Identification of 1-chloro-2-formyl indenes and tetralenes as novel antistaphylococcal agents exhibiting sortase a inhibition

Applied Microbiology and Biotechnology

Volumn 98, Issue 5, 2014, Pages 2041-2051

  Kahlon, Amandeep Kaur ^a   Negi, Arvind S ^a   Kumari, Ruma ^b   Srivastava, Kishore K ^b   Kumar, Shiv ^a   Darokar, Mahendra P ^a   Sharma, Ashok ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Anti infectives; Antibacterials; Indenes; Sortase A; Staphylococcus aureus; Tetralenes

Indexed keywords

ANTI-INFECTIVES; ANTIBACTERIALS; INDENES; SORTASE A; STAPHYLOCOCCUS AUREUS; TETRALENES;

ASSAYS; BACTERIA; CELL CULTURE; COLORIMETRIC ANALYSIS; CYTOTOXICITY;

POLYCYCLIC AROMATIC HYDROCARBONS;

1 CHLORO 2 FORMYL INDENE DERIVATIVE; INDENE DERIVATIVE; OXACILLIN; SORTASE; TETRACYCLINE; UNCLASSIFIED DRUG; VANCOMYCIN;

BACTERIUM; CHEMICAL BINDING; COLORIMETRY; DRUG RESISTANCE; ENZYME ACTIVITY; EXCRETION; INHIBITOR; MOLECULAR ANALYSIS;

AGAR GEL ELECTROPHORESIS; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIAL VIRULENCE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG SCREENING; ENZYME INHIBITION; HUMAN; HUMAN CELL; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MYCOBACTERIUM TUBERCULOSIS; STAPHYLOCOCCUS AUREUS;

AMINOACYLTRANSFERASES; ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CELL LINE; CELL SURVIVAL; COMPUTATIONAL BIOLOGY; CYSTEINE ENDOPEPTIDASES; DNA, BACTERIAL; ENZYME INHIBITORS; HUMANS; INDENES; MICROBIAL SENSITIVITY TESTS; MOLECULAR DOCKING SIMULATION; MOLECULAR SEQUENCE DATA; SEQUENCE ANALYSIS, DNA; STAPHYLOCOCCUS AUREUS;

EID: 84896699155     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-5036-1     Document Type: Article

References (27)

1. Bentley ML, Gaweska H, Kielec JM, McCafferty DG (2007) Engineering the substrate specificity of Staphylococcus aureus sortase A, the β6/ β7 loop from SrtB confers NPQTN recognition to SrtA. J Biol Chem 282:6571-6581 (Pubitemid 47100853)
2. Bentley ML, Lamb EC, McCafferty DG (2008) Mutagenesis studies of substrate recognition and catalysis in the sortase A transpeptidase from Staphylococcus aureus . J Biol Chem 283:14762-14771
3. Chanda D, Saikia D, Kumar JK, Thakur JP, Agarwal J, Chanotiya CS, Shanker K, Negi AS (2011) 1-Chloro-2-formyl indenes and tetralenes as antitubercular agents. Bioorg Medicinal Chem Lett 21:3966-3969
4. Elgalai I, Foster HA (2003) Comparison of adhesion of wound isolates of Staphylococcus aureus to immobilized proteins. J Appl Microbiol 94:413-420 (Pubitemid 36315033)
5. Frankel BA, Bently M, Kruger RG, McCafferty DG (2004) Vinylsulfones: inhibitors of SrtA, a transpeptidase required for cell wall protein anchoring and virulence in Staphylococcus aureus. J Am Chem Soc 126:3404-3405 (Pubitemid 38366714)
6. Huang X, Aulabaugh A, Ding W, Kapoor B, Alksne L, Tabei K, Ellestad G (2003) Kinetic mechanism of Staphylococcus aureus sortase SrtA. Biochemistry 42:11307-11315 (Pubitemid 37158898)
7. Joubert A, Van der Kooy F, Meyer JJM, Lall N (2006) HPLC in the comparative study of the content of naphthoquinones (quinonoid constituents) in Euclea species of South Africa. Chromatographia 64:399-403 (Pubitemid 44521400)
8. Kim SW, Chang IM, Oh KB (2002) Inhibition of the bacterial surface protein anchoring transpeptidase sortase by medicinal plants. Biosci Biotechnol Biochem 66:2751-2754
9. Lin WY, Peng CF, Tsai IL, Chen JJ, Cheng MJ, Chen IS (2005) Antitubercular constituents from the roots of Engelhardia roxburghiana. Planta Med 71:171-175
10. Lindsay JA, Holden MTG (2004) Staphylococcus aureus: superbug, super genome? Trends Microbiol 12:378-385 (Pubitemid 38987825)
11. Machida K, Matsuoka E, Kasahara T, Kikuchi M (2005) Studies on the constituents of Juglans species. I. Structural determination of (4S)-and (4R)-4-hydroxy-a-tetralone derivatives from the fruit of Juglans mandshurica M axim. var. sieboldiana Makino. Chem Pharm Bull 53:934-937 (Pubitemid 41327683)
12. Maresso AW, Schneewind O (2008) Sortase as a target of anti-infective therapy. Pharmacol Rev 60:128-141 (Pubitemid 351439219)
13. Maresso AW, Wu R, Kern JW, Zhang R, Dorota J, Missiakas DM, Duban ME, Joachimiak A, Schneewind O (2007) Activation of inhibitors by sortase triggers irreversible modification of the active site. J Biol Chem 282:23129-23139 (Pubitemid 47311911)
14. Mazmanian SK, Liu G, Lenoy ER, Schneewind O (2000) Staphylococcus aureus sortase mutants defective in the display of surface proteins and in the pathogenesis of animal infections. Proc Natl Acad Sci USA 97:5510-5515 (Pubitemid 30313749)
15. Mazmanian SK, Liu G, Ton-That H, Schneewind O (1999) Staphylococcus aureus sortase, an enzyme that anchors surface proteins to the cell wall. Science 285:760-763
16. Park BS, Kim JG, Kim MR, Lee SE, Takeoka GR, Oh KB, Kim JH (2005) Curcuma longa L. constituents inhibit sortase A and Staphylococcus aureus cell adhesion to fibronectin. J Agric Food Chem 53:9005 -9009
17. Perry AM, Ton-That H, Mazmanian SK, Schneewind O (2002) Anchoring of surface proteins to the cell wall of Staphylococcus aureus III. Lipid II is an in vivo peptidoglycan substrate for sortase-catalyzed surface protein anchoring. J Biol Chem 277:16241-16248 (Pubitemid 34967912)
18. Ruhland A, Brendel M (1979) Mutagenesis by cytostatic alkylating agents in yeast strains of differing repair capacities. Genetics 92:83-97
19. Suree N, Yi SW, Thieu W, Marohn M, Damoiseaux R, Chan A, Jung ME, Clubb RT (2009) Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors. Bioorg Med Chem 17:7174-7185
20. Tian BX, Eriksson LA (2011) Catalytic mechanism and roles of Arg197 and Thr183 in the Staphylococcus aureus sortase A enzyme. J Phys Chem B 115:13003-13011
21. Ton-That H, Liu G, Mazmanian SK, Faull KF, Schneewind O (1999) Purification and characterization of sortase, the transpeptidase that cleaves surface proteins of Staphylococcus aureus at the LPXTG motif. Proc Natl Acad Sci USA 96:12424-12429 (Pubitemid 29513518)
22. Upadhyay HC, Dwivedi GR, Darokar MP, Chaturvedi V, Srivastava SK (2012) Bioenhancing and antimycobacterial agents from Ammania multiflora. Planta Med 78:79-81
23. Venkatachalam CM, Jiang X, Oldfield T, Waldman M (2003) LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites. J Mol Graph Model 21:289-307 (Pubitemid 35441326)
24. Woerdenbag HJ, Merfort I, Passreiter CM, Schmidt TJ, Willuhn G, Van Uden WV, Pras N, Kampinga HH, Konings AWT (1994) Cytotoxicity of flavonoids and sesquiterpene lactones from Arnica species against the GLC4 and the COLO 320 cell lines. Planta Med 60:434-437 (Pubitemid 24330771)
25. Wu CC, Peng CF, Tsai IL, Abd El-Razek MH, Huang HS, Chen IS (2007) Secondary metabolites from the roots of Engelhardia roxburghiana and their antitubercular activities. Phytochemistry 68:1338-1343 (Pubitemid 46602455)
26. Zerovosen A, Lu WP, Chen Z, White RE, Demuth TP Jr, Frere JM (2004) Interactions between penicillin-binding proteins (PBPs) and two novel classes of PBP inhibitors, arylalkylidene rhodanines and arylalkylidene iminothiazolidin-4-ones. Antimicrob Agents Chemother 48:961-969 (Pubitemid 38280350)
27. Zong YN, Bice TW, Ton-That H, Schneewind O, Narayana SV (2004) Crystal structures of Staphylococcus aureus sortase A and its substrate complex. J Biol Chem 279:31383-31389 (Pubitemid 39037805)