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Anticandidal cytotoxicity, antitumor activities, and purified cell wall modulation by novel Schiff base ligand and its metal (II) complexes against some pathogenic yeasts

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Abstract

The preparation of metal (II) complexes [CoCl2·6H2O, Ni(CH3COO)2·4H2O, Cu(CH3COO)2·2H2O, and Zn (CH3COO)2 ·2H2O] with 2[N-(cinnamlidene) amino]-5-nitro phenol as a novel ligands and their biological evaluation against candida species was studied. The inhibitory effects of the tested metal complexes were tested against six pathogenic yeasts (Candida albicans, C. fructus, C. glabrata, C. oleophila, C. parapsilosis, and C. tropicalis). The effect of the most efficient metal complex (Zn(II) complex) was more pronounced at 1.25 μg/ml, while Ni(II) complex was exhibited the least suppressive effect. Co(II) and Zn(II) complexes act as potential antitumor agents, while Zn(II) complex has shown promising cytotoxic activity with slow candidal respiration rate. Addition of Zn(II) complex leading to suppression of cell wall components in all candidal cells accompanied with leaking out of amino acids. Purification of the cell wall mannoprotein of C. glabrata treated with Zn(II) complex was established, resulting one pure fissured protein peak. Cell wall protein modulation was showed by appearance of two new protein bands with molecular weights of 72 and 39 KDa in C. glabrata cells treated with Zn(II) complex compared with one pure protein band 55.6 KDa in the non treated yeast cell.

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References

  • Altork W, Al-sarany A, Al-Hosseny M (2002) Bacteria, 1st edn. Dar El-eman, Almadena Almenawra, Saudi Arabia

    Google Scholar 

  • Asia K, Tsuchimori N, Okonogi J, Perfect O, Yoshida Y (1999) Formation of azole-resistant Candida albicans by mutation of sterol 14-demethylase P450. Antimicrob Agents Chemother 43:1163–1169

    Google Scholar 

  • Benallaoua S, Nguyen V, DeMeo M, Coulon J, Dumenil G, Bonaly R (1990) The mode of action of a nonpolyenic antifungal (desertomycin) produced by a strain of Streptomyces spectabilis. Can J Microbiol 36:609–616

    PubMed  CAS  Google Scholar 

  • Bindu P, Kurup M, Satyakeerty T (1998) EPR, cyclic voltammetric and biological activities of copper (II) complexes of salicylaldehyde N(4)-substituted thiosemicarbazone and heterocyclic bases. Polyhedron 18:321–331

    Article  Google Scholar 

  • Casanova M, Lopez-Ribot J, Sentandreu R (1992) Characterization of cell wall proteins from yeast and mycelial cells of Candida albicans by labeling with biotin: comparison with other techniques. Infect Immun 60:4898–4906

    PubMed  CAS  Google Scholar 

  • Chandra S, Sangeetika X (2004) EPR, magnetic and spectral studies of copper (II) and nickel (II) complexes of schiff base macrocyclic ligand derived from thiosemicarbazide and glyoxal. Spectrochim Acta 60:147–153

    Article  CAS  Google Scholar 

  • Chen J, Huang G, Liu Z, Afr T, Asiabi E, Sinn S, Padhye Y (2004) The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells. Toxicol Appl Pharmacol 197:40–48

    Article  PubMed  CAS  Google Scholar 

  • Chohan ZH (2005) Antibacterial and antifungal ferrocene incorporated dithiothione and dithioketone compounds. Appl Organomet Chem 20:112–116

    Article  CAS  Google Scholar 

  • Chohan Z, Praveen M (2001) Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1,1′-disubstituted ferrocene-derived Schiff-base ligands and their Co(II), Cu(II), Ni(II) and Zn(II) complexes. Appl Organomet Chem 15:617–625

    Article  CAS  Google Scholar 

  • Chohan ZH, Supuran CT (2005) Organometallic compounds with biologically active molecules: in vitro antibacterial and antifungal activity of some 1,1′-(dicarbohydrazono) ferrocenes and their cobalt(II), copper(II), nickel(II) and zinc(II) complexes. Appl Organomet Chem 19:1207–1214

    Article  CAS  Google Scholar 

  • Coyle B, Kavanagh K, McCann M, Devereux M, Geraghty M (2003) Mode of anti-fungal activity of 1,10-phenanthroline and its Cu(II), Mn(II) and Ag(I) complexes. BioMetals 16:321–329

    Article  PubMed  CAS  Google Scholar 

  • Del Campo R, Criado J, García E, Hermosa M, Jiménez-Sánchez A, Manzano J, Monte E, Rodríguez-Fernández E, Sanz F (2002) Thiourea derivatives and their nickel (II) and platinum (II) complexes antifungal activity. J Inorg Biochem 89:74–82

    Article  PubMed  CAS  Google Scholar 

  • Dilovic I, Rubcˇic V, Vrdoljak S, Kraljevic M, Kralj I, Piantanidab P, Cindric M (2008) Novel thiosemicarbazone derivatives as potential antitumor agents: Synthesis, physicochemical and structural properties, DNA interactions and antiproliferative activity. Bioorg Med Chem 16:5189–5198

    Article  PubMed  CAS  Google Scholar 

  • Douglas LJ (2003) Candida biofilms and their role in infection. Trends Microbiol 11:30–36

    Article  PubMed  CAS  Google Scholar 

  • Dubois M, Gilles J, Hamilton P, Smith F (1956) Colorimetric method for determination of sugar and related substances. Anal Chem 28:350–356

    Article  CAS  Google Scholar 

  • Elespura RK, White RJ (1983) Biochemical properties of prophage induction assay, a rapid test for antitumor agents that interact with DNA. Cancer Res 43:2819–2830

    Google Scholar 

  • Eshwika A, Coyle B, Devereux M, McCann M, Kavanagh K (2004) Metal complexes of 1,10-phenanthroline-5,6-dione alter the susceptibility of the yeast Candida albicans to Amphotericin B and Miconazole. Biometals 17:415–422

    Article  PubMed  CAS  Google Scholar 

  • Frey GD, Bell ZR, Jeffery JC, Ward MD (2001) Complexes of ruthenium (III) and chromium (III) with a new tetradentate N2O2-donor ligand: crystal structures, redox properties and spectroelectrochemistry. Polyhedron 20:3231–3237

    Article  CAS  Google Scholar 

  • Garcia-Sanchez S, Aubert I, Iraqui G, Janbon J, Ghigo M, Enfert C (2004) Biofilms of Candida albicans: a developmental state associated with specific and stable gene expression patterns. Eukaryot Cell 3:536–545

    Article  PubMed  CAS  Google Scholar 

  • Golcu A, Tumer M, Demirelli H, Wheatley R (2005) Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorg Chem Acta 358:1785–1797

    Article  CAS  Google Scholar 

  • Groot P, de Boer A, Cunningham J, Dekker H, de Jong L, Hellingwerf K, de Koster C, Klis F (2004) Proteomic analysis of Candida albicans cell walls reveals covalently bound carbohydrate-active enzymes and adhesins. Eukaryot Cell 3:955–965

    Article  PubMed  CAS  Google Scholar 

  • Holmes AR, Cannon RD, Shepherd MG (1992) Mechanisms of aggregation accompanying morphogenesis in Candida albicans. Oral Microbiol Immunol 7:32–37

    Article  PubMed  CAS  Google Scholar 

  • Kapteyn J, Hoyer L, Hecht J, Müller W, Andel A, Verkleij A, Makarow M, Ende H, Klis F (2000) The cell wall architecture of Candida albicans wild-type cells and cell wall-defective mutants. Mol Microbiol 35:601–611

    Article  PubMed  CAS  Google Scholar 

  • Khandar AA, Hosseini-Yazdi SA, Zarei SA (2005) Synthesis, characterization and X-ray crystal structures of copper (II) and nickel (II) complexes with potentially hexadentate Schiff base ligands. Inorg Chem Acta 358:3211–3217

    Article  CAS  Google Scholar 

  • Laemmli U (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680–685

    Article  PubMed  CAS  Google Scholar 

  • Lippard SJ, Berg JM (1999) Principles of bioinorganic chemistry. University Science Books, Mill Valley, CA

    Google Scholar 

  • Lo′pez-Sandoval H, Milton E, Lemos L, Garza-Velasco R, Mele′ndez I, Macı′as P, Gracia-Mora I, Barba-Behrens N (2008) Synthesis, structure and biological activities of cobalt(II) and zinc(II) coordination compounds with 2-benzimidazole derivatives. J Inorg Biochem 102:1267–1276

    Article  CAS  Google Scholar 

  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–275

    PubMed  CAS  Google Scholar 

  • Mascharak PK (2002) Structural and functional models of nitrile hydratase. Coord Chem Rev 225:201–214

    Article  CAS  Google Scholar 

  • McCann M, Geraghty M, Devereux M, O’Shea D, Mason J, O’Sullivan L (2000) Insights into the mode of action of the anti-candida activity of 1,10-phenanthroline and its metal chelates. Metal-Based Drugs 7:185–193

    Article  PubMed  CAS  Google Scholar 

  • McClare CW (1971) An accurate and convenient organic phosphorus assay. Anal Biochem 39:527–530

    Article  PubMed  CAS  Google Scholar 

  • Mendoza CG, Villanueva JR (1963) Preparation cell walls of yeast. Can J Microbiol 9:141–142

    Article  Google Scholar 

  • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63

    Article  PubMed  CAS  Google Scholar 

  • Munnecke D, Johnson L, Talbot H, Barik S (1982) Microbial metabolism and enzymology of selected pesticides. In: Chakrabarty AM (ed) Biodegradation and detoxification of environmental pollutants. CRC Press, Boca Raton

    Google Scholar 

  • Newton S, Lau C, Gurcha S, Besra G, Wright C (2002) The evaluation of forty-three plant species for in vitro antimycobacterial activities, isolation of active constituents from Psoralea corylifolia and Sanguinaria canadensis. J Ethnopharmacol 79:57–67

    Article  PubMed  Google Scholar 

  • Ouf SA, Sharaf EF, Sumner DR (1999) Interaction of pine needle soil amendment with microbial antagonists on pathogenicity and some metabolic activities of Rhizoctonia solani. Acta Microbiol Polon 482:173–183

    Google Scholar 

  • Peat S, Whelan A, Edwards T (1961) Polysaccharides of bakers yeast. IV. Mannan. J Chem Soc 1:28–35

    Google Scholar 

  • Powderly WG, Mayer KH, Perfect JR (1999) Diagnosis and treatment of oropharyngeal candidiasis in patients infected with HIV. AIDS Res Hum Retrov 15(1):405–1412

    Google Scholar 

  • Rehman S, Chohan Z, Gulnaz F, Supuran C (2005) In vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes. J Enz Inhib Med Chem 20:333–340

    Article  CAS  Google Scholar 

  • Salie F, Eagles P, Leng H (1996) Preliminary antimicrobial screening of four South African Asteraceae species. J Ethnopharmacol 52:27–33

    Article  PubMed  CAS  Google Scholar 

  • Schmourlo G, Mendonça-Filho R, Alviano C, Costa S (2005) Screening of antifungal agents using ethanol precipitation and bioautography of medicinal and foods plants. J Ethnopharmacol 96:563–568

    Article  PubMed  Google Scholar 

  • Singh N, Singh S, Shrivastav A, Singh S (2001) Spectral, magnetic and biological studies of 1,4-dibenzoyl-3-thiosemicarbazide complexes with some first row transition metal ions. Proc Ind Acad Sci 113:257–273

    Article  CAS  Google Scholar 

  • Sternberg S (1994) The emerging fungal threat. Science 266:1632–1634

    Article  PubMed  CAS  Google Scholar 

  • Thangadurai T, Natarajan K (2002) Antibacterial activity of ruthenium(II) carbonyl complexes containing tetradentate Schiff base. Trans Met Chem 27:485–489

    Article  CAS  Google Scholar 

  • Valentin E, Herrero E, Pastor F, Sentandreu R (1984) Solubilization and analysis of mannoprotein molecules from the cell wall of Saccharomyces cerevkiae. J Gen Microbiol 130:1419–1428

    CAS  Google Scholar 

  • Vigato P, Tamburini S, Fenton D (1990) The activation of small molecules by dinuclear complexes of copper and other metals. Coord Chem Rev 106:25–70

    Article  CAS  Google Scholar 

  • Winder K, Eggum O (1966) Protein analysis: s description of the method used at the department of animal physiology in Copenhagen. Acta Agr Scand 16:11–15

    Google Scholar 

  • Wu J, Zh L, Yuan L (2004) Synthesis and DNA interaction studies of a binuclear ruthenium (II) complex with 2,9-bis(2-imidazo[4, 5-f][1,10]phenanthroline)-1,10-phenanthroline as bridging and intercalating ligand. J Inorg Biochem 98:41–45

    Article  PubMed  CAS  Google Scholar 

  • Xue N, Yang X, Wu R, Chen J, He Q, Yang B, Luc X, Hua Y (2008) Synthesis and biological evaluation of imidazole-2-one derivatives as potential antitumor agents. Bioorg Med Chem 16:2550–2557

    Article  PubMed  CAS  Google Scholar 

  • Yun D, Zhoa Y, Pardo J, Narasimhan M, Damsz B, Lee H, Abab L, D’Urzo M, Hasegawa P, Bressan RA (1997) Stress proteins on the yeast cell surface determine resistance to osmotin, a plant antifungal protein. Proc Natl Acad Sci USA 94:7082–7087

    Article  PubMed  CAS  Google Scholar 

  • Zanello P, Tamburini S, Vigato P, Mazzochin G (1987) Syntheses, structure and electrochemical characterization of homo- and heterodinuclear copper complexes with compartmental ligands. Coord Chem Rev 77:165–273

    Article  CAS  Google Scholar 

  • Zhang J, Liu L, Gong Y, Zheng X, Yang M, Cui J, Shen S (2008) Synthesis, characterization and antitumor activity of new type binuclear platinum(II) complexes. Eur J Med Chem 5:2322–2327

    Google Scholar 

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Acknowledgment

The author thanks Dr. Amel F. El-Husseiny in the Department of Chemistry, Faculty of Science, Alexandria University, Egypt for chemical analyses and helpful discussions.

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  1. Department of Botany, Faculty of Science, Cairo University, Giza, 12613, Egypt

    Neveen S. Geweely

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Correspondence to Neveen S. Geweely.

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Communicated by Erko Stackebrandt.

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Geweely, N.S. Anticandidal cytotoxicity, antitumor activities, and purified cell wall modulation by novel Schiff base ligand and its metal (II) complexes against some pathogenic yeasts. Arch Microbiol 191, 687–695 (2009). https://doi.org/10.1007/s00203-009-0497-4

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