Impaired ergosterol biosynthesis mediated fungicidal activity of Co(II) complex with ligand derived from cinnamaldehyde

Chemico-Biological Interactions

Volumn 247, Issue , 2016, Pages 64-74

  Shreaz, Sheikh ^a   Shiekh, Rayees A ^b   Raja, Vaseem ^c   Wani, Waseem A ^d   Behbehani, Jawad M ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

^b TAIBAH UNIVERSITY   (Saudi Arabia)

^c JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

^d UNIVERSITI TEKNOLOGI MALAYSIA   (Malaysia)

Author keywords

Anticandidal activity; Candida; Cinnamaldehyde; Co(II) complex; Ergosterol biosynthesis

Indexed keywords

CINNAMALDEHYDE; COPPER COMPLEX; ERGOSTEROL; FLUCONAZOLE; SCHIFF BASE; ACROLEIN; COBALT; FUNGICIDE; LIGAND;

ANIMAL CELL; ARTICLE; CANDIDA; CONDUCTANCE; CONFOCAL LASER MICROSCOPY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DISK DIFFUSION; DRUG STRUCTURE; FUNGAL STRAIN; FUNGICIDAL ACTIVITY; FUNGUS GROWTH; GROWTH INHIBITION; INFRARED SPECTROSCOPY; LIGAND BINDING; LIPOGENESIS; LIPOPHILICITY; MASS SPECTROMETRY; NONHUMAN; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; TRANSMISSION ELECTRON MICROSCOPY; ANALOGS AND DERIVATIVES; ANIMAL; BIOSYNTHESIS; CELL LINE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY;

ACROLEIN; ANIMALS; CELL LINE; COBALT; ERGOSTEROL; FUNGICIDES, INDUSTRIAL; LIGANDS; MICROSCOPY, ELECTRON, TRANSMISSION; PROTON MAGNETIC RESONANCE SPECTROSCOPY; RATS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED;

EID: 84957589246     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2016.01.015     Document Type: Article

References (57)

1. M.A. Kabir, and Z. Ahmad Candida infections and their prevention ISRN. Pre. Med. 2013 2013 1 13
2. M.A. Kabir, M.A. Hussain, and Z. Ahmad Candida albicans: a model organism for studying fungal pathogens ISRN. Microbiol. 2012 2012 1 15
3. F.C. Odds Candida and Candidosis second ed. 1988 Bailliere Tindall London, UK
4. M.H. Miceli, J.A. Diaz, and S.A. Lee Emerging opportunistic yeast infections Lancet Infec. Dis. 11 2011 142 151
5. M.A. Pfaller, P.G. Pappas, and J.R. Wingard Invasive fungal pathogens: current epidemiological trends Clin. Infect. Dis. 43 2006 S3 S14
6. H.P. Koeffler, and D.W. Golde Amphotericin inhibition of hematopoiesis in vitro Am. J. Hematol. 3 1977 57 62
7. T.C. Meeker, M.S. Siegel, F.M. Shiota, J.J. Crowley, and R.W. McGuffin Toxicity of amphotericin B, miconazole and ketoconazole to human granulocyte progenitor cells in vitro Antimicrob. Agents Chemother. 23 1983 169 171
8. + extrusion activity and ultrastructure of Candida J. Med. Microbiol. 62 2013 232 240
9. X.M. Xie, K. Long, and J.R. Fang Effects of cinnamaldehyde and citral on ergosterol biosynthesis in Aspergillus fumigatus cell membrane Chin. Trad. Herb. Drugs 37 2006 530 532
10. J.M. Quale, D. Landman, M.M. Zaman, S. Burney, and S.S. Sathe In vitro activity of Cinnamomum zeylanicum against azole resistant and sensitive Candida species and a pilot study of cinnamon for oral candidiasis Am. J. Chin. Med. 24 1996 103 109
11. U. Julnar, K. Sawsan, B. Pascale, B.M. Yolla, and N.C. Hania Comparative study on the effect of cinnamon and clove extracts and their main components on different types of ATPases Hum. Exp. Toxicol. 22 2003 335 362
12. M.S.A. Khan, I. Ahmad, and S.S. Cameotra Phenyl aldehyde and propanoids exert multiple sites of action towards cell membrane and cell wall targeting ergosterol in Candida albicans Amb. Express 3 2013 1 16
13. S. Shreaz, B. Rimple, K. Neelofar, S. Muralidhar, F.B. Seemi, M. Nikhat, and L.A. Khan Spice oil cinnamaldehyde exhibits potent anticandidal activity against fluconazole resistant clinical isolates Fitoterapia 82 2011 1012 1020
14. M. Narumol Growth inhibition of Aspergillus niger by cinnamaldehyde and eugenol Walailak J. Sci. Tech. 4 2007 41 51
15. S. Shreaz, B. Rimple, K. Neelofar, I.K. Maurya, S.I. Ahmad, S. Muralidhar, M. Nikhat, and L.A. Khan Cinnamic aldehydes affect hydrolytic enzyme secretion and morphogenesis in oral Candida isolates Microb. Pathog. 52 2012 251 258
16. W.C. Still, and I. Galynker Chemical consequences of conformation in macrocyclic compounds: an effective approach to remote asymmetric induction Tetrahedron 37 1981 3981 3996
17. M. Wang, L.F. Wang, Y.Z. Li, and Q.X. Li Antitumor activity of transition metal complexes with the thiosemicarbazone derived from 3-acetylumbelliferone Transit. Metal. Chem. 26 2001 307 310
18. M.K.S. Abou In vitro antibacterial, antifungal activity of some transition metal complexes of thiosemicarbazone Schiff base (HL) derived from N4-(7'-chloroquinolin-4'-ylamino) thiosemicarbazide J. Enz. Inhib. Med. Chem. 23 2008 493 503
19. E. Labisbal, A. Sousa, A. Castineiras, J.A. García-Vázquez, J. Romero, and D.X. West Spectral and structural studies of metal complexes of tin 3-hexamethyleneiminyl thiosemicarbazone prepared electrochemically Polyhedron 19 2000 1255 1262
20. 2O phen=1,10- phenanthroline Inorg. Chim. Acta 293 1999 160 166
21. S.N. Madhavan, A. Dasan, and S.J. Raphael Synthesis, characterization, antifungal, antibacterial and DNA cleavage studies of some heterocyclic Schiff base metal complexes J. Saud. Chem. Soc. 16 2012 83 88
22. B. Sabrina, L. Anne, D. Safia, B.B. Ouassini, A.K. Mustayeen, and B. Gillies Synthesis, characterisation and antifungal activity of a series of Cobalt (II) and Nickel (II) complexes with ligands derived from reduced N, N′-o-Phenylenebis(Salicylideneimine) Transit. Metal. Chem. 33 2008 511 516
23. S. Shreaz, R.A. Sheikh, B. Rimple, A.A. Hashmi, M. Nikhat, and L.A. Khan Anticandidal activity of cinnamaldehyde, its ligand and Ni(II) complex: effect of increase in ring and side chain Microb. Pathog. 49 2010 75 82
24. A.D. Khalaji, and M. Weil Crystal structure of N, N′- Bis (trans-cinnamaldehyde) ethylene- diimine Anal. Sci. 23 2007 187 188
25. N.C.C.L.S Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard M27-a2 vol. 30 2002 National Committee on Clinical Laboratory Standards Wayne, PA
26. S. Shreaz, B. Rimple, K. Neelofar, M. Sumathi, F.B. Seemi, M. Nikhat, and L.A. Khan Exposure of Candida to p-anisaldehyde inhibits its growth and ergosterol biosynthesis J. Gen. Appl. Microbiol. 57 2011 129 136
27. O.N. Breivik, and J.L. Owades Spectrophotometric semi-micro determination of ergosterol in yeast J. Agr. Food Chem. 5 1957 360 363
28. R. Vaseem, S. Shreaz, and W.A. Siddiqui Curcuma longa rhizome extract as a promising source of anticandidal agents Adv. Sci. Lett. 20 2014 1644 1649
29. C. Pina-Vaz, F. Sansonetty, A.G. Rodrigues, S. Costa-Oliveira, C. Tavares, and J. Martinez-de-Oliveira Cytometric approach for a rapid evaluation of susceptibility of Candida strains to antifungals Clin. Microbiol. Infect. 7 2001 609 618
30. D. Mares Electron microscopy of Microsporum cookie after in vitro treatment with protoanemonin: a combined SEM and TEM study Mycopathologia 108 1989 37 46
31. S. Kaneshima, S. Koga, and K. Tanaka A simple method for cellular identification of free cells by light microscopy and scanning electron microscopy J. Electron. Microsc. 26 1977 355 358
32. M. Borgers, M.A. Van de Ven, and J. Van Cutsem Structural degeneration of Aspergillus fumigatus after exposure to saperconazole J. Med. Vet. Mycol. 27 1989 381 389
33. M.K. Gupta, T.V. Neelakantan, M. Sanghamitra, R.K. Tyagi, A. Dinda, S. Mualik, C.K. Mukhopadhyay, and S.K. Goswami An assessment of the role of reactive oxygen species and redox signaling in norepinephrine-induced apoptosis and hypertrophy of H9c2 cardiac myoblasts Antioxid. Redox. Signal 8 2006 1081 1093
34. W.J. Geary Use of conductivity measurements in organic solvents for the characterization of coordination compounds Coord. Chem. Rev. 7 1971 81 122
35. S. Chandra, L.K. Gupta, and D. Jain Spectroscopic studies on Mn(II), Co(II), Ni(II) and Cu(II) complexes with N-donor tetra-dentate (N4) macrocyclic ligand derived from Ethyl-cinnamate moiety Spectrochim. Acta 60 2004 2411 2417
36. R.A. Shiekh, I.A. Rahman, M.A. Malik, N. Luddin, S.M. Masudi, and S.A. Al-Thabaiti Transition metal complexes with mixed Nitrogen-Sulphur (N-S) donor macrocyclic Schiff base ligand: synthesis, spectral, electrochemical and antimicrobial Studies Int. J. Electrochem. Sci. 8 2013 6972 6987
37. K. Nakamoto Infrared Spectra of Inorganic and Coordination Compounds 1970 Wiley Interscience New York
38. M. Shakir, S.P. Varkey, and P.S. Hameed Divalent, cobalt, nickel, copper and zinc complexes of tetra-azamacrocycles bearing polyamide groups: synthesis and characterization Polyhedron 12 1993 2775 2780
39. A. Chaudhary, and R.V. Singh Synthetic, spectroscopic and toxicological aspects of novel eighteen to twenty two membered tetra-aza macro cycles and their bivalent manganese complexes Indian J. Chem. 43 2004 2529 2535
40. W. Kemp Organic Spectroscopy 1975 Macmillan Press Ltd
41. R.A. Sheikh, S. Shreaz, G.S. Sharma, L.A. Khan, and A.A. Hashmi Synthesis, characterization and antimicrobial screening of a novel organylborate ligand, potassium hydro (phthalyl) (salicylyl) borate and its Co(II), Ni(II), and Cu(II) complexes J. Saudi. Chem. Soc. 16 4 2012 353 361
42. M. Yamashita, and J.D. Fenn Negative ion production with the electro spray ion source J. Phys. Chem. 88 1984 4451 4459
43. R.A. Shiekh, I.A. Rahman, M.A. Malik, S.M. Masudi, and N. Luddin Synthesis, spectral, electrochemical and biological studies of Nitrogen donor macrocyclic ligand and its transition metal complexes Int. J. Electrochem. Sci. 7 2012 12829 12845
44. A.B.P. Lever second ed. Inorganic Electronic Spectroscopy vol. 2 1984 Elsevier Amsterdam 507 520
45. B.N. Figgis, and J. Lewis Progress in Inorganic Chemistry 1964 Wiley Interscience New York
46. S. Chandra, and L.K. Gupta Modern spectroscopic techniques in the characterization of Schiff base macrocyclic ligand and its complexes with transition metals Spectrochim. Acta. A. 62 2005 307 312
47. W.A. Zoubi Biological activities of Schiff bases and their complexes: a review of recent works Int. J.Org. Chem. 3 2013 73 95
48. I. Ali, W.A. Wani, and K. Saleem Empirical formulae to molecular structures of metal complexes by molar conductance Synth. React. Inorg. Metal Org. Nano Met. Chem. 43 2013 1162 1170
49. B.F. Dupont, F. Dromer, and L. Improvisi The problem of azole resistance in Candida J. Mycol. Med. 6 1996 12 18
50. D. Sanglard, F. Ische, T. Parkinson, D. Falconer, and J. Bille Candida albicans mutations in the ergosterol biosynthetic pathway and resistance to several antifungal agents Antimicrob. Agents Chemother. 47 2003 2404 2412
51. C.A. Kauffman, and P.L. Carver Antifungal agents in the 1990s current status and future developments Drugs 53 1997 539 549
52. B.E. Cohen Amphotericin B toxicity and lethality: a tale of two channels Int. J. Pharm. 162 1998 95 106
53. H.B. Singh, M. Srivastava, A.B. Singh, and A.K. Srivastava Cinnamon bark oil, a potent fungi toxicant against fungi causing respiratory tract mycoses Eur. J. Allergy Clin. Immunol. 50 1995 995 999
54. A.O. Gill, and R.A. Holley Mechanisms of bactericidal action of cinnamaldehyde against Listeria monocytogenes and of eugenol against L. monocytogenes and Lactobacillus sakei Appl. Environ. Microb. 70 2004 5750 5755
55. K.H. Bang, D.W. Lee, H.M. Park, and Y.H. Rhee Inhibition of fungal cell wall synthesizing enzymes by trans- cinnamaldehyde Biosci. Biotechnol. Biochem. 64 2000 1061 1063
56. Y.W. Sheng, P.F. Chen, and S.T. Chang Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi Bioresour. Technol. 96 2005 813 818
57. Z.H. Chohan, H. Pervez, A. Rauf, K.M. Khan, and C.T. Supuran Isatins-Derived antibacterial and antifungal compounds and their Transition Metal Complexes J. Enz. Inhib. Med. Chem. 19 2004 417 423