Pathogenic Gram-positive bacteria are highly sensitive to triphenylphosphanegold(O-alkylthiocarbamates), Ph3PAu[SC(OR)=N(p- tolyl)] (R = Me, et and iPr)

Gold Bulletin

Volumn 46, Issue 3, 2013, Pages 145-152

  Yeo, Chien Ing ^a   Sim, Jiun Horng ^b   Khoo, Chai Hoon ^b   Goh, Zheng Jie ^b   Ang, Kok Pian ^b   Cheah, Yoke Kqueen ^b   Fairuz, Zainal Abidin ^a   Halim, Siti Nadiah Binti Abdul ^a   Ng, Seik Weng ^a,c   Seng, Hoi Ling ^a   Tiekink, Edward R T ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Antimicrobial activity; Gold(I) compounds; Gram positive bacteria; Metal based drugs; Phosphanegold thiolates; Thiocarbamides

Indexed keywords

ANTI-MICROBIAL ACTIVITY; GRAM-POSITIVE BACTERIUM; METAL-BASED DRUGS; THIOCARBAMIDES; THIOLATES;

GOLD;

BACILLI;

EID: 84885166552     PISSN: 00171557     EISSN: 21907579     Source Type: Journal    
DOI: 10.1007/s13404-013-0091-z     Document Type: Article

References (53)

1. Hemaiswarya S, Kruthiventi AK, Doble M (2008) Synergism between natural products and antibiotics against infectious diseases. Phytomedicine 15:639-652. doi: 10.1016/j.phymed.2008.06.008
2. Editor (2013) Editorial: the antibiotic alarm. Nature. doi: 10.1038/495141a
3. Jones RN, Pfaller MA (1998) Bacterial resistance: a worldwide problem. Diagn Microbiol Infect Dis 31:379-388. doi: 10.1016/S0732-8893(98)00037-6
4. Pfaller MA, Jones RN, Doern GV, Sader HS, Kugler KC, Beach ML (1999) Survey of blood stream infections attributable to Gram-positive cocci: frequency of occurrence and antimicrobial susceptibility of isolates collected in 1997 in the United States, Canada, and Latin America from the SENTRY Antimicrobial Surveillance Program. SENTRY Participants Group. Diagn Microbiol Infect Dis 33:283-297. doi: 10.1016/S0732-8893(98)00149-7
5. Otto M (2010) Staphylococcus colonization of the skin and antimicrobial peptides. Expert Rev Dermatol 5:183-195. doi: 10.1586/edm.10.6
6. Jones RN (2003) Global epidemiology of antimicrobial resistance among community-acquired and nosocomial pathogens: a five-year summary from the SENTRY Antimicrobial Surveillance Program (1997-2001). Semin Respir Crit Care Med 24:121-134. doi: 10.1055/s-2003-37923
7. Eisler E (2003) Chrysotherapy: a synoptic review. Inflamm Res 52:487-501. doi: 10.1007/s00011-002-1208-2
8. Kean WF, Kean IRL (2008) Clinical pharmacology of gold. Inflammopharmacology 16:112-125. doi: 10.1007/s10787-007-0021-x
9. Pacheco EA, Tiekink ERT, Whitehouse MW (2009) Gold compounds and their applications in medicine. In: Mohr F (ed) Gold chemistry. Applications and future directions in the life sciences. Wiley, Germany, pp 283-319
10. Berners-Price SJ (2011) Gold-based therapeutic agents: a new perspective. In: Alessio E (ed) Bioinorganic medicinal chemistry. Wiley, Weinheim, pp 197-222
11. Bhabak K, Bhuyan BJ, Mugesh G (2011) Bioinorganic and medicinal chemistry: aspects of gold(I)-protein complexes. Dalton Trans 40:2099-2111. doi: 10.1039/C0DT01057J
12. Trávníček Z, Štarha P, Vančo J, Šilha T, Hošek J, Suchý P Jr, Prazanova G (2012) Anti-inflammatory active gold(I) complexes involving 6-substituted-purine derivatives. J Med Chem 55:4568-4579. doi: 10.1021/jm201416p
13. Pacheco EA, Tiekink ERT, Whitehouse MW (2009) Biomedical applications of gold and gold compounds. In: Corti C, Holliday R (eds) Gold: science and applications. CRC Press, Boca Raton, pp 217-230
14. Berners-Price SJ, Filipovska A (2011) Gold compounds as therapeutic agents for human diseases. Metallomics 3:863-873. doi: 10.1039/c1mt00062d
15. Ott I (2009) On the medicinal chemistry of gold complexes as anticancer drugs. Coord Chem Rev 253:1670-1681. doi: 10.1016/j.ccr.2009.02.019
16. Fregona D, Ronconi L, Aldinucci D (2009) Groundbreaking gold(III) anticancer agents. Drug Discov Today 14:1075-1076
17. Tiekink ERT (2002) Gold derivatives for the treatment of cancer. Crit Rev Hematol Oncol 42:225-248. doi: 10.1016/S1040-8428(01)00216-5
18. Tiekink ERT (2003) Gold compounds in medicine: potential anti-tumour agents. Gold Bull 36:117-124. doi: 10.1007/BF03215502
19. Fricker SP (1996) Medical uses of gold compounds: past, present and future. Gold Bull 29:53-60. doi: 10.1007/BF03215464
20. Che C-M, Sun RW-Y (2011) Therapeutic applications of gold complexes: lipophilic gold(III) cations and gold(I) complexes for anti-cancer treatment. Chem Commun 47:9554-9560. doi: 10.1039/C1CC10860C
21. Milacic V, Dou QP (2009) The tumor proteasome as a novel target for gold(III) complexes: implications for breast cancer therapy. Coord Chem Rev 253:1649-1660. doi: 10.1016/j.ccr.2009.01.032
22. Bindoli A, Rigobello MP, Scutari G, Gabbiani C, Casini A, Messori L (2009) Thioredoxin reductase: a target for gold compounds acting as potential anticancer drugs. Coord Chem Rev 253:1692-1707. doi: 10.1016/j.ccr.2009.02.026
23. Gabbiani C, Cinellu MA, Maiore L, Massai L, Scaletti F (2012) Chemistry and biology of three representative gold(III) compounds as prospective anticancer agents. Inorg Chim Acta 393:115-124. doi: 10.1016/j.ica.2012.07.016
24. Madeira JM, Gibson DL, Kean WF, Klegeris A (2012) The biological activity of auranofin: implications for novel treatment of diseases. Inflammopharmacology 20:297-306. doi: 10.1007/s10787-012-0149-1
25. Novelli F, Recine M, Sparatore F, Juliano C (1999) Gold(I) complexes as antimicrobial agents. Il Farmaco 54:232-236. doi: 10.1016/S0014-827X(99)00019-1
26. Noguchi R, Hara A, Sugie A, Nomiya K (2006) Synthesis of novel gold(I) complexes derived by AgCl-elimination between [AuCl(PPh3)] and silver(I) heterocyclic carboxylates, and their antimicrobial activities. Molecular structure of [Au(R, S-Hpyrrld)(PPh3)] (H2pyrrld = 2-pyrrolidone-5-carboxylic acid). Inorg Chem Commun 9:355-359. doi: 10.1016/j.inoche.2006.01.001
27. Marques LL, Oliveira GMD, Lang ES, Campos MMAD, Gris LRS (2007) New gold(I) and silver(I) complexes of sulfamethoxazole: synthesis, X-ray structural characterization and microbiological activities of triphenylphosphine(sulfamethoxazolato-N2)gold(I) and (sulfamethoxazolato) silver(I). Inorg Chem Commun 10:1083-1087. doi: 10.1016/j.inoche.2007.06.005
28. Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P (2007) Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc 129:15042-15053. doi: 10.1021/ja075889z
29. 2] in the solid state, and their antimicrobial activities. J Chem Soc Dalton Trans 2000:2091-2097. doi: 10.1039/B001664K
30. Corbi PP, Quintão FA, Ferraresi DKD, Lustri WR, Amaral AC, Massabni AC (2010) Chemical, spectroscopic characterization, and in vitro antibacterial studies of a new gold(I) complex with N-acetyl-l-cysteine. J Coord Chem 63:1390-1397. doi: 10.1080/00958971003782608
31. Barreiro E, Casas JS, Couce MD, Sánchez A, Seoane R, Perez-Estévez A, Sordo J (2012) Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates. Gold Bull 45:23-34. doi: 10.1007/s13404-011-0040- 7
32. 1. Synthesis, characterisation, and biological activity of gold(III)-thiosalicylate and -salicylate complexes. J Organomet Chem 560:233-243. doi: 10.1016/S0022-328X(98)00493-8
33. 2 synthon - solid-state (X-ray crystallography), solution (NMR) and gas-phase (theoretical) structures of O-methyl-N-aryl-thiocarbamides. CrystEngComm 7:682-689. doi: 10.1039/B514254G
34. Hall VJ, Siasios G, Tiekink ERT (1993) Triorganophosphinegold(I) carbonimidothioates. Aust J Chem 46:561-570. doi: 10.1071/CH9930561
35. CrysAlisPro (2010) Agilent Technologies, Yarnton, Oxfordshire, England
36. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A64:112-122. doi: 10.1107/S0108767307043930
37. Farrugia LJ (2012) WinGX and ORTEP for Windows: an update. J Appl Crystallogr 45:849-854. doi: 10.1107/S0021889812029111
38. Gans J, Shalloway D (2001) Qmol: a program for molecular visualization on Windows based PCs. J Mol Graph Model 19:557-559. doi: 10.1016/S1093-3263(01) 00090-0
39. Spek AL (2003) Single-crystal structure validation with the program PLATON. J Appl Crystallogr 36:7-13. doi: 10.1107/S0021889802022112
40. Brandenburg K (2006) DIAMOND. Crystal Impact GbR, Bonn
41. 2-4. CrystEngComm 10:548-564. doi: 10.1039/b717198f
42. Tadbuppa PP, Tiekink ERT (2009) [(Z)-O-Ethyl-N-(p-tolyl)thiocarbamato- κS](triphenylphosphine)-κP]gold(I). Acta Crystallogr E 65:m1587. doi: 10.1107/S1600536809047618
43. 4, Fc). Inorg Chem 45:8165-8174. doi: 10.1021/ic0608243
44. Caracelli I, Zukerman-Schpector J, Tiekink ERT (2013) Supramolecular synthons based on gold.π(arene) interactions. Gold Bull. doi: 10.1007/s13404-013-0088-7
45. iii = 3.515(3) Å, angle at H = 131. Symmetry operations: i, 2-x, +y, -z; ii, 2-x, -+y, -z; and iii, x, 1-y, +z
46. Schneewind O, Missiakas DM (2012) Protein secretion and surface display in Gram positive bacteria. Phil Trans R Soc B 367:1123-1139. doi: 10.1098/rstb.2011.0210
47. Pankey GA, Sabath LD (2004) Clinical relevance of bacteriostatic versus bactericidal mechanisms of action in the treatment of Gram-positive bacterial infections. Clin Infect Dis 38:864-870. doi: 10.1086/381972
48. Levison ME (2004) Pharmacodynamics of antimicrobial drugs. Infect Dis Clin N Am 18:451-465. doi: 10.1016/j.idc.2004.04.012
49. French GL (2006) Bactericidal agents in the treatment of MRSA infections - the potential role of daptomycin. J Antimicrob Chemother 58:1107-1117. doi: 10.1093/jac/dkl393
50. Klastersky J (1986) Concept of empiric therapy with antibiotic combinations. Am J Med 80:2-12
51. Brown AE (1984) Neutropenia, fever, and infection. Am J Med 76:421-428. doi: 10.1016/0002-9343(84)90661-2
52. Pizzo PA, Hathorn JW, Hiemenz J, Browne M, Commers J, Cotton D, Gress J, Longo D, Marshall D, McKnight J, Rubin M, Skelton J, Thaler M, Wesley R (1986) A randomized trial comparing ceftazidime alone with combination antibiotic therapy in cancer patients with fever and neutropenia. N Engl J Med 315:552-558. doi: 10.1056/NEJM198608283150905
53. Arias CA, Contreras GA, Murray BE (2010) Management of multidrug-resistant enterococcal infections. Clin Microbiol Infect 16:555-562. doi: 10.1111/j.1469-0691.2010.03214.x