Inhibition of Streptococcus pneumoniae adenylate kinase by some 5-arylidene-thiazolidin-4-on-2-thione derivates

Open access

Abstract

Adenylat kinase is an ubiquitous enzyme found in prokaryotes and eukaryotes. In the present study we examined the inhibition of Streptococcus pneumoniae adenylate kinase (AKSP) by six 5-arylidene-thiazolidin-4- on-2-thione derivates using 2, 4-dinitrophenylhydrazine colorimetric assay. Inhibition of AKSP activity with synthetic compounds was performed against recombinant enzyme over-expressed in E. coli. The compound C10H6BrNOS2 with the bromine atom in -ortho position has shown the most efficient inhibitory activity; I50 value (the inhibitor concentration that leads to 50% activity inhibition) was 0.067mM.

1. Oakhill JS, Scott JW, Kemp BE. AMPK functions as an adenylate charge-regulated protein kinase. Trends Endocrinol Metab. 2012; 23(3):125-32

2. Daily MD, Phillips GN Jr, Cui Q. Interconversion of functional motions between mesophilic and thermophilic adenylate kinases. PLoS Comput Biol. 2011; 7(7):e1002103. Epub 2011 Jul 14

3. Lehmann-Munier H, Chenal-Francisque V, Ionescu M, Christova P, Foulon J, Carniel E, et al. Relationship between bacterial virulence and nucleotide metabolism: a mutation in the adenylate kinase gene renders Yersinia pestis avirulent. Biochem J. 2003; 373(2): 515-22

4. Saint-Girons I, Gilles AM, Margarita D, Michelson S, Monnot M, Fermandjian S, et al. Structural and catalytic 98 characteristics of Escherichia coli adenylate kinase. J. Biol. Chem. 1987; 262(2): 622-9

5. Tuck KL, Saldanha SA, Birch LM, Smith AG, Abell C. The design and synthesis of inhibitors of pantothenate synthetase. Org Biomol Chem. 2006; 4(19):3598-610

6. Buchko GW, Robinson H, Abendroth J, Staker BL, Myler PJ. Structural characterization of Burkholderia pseudomallei adenylate kinase (Adk): profound asymmetry in the crystal structure of the 'open' state. Biochem Biophys Res Commun. 2010; 394(4):1012-7

7. Altschul SF, Madden TL, Schaffer AA, Zhang J, Zhang Z, Miller W, et al. Gapped BLAST and PSIBLAST: a new generation of protein database search programs. Nucleic Acids Res. 1997; 25(17): 3389-402

8. Thompson JD, Higgins DG, Gibson TJ. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, positionspecific gap penalties and weight matrix choice. Nucleic Acids Res. 1994; 22: 4673-80

9. Crowe J, Dobeli H, Gentz R, Hochuli E, Stuber D, Henco K. 6xHis-Ni-NTA chromatography as a superior technique in recombinant protein expression/purification. Methods Mol. Biol. 1994; 31:371-87

10. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976; 72: 248-54

11. Laemmli UK Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970; 227(5259): 680-685

12. Oniga O, Moldovan C, Muntean A, Verite P, Ionescu M, Tiperciuc B. Synthesis and antibacterial activity of some 5-aryliden-2-thioxo-thiazolydin-4-one. Revista de Medicina si Farmacie 2004; 50, Supl.II: 183-186

13. Ionescu M, Radulescu AZ, Moldovan C, Banciu HL, Ghiran D. Inhibition of E.coli adenylate kinase by some 5- aryliden-2-thioxo-thiazolydin-4-one derivatives. Clujul Medical 2005; 3:638-41.

14. Grochowski LL, Censky K, Xu H, White RH. A new class of adenylate kinase in methanogens is related to uridylate kinase. Arch Microbiol. 2012;194(2):141-5. Epub 2011 Oct 15.

15. Bae E, Phillips GN Jr. Structures and analysis of highly homologous psychrophilic, mesophilic, and thermophilic adenylate kinases. J.Biol Chem. 2004; 279(27):28202-8

16. Vicini P, Geronikaki A, Anastasia K, Incerti M, Zani F. Synthesis and antimicrobial activity of novel 2- thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg Med Chem. 2006;14(11):3859-64

17. Segall-Shapiro TH, Nguyen PQ, Dos Santos ED, Subedi S, Judd J, Suh J, et al. Mesophilic and hyperthermophilic adenylate kinases differ in their tolerance to random fragmentation. J Mol Biol. 2011; 406(1):135-48.

18. Gilles AM, Glaser P, Perrier V, Meier A, Longin R, Sebald M, et al. Zinc, a structural component of adenylate kinases from gram-positive bacteria. J Bacteriol. 1994; 176(2):520-3.

19. Gresh N. Development, validation, and applications of anisotropic polarizable molecular mechanics to study ligand and drug-receptor interactions. Curr Pharm Des. 2006; 12(17):2121-58.

20. Kistler KA, Matsika S. The fluorescence mechanism of 5-methyl-2-pyrimidinone: an ab initio study of a fluorescent pyrimidine analog. Photochem Photobiol. 2007; 83(3):611-24.

21. Seclaman E, Bora A, Avram S, Simon Z, Kurunczi L. MTD-PLS and docking study for a series of substituted 2-phenylindole derivatives with oestrogenic activity. Chemical Papers. 2011; 65 (4): 566-576.

22. Miura K, Inouye S, Sakai K, Takaoka H, Kishi F, Tabuchi M, et al. Cloning and characterization of adenylate kinase from Chlamydia pneumoniae. J Biol Chem. 2001; 276(16):13490-8.

23. Oakhill JS, Steel R, Chen ZP, Scott JW, Ling N, Tam S, et al. AMPK is a direct adenylate charge-regulated protein kinase. Science. 2011; 332(6036):1433-5.

Revista Romana de Medicina de Laborator

Romanian Journal of Laboratory Medicine

Journal Information


IMPACT FACTOR 2018: 0,800
5-year IMPACT FACTOR: 0,655



CiteScore 2017: 0.31

SCImago Journal Rank (SJR) 2018: 0.194
Source Normalized Impact per Paper (SNIP) 2018: 0.306

Cited By

Metrics

All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 160 132 10
PDF Downloads 68 61 6