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Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines

Authorized Users Only
2011
Authors
Krstić, Milena
Sovilj, Sofija P.
Grgurić-Šipka, Sanja
Radosavljević-Evans, Ivana
Borozan, Sunčica
Santibanez, Juan
Article (Published version)
Metadata
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Abstract
Three new ruthenium(II) complexes 1-3 containing N-alkylphenothiazine molecules were synthesized by reaction of [RuCl2(eta(6)-P-cymene)](2) with chlorpromazine hydrochloride (1), trifluoperazine dihydrochloride (2) or thioridazine hydrochloride (3). The compounds of the general formula L[RuCl3(eta(6)-p-cymene)] were characterized by elemental analysis and spectroscopic methods (FT-IR, UV-Vis, H-1 and C-13 NMR). Complex 2 was structurally characterized by single crystal X-ray diffraction. In vitro cytotoxic activity of complexes 1-3 were assayed in four human carcinoma cell lines MCF-7, MDA-MB-453 (breast carcinoma), SW-480 (colon carcinoma) and IM9 (myeloma multiple cells). The highest cytotoxicity (12.1 lt = IC50 lt = 17.3 mu M) and induced a total (SW-480) or almost total cell death (MCF-7. MDA-MB-453) at 25 mu M in 48 h of treatment were observed for complex 2. The influence of three different doses (0.4, 4.5 and 90.4 mu M/kg bw) of complex 2 on activities of antioxidants enzymes ...(superoxide dismutase (SOD) and catalase (CAT)) and lactate dehydrogenase (LDH) were investigated under physiological conditions. The effects on nitrite production (NO2-) and level of erythrocytes malondialdehyde (MDA) in rats blood were evaluated, too.

Keywords:
Ruthenium complexes / p-Cymene / N-Alkylphenothiazines / Single crystal X-ray diffraction / Cytotoxicity / Antioxidant enzymes
Source:
European Journal of Medicinal Chemistry, 2011, 46, 9, 4168-4177
Publisher:
  • Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
Funding / projects:
  • Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-172014)

DOI: 10.1016/j.ejmech.2011.06.019

ISSN: 0223-5234

PubMed: 21741132

WoS: 000295237400066

Scopus: 2-s2.0-80052929773
[ Google Scholar ]
12
11
URI
http://rimi.imi.bg.ac.rs/handle/123456789/371
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
Institut za medicinska istraživanja
TY  - JOUR
AU  - Krstić, Milena
AU  - Sovilj, Sofija P.
AU  - Grgurić-Šipka, Sanja
AU  - Radosavljević-Evans, Ivana
AU  - Borozan, Sunčica
AU  - Santibanez, Juan
PY  - 2011
UR  - http://rimi.imi.bg.ac.rs/handle/123456789/371
AB  - Three new ruthenium(II) complexes 1-3 containing N-alkylphenothiazine molecules were synthesized by reaction of [RuCl2(eta(6)-P-cymene)](2) with chlorpromazine hydrochloride (1), trifluoperazine dihydrochloride (2) or thioridazine hydrochloride (3). The compounds of the general formula L[RuCl3(eta(6)-p-cymene)] were characterized by elemental analysis and spectroscopic methods (FT-IR, UV-Vis, H-1 and C-13 NMR). Complex 2 was structurally characterized by single crystal X-ray diffraction. In vitro cytotoxic activity of complexes 1-3 were assayed in four human carcinoma cell lines MCF-7, MDA-MB-453 (breast carcinoma), SW-480 (colon carcinoma) and IM9 (myeloma multiple cells). The highest cytotoxicity (12.1  lt = IC50  lt = 17.3 mu M) and induced a total (SW-480) or almost total cell death (MCF-7. MDA-MB-453) at 25 mu M in 48 h of treatment were observed for complex 2. The influence of three different doses (0.4, 4.5 and 90.4 mu M/kg bw) of complex 2 on activities of antioxidants enzymes (superoxide dismutase (SOD) and catalase (CAT)) and lactate dehydrogenase (LDH) were investigated under physiological conditions. The effects on nitrite production (NO2-) and level of erythrocytes malondialdehyde (MDA) in rats blood were evaluated, too.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines
EP  - 4177
IS  - 9
SP  - 4168
VL  - 46
DO  - 10.1016/j.ejmech.2011.06.019
UR  - conv_2586
ER  - 
@article{
author = "Krstić, Milena and Sovilj, Sofija P. and Grgurić-Šipka, Sanja and Radosavljević-Evans, Ivana and Borozan, Sunčica and Santibanez, Juan",
year = "2011",
abstract = "Three new ruthenium(II) complexes 1-3 containing N-alkylphenothiazine molecules were synthesized by reaction of [RuCl2(eta(6)-P-cymene)](2) with chlorpromazine hydrochloride (1), trifluoperazine dihydrochloride (2) or thioridazine hydrochloride (3). The compounds of the general formula L[RuCl3(eta(6)-p-cymene)] were characterized by elemental analysis and spectroscopic methods (FT-IR, UV-Vis, H-1 and C-13 NMR). Complex 2 was structurally characterized by single crystal X-ray diffraction. In vitro cytotoxic activity of complexes 1-3 were assayed in four human carcinoma cell lines MCF-7, MDA-MB-453 (breast carcinoma), SW-480 (colon carcinoma) and IM9 (myeloma multiple cells). The highest cytotoxicity (12.1  lt = IC50  lt = 17.3 mu M) and induced a total (SW-480) or almost total cell death (MCF-7. MDA-MB-453) at 25 mu M in 48 h of treatment were observed for complex 2. The influence of three different doses (0.4, 4.5 and 90.4 mu M/kg bw) of complex 2 on activities of antioxidants enzymes (superoxide dismutase (SOD) and catalase (CAT)) and lactate dehydrogenase (LDH) were investigated under physiological conditions. The effects on nitrite production (NO2-) and level of erythrocytes malondialdehyde (MDA) in rats blood were evaluated, too.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines",
pages = "4177-4168",
number = "9",
volume = "46",
doi = "10.1016/j.ejmech.2011.06.019",
url = "conv_2586"
}
Krstić, M., Sovilj, S. P., Grgurić-Šipka, S., Radosavljević-Evans, I., Borozan, S.,& Santibanez, J.. (2011). Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 46(9), 4168-4177.
https://doi.org/10.1016/j.ejmech.2011.06.019
conv_2586
Krstić M, Sovilj SP, Grgurić-Šipka S, Radosavljević-Evans I, Borozan S, Santibanez J. Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines. in European Journal of Medicinal Chemistry. 2011;46(9):4168-4177.
doi:10.1016/j.ejmech.2011.06.019
conv_2586 .
Krstić, Milena, Sovilj, Sofija P., Grgurić-Šipka, Sanja, Radosavljević-Evans, Ivana, Borozan, Sunčica, Santibanez, Juan, "Synthesis, structural and spectroscopic characterization, in vitro cytotoxicity and in vivo activity as free radical scavengers of chlorido(p-cymene) complexes of ruthenium(II) containing N-alkylphenothiazines" in European Journal of Medicinal Chemistry, 46, no. 9 (2011):4168-4177,
https://doi.org/10.1016/j.ejmech.2011.06.019 .,
conv_2586 .

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