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
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2011
Authors
Krstić, MilenaSovilj, Sofija P.
Grgurić-Šipka, Sanja
Radosavljević-Evans, Ivana
Borozan, Sunčica
Santibanez, Juan F.
Article (Published version)
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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 enzymesSource:
European Journal of Medicinal Chemistry, 2011, 46, 9, 4168-4177Publisher:
- 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-MESTD-Basic Research (BR or ON)-172014)
DOI: 10.1016/j.ejmech.2011.06.019
ISSN: 0223-5234
PubMed: 21741132
WoS: 000295237400066
Scopus: 2-s2.0-80052929773
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Institut za medicinska istraživanjaTY - JOUR AU - Krstić, Milena AU - Sovilj, Sofija P. AU - Grgurić-Šipka, Sanja AU - Radosavljević-Evans, Ivana AU - Borozan, Sunčica AU - Santibanez, Juan F. 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 ER -
@article{ author = "Krstić, Milena and Sovilj, Sofija P. and Grgurić-Šipka, Sanja and Radosavljević-Evans, Ivana and Borozan, Sunčica and Santibanez, Juan F.", 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" }
Krstić, M., Sovilj, S. P., Grgurić-Šipka, S., Radosavljević-Evans, I., Borozan, S.,& Santibanez, J. F.. (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
Krstić M, Sovilj SP, Grgurić-Šipka S, Radosavljević-Evans I, Borozan S, Santibanez JF. 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 .
Krstić, Milena, Sovilj, Sofija P., Grgurić-Šipka, Sanja, Radosavljević-Evans, Ivana, Borozan, Sunčica, Santibanez, Juan F., "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 . .