Synthesis and Antitumor and Surface Activity of Novel Tetrachloro Metallate Complexes of Sulfaquinoxaline with Co(II), Cu(II), or Sn(II) Chlorides

Nashwa Saleh; Manal Khowdiary; Abdel Fattah Badawi

doi:10.3139/113.110313

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Synthesis and Antitumor and Surface Activity of Novel Tetrachloro Metallate Complexes of Sulfaquinoxaline with Co(II), Cu(II), or Sn(II) Chlorides

Nashwa Saleh , Manal Khowdiary und Abdel Fattah Badawi

Veröffentlicht/Copyright: 22. Juli 2014

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Aus der Zeitschrift Tenside Surfactants Detergents Band 51 Heft 4

Abstract

New sulfonamide tetrachloro metallate complexes that might possess strong carbonic anhydrase (CA) inhibitory properties were synthesized by the reaction of 4-amino-N-(quinoxalin-2-yl) benzene sulfonamide (sulfaquinoxaline) hydrochloride with different metal chlorides, i.e. CoCl₂, CuCl₂ or SnCl₂. The produced metal complexes of the sulfonamide derivative, containing divalent cations, were characterized by standard procedures. These metal complexes might possess topical antiglaucoma properties which might make them more effective as pharmacological agents. The synthesized complexes exhibited significant cytotoxic activity against colon HCT-116 human cell line. Surface properties of these surfactants were investigated. The surface properties studies included critical micelle concentration (CMC), maximum surface excess (Γ_max), minimum surface area (A_min). Free energy of micellization (ΔG°_mic) and adsorption (ΔG°_ads) were calculated.

Kurzfassung

Neue Sulfonamidtetra chlorometallat-Komplexe, die Carboanhydrase (CA) deutlich hemmen können, wurden in einer Reaktion des 4-Amino-N-2-quinoxalinylbenzensulfonamidhydrochlorids (= Sulfaquinoxalinhydrochlorid) mit verschiedenen Metallchloriden (CoCl₂, CuCl₂ oder SnCl₂) synthetisiert. Die synthetisierten Metall-Komplexe der Sulfonamidderivate enthalten divalente Kationen und wurden mit Standardverfahren charakterisiert. Die Metallkomplexe könnten lokal gegen Glaukom wirken, was sie als pharmakologische Agenzien noch effektiver macht. Die synthetisierten Komplexe sind signifikant zytotoxisch aktiv gegen die humane kolorektale Karzinom-Zelllinie HCT-116. Die Oberflächeneigenschaften dieser Tenside wurden untersucht. Hierzu gehören die kritische Mizellbildungskonzentration (CMC), der maximale Oberflächenüberschuss (Γ_max) und der minimale Platzbedarf an der Oberfläche (A_min). Die freien Energien der Mizellenbildung (ΔG°_mic) und der Adsorption (ΔG°_ads) wurden auch berechnet.

Key words: critical micelle concentration; sulfaquinoxaline tetrachlorometallate complex; carbonic anhydrase; in-vitro antitumor activity

Stichwörter: Kritische Mizellbildungskonzentration; Sulfonamid tetrachlorometallat-Komplex; Carboanhydrase; in-vitro-Antitumoraktivität

* Correspondence address Prof. Manal Mohmed Khowdiary, Elzomer St., Egyptian Petroleum Institute, Naser City, Cairo, Egypt, Tel.: 00966504348073, E-mail: khaled.reda.2020@hotmail.com

M. M. Kowdiary: She received his Ph.D. for the thesis “Synthesis and evaluation of some quaternary ammonium surfactants” from Ain Shams University in the year 2000. Now she is a Assoc. professor of Applied Organic Phiscal chemistry, petrochemicals Department, Egyptian Petroleum Research Institute. she is interested in several fields of surfactant applications, including:, emulsification, solubilization, corrosion inhibition of metals. He is also interested in the biological activity of surfactants and their metal complexes towards bacteria, fungi and tumors. Her activities now are concerned on studying the interaction of different types of surfactants with protein and macromolecules in short and long term measurements using new measurements methodology.

Dr. Nashwa Mostafa Saleh: Lecturer of Organic Chemistry, Faculty of Science, Al-Azhar University (Girl's branch). Her research interests are in the areas of both Environmental Chemistry and Medicinal Chemistry with special emphasis on antitumor agents. Her current research involves investigations on metal based drugs. Additional interests include the development of biocides and investigation of Nanotechnology for destruction of tumors.

Dr. Abdel Fattah M. Badawi is Professor of Applied Organic Chemistry in the Egyptian Petroleum Research Institute (Applied Surfactant Laboratory). He participated in the research of Applied Surfactant, Metallosurfactant Chemistry and Nanotechnology. Her research interests are in the areas of both Environmental Chemistry and Medicinal Chemistry with special emphasis on antitumor agents. His current research involves investigations on metal based drugs. Additional interests include the development of biocides and investigation of Nanotechnology for destruction of tumors.

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Received: 2013-09-05

Revised: 2014-01-30

Published Online: 2014-07-22

Published in Print: 2014-07-15

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https://doi.org/10.3139/113.110313

Schlagwörter für diesen Artikel

critical micelle concentration; sulfaquinoxaline tetrachlorometallate complex; carbonic anhydrase; in-vitro antitumor activity