Antifungal activity of α-methyl trans cinnamaldehyde, its ligand and metal complexes: Promising growth and ergosterol inhibitors

BioMetals

Volumn 24, Issue 5, 2011, Pages 923-933

  Shreaz, Sheikh ^a   Sheikh, Rayees A ^a   Bhatia, Rimple ^a   Neelofar, Khan ^a   Imran, Sheikh ^a   Hashmi, Athar A ^a   Manzoor, Nikhat ^a   Basir, Seemi F ^a   Khan, Luqman A ^a  

^a JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

Author keywords

methyl trans cinnamaldehyde; Candida; Ergosterol; Metal complexes; PM ATPase

Indexed keywords

ALPHA METHYL CINNAMALDEHYDE; CINNAMALDEHYDE DERIVATIVE; COBALT COMPLEX; ERGOSTEROL; HYDROGEN; LIGAND; NICKEL COMPLEX; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA KRUSEI; CANDIDA TROPICALIS; CLINICAL EFFECTIVENESS; CONTROLLED STUDY; CYTOTOXICITY TEST; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; FUNGUS GROWTH; INFRARED SPECTROMETRY; INFRARED SPECTROSCOPY; LIQUID CULTURE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SENSITIVITY ANALYSIS;

ACROLEIN; ANIMALS; ANTIFUNGAL AGENTS; CANDIDA; CELL SURVIVAL; COBALT; DOSE-RESPONSE RELATIONSHIP, DRUG; ERGOSTEROL; LIGANDS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYOBLASTS, CARDIAC; NICKEL; ORGANOMETALLIC COMPOUNDS; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

CANDIDA; CANDIDA ALBICANS; CANDIDA TROPICALIS; RATTUS;

EID: 80052408032     PISSN: 09660844     EISSN: 15728773     Source Type: Journal    
DOI: 10.1007/s10534-011-9447-0     Document Type: Article

References (27)

1. A Ahmad A Khan N Manzoor LA Khan 2010 Evolution of ergosterol biosynthesis inhibitors as fungicidal against Candida Microb Pathog 48 35 41 19835945 10.1016/j.micpath.2009.10.001 1:CAS:528:DC%2BD1MXhs1Wjt7rF
2. SBA Arthington H Jradi T Desai CJ Morrison 1999 Quantification of ergosterol content: novel method for determination of fluconazole susceptibility of Candida albicans J Clin Microbiol 37 3332 3337 (Pubitemid 29455229)
3. KH Bang DW Lee HM Park YH Rhee 2000 Inhibition of fungal cell wall synthesizing enzymes by trans-cinnamaldehyde Biosci Biotechnol Biochem 64 1061 1063 10879482 10.1271/bbb.64.1061 1:CAS:528:DC%2BD3cXjvFOqt7o%3D
4. AM Ben-Josef EK Manavathu D Platt JD Sobel 2000 Proton translocating ATPase mediated fungicidal activity of a novel complex carbohydrate: CAN-296 Int J Antimicro Agents 13 287 295 10.1016/S0924-8579(99)00140-5 1:CAS:528:DC%2BD3cXhslWlurc%3D (Pubitemid 30072745)
5. A Chaudhary RV Singh 2004 Synthetic, Spectroscopic and toxicological aspects of novel eighteen to twenty two membered tetraaza macrocycles and their bivalent manganese complexes Indian J Chem 43 2529 2535 (Pubitemid 40128730)
6. SS Cheng J Liu E Chang ST Chang 2008 Antifungal activity of cinnamaldehyde and Eugenol congeners against wood-rot fungi Biores Tech 99 5145 5149 10.1016/j.biortech.2007.09.013 1:CAS:528:DC%2BD1cXks1Gjsrc%3D (Pubitemid 351503814)
7. ZH Chohan H Pervez A Rauf KM Khan CT Supuran 2004 Isatins-derived antibacterial and antifungal compounds and their transition metal complexes J Enz Inhib Med Chem 19 417 423 10.1080/14756360410001710383 1:CAS:528: DC%2BD2cXhtFSnsbfK (Pubitemid 40045502)
8. +-ATPase- mediated proton pumping in Cryptococcus neoformans by a novel conjugated Styryl ketone. J Antimicrob Chemother 47 491 494 10.1093/jac/47.4.491 (Pubitemid 32303422)
9. AO Gill RA Holley 2004 Mechanisms of bactericidal action of cinnamaldehyde against Listeria monocytogenes and of eugenol against L. monocytogenes and Lactobacillus sakei Appl Biochem Biotechnol 70 5750 5755 1:CAS:528:DC%2BD2cXosl2itL0%3D (Pubitemid 39471813)
10. AK Gupta E Thomas 2003 New antifungal agents Dermatol Clin 2 565 576 (Pubitemid 37022679)
11. MK Gupta TV Neelakantan M Sanghamitra RK Tyagi A Dinda S Mualik CK Mukhopadhyay SK Goswami 2006 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 1081 1093 16771697 10.1089/ars.2006.8.1081 1:CAS:528:DC%2BD28XlsFOnuro%3D (Pubitemid 44036524)
12. Kemp W (1975) Organic spectroscopy. Macmillan Press Ltd, London
13. AD Khalaji M Weil 2007 Crystal structure of N, N′- Bis (trans-cinnamaldehyde) ethylenediimine Anal Sci 2 187 188
14. A Kohli Smriti K Mukhopadhyay A Rattan R Prasad 2002 In vitro low-level resistance to azoles in Candida albicans is associated with changes in membrane lipid fluidity and asymmetry Antimicrob Agents Chemother 46 1046 1052 11897588 10.1128/AAC.46.4.1046-1052.2002 1:CAS:528:DC%2BD38XisVSjtL4%3D (Pubitemid 34260349)
15. JA Kwon CB Yu HD Park 2003 Bacterial effects and inhibition of cell separation of cinnamic aldehyde on B. cereus Lett Appl Microbiol 37 61 65 12803558 10.1046/j.1472-765X.2003.01350.x 1:CAS:528:DC%2BD3sXlvFCjs7k%3D (Pubitemid 36783082)
16. Nakamoto K (1970) Infrared spectra of inorganic and coordination compounds. Wiley Interscience, New York
17. MH Nguyen JE Peacock AJ Morris Jr DC Tanner ML Nguyen DR Snydman MM Wagener MG Rinaldi VL Yu 1996 The changing face of candidemia: emergence of non-Candida albicans species and antifungal resistance Am J Med 100 617 623 8678081 10.1016/S0002-9343(95)00010-0 1:STN:280:DyaK283ptFWitQ%3D%3D (Pubitemid 26243671)
18. FC Odds AJ Brown NA Gow 2003 Antifungal agents: mechanisms of action Trends Microbiol 11 272 279 12823944 10.1016/S0966-842X(03)00117-3 1:CAS:528:DC%2BD3sXkvVCmsLk%3D (Pubitemid 36725017)
19. LS Ooi Y Li SL Kam H Wang EY Wong VE Ooi 2006 Antimicrobial activities of cinnamon oil and cinnamaldehyde from the Chinese medicinal herb Cinnamomum cassia Blume Am J Chin Med 34 511 522 16710900 10.1142/S0192415X06004041 1:CAS:528:DC%2BD28XksFKnt7o%3D (Pubitemid 43740987)
20. MA Pfaller RN Jones SA Messer MB Edmond RP Wenzel 1998 National surveillance of nosocomial blood stream infection due to species of Candida other than Candida albicans: frequency of occurrence and antifungal susceptibility in the SCOPE Program Diagn Microbiol Infect Dis 30 121 129 9554180 10.1016/S0732-8893(97)00192-2 1:STN:280:DyaK1c3hsVOqug%3D%3D (Pubitemid 28102867)
21. B Rashid N Manzoor M Amin LA Khan 2004 Effect of glucose, its analogs and some amino acids on Pre-steady state kinetics of ATP hydrolysis by PM-ATPase of pathogenic yeast C. albicans Korean J Biol Sci 8 307 312 1:CAS:528: DC%2BD2MXht1ens7Y%3D
22. R Serrano 1980 Effect of ATPase inhibitors on the proton pump of respiratory deficient yeast Eur J Biochem 105 419 424 6247154 10.1111/j.1432-1033.1980.tb04516.x 1:CAS:528:DyaL3cXhvFCiurc%3D
23. S Sheikh RA Sheikh R Bhatia AA Hashmi N Manzoor LA Khan 2010 Anticandidal activity of cinnamaldehyde, its ligand and Ni (II) complex: effect of increase in ring and side chain Microb Pathog 49 75 82 20399846 10.1016/j.micpath.2010. 03.013
24. O Shimokawa H Nakayama 1992 Increased sensitivity of Candida albicans cells accumulating 14 alpha- methylated sterols to active oxygen: possible relevance to in vivo efficacies of azole antifungal agents Antimicrob Agents Chemother 36 1626 1629 1329623 1:CAS:528:DyaK38Xlt1yjurk%3D
25. AM Vimala RS Raymond 1997 Mechanism of cinnamaldehyde sensitization Contact Dermat 3 16 18
26. SE Walsh JY Mailard AD Russell CE Catrenich DL Charbonneau RG Bartolo 2003 Activity and mechanism of selected biocidal agents on Gram-positive and negative bacteria J Appl Microbiol 94 240 247 12534815 10.1046/j.1365-2672.2003. 01825.x 1:CAS:528:DC%2BD3sXhsFOrtbw%3D (Pubitemid 36120948)
27. SY Wang PF Chen ST Chang 2005 Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi Biores Tech 96 813 818 10.1016/j.biortech.2004.07.010 1:CAS:528:DC%2BD2cXhtVOqs7bO (Pubitemid 40017784)