TY  - JOUR
AU  - Ceballos-Torres, Jesus
AU  - del Hierro, Isabel
AU  - Prashar, Sanjiv
AU  - Fajardo, Mariano
AU  - Mijatović, Sanja
AU  - Maksimović-Ivanić, Danijela
AU  - Kaluđerović, Goran N.
AU  - Gomez-Ruiz, Santiago
PY  - 2014
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2139
AB  - Four alkenyl-substituted titanocene dichloride complexes
   {[}Ti(eta(5)-C5H5)\{eta(5)-C5H4(CMeR(CH2CH2CH=CH2))\}Cl-2] (R = Me (8),
   Ph (9)) and
   {[}Ti(eta(5)-C5H5)\{eta(5)-C5H3(CMeR(CH2CH2CH=CH2))(SiMe3)\}] (R = Me
   (10), Ph (11)) have been synthesized and characterized.
   The cytotoxic activity of 8-11 has been tested against human tumour cell
   lines from four different tissue origins {[}8505C (anaplastic thyroid
   cancer), DLD-1 (colon cancer), FaDu (head and neck cancer), A2780
   (ovarian cancer) and A549 (lung carcinoma)] and compared with those of
   the reference complexes {[}Ti(eta(5)-C5H5)(2)Cl-2] and cisplatin. The
   majority of the studied titanocene compounds are more active than the
   reference complex {[}Ti(eta(5)-C5H5)(2)Cl-2] indicating that the
   presence of alkenyl substituents leads to an increase in the cytotoxic
   activity. In addition, the presence of a trimethylsilyl group on the
   cyclopentadienyl ring also leads to an increase in the cytotoxic
   activity of 10 with respect to 8. The contrary is observed for 9 and 11
   (except on the DLD-1 cell line) with 9 (without -SiMe3) being more
   active than 11 (with -SiMe3). However, all synthesized complexes,
   exhibited lower cytotoxic activity than cisplatin.
   Stability and binding studies based on cyclic voltammetry and UV-visible
   spectroscopy have been carried out in order to explore possible
   interactions between titanocene derivatives and various intracellular
   molecules, such as the nitrogenous bases cytosine and thymine, the
   nucleotides adenosine and guanosine, and single-strand fish sperm DNA
   (FS-DNA). These experiments have allowed us to construct models to
   examine the interactions and action mechanisms of titanocene complexes
   inside the cells. In addition, this is one of the first studies on the
   interactions of titanocene derivatives with DNA fragments using cyclic
   voltammetry. (c) 2014 Elsevier B.V. All rights reserved.
T2  - Journal of Organometallic Chemistry
T1  - Alkenyl-substituted titanocene dichloride complexes: Stability studies,
 binding and cytotoxicity
VL  - 769
DO  - 10.1016/j.jorganchem.2014.06.031
SP  - 46
EP  - 57
ER  - 

@article{
author = "Ceballos-Torres, Jesus and del Hierro, Isabel and Prashar, Sanjiv and Fajardo, Mariano and Mijatović, Sanja and Maksimović-Ivanić, Danijela and Kaluđerović, Goran N. and Gomez-Ruiz, Santiago",
year = "2014",
abstract = "Four alkenyl-substituted titanocene dichloride complexes
   {[}Ti(eta(5)-C5H5)\{eta(5)-C5H4(CMeR(CH2CH2CH=CH2))\}Cl-2] (R = Me (8),
   Ph (9)) and
   {[}Ti(eta(5)-C5H5)\{eta(5)-C5H3(CMeR(CH2CH2CH=CH2))(SiMe3)\}] (R = Me
   (10), Ph (11)) have been synthesized and characterized.
   The cytotoxic activity of 8-11 has been tested against human tumour cell
   lines from four different tissue origins {[}8505C (anaplastic thyroid
   cancer), DLD-1 (colon cancer), FaDu (head and neck cancer), A2780
   (ovarian cancer) and A549 (lung carcinoma)] and compared with those of
   the reference complexes {[}Ti(eta(5)-C5H5)(2)Cl-2] and cisplatin. The
   majority of the studied titanocene compounds are more active than the
   reference complex {[}Ti(eta(5)-C5H5)(2)Cl-2] indicating that the
   presence of alkenyl substituents leads to an increase in the cytotoxic
   activity. In addition, the presence of a trimethylsilyl group on the
   cyclopentadienyl ring also leads to an increase in the cytotoxic
   activity of 10 with respect to 8. The contrary is observed for 9 and 11
   (except on the DLD-1 cell line) with 9 (without -SiMe3) being more
   active than 11 (with -SiMe3). However, all synthesized complexes,
   exhibited lower cytotoxic activity than cisplatin.
   Stability and binding studies based on cyclic voltammetry and UV-visible
   spectroscopy have been carried out in order to explore possible
   interactions between titanocene derivatives and various intracellular
   molecules, such as the nitrogenous bases cytosine and thymine, the
   nucleotides adenosine and guanosine, and single-strand fish sperm DNA
   (FS-DNA). These experiments have allowed us to construct models to
   examine the interactions and action mechanisms of titanocene complexes
   inside the cells. In addition, this is one of the first studies on the
   interactions of titanocene derivatives with DNA fragments using cyclic
   voltammetry. (c) 2014 Elsevier B.V. All rights reserved.",
journal = "Journal of Organometallic Chemistry",
title = "Alkenyl-substituted titanocene dichloride complexes: Stability studies,
 binding and cytotoxicity",
volume = "769",
doi = "10.1016/j.jorganchem.2014.06.031",
pages = "46-57"
}

Ceballos-Torres, J., del Hierro, I., Prashar, S., Fajardo, M., Mijatović, S., Maksimović-Ivanić, D., Kaluđerović, G. N.,& Gomez-Ruiz, S.. (2014). Alkenyl-substituted titanocene dichloride complexes: Stability studies,
 binding and cytotoxicity. in Journal of Organometallic Chemistry, 769, 46-57.
https://doi.org/10.1016/j.jorganchem.2014.06.031

Ceballos-Torres J, del Hierro I, Prashar S, Fajardo M, Mijatović S, Maksimović-Ivanić D, Kaluđerović GN, Gomez-Ruiz S. Alkenyl-substituted titanocene dichloride complexes: Stability studies,
 binding and cytotoxicity. in Journal of Organometallic Chemistry. 2014;769:46-57.
doi:10.1016/j.jorganchem.2014.06.031 .

Ceballos-Torres, Jesus, del Hierro, Isabel, Prashar, Sanjiv, Fajardo, Mariano, Mijatović, Sanja, Maksimović-Ivanić, Danijela, Kaluđerović, Goran N., Gomez-Ruiz, Santiago, "Alkenyl-substituted titanocene dichloride complexes: Stability studies,
 binding and cytotoxicity" in Journal of Organometallic Chemistry, 769 (2014):46-57,
https://doi.org/10.1016/j.jorganchem.2014.06.031 . .