Jump to main content
Jump to site search

Issue 28, 2018
Previous Article Next Article

Versatile coordination of acetazolamide to ruthenium(II) p-cymene complexes and preliminary cytotoxicity studies

Author affiliations

Abstract

The carbonic anhydrase inhibitor acetazolamide (AcmH2) reacted with [(η6-p-cymene)RuCl(μ-Cl)]2 to afford [(η6-p-cymene)RuCl2N-AcmH2)], 1A, in near-quantitative yield. In methanol, 1A exists in equilibrium with 1B, being probably a coordination isomer, as established by VT 1H-EXSY NMR spectroscopy. DFT calculations pointed to a higher stability of 1A with respect to 1B. [(η6-p-cymene)RuCl(κ2N,N′-AcmH)], 2, was obtained in 86% yield from [(η6-p-cymene)RuCl(μ-Cl)]2 and AcmH2 in the presence of NaOH. The reactions of 2 with AgNO3 (in water), pta/AgNO3 or pta/AgOTf/Et3N (in methanol) afforded the nitrate-coordinated complex [(η6-p-cymene)Ru(κO-NO3)(κ2N,N′-AcmH)], 3, the salt [(η6-p-cymene)Ru(κ2N,N′-AcmH)(κP-pta)]NO3, [4]NO3, and the zwitterion [(η6-p-cymene)Ru(κ2N,N′-Acm)(κP-pta)], 5, respectively, in high yields (pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane). The reactions of 5 with Brønsted acids yielded the protonated-pta species [(η6-p-cymene)Ru(κ2N,N′-Acm)(κP-ptaH)]X [6]X (X = NO3, TsO). All compounds were fully characterized by analytical and spectroscopic methods, and the structures of 1A, 2 and 5 were elucidated by X-ray diffraction. The stability of the compounds was investigated in aqueous media and 2 and 5 were evaluated for their cytotoxicity towards human ovarian A2780 and A2780cisR cancer cells and non-tumorigenic HEK-293 cells.

Graphical abstract: Versatile coordination of acetazolamide to ruthenium(ii) p-cymene complexes and preliminary cytotoxicity studies

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Apr 2018, accepted on 22 Jun 2018 and first published on 28 Jun 2018


Article type: Paper
DOI: 10.1039/C8DT01555D
Citation: Dalton Trans., 2018,47, 9367-9384

  •   Request permissions

    Versatile coordination of acetazolamide to ruthenium(II) p-cymene complexes and preliminary cytotoxicity studies

    L. Biancalana, L. K. Batchelor, G. Ciancaleoni, S. Zacchini, G. Pampaloni, P. J. Dyson and F. Marchetti, Dalton Trans., 2018, 47, 9367
    DOI: 10.1039/C8DT01555D

Search articles by author

Spotlight

Advertisements