Antifungal effect of 4-arylthiosemicarbazides against Candida species. Search for molecular basis of antifungal activity of thiosemicarbazide derivatives
Tóm tắt
The in vitro antifungal potency of six series of 4-arylthiosemicarbazides was evaluated. Two isoquinoline derivatives with an ortho-methoxy or ortho-methyl group at the phenyl ring were the most potent antifungal agents. Molecular modeling studies and docking of all 4-arylthiosemicarbazides into the active sites of sterol 14α-demethylase (CYP51), topoisomerase II (topo II), l-glutamine: d-fructose-6-phosphate amidotransferase (GlcN-6-P), secreted aspartic proteinase (SAP), N-myristoyltransferase (NMT), and UDP-N-acetylmuramoyl-l-alanine:d-glutamate ligase (MurD) indicated the importance of both structural and electronic factors in ligand recognition and thus for the antifungal effectiveness of 4-arylthiosemicarbazides. A possible antifungal target was identified (NMT) and isoquinoline-thiosemicarbazides showed more favorable affinity than the native ligand.
Tài liệu tham khảo
Pfaller MA, Diekma DJ (2007) Epidemiology of invasive candidiasis: persistent public health problem. Clin Microbiol Rev 20:133–163
Negri M, Martins M, Henriques M, Svidzinski TI, Azeredo J, Oliveira R (2010) Examination of potential virulence factors of Candida tropicalis clinical isolates from hospitalized patients. Mycopathologia 169:175–182
Borg-von Zepelin M, Kunz L, Rüchel R, Reichard U, Weig M, Gross U (2007) Epidemiology and antifungal susceptibilities of Candida spp. to six antifungal agents: results from a surveillance study on fungaemia in Germany from July 2004 to August 2005. J Antimicrob Chemother 60:424–428
Mercedes Panizo M, Reviakina V, Dolande M, Selgrad S (2008) Candida spp. in vitro susceptibility profile to four antifungal agents. Resistance surveillance study in Venezuelan strains. Med Mycol 24:1–7
Richardson M, Lass-Flörl C (2008) Changing epidemiology of systemic fungal infections. Clin Microbiol Infect 14:5–24
Pappas PG, Kauffman CA, Andes D, Benjamin DK Jr, Calandra TF, Edwards JE Jr, Filler JF, Kullberg BJ, Ostrosky-Zeichner L, Reboli AC, Rex JH, Walsh TJ, Sobel JD (2009) Clinical practice guidelines for the management of candidiasis: 2009 update by the Infectious Diseases Society of America. Clin Infect Dis 48:503–535
Pfaller MA, Diekema DJ, Jones RN, Sader HS, Fluit AC, Hollis RJ, Messer SA (2001) International surveillance of bloodstream infections due to Candida species: frequency of occurrence and in vitro susceptibilities to fluconazole, ravuconazole, and voriconazole of isolates collected from 1997 through 1999 in the SENTRY antimicrobial surveillance program. J Clin Microbiol 39:3254–3259
Wisplinghoff H, Bischoff T, Tallent SM, Seifert H, Wenzel RP, Edmond MB (2004) Nosocomial bloodstream infections in US hospitals: analysis of 24,179 cases from a prospective nationwide surveillance study. Clin Infect Dis 39:309–317
Méan M, Marchetti O, Calandra T (2008) Bench-to-bedside review: Candida infections in the intensive care unit. Crit Care 12:204–212
Lass-Flörl C (2009) The changing face of epidemiology of invasive fungal disease in Europe. Mycoses 52:197–205
Diekema DJ, Messer SA, Brueggemann AB, Coffman SL, Doern GV, Herwaldt LA, Pfaller MA (2002) Epidemiology of candidemia: 3-year results from the emerging infections and the epidemiology of Iowa organisms study. J Clin Microbiol 40:1298–1302
Kao AS, Brandt ME, Pruitt WR, Conn LA, Perkins BA, Stephens DS, Baughman WS, Reingold AL, Rothrock GA, Pfaller MA, Pinner RW, Hajjeh RA (1999) The epidemiology of candidemia in two United States cities: results of a populationbased active surveillance. Clin Infect Dis 29:1164–1170
Tortorano AM, Kibbler C, Peman J, BernhardtH KL, Grillot R (2006) Candidaemia in Europe: epidemiology and resistance. Int J Antimicrob Agents 27:359–366
Enoch DA, Ludlam HA, Brown NMJ (2006) Invasive fungal infections: a review of epidemiology and management options. J Med Microbiol 55:809–818
Blot S, Vandewoude K (2004) Management of invasive candidiasis in critically ill patients. Drugs 64:2159–2175
Hakki M, Staab JF, Marr KF (2006) Emergence of a Candida krusei isolate with reduced susceptibility to caspofungin during therapy. Antimicrob Agents Ch 50:2522–2524
Moudgal V, Little T, Boikov D, Vazquez JA (2005) Multiechinocandin- and Multiazole-resistant Candida parapsilosis isolates serially obtained during therapy for prosthetic valve endocarditis. Antimicrob Agents Chemother 49:767–769
Arendrup MC, Fuursted K, Gahrn-Hansen B, Jensen IM, Knudsen JD, Lundgren B, Schonheyder HC, Tvede MJ (2005) Seminational surveillance of fungemia in Denmark: notably high rates of fungemia and numbers of isolates with reduced azole susceptibility. J Clin Microbiol 43:4434–4340
Hobson RPJ (2003) The global epidemiology of invasive Candida infections—is the tide turning? J Hosp Infect 55:159–168
Verweij PE, Snelders E, Kema GHJ, Mellado E, Melchers JGM (2009) Azole resistance in Aspergillus fumigatus: a side-effect of environmental fungicide use? Lancet Infect Dis 6:789–795
Groll AH, De Lucca AJ, Walsh TJ (1998) Emerging targets for the development of novel antifungal therapeutics. Trends Microbiol 6:117–124
Sheehan DJ, Hitchcock CA, Sibley CM (1999) Current and emerging azole antifungal agents. Clin Microbiol Rev 12:40–79
Schiaffella F, Macchiarulo A, Milanese L, Vecchiarelli A, Costantino G, Pietrella D, Fringuelli R (2005) Design, synthesis, and microbiological evaluation of new Candida albicans CYP51 inhibitors. J Med Chem 48:7658–7666
Siwek A, Stączek P, Stefańska J (2011) Synthesis and structure-activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides. Eur J Med Chem 46:5717–5726
Siwek A, Wujec M, Dobosz M, Wawrzycka-Gorczyca I (2010) Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides. Heteroatom Chem 21:521–532
Siwek A, Wujec M, Stefańska J, Paneth P (2009) Antimicrobial properties of 4-aryl-(2-methyl-furan-3-yl)-Δ2-1H-1,2,4-triazole-thiones. Phosphorus Sulfur 184:3149–3159
Wawrzycka I, Siwek A, Kosikowska U, Malm A (2011) Synthesis and crystal structure of N-butyl-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,3,4-thiadiazol-2-amine and 5-isoquinolin-3-yl-N-(2-methylphenyl)-1,3,4-thiadiazol-2-amine. Z Kristallogr 226:297–302
Çapan G, Ulusoy N, Ergenç N, Kiraz M (1999) New 6-Phenylimidazo2,1-b]thiazole derivatives: synthesis and antifungal activity. Monatsh Chem 130:1399–1407
Dogan HN, Rollas S, Erdeniz H (1998) Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphthoic acid hydrazide derivatives. Farmaco 53:462–467
Farag AM, Mayhoub AS, Barakat SE, Bayomi AH (2008) Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial. Bioorg Med Chem 16:4569–4578
Siwek A, Stefańska J (2011) Antimicrobial activity and SAR study of some novel thiosemicarbazide derivatives bearing piperidine moiety. Med Chem 7:690–696
Salgın-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, Kılıç E, Işık S, Aktay G, Özalp M (2007) 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 15:5738–5751
Wujec M, Kosikowska U, Paneth P, Malm A (2007) Reaction of hydrazide of (tetrazol-5-yl)acetic acid with isothiocyanates and antimicrobial investigations of newly-obtained compouns. Heterocycles 71:2617–2626
Cunha S, Macedo FC Jr, Costa GAN, Rodrigues MT Jr, Verde RBV, de Souza Neta LC, Vencato I, Lariucci C, Sá FP (2007) Antimicrobial activity and structural study of disubstituted thiourea derivatives. Monatsh Chem 138:511–516
Kadi AA (2011) Synthesis and antimicrobial activity of some new quinazolin-4(3H)-one derivatives. J Saudi Chem Soc 15:95–100
Al-Saadi MS, Faidallah HM, Rostom SAF (2008) Synthesis and biological evaluation of some 2,4,5-trisubstituted thiazole derivatives as potential antimicrobial and anticancer agents. Arch Pharm 341:424–434
Jalilian AR, Sattari S, Bineshmarvasti M, Shafiee A, Daneshtalab M (2000) Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo-4H-1,2,4-triazoles and 1,2,3-thiadiazolo-4H-1,2,4-triazoles. Arch Pharm 333:347–354
Ruge E, Korting HC, Borelli C (2005) Current state of three-dimensional characterisation of antifungal targets and its use for molecular modelling in drug design. Int J Antimicrob Ag 26:427–441
Sheng Ch XuH, Wang W, Cao Y, Dong G, Wang S, Che X, Ji H, Miao Z, Yao J, Zhang W (2010) Design, synthesis and antifungal activity of isosteric analogues of benzoheterocyclic N-myristoyltransferase inhibitors. Eur J Med Chem 45:3531–3540
Balladka KS, Bettadapura GK, Chenna GD, Basavapattana RB, Hanumanthappa M (2010) Synthesis, characterization, in vitro and molecular docking studies of new 2,5-dichloro thienyl substituted thiazole derivatives for antimicrobial properties. Eur J Med Chem 45:3490–3496
Khan SI, Nimrod AC, Mehrpooya M, Nitiss L, Walker LA, Clark AM (2002) Antifungal activity of eupolauridine and its action on DNA topoisomerases. Antimicrob Agents Ch 46:1785–1792
Clinical and Laboratory Standards Institute (2006) Performance standards for antimicrobial disc susceptibility tests; approved standard M2-A9. Clinical and Laboratory Standards Institute, Wayne, PA
Clinical and Laboratory Standards Institute (2006) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard M7-A7. Clinical and Laboratory Standards Institute, Wayne, PA
HyperChem 8.0.3 (2007) HyperCube, Gainsville, FL
Jorgensen WL, Maxwell DS, Tirado-Rives J (1996) Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J Am Chem Soc 118:11225–11236
Jorgensen WL, McDonald NA (1998) Development of an all-atom force field for heterocycles. Properties of liquid pyridine and diazenes. J Mol Struct (THEOCHEM) 424:145–155
Rocha GB, Freire RO, Simas AM, Stewart JJP (2006) Rm1: A reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I. J Comput Chem 27:1101–1111
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian03, Revision D.01. Gaussian, Wallingford, CT
Dennington II R, Keith T, Millam J, Eppinnett K, Hovell WL, Gilliland R (2003) GaussView, Version 3.0. Semichem, Shawnee Mission, KS
Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, Defrees DJ, Pople JA (1982) Self-consistent molecular orbital methods XXIII. A polarization-type basis set for second-row elements. J Chem Phys 77:3654–3665
Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28:213–222
Trott O, Olson AJ (2010) AutoDockVina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem 31:455–461
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The Protein Data Bank. Nucleic Acids Res 28:235–242; http://www.pdb.org
Podust LM, von Kries JP, Nasser Eddine A, Kim Y, Yermalitskaya LV, Kuehne R, Ouellet H, Warrier T, Alteköster M, Lee J-S, Rademann J, Oschkinat H, Kaufmann SHE, Waterman MR (2007) Small-molecule scaffolds for CYP51 inhibitors identified by high-throughput screening and defined by X-ray crystallography. Antimicrob Agents Chemother 51:3915–3923
Classen S, Olland S, Berger JM (2003) Structure of the topoisomerase II ATPase region and its mechanism of inhibition by the chemotherapeutic agent ICRF-187. Proc Natl Acad Sci USA 100:10629–10634
Isupov MN, Obmolova G, Butterworth S, Badet-Denisot MA, Badet B, Polikarpov I, Littlechild JA, Teplyakov A (1996) Substrate binding is required for assembly of the active conformation of the catalytic site in Ntn amidotransferases: evidence from the 1.8 A crystal structure of the glutaminase domain of glucosamine 6-phosphate synthase. Structure 4:801–810
Cutfield SM, Dodson EJ, Anderson BF, Moody PC, Marshall CJ, Sullivan PA, Cutfield JF (1995) The crystal structure of a major secreted aspartic proteinase from Candida albicans in complexes with two inhibitors. Structure 3:1261–1271
Sogabe S, Masubuchi M, Sakata K, Fukami TA, Morikami K, Shiratori Y, Ebiike H, Kawasaki K, Aoki Y, Shimma N, D'Arcy A, Winkler FK, Banner DW, Ohtsuka T (2002) Crystal structures of Candida albicans N-myristoyltransferase with two distinct inhibitors. Chem Biol 9:1119–1128
Bertrand JA, Auger G, Fanchon E, Martin L, Blanot D, van Heijenoort J, Dideberg O (1997) Crystal structure of UDP-N-acetylmuramoyl-l-alanine:d-glutamate ligase from Escherichia coli. EMBO J 16:3416–3425
Ezabadi IR, Camoutsis C, Zoumpoulakis P, Geronikaki A, Soković M, Glamoćilija J, Ćirić A (2008) Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: Synthesis biological evaluation, lipophilicity, and conformational studies. Bioorg Med Chem 16:1150–1161
Kuş C, Ayhan-Kılcıgil G, Özbey S, Kaynak FB, Kaya M, Çoban T, Can-Eke B (2008) Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Bioorg Med Chem 16:4294–4303
Önkol T, Doğruer DS, Uzun L, Adak S, Özkan S, Şahin MFJ (2008) Synthesis and antimicrobial activity of new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Enzyme Inhib Med Chem 23:277–284
Shams HZ, Mohareb RM, Helal MH, Mahmoud AE (2007) Synthesis, structure elucidation, and biological evaluation of some fused and/or pendant thiophene, pyrazole, imidazole, thiazole, triazole, triazine, and coumarin systems based on cyanoacetic 2-(benzoylamino)thioxomethyl. hydrazide. Phosphorus Sulfur 182:237–263
Babu KS, Li XC, Jacob MR, Zhang Q, Khan SI, Ferreira D, Clark AM (2006) Synthesis, antifungal activity, and structure-activity relationships of coruscanone A analogues. J Med Chem 49:7877–7886