Drug resistance reversal potential of ursolic acid derivatives against nalidixic acid- and multidrug-resistant Escherichia coli

Chemical Biology and Drug Design

Volumn 86, Issue 3, 2015, Pages 272-283

  Dwivedi, Gaurav Raj ^a   Maurya, Anupam ^a   Yadav, Dharmendra Kumar ^a   Khan, Feroz ^a   Darokar, Mahendra P ^a   Srivastava, Santosh Kumar ^a  

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

Author keywords

ester analog; multidrug resistant; nalidixic acid; non antibiotics; tetracycline; triterpenoids

Indexed keywords

3 O ACETYL URS 12 EN 28 ISOPROPRYL ESTER DERIVATIVE; 3 O ACETYL URS 12 EN 28 N BUTYL ESTER DERIVATIVE; ADENOSINE TRIPHOSPHATASE; ANTIINFECTIVE AGENT; CARRIER PROTEIN; NALIDIXIC ACID; RESERPINE; TETRACYCLINE; UNCLASSIFIED DRUG; URSOLIC ACID; URSOLIC ACID DERIVATIVE; ENZYME INHIBITOR; TRITERPENE;

ACETYLATION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATE; BINDING AFFINITY; CELL VIABILITY; COLUMN CHROMATOGRAPHY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG POTENCY; DRUG POTENTIATION; DRUG STRUCTURE; ENZYME INHIBITION; ESCHERICHIA COLI; GRAM NEGATIVE INFECTION; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR MODEL; MULTIDRUG RESISTANCE; NONHUMAN; PRIORITY JOURNAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; COMBINATION DRUG THERAPY; DRUG DEVELOPMENT; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST;

ESCHERICHIA COLI; NEGIBACTERIA;

ADENOSINE TRIPHOSPHATASES; ANTI-BACTERIAL AGENTS; DRUG DISCOVERY; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG SYNERGISM; DRUG THERAPY, COMBINATION; ENZYME INHIBITORS; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; NALIDIXIC ACID; TETRACYCLINE; TRITERPENES;

EID: 84939266822     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12491     Document Type: Article

References (51)

1. Nikaido H., (2009) Multidrug resistance in bacteria. Annu Rev Biochem; 78: 119-146.
2. Pages J.M., Amaral L., (2009) Mechanisms of drug efflux and strategies to combat them: challenging the efflux pump of Gram-negative bacteria. Biochim Biophys Acta; 1794: 826-833.
3. Piddock L.J., (2006) Multidrug-resistance efflux pumps not just for resistance. Nat Rev Microbiol; 4: 629-636.
4. (2013) Multidrug-resistant organism & Clostridium difficile infection (MDRO/CDI) module. Centers for Disease Control and Prevention (CDC); 12: 2-42.
5. Peleg A.Y., Hooper D.C., (2010) Hospital-acquired infections due to gram-negative bacteria. N Engl J Med; 362: 1804-1813.
6. Gaynes R., Edwards J.R., (2005) Overview of nosocomial infections caused by Gram negative bacilli. Clin Infect Dis; 41: 848-854.
7. Van der Donk C.F., van de Bovenkamp J.H., De Brauwer E.I., (2012) Antimicrobial resistance and spread of multi drug resistant Escherichia coli isolates collected from nine urology services in the Euregion Meuse-Rhine. PLoS ONE; 7: e47707.
8. Hawkey P.M., Jones A.M., (2009) The changing epidemiology of resistance. J Antimicrob Chemother; 64 (S1): i3-i10.
9. Datta S., Wattal C., Goel N., (2012) A ten year analysis of multidrug resistant blood stream infections caused by Escherichia coli & Klebsiella pneumoniae in tertiary care hospital. Indian J Med Res; 135: 907-912.
10. Gibbons S., (2005) Plants as a source of bacterial resistance modulators and anti-infective agents. Phytochem Rev; 4: 63-78.
11. Khanuja S.P.S., Arya J.S., Srivastava S.K., Shasany A.K., Kumar S., Ranganathan T., Darokar M.P., Kumar S., (2006) Antibiotic pharmaceutical composition with lysergol as bio-enhancer and method of treatment. US Patent, 20070060604.
12. Khanuja S.P.S., Arya J.S., Tiruppadiripulivur R.S.K., Saikia D., Kaur H., Singh M., Gupta S.C., Shasany A.K., Darokar M.P., Srivastava S.K., Gupta M.M., Verma S.C., Pal A., (2005) Novel Nitrite Glycosides useful as a bio-enhancer of drugs and nutrients process of its isolation from Moringa oleifera. US Patent 6,858,588.
13. Maurya A., Dwivedi G.R., Darokar M.P., Srivastava S.K., (2013) Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid resistant Escherichia coli. Chem Biol Drug Des; 81: 484-490.
14. Hu Y., Coates A.R., (2013) Enhancement by novel anti-methicillin resistant Staphylococcus aureus compound HT61 of the activity of neomycin, gentamicin, mupirocin and chlorhexidine: in vitro and in vivo studies. J Antimicrob Chemother; 68: 374-384.
15. Gertsch J., (2011) Botanical drugs, synergy, and network pharmacology: forth and back to intelligent mixtures. Planta Med; 77: 1086.
16. Jia J., Zhu F., Ma F., Cao F., Li Y.X., (2009) Mechanisms of drug combinations: interaction and network perspectives. Nat Rev Drug Discov; 8: 111-128.
17. Mazumder K., Tanaka K., Fukase K., (2013) Cytotoxic activity of ursolic acid derivatives obtained by isolation and oxidative derivatization. Molecules; 18: 8929-8944.
18. Babalola I.T., Shode F.O., (2013) Ubiquitous ursolic acid: a potential pentacyclic triterpene natural product. J Pharm Phytochem; 2: 214-222.
19. Akbarsha M.A., Palanisamy M., Murugaian P., Latha P.N.L., (1998) Ursolic acid generates symplasts in rat spermatogenic clones. Phytother Res; 12: 32-36.
20. Chattopadhyaya D., Dungdung S.R., Mandal A.B., Majumder G.C., (2005) A potent sperm motility-inhibiting activity of bioflavonoids from an ethnomedicine of Onge, Alstonia macrophylla Wall ex A. DC, leaf extract. Contraception; 71: 372-378.
21. Messner B., Zeller I., Ploner C., Frotschnig S., Ringer T., Steinacher-Nigisch A., Ritsch A., Laufer G., Huck C., Bernhard D., (2011) Ursolic acid causes DNA-damage, p53-mediated, mitochondria- and caspase-dependent human endothelial cell apoptosis, and accelerates atherosclerotic plaque formation in vivo. Atherosclerosis; 2: 402-408.
22. Upadhyay H.C., Dwivedi G.R., Darokar M.P., Chaturvedi V., Srivastava S.K., (2012) Bioenhancing and antimycobacterial agents from Ammannia multiflora. Planta Med; 78: 79-81.
23. Gupta V.K., Verma S., Pal A., Srivastava S.K., (2013) In vivo efficacy and synergistic interaction of 16α-hydroxycleroda-3, 13 (14) Z-dien-15, 16-olide, a clerodane diterpene from Polyalthia longifolia against methicillin-resistant Staphylococcus aureus. Appl Microbiol Biotechnol; 97: 9121-9131.
24. Dwivedi G.R., Upadhyay H.C., Yadav D.K., (2013) 4-Hydroxy-α-tetralone and its derivative as drug resistance reversal agents in multi drug resistant Escherichia coli. Chem Biol Drug Des; 83: 482-492.
25. Kumar S., (1976) Properties of adenyl cyclase and cyclic adenosine 3′,5′-monophosphate receptor protein deficient mutants of Escherichia coli. J Bacteriol; 125: 545-555.
26. Dwivedi G.R., (2013) Studies on efflux pumps for high throughput screening of phytomolecules combating bacterial multidrug resistant infections. PhD Thesis. Faizabad, India: Dr. R. M. L. Avadh University.
27. Clinical Laboratory Standards Institute (CLSI) (2012) Performance Standards for Antimicrobial Susceptibility Testing. 22nd Informational Supplement testing M100-S15. Wayne, PA: CLSI.
28. Stermitz F.R., Lorenz P., Tawara J.N., Zenewicz L.A., Lewis K., (2000) Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5′-methoxyhydnocarpin, a multidrug pump inhibitor. Proc Natl Acad Sci; 97: 1433-1437.
29. Eliopoulos G.M., Wennersten C.B., (2002) Antimicrobial activity of quinupristin-dalfopristin combined with other antibiotics against vancomycin resistant enterococci. Antimicrob Agents Chemother; 46: 1319-1324.
30. Eliopoulus G.M., Moellering R.C.J., (1996) Antimicrobial combinations. In:, Lorian V., editor. Antibiotics in Laboratory Medicine, 4th edn. Baltimore, MD: Williams & Wilkins; p. 330-336.
31. Viveiros M., Rodrigues L., Martins M., Couto I., Spengler G., Martins A., Amaral L., (2010) Evaluation of efflux activity of bacteria by a semi-automated fluorometric system. Methods Mol Biol; 642: 159-172.
32. Suzuki Y., Ueno S., Ohnuma R., Koyama N., (2005) Cloning, sequencing and functional expression in E. coli of the gene for a P-type Na+- ATPase of the facultative anaerobic alkaliphile, Exiguobacterium auranticum. Biochim Biophys Acta; 1727: 162-168.
33. Glavinas H., Méhn D., Jani M., Oosterhuis B., Herédi-Szabõ K., (2008) Utilization of membrane vesicle preparations to study drug-ABC transporter interactions. Expert Opin Drug Metab Toxicol; 4: 721-732.
34. Yadav D.K., Ahmad I., Shukla A., Khan F., Negi A.S., Gupta A., (2014) QSAR and docking studies on Chalcone derivatives for anti-tubercular activity against M. tuberculosis H37Rv. J Chemom; 28: 499-507.
35. Yadav D.K., Khan F., (2013) QSAR, docking and ADMET studies of camptothecin derivatives as inhibitors of DNA topoisomerase-I. J Chemom; 27: 21-33.
36. Livermore D.M., (2009) Has the era of untreatable infections arrived? J Antimicrob Chemother; 64 (S1): i29-i36.
37. Infectious Diseases Society of America (2010) The 10 × '20 Initiative: pursuing a global commitment to develop 10 new antibacterial drugs by 2020. Clin Infect Dis; 50: 1081-1083.
38. Spellberg B., Bartlett J.G., Gilbert D.N., (2013) The future of antibiotics and resistance. N Engl J Med; 368: 299-302.
39. Hassani M., (2014) The crisis of resistant Gram-negative bacterial infections: is there any hope for ES KAPE? Clin Infect Dis; 1: 1005.
40. Li H.Z., Nikaido H., (2004) Efflux-mediated drug resistance in bacteria. Drugs; 64: 159-204. 35.
41. Garvey M.I., Piddock L.V.J., (2008) The efflux pump inhibitor reserpine selects multidrug resistant Streptococcus pneumoniae strains that overexpress the ABC transporters PatA and PatB. Antimicrob Agents Chemother; 52: 1677-1685.
42. Khan I.A., Mirza Z.M., Kumar A., Verma V., Qazi G.N., (2006) Piperine, a phytochemical potentiator of ciprofloxacin against Staphylococcus aureus. Antimicrob Agents Chemother; 50: 810-812.
43. Kalia N.P., Mahajan P., Mehra R., Nargotra A., Sharma J.P., Koul S., Khan I.A., (2012) Capsaicin, a novel inhibitor of the NorA efflux pump, reduces the intracellular invasion of Staphylococcus aureus. J Antimicrob Chemother; 67: 2401-2408.
44. Viveiros M., Dupont M., Rodrigues L., Couto I., Davin-Regli A., (2007) Antibiotic stress, genetic response and altered permeability of E. coli. PLoS ONE; 2: e36.
45. Viveiros M., Jesus A., Brito M., Leandro C., Martins M., Ordway D., (2005) Inducement and reversal of tetracycline resistance in Escherichia coli K-12 and expression of proton gradient-dependent multidrug efflux pump genes. Antimicrob Agents Chemother; 49: 3578-3582.
46. Lubelski J., Konings W.N., Driessen A.J.M., (2007) Distribution and physiology of ABC-TypeTransporters contributing to multidrug resistance in bacteria. Microbiol Mol Biol Rev; 71: 463-476.
47. Kobayashi N., Nishino K., Yamaguchi A., (2001) Novel macrolide-specific ABC-type efflux transporter in Escherichia coli. J Bacteriol; 183: 5639-5644.
48. Martins M., Couto I., Viveiros M., Amaral L., (2010) Identification of efflux-mediated multidrug resistance in bacterial clinical isolates by two simple methods. Methods Mol Biol; 642: 143-157.
49. Marquez B., (2005) Bacterial efflux systems and efflux pumps inhibitors. Biochimie; 87: 1137-1147.
50. Viveiros M., Martins M., Couto I., (2008) New methods for the identification of efflux mediated MDR bacteria, genetic assessment of regulators and efflux pump constituents, characterization of efflux systems and screening for inhibitors of efflux pumps. Curr Drug Targets; 9: 760-778.
51. Hurdle J.G., O'Neill A.J., Chopra I., Lee R.E., (2011) Targeting bacterial membrane function: an underexploited mechanism for treating persistent infections. Nat Rev Microbiol; 9: 62-75.