, 2008, 102, 8, 1558-1570Publisher:
- Elsevier
Funding / 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: 000258012000002
Scopus: 2-s2.0-47049100123
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Institution/Community
IHTMTY - JOUR AU - Gomez-Ruiz, Santiago AU - Kaluđerović, Goran N. AU - Prashar, Sanjiv AU - Polo-Ceron, Dorian AU - Fajardo, Mariano AU - Žižak, Željko AU - Sabo, Tibor AU - Juranić, Zorica PY - 2008 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4130 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(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. PB - Elsevier 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 and Sabo, Tibor and Juranić, Zorica", 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(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.", publisher = "Elsevier", 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., Sabo, T.,& Juranić, Z.. (2008). Cytotoxic studies of substituted titanocene and ansa-titanocene anticancer drugs. in Journal of Inorganic Biochemistry Elsevier., 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 Ž, Sabo T, Juranić Z. 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, Sabo, Tibor, Juranić, Zorica, "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 . .