Novel long-chain compounds with both immunomodulatory and MenA inhibitory activities against Staphylococcus aureus and its biofilm

Scientific Reports

Volumn 7, Issue , 2017, Pages

  Choi, Seoung Ryoung ^a   Frandsen, Joel ^a   Narayanasamy, Prabagaran ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CYTOKINE; ENZYME INHIBITOR; FARNOQUINONE; IMMUNOLOGIC FACTOR; TRANSFERASE;

AEROBIC BACTERIUM; ANTAGONISTS AND INHIBITORS; BIOFILM; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; HUMAN; MACROPHAGE; METABOLISM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TEST; MICROBIAL VIABILITY; SECRETION (PROCESS); SYNTHESIS; THP-1 CELL LINE;

ALKYL AND ARYL TRANSFERASES; ANTI-BACTERIAL AGENTS; BACTERIA, AEROBIC; BIOFILMS; CYTOKINES; ENZYME INHIBITORS; HUMANS; IMMUNOLOGIC FACTORS; MACROPHAGES; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; MICROBIAL VIABILITY; THP-1 CELLS; VITAMIN K 2;

EID: 85009064477     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep40077     Document Type: Article

References (37)

1. Dam, H. The antihaemorrhagic vitamin of the chick: occurance and chemical nature. Nature 135 652-653 (1935).
2. MacCorquodale, D. W., Binkley, S. B., Thayer, S. A. & Doisy, E. A. Constitution of vitamin K1. J. Am. Chem. Soc. 61, 1928-1929, doi: 10.1021/ja01876a510 (1939).
3. Meganathan, R. Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm 61, 173-218 (2001).
4. Hiratsuka, T. et al. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science (Washington, DC, US) 321, 1670-1673, doi: 10.1126/science.1160446 (2008).
5. Bentley, R. & Meganathan, R. Biosynthesis of vitamin K (menaquinone) in bacteria. Microbiol. Rev. 46, 241-280 (1982).
6. Choi, S. R. et al. Discovery of bicyclic inhibitors against menaquinone biosynthesis. Future Med Chem 8, 11-16, doi: 10.4155/ fmc.15.168 (2016).
7. Choi, S. R., Larson, M. A., Hinrichs, S. H. & Narayanasamy, P. Development of potential broad spectrum antimicrobials using C-symmetric 9-fluorenone alkyl amine. Bioorganic & medicinal chemistry letters, doi: 10.1016/j.bmcl.2016.02.087 (2016).
8. Li, X. et al. CoA Adducts of 4-Oxo-4-Phenylbut-2-enoates: Inhibitors of MenB from the M. tuberculosis Menaquinone Biosynthesis Pathway. ACS medicinal chemistry letters 2, 818-823, doi: 10.1021/ml200141e (2011).
9. Matarlo, J. S. et al. A Methyl 4-Oxo-4-phenylbut-2-enoate with in Vivo Activity against MRSA that Inhibits MenB in the Bacterial Menaquinone Biosynthesis Pathway. ACS Infect Dis 2, 329-340, doi: 10.1021/acsinfecdis.6b00023 (2016).
10. Lu, X., Zhang, H., Tonge, P. J. & Tan, D. S. Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis. Bioorg. Med. Chem. Lett. 18, 5963-5966, doi: 10.1016/j.bmcl.2008.07.130 (2008).
11. Lu, X. et al. Stable analogues of OSB-AMP: potent inhibitors of MenE, the o-succinylbenzoate-CoA synthetase from bacterial menaquinone biosynthesis. Chembiochem 13, 129-136 (2012).
12. Matarlo, J. S. et al. Mechanism of MenE inhibition by acyl-adenylate analogues and discovery of novel antibacterial agents. Biochemistry 54, 6514-6524, doi: 10.1021/acs.biochem.5b00966 (2015).
13. Fang, M. et al. Succinylphosphonate esters are competitive inhibitors of MenD that show active-site discrimination between homologous alpha-ketoglutarate-decarboxylating enzymes. Biochemistry 49, 2672-2679, doi: 10.1021/bi901432d (2010).
14. Pulaganti, M., Banaganapalli, B., Mulakayala, C., Chitta, S. K. & C., M. A. Molecular modeling and docking studies of O-succinylbenzoate synthase of M. tuberculosis-a potential target for antituberculosis drug design. Appl Biochem Biotechnol 172, 1407-1432, doi: 10.1007/s12010-013-0569-4 (2014).
15. Debnath, J. et al. Discovery of selective menaquinone biosynthesis inhibitors against Mycobacterium tuberculosis. J Med Chem 55, 3739-3755 (2012).
16. Kurosu, M., Narayanasamy, P., Biswas, K., Dhiman, R. & Crick, D. C. Discovery of 1, 4-Dihydroxy-2-naphthoate Prenyltransferase Inhibitors: New Drug Leads for Multidrug-Resistant Gram-Positive Pathogens. J. Med. Chem. 50, 3973-3975, doi: 10.1021/ jm070638m (2007).
17. Kurosu, M. & Crick, D. C. MenA is a promising drug target for developing novel lead molecules to combat Mycobacterium tuberculosis. Med. Chem. 5, 197-207, doi: 10.2174/157340609787582882 (2009).
18. Dhiman, R. K. et al. Menaquinone synthesis is critical for maintaining mycobacterial viability during exponential growth and recovery from nonreplicating persistence. Mol. Microbiol. 72, 85-97, doi: 10.1111/j.1365-2958.2009.06625.x (2009).
19. Matsumoto, K. et al. Cytotoxic benzophenone derivatives from Garcinia species display a strong apoptosis-inducing effect against human leukemia cell lines. Biol. Pharm. Bull. 26, 569-571, doi: 10.1248/bpb.26.569 (2003).
20. Kuete, V. et al. Cytotoxicity and modes of action of four naturally occurring benzophenones: 2, 2', 5, 6'-Tetrahydroxybenzophenone, guttiferone E, isogarcinol and isoxanthochymol. Phytomedicine 20, 528-536, doi: 10.1016/j.phymed.2013.02.003 (2013).
21. Baggett, S., Mazzola, E. P. & Kennelly, E. J. The benzophenones: isolation structural elucidation and biological activities. Stud. Nat. Prod. Chem. 32, 721-771 (2005).
22. Proctor, R. A. et al. Small colony variants: a pathogenic form of bacteria that facilitates persistent and recurrent infections. Nat Rev Microbiol 4, 295-305, doi: 10.1038/nrmicro1384 (2006).
23. Proctor, R. A. et al. Staphylococcus aureus Small Colony Variants (SCVs): a road map for the metabolic pathways involved in persistent infections. Front Cell Infect Microbiol 4, 99, doi: 10.3389/fcimb.2014.00099 (2014).
24. Haussler, S. et al. Highly adherent small-colony variants of Pseudomonas aeruginosa in cystic fibrosis lung infection. J Med Microbiol 52, 295-301, doi: 10.1099/jmm.0.05069-0 (2003).
25. Wellinghausen, N. et al. Characterization of clinical Enterococcus faecalis small-colony variants. J Clin Microbiol 47, 2802-2811, doi: 10.1128/jcm.00485-09 (2009).
26. Proctor, R. A. et al. Staphylococcal small colony variants have novel mechanisms for antibiotic resistance. Clin Infect Dis 27 Suppl 1, S68-74 (1998).
27. Olson, M. E., Ceri, H., Morck, D. W., Buret, A. G. & Read, R. R. Biofilm bacteria: formation and comparative susceptibility to antibiotics. Can J Vet Res 66, 86-92 (2002).
28. Scheller, J., Chalaris, A., Schmidt-Arras, D. & Rose-John, S. The pro- and anti-inflammatory properties of the cytokine interleukin-6. Biochim Biophys Acta 1813, 878-888, doi: 10.1016/j.bbamcr.2011.01.034 (2011).
29. Fei, Y. et al. The combination of a tumor necrosis factor inhibitor and antibiotic alleviates staphylococcal arthritis and sepsis in mice. J Infect Dis 204, 348-357, doi: 10.1093/infdis/jir266 (2011).
30. Lee, J., Hartman, M. & Kornfeld, H. Macrophage apoptosis in tuberculosis. Yonsei Med J 50, 1-11 (2009).
31. Keane, J., Remold, H. G. & Kornfeld, H. Virulent Mycobacterium tuberculosis strains evade apoptosis of infected alveolar macrophages. J Immunol 164, 2016-2020 (2000).
32. Balcewicz-Sablinska, M. K., Keane, J., Kornfeld, H. & Remold, H. G. Pathogenic Mycobacterium tuberculosis evades apoptosis of host macrophages by release of TNF-R2, resulting in inactivation of TNF-α . J. Immunol. 161, 2636-2641 (1998).
33. Kreckler, L. M., Wan, T. C., Ge, Z. D. & Auchampach, J. A. Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther 317, 172-180, doi: 10.1124/ jpet.105.096016 (2006).
34. Kreckler, L. M., Gizewski, E., Wan, T. C. & Auchampach, J. A. Adenosine suppresses lipopolysaccharide-induced tumor necrosis factor-alpha production by murine macrophages through a protein kinase A- and exchange protein activated by cAMP-independent signaling pathway. J Pharmacol Exp Ther 331, 1051-1061, doi: 10.1124/jpet.109.157651 (2009).
35. Lopez-Castejon, G. & Brough, D. Understanding the mechanism of IL-1beta secretion. Cytokine Growth Factor Rev 22, 189-195, doi: 10.1016/j.cytogfr.2011.10.001 (2011).
36. Bose, J. L., Lehman, M. K. K., Fey, P. D. & Bayles, K. W. In PLoS One Vol. 7 (ed H. Ton-That) (2012).
37. Narayanasamy, P., Switzer, B. L. & Britigan, B. E. Prolonged-acting, Multi-targeting Gallium Nanoparticles Potently Inhibit Growth of Both HIV and Mycobacteria in Co-Infected Human Macrophages. Scientific reports 5, 8824, doi: 10.1038/srep08824 (2015).