N, N′-Olefin Functionalized Bis-Imidazolium Gold(I) Salt Is an Efficient Candidate to Control Keratitis-Associated Eye Infection

PLoS ONE

Volumn 8, Issue 3, 2013, Pages

  Samanta, Tapastaru ^a   Roymahapatra, Gourisankar ^a,f   Porto, William F ^c   Seth, Saikat ^d   Ghorai, Sudipta ^d   Saha, Suman ^e   Sengupta, Jayangshu ^e   Franco, Octávio L ^c   Dinda, Joydev ^a   Mandal, Santi M ^b  

^a HALDIA INSTITUTE OF TECHNOLOGY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY   (India)

^c UCB PHARMA   (Belgium)

^d Department of Chemistry   (India)

^e ARAVIND EYE HOSPITAL   (India)

^f Global Institute of Science and Technology   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLINE]GOLD BROMIDE; 3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLINE]GOLD HEXAFLUOROPHOSPHATE; 3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLINE]SILVER BROMIDE; 3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLINE]SILVER HEXAFLUOROPHOSPHATE; 3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLIUM]BROMIDE; 3,3' (4 PHENYLENEDIMETHYLENE)BIS[1 (2 METHYL ALLYL)IMIDAZOLIUM]HEXAFLUOROPHOSPHATE SALT; ALKENE; AMPHOTERICIN B; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; BIS IMIDAZOLIUM GOLD SALT; CARBENOID; CEFTAZIDIME; FLUCONAZOLE; IMIDAZOLE DERIVATIVE; PIPERACILLIN; UNCLASSIFIED DRUG; VANCOMYCIN; VORICONAZOLE; GOLD; IMIDAZOLE;

ANIMAL CELL; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BACTERIAL GROWTH; BACTERIAL KERATITIS; CANDIDA ALBICANS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTALLOGRAPHY; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; EX VIVO STUDY; GOAT; GROWTH INHIBITION; HUMAN; HUMAN CELL; KERATOMYCOSIS; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOUSE; NONHUMAN; PSEUDOMONAS AERUGINOSA; SCANNING ELECTRON MICROSCOPY; STAPHYLOCOCCUS AUREUS; ANIMAL; BIOFILM; CHEMISTRY; CONTACT LENS; EXTENDED WEAR CONTACT LENS; EYE INFECTION; KERATITIS; MICROBIOLOGY; SYNTHESIS; TUMOR CELL LINE;

ALKENES; ANIMALS; ANTI-INFECTIVE AGENTS; BIOFILMS; CELL LINE, TUMOR; CONTACT LENSES; CONTACT LENSES, EXTENDED-WEAR; EYE INFECTIONS; GOLD; HUMANS; IMIDAZOLES; KERATITIS; MICE;

EID: 84875017452     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0058346     Document Type: Article

References (31)

1. Willcox MD, (2011) Review of resistance of ocular isolates of Pseudomonas aeruginosa and Staphylococci from keratitis to ciprofloxacin, gentamicin and cephalosporins. Clin Exp Optom 94: 161-168.
2. Sengupta J, Saha S, Khetan A, Sarkar SK, Mandal SM, (2012) Effects of lactoferricin B against keratitis-associated fungal biofilms. J Infect Chemother 18: 698-703.
3. Mellon MG, Benbrook C, Benbrook KL (2001) Hogging It! Estimates of Antimicrobial Abuse in Livestock (Cambridge, MA: Union of Concerned Scientists). Available: http://www.ucsusa.org/food_and_environment/antibiotics_and_food/hogging-it-estimates-of-antimicrobial-abuse-in-livestock.html. Accessed 2008 Mar 12.
4. Tenover FC, (2006) Mechanisms of Antimicrobial Resistance in Bacteria. Am J Med 119: S3-S10.
5. Roymahapatra G, Mandal SM, Porto WF, Samanta T, Giri S, et al. (2012) Pyrazine functionalized Ag(I) and Au(I)-NHC complexes are potential antibacterial agents. Curr Med Chem19: 4184-4193.
6. Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ, (2009) The medicinal applications of imidazolium carbene-metal complexes. Chem Rev 109: 3859-3884.
7. Hermann WA, (2002) N-Heterocyclic carbene as ligands for metal complexes- challenging phsphene ligands in homogenious catalysts. Angew Chem Int Ed 41: 1290-1309.
8. Knapp AR, Panzner MJ, Medvetz DA, Wright BD, Tessier CA, et al. (2010) Synthesis and antimicronial studies of silver N-heterocyclic carbene complexes bearing a methyl benzoate substituent. Inorganica Chim.Acta 364: 125-131.
9. Huang W, Zhang,R, Zou G, Tang J, Sun J, (2007) An iodide/anion exchange route to benzimidazolylidene silver complexes from benzimidazolium iodide: Crystal structures of N,N′-dibutylbenzimidazolylidene silver chloride, bromide, cyanide and nitrate. J Organomet Chem 692: 3804-3809.
10. Schuster O, Yang L, Raubenheimer HG, Albrecht M, (2009) Beyond conventional N-heterocyclic carbenes: abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization. Chem Rev 109: 3445-3478.
11. Lillo V, Mas-Marzá E, Segarra AM, Carbó JJ, Bo C, et al. (2007) Palladium-NHC complexes do catalyse the diboration of alkenes: mechanistic insights Chem Commun. 32: 3380-3382.
12. Hahn EF, Heidrich B, Hepp A, Pape T, (2007) Coordination compounds of N,N′-olefin functionalized imidazolin-2-ylidenes. J Organomet Chem 692: 4630-4638.
13. Sheldrick GM (1997) SHELX76, Programme for refinement of crystal structures,University of Gottingen, Germany. Available: http://shelx.uni-ac.gwdg.de/SHELX/.
14. Gaussian 03, Revision E.01, (2004) Gaussian, Inc., Wallingford CT.
15. Saha S, Banerjee D, Khetan A, Sengupta J, (2009) Epidemiological profile of fungal keratitis in urban population of West Bengal, India. Oman J Ophthalmol 2: 114-118.
16. Clinical and Laboratory Standards Institute Performance standards for antimicrobial susceptibility testing (2007) Seventeenth informational supplement Document M100-S17. CLSI, Wayne, PA: CLSI.
17. Mitchell BM, Wu TG, Jackson BE, Wilhelmus KR, (2007) Candida albicans strain-dependent virulence and Rim13p-mediated filamentation in experimental keratomycosis. Invest Ophthalmol Vis Sci 48: 774-780.
18. Croes S, Deurenberg RH, Boumans ML, Beisser PS, Neef C, et al. (2009) Staphylococcus aureus biofilm formation at the physiologic glucose concentration depends on the S. aureus lineage. BMC Microbiol 9: 229-237.
19. Sahu K, Bansal H, Mukherjee C, Sharma M, Gupta PK, (2009) Atomic force microscopic study on morphological alterations induced by photodynamic action of Toluidine Blue O in Staphylococcus aureus and Escherichia coli. J Photochem Photobiol B 96: 9-16.
20. Jo S, Lim JB, Klauda JB, Im W, (2009) CHARMM-GUI Membrane Builder for Mixed Bilayers and Its Application to Yeast Membranes. Biophys J 9: 50-58.
21. Murzyn K, Rog T, Pasenkiewicz-Gierula T, (2005) Phosphatidylethanolamine-phosphatidylglycerol bilayer as a model of the inner bacterial membrane. Biophys J 88: 1091-1103.
22. Bikadi Z, Hazai I, Malik D, Jemnitz K, Zsuzsa V, et al. (2011) Predicting p-glycoprotein-mediated drug transport based on support vector machine and three-dimensional crystal structure of p-glycoprotein. Plos One 6(10): e25815.
23. Lu P, Hontecillas R, Horne WT, Carbo A, Viladomiu M, et al. (2012) Computational modeling-based discovery of novel classes of anti-inflammatory drugs that target lanthionine synthetase c-like protein 2. PLoS One 7(4): e34643.
24. Platania CBM, Salomone S, Leggio GM, Drago F, Bucolo C, (2012) Homology modeling of dopamine D2 and D3 receptors: molecular dynamics refinement and docking evaluation. PLoS One 7(9): e44316.
25. Mandal SM, Migliolo L, Das S, Mandal M, Franco OL, et al. (2012) Identification and characterization of a bactericidal and proapoptotic peptide from Cycas revoluta seeds with DNA binding properties. J Cell Biochem 113(1): 184-193.
26. Barnes NA, Brisdon AK, Brown WFR, Cross WI, Crossley IR, et al. (2011) Synthesis of gold(I) fluoroalkyl and fluoroalkenyl-substituted phosphine complexes and factors affecting their cryst7al packing. Dalton Trans 40: 1743-1750.
27. Poole K, (2004) Efflux-mediated multiresistance in Gram-negative bacteria. Clin Microbiol Infect 10: 12-26.
28. Parthasarathi R, Padmanabhan J, Subramanian V, Maiti B, Chattaraj PK, (2003) Chemical reactivity profiles of two selected polychlorinated biphenyls. J Phys Chem A 107: 10346-10352.
29. Arulmozhiraja S, Selvin PC, Fujiti TJ, (2002) Structures, potential energy curves and torsional barrier heights for selected polychlorinated biphenyls: a density functional theory study. J Phys Chem A 106: 1765-1769.
30. Berners-Price SJ, Mirabelli CK, Jhonson RK, McCabe LF, Sung CM, et al. (1986) In Vivo antitumor activity and in vitro cytotoxic properties of bis[1,2-bis(diphenylphosphino)ethane]gold(i) chloride. Cancer Res 46: 5486-5493.
31. Özdemir I, Denizci A, Öztürk HT, Çetinkaya B, (2004) Synthetic and antimicrobial studies on new gold(I) complexes of imidazolidin-2-ylidenes. Appl Organomet Chem 18: 318-322.