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Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes

Authorized Users Only
2008
Authors
Gómez-Ruiz, Santiago
Kaluđerović, Goran N.
Prashar, Sanjiv
Hey-Hawkins, Evamarie
Erić, Aleksandra
Žižak, Željko
Juranić, Zorica
Article (Published version)
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Abstract
The reaction of 3-methoxyphenylacetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5- dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV) chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence of triethylamine yielded the compounds [SnPh3(3-MPA)] (1), [SnPh3(4-MPA)] (2), [SnPh3(DMFU)] (3), [SnPh3(BZDO)] (4), [SnPh2(3-MPA)2] (5), [SnPh2(4-MPA)2] (6), [SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8), respectively. The tetranuclear complex [{Me2(DMFU)SnOSn(DMFU)Me2}2] (9) was prepared by the reaction of dimethyltin(IV) oxide and 2,5- dimethyl-3-furoic acid (DMFUH). The molecular structures of 3, 4 and 9, were determined by X-ray diffraction studies. The cytotoxic activity of the carboxylic acids (3-MPAH, 4-MPAH, BZDOH and DMFUH) and di (5–8) and triphenyltin(IV) complexes (2–4) was tested against tumor cell lines human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal immun...ocompetent cells, peripheral blood mononuclear cells PBMC. Triphenyltin(IV) complexes show higher activities than the diphenyltin(IV) derivatives. The most active compound is [SnPh3(DMFU)] (3) with IC50 value of 0.15 } 0.01, 0.051 } 0.004, 0.074 } 0.004, 0.20 } 0.01, 0.15 } 0.02 on HeLa, K562, Femx, rested and stimulated PBMC, respectively, while the most selective are [SnPh2(3-MPA)2] (5), [SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8). Compounds 3, 5, 7 and 8 present higher activities than cisplatin in all the tested cells and relative high selectivity especially on K562 cells.

Keywords:
Anticancer drugs / Tin / Adenocarcinoma HeLa / Human myelogenous leukemia K562 / Human malignant melanoma Fem-x
Source:
Journal of Inorganic Biochemistry, 2008, 102, 12, 2087-2096
Publisher:
  • Elsevier
Funding / projects:
  • Ministerio de Educación y Ciencia, Spain (Grant No. CTQ2005-07918-C02- 02/BQU)
  • 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.2008.07.009

ISSN: 0162-0134

PubMed: 18760840

WoS: 000261429700009

Scopus: 2-s2.0-55549104361
[ Google Scholar ]
87
76
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4125
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Gómez-Ruiz, Santiago
AU  - Kaluđerović, Goran N.
AU  - Prashar, Sanjiv
AU  - Hey-Hawkins, Evamarie
AU  - Erić, Aleksandra
AU  - Žižak, Željko
AU  - Juranić, Zorica
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4125
AB  - The reaction of 3-methoxyphenylacetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5-
dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV)
chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence of triethylamine yielded the compounds
[SnPh3(3-MPA)] (1), [SnPh3(4-MPA)] (2), [SnPh3(DMFU)] (3), [SnPh3(BZDO)] (4), [SnPh2(3-MPA)2] (5),
[SnPh2(4-MPA)2] (6), [SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8), respectively. The tetranuclear complex
[{Me2(DMFU)SnOSn(DMFU)Me2}2] (9) was prepared by the reaction of dimethyltin(IV) oxide and 2,5-
dimethyl-3-furoic acid (DMFUH). The molecular structures of 3, 4 and 9, were determined by X-ray diffraction
studies. The cytotoxic activity of the carboxylic acids (3-MPAH, 4-MPAH, BZDOH and DMFUH)
and di (5–8) and triphenyltin(IV) complexes (2–4) was tested against tumor cell lines human adenocarcinoma
HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal
immunocompetent cells, peripheral blood mononuclear cells PBMC. Triphenyltin(IV) complexes show
higher activities than the diphenyltin(IV) derivatives. The most active compound is [SnPh3(DMFU)] (3)
with IC50 value of 0.15  } 0.01, 0.051  } 0.004, 0.074  } 0.004, 0.20  } 0.01, 0.15  } 0.02 on HeLa, K562, Femx,
rested and stimulated PBMC, respectively, while the most selective are [SnPh2(3-MPA)2] (5),
[SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8). Compounds 3, 5, 7 and 8 present higher activities than cisplatin
in all the tested cells and relative high selectivity especially on K562 cells.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes
VL  - 102
IS  - 12
SP  - 2087
EP  - 2096
DO  - 10.1016/j.jinorgbio.2008.07.009
ER  - 
@article{
author = "Gómez-Ruiz, Santiago and Kaluđerović, Goran N. and Prashar, Sanjiv and Hey-Hawkins, Evamarie and Erić, Aleksandra and Žižak, Željko and Juranić, Zorica",
year = "2008",
abstract = "The reaction of 3-methoxyphenylacetic acid (3-MPAH), 4-methoxyphenylacetic acid (4-MPAH), 2,5-
dimethyl-3-furoic acid (DMFUH) or 1,4-benzodioxane-6-carboxylic acid (BZDOH) with triphenyltin(IV)
chloride (1:1) or diphenyltin(IV) dichloride (2:1) in the presence of triethylamine yielded the compounds
[SnPh3(3-MPA)] (1), [SnPh3(4-MPA)] (2), [SnPh3(DMFU)] (3), [SnPh3(BZDO)] (4), [SnPh2(3-MPA)2] (5),
[SnPh2(4-MPA)2] (6), [SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8), respectively. The tetranuclear complex
[{Me2(DMFU)SnOSn(DMFU)Me2}2] (9) was prepared by the reaction of dimethyltin(IV) oxide and 2,5-
dimethyl-3-furoic acid (DMFUH). The molecular structures of 3, 4 and 9, were determined by X-ray diffraction
studies. The cytotoxic activity of the carboxylic acids (3-MPAH, 4-MPAH, BZDOH and DMFUH)
and di (5–8) and triphenyltin(IV) complexes (2–4) was tested against tumor cell lines human adenocarcinoma
HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x and normal
immunocompetent cells, peripheral blood mononuclear cells PBMC. Triphenyltin(IV) complexes show
higher activities than the diphenyltin(IV) derivatives. The most active compound is [SnPh3(DMFU)] (3)
with IC50 value of 0.15  } 0.01, 0.051  } 0.004, 0.074  } 0.004, 0.20  } 0.01, 0.15  } 0.02 on HeLa, K562, Femx,
rested and stimulated PBMC, respectively, while the most selective are [SnPh2(3-MPA)2] (5),
[SnPh2(DMFU)2] (7) and [SnPh2(BZDO)2] (8). Compounds 3, 5, 7 and 8 present higher activities than cisplatin
in all the tested cells and relative high selectivity especially on K562 cells.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes",
volume = "102",
number = "12",
pages = "2087-2096",
doi = "10.1016/j.jinorgbio.2008.07.009"
}
Gómez-Ruiz, S., Kaluđerović, G. N., Prashar, S., Hey-Hawkins, E., Erić, A., Žižak, Ž.,& Juranić, Z.. (2008). Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes. in Journal of Inorganic Biochemistry
Elsevier., 102(12), 2087-2096.
https://doi.org/10.1016/j.jinorgbio.2008.07.009
Gómez-Ruiz S, Kaluđerović GN, Prashar S, Hey-Hawkins E, Erić A, Žižak Ž, Juranić Z. Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes. in Journal of Inorganic Biochemistry. 2008;102(12):2087-2096.
doi:10.1016/j.jinorgbio.2008.07.009 .
Gómez-Ruiz, Santiago, Kaluđerović, Goran N., Prashar, Sanjiv, Hey-Hawkins, Evamarie, Erić, Aleksandra, Žižak, Željko, Juranić, Zorica, "Study of the cytotoxic activity of di and triphenyltin(IV) carboxylate complexes" in Journal of Inorganic Biochemistry, 102, no. 12 (2008):2087-2096,
https://doi.org/10.1016/j.jinorgbio.2008.07.009 . .

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