The University of Southampton
University of Southampton Institutional Repository

Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex

Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex
Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex
Cytotoxic tests recently performed at National Cancer Institute, NCI (USA), on [Cu(HPIR)2(DMF)2], 1, (H2PIR = piroxicam, 4-hydroxy-2-methyl-N-pyridin-2-yl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) a widely used non-steroidal anti-inflammatory drug, NSAID [see R. Cini, G. Giorgi, A. Cinquantini, C. Rossi, M. Sabat, Inorg. Chem. 29 (1990) 5197–5200, for synthesis and structural characterization, DMF = dimethylformamide] (NSC #624662) by using a panel of ca. 50 human cancer cells, showed growth inhibition factor GI50 values as low as 20 ?M against several cancer lines, with an average value 54.4 ?M. The activity of 1 is larger against ovarian cancer cells, non-small lung cancer cells, melanoma cancer cells, and central nervous system cancer cells. The widely used anticancer drug carboplatin (cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II)) (NSC #241240) has average GI50 value of 102 ?M. The reactions of copper(II)–acetate with other NSAIDs from the oxicam family were tested and crystalline complexes were obtained and characterized. Isoxicam (H2ISO = 4-hydroxy-2-methyl-N-(5-methylisoxazol-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) produced [Cu(HISO)2] · 0.5DMF, 2 · 0.5DMF (DMF = dimethylfomamide). The coordination arrangement is square-planar and the HISO? anions behave as ambi-dentate chelators via O(amide),N(isoxazole) and O(enolate),O(amide) donors. Meloxicam (H2MEL = 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) produced [Cu(HMEL)2(DMF)] · 0.25H2O, 3 · 0.25H2O. The coordination arrangement is square-pyramidal, the equatorial donors being O(amide),N(thiazole) from two HMEL? anions and the apical donor being O(DMF). Unexpectedly, cinnoxicam (HCIN = 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-1,2-benzothiazin-4-yl-(3-phenylacrylate)) produced [Cu(MBT)2(PPA)2] (MBT = 3-(methoxycarbonyl)-2-methyl-2H-1,2-benzothiazin-4-olate 1,1-dioxide, PPA = 3-phenyl-N-pyridin-2-ylacrylamide).
thiosemicarbazones, piroxicam, oxicam, crystal-structure, n-(2-pyridyl)-3-phenyl-2-propene, cytotoxic activity, nickel(ii), molecular-structure, indomethacin, anti-inflammatory drugs, cobalt(ii), diffraction, x-ray structures, amide, non-steroidal, metal-complexes, cu complexes
0162-0134
1140-1152
Cini, R.
a216ad24-d747-425e-8429-7b86eabe7a85
Tamasi, G.
ce381360-29a2-4324-8a1c-6656f3e3abbe
Defazio, S.
5222ea95-a7a7-40de-a1c2-6387fd7f73bd
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Cini, R.
a216ad24-d747-425e-8429-7b86eabe7a85
Tamasi, G.
ce381360-29a2-4324-8a1c-6656f3e3abbe
Defazio, S.
5222ea95-a7a7-40de-a1c2-6387fd7f73bd
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Cini, R., Tamasi, G., Defazio, S. and Hursthouse, M.B. (2007) Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex. Journal of Inorganic Biochemistry, 101 (8), 1140-1152. (doi:10.1016/j.jinorgbio.2007.04.015).

Record type: Article

Abstract

Cytotoxic tests recently performed at National Cancer Institute, NCI (USA), on [Cu(HPIR)2(DMF)2], 1, (H2PIR = piroxicam, 4-hydroxy-2-methyl-N-pyridin-2-yl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) a widely used non-steroidal anti-inflammatory drug, NSAID [see R. Cini, G. Giorgi, A. Cinquantini, C. Rossi, M. Sabat, Inorg. Chem. 29 (1990) 5197–5200, for synthesis and structural characterization, DMF = dimethylformamide] (NSC #624662) by using a panel of ca. 50 human cancer cells, showed growth inhibition factor GI50 values as low as 20 ?M against several cancer lines, with an average value 54.4 ?M. The activity of 1 is larger against ovarian cancer cells, non-small lung cancer cells, melanoma cancer cells, and central nervous system cancer cells. The widely used anticancer drug carboplatin (cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II)) (NSC #241240) has average GI50 value of 102 ?M. The reactions of copper(II)–acetate with other NSAIDs from the oxicam family were tested and crystalline complexes were obtained and characterized. Isoxicam (H2ISO = 4-hydroxy-2-methyl-N-(5-methylisoxazol-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) produced [Cu(HISO)2] · 0.5DMF, 2 · 0.5DMF (DMF = dimethylfomamide). The coordination arrangement is square-planar and the HISO? anions behave as ambi-dentate chelators via O(amide),N(isoxazole) and O(enolate),O(amide) donors. Meloxicam (H2MEL = 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide) produced [Cu(HMEL)2(DMF)] · 0.25H2O, 3 · 0.25H2O. The coordination arrangement is square-pyramidal, the equatorial donors being O(amide),N(thiazole) from two HMEL? anions and the apical donor being O(DMF). Unexpectedly, cinnoxicam (HCIN = 2-methyl-1,1-dioxido-3-[(pyridin-2-ylamino)carbonyl]-2H-1,2-benzothiazin-4-yl-(3-phenylacrylate)) produced [Cu(MBT)2(PPA)2] (MBT = 3-(methoxycarbonyl)-2-methyl-2H-1,2-benzothiazin-4-olate 1,1-dioxide, PPA = 3-phenyl-N-pyridin-2-ylacrylamide).

Full text not available from this repository.

More information

Published date: 2007
Keywords: thiosemicarbazones, piroxicam, oxicam, crystal-structure, n-(2-pyridyl)-3-phenyl-2-propene, cytotoxic activity, nickel(ii), molecular-structure, indomethacin, anti-inflammatory drugs, cobalt(ii), diffraction, x-ray structures, amide, non-steroidal, metal-complexes, cu complexes

Identifiers

Local EPrints ID: 54268
URI: https://eprints.soton.ac.uk/id/eprint/54268
ISSN: 0162-0134
PURE UUID: a3b6df42-e7b4-499f-962a-a88835dfa054

Catalogue record

Date deposited: 31 Jul 2008
Last modified: 13 Mar 2019 20:39

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×