IN VITRO ANTIBACTERIAL ACTIVITY OF PHOSPHATE ESTERS SCREENED BY BROTH DILUTION ASSAY METHOD

Authors

  • Mithilesh Kumari Gupta School of Studies in Chemistry, Pt. Ravishankar Shukla University, Raipur C. G. 492010 India
  • S. K. Jadhav School of Studies in Biotechnology, Pt. Ravishankar Shukla University, Raipur C. G. 492010 India
  • S. A. Bhoite School of Studies in Chemistry, Pt. Ravishankar Shukla University, Raipur C. G. 492010 India

Keywords:

MIC, MBC, Antibacterial activity, Broth dilution assay

Abstract

Objective: The present study was formulated in order to determine the novelty and the potency of the synthesized phosphate esters in terms of their antibacterial activity.

Methods: Mono-6-chloro-2,4-dinitroaniline phosphate and di-2-methyl-5-nitroaniline phosphate were screened for antibacterial activity against four pathogenic bacterial strains Staphylococcus aureus MTCC 3160, Klebsiella oxytoca ATCC 13182, Bacillus subtilis BAB 2437 and Bacillus licheniformis MS 17. Antibacterial activity was evaluated by the broth dilution assay method at different concentrations (50-2000µg/ml) of phosphate esters. Solutions of mono-and di phosphate esters were prepared in water and DMSO respectively. Growth of inoculums was noted in terms of optical density.

Results: Di-2-methyl-5-nitroaniline phosphate was found more active than mono-6-chloro-2,4-dinitroaniline phosphate against selected bacterial strains. The minimum inhibitory concentration (MIC) of both phosphate esters was found in the range of 25 to 50 µg/ml. Minimum bactericidal concentration (MBC) of mono-6-chloro-2,4-dinitroaniline phosphate was found in the range of 1000 to 1500µg/ml against Staphylococcus aureus, Klebsiella oxytoca, Bacillus subtilis and Bacillus licheniformis. Di-2-methyl-5-nitroaniline phosphate showed MBC of 500 and 400 µg/ml against Staphylococcus aureus and Klebsiella oxytoca respectively, and 1000 µg/ml against Bacillus subtilis and Bacillus licheniformis.

Conclusion: Both the phosphate esters have exhibited significant antibacterial activity, therefore these compounds may be a good antibacterial agent.

 

Downloads

Download data is not yet available.

References

Castillo Exposito JA. A thesis on studies on antimicrobial activity of arginine based surfactants and chemoenzymatic synthesis of novel amphiphites based on L-Arginine and D-Fagomine; 2006.

Tevover FC. Mechanism of antimicrobial resistance in bacteria. Am J Med 2006;119:S3-S10.

Saga T, Guchi KY. History of antimicrobial agents and resistant bacteria. JMAJ 2009;52:103-8.

Pokalwar RU, Hangarge RV, Maske PV, Shingare MS. Synthesis and antibacterial activities of a-hydroxyphosphonates and a-acetyloxyphosphonates derived from 2-chloroquinoline-3-carbaldehyde. General Papers ARKIVOC 2006;11;196-204.

Banjara RA, Jadhav SK, Bhoite SA. In vitro antibacterial activity of mono-2-ethylaniline phosphate ester. Asian J Exp Biol Sci 2012;3:772-7.

Khasiyatullina NR, Mironov VF, Bogdanov AV, Zabov VV, Voloshina AD, Kulik NV, Konovalov AI. Synthesis and antibacterial and antifungal properties of some phosphorus-containing 1,2-dihydroxynaphthalenes. Pharm Chem J 2009;43:20-3.

Harastani HH, Araj GF, Tokajian ST. Molecular characteristics of Staphylococcus aureus isolated from a mojor hospital in Lebanon. Int J Infect Dis 2014;19:33-8.

David MZ, Daum RS. Community-associated methicillin-resistant Staphylococcus aureus: epidemiology and clinical consequences of an emerging epidemic. Clin Microbiol Rev 2010;23:616–87.

Murray PR, Baron EJ, Jorgensen JH, Landry ML, Pfaller MA, Yolken RH. Manual of clinical microbiology (8th ed.). Herdon, VA, United States of America: American Society for Microbiology; 2003.

Le Loir Y, Baron F, Gautier M. Staphylococcus aureus and food poisoning. Genet Mol Res 2003;2:63-76.

Monecke S, Coombs G, Shore AC, Coleman DC, Akpaka P, Borg M. A ï¬eld guide to pandemic, epidemic and sporadic clones of methicillin-resistant Staphylococcus aureus. PLoS One 2011;6:e17936.

Högenauer C. Klebsiella oxytoca as a causative organism of antibiotic-associated hemorrhagic colitis. N Engl J Med 2006;355:2418–26.

Zollner-Schwetz I. Role of Klebsiella oxytoca in antibiotic associated diarrhea. Clin Infect Dis 2008;47:e74-8.

Savino F, Cordisco L, Tarasco V, Calabrese R, Palumeri E. Molecular identification of coliform bacteria from colicky breastfed infants. Acta Paediatr 2009;98:1582–8.

Hoffmann KM, Deutschmann A, Weitzer C, Joainig M, Zechner E. Antibiotic-associated hemorrhagic colitis caused by cytotoxin-producing Klebsiella oxytoca. Peds 2010;125:e960–3.

Savino F, Cordisco L, Tarasco V, Locatelli E, Di Gioia D. Antagonistic effect of Lactobacillus strains against gas-producing coliforms isolated from colicky infants. BMC Microbiol 2011;11:157.

Oggioni MR, Pozzi G, Valensin PE, Galieni P, Bigazzi C. Recurrent septicemia in an immunocompromised patient due to probiotic strains of Bacillus subtilis. J Clin Microbiol 1998;36:325–6.

Ryan KJ, Ray CG. Sherris medical microbiology. 4th ed. McGraw Hill; 2004. p. 8529-9.

Banyko J, Vyletelova M. Determining the source of Bacillus cereus and Bacillus licheniformis isolated from raw milk, pasteurized milk and Yoghurt. Soc Appl Microbiol Lett Appl Microbiol 2009;48:318-23.

De Clerck E, De Vos P. Genotypic diversity among Bacillus licheniformis strains from various sources. FEMS Microbiol Lett 2004;231:91-8.

Nieminen T, Rintaluoma N, Andersson M, Taimisto AM, Ali-Vehmas T, Seppala A, et al. Toxinogenic Bacillus pumilus and Bacillus licheniformis from mastitic milk. Vet Microbiol 2007;124:329-39.

Mikkola R, Kolari M, Andersson MA, Helin J, Salkinoja-Salonen MS. Toxic lactonic lipopeptide from food poisoning isolates of Bacillus licheniformis. Eur J Biochem 2000;267:4068-74.

Westheimer FH. Why nature chose phosphates. Science 1987;235:1173-8.

Kumar KS, Reddy CB, Reddy MVN, Reddy CS. Green chemical synthesis of á½°-hydroxyphosphonates. Org Commun 2012;5:2:50-7.

Ali RM, Hammed AS, Ameer AA. Synthesis of some new phosphate esters containing three 1.3.4-oxa diazole units and studying their biological activity. Nat J Chem 2005;19:426-39.

Shivananda MK, Shet PM. Synthesis, characterization and antibacterial activity studies of some triazolothiadiazolylquinolines. J Chem Pharm Res 2011;3:61-6.

Fleisher D, Bong R, Stewart BH. Improved oral drug delivery: solubility limitations overcome by the use of Prodrug. Adv Drug Delivery Rev 1996;19:115-30.

Chang S, Griesgraber GW, Southern PJ, Wagner CR. Amino acid phosphoramidate monoesters of 3′-azido-3′-deoxythymidine: Relationship between antiviral potency and intracellular metabolism. J Med Chem 2001;44:223-31.

Schultz C. Prodrugs of biologically active phosphate esters. Bioorg Med Chem 2003;11:885-98.

Kumpulainen H, Jarvinen T, Saari R, Lehtonen M, Vepsalainen J. An efficient strategy for the synthesis of 1-chloroethyl phosphates and phosphoramidates. J Org Chem 2005;70:9056-8.

Hassall KA. The chemistry of pesticides: Their metabolism, mode of action and uses in crop protection, The Macmillan Press Ltd. London; 1983. p. 236-40.

Lorencova E, Vltavska P, Budinsky P, Koutny M. Antibacterial effect of phosphates and phosphonates with different chain length. J Environ Sci Health A Tox Hazardd Subst Environ Eng 2012;47:2241-5.

Srinivasulu K, Kumar MA, Raju CN, Reddy CS. Synthesis and bioactivity of some new-2-substituted-3,4-dihydro-1-(9H-carbazol-4-yloxy)methyl-3-[2-(2-methoxyphenoxy) ethyl]-1,3,2λoxazaphosphole-2-oxides, Sulfidesand selenides. Arkivoc 2007;14:100-9.

Awadhiya P. A thesis on synthesis, characterization and kinetics of hydrolysis of some organic phosphate esters. Pt. Ravishankar Shukla University, Raipur; 2009.

Kahan JS, Kahan FM, Goegelman R, Currie SA, Jackson M, Stapley EO, et al. Thienamycin, a new beta-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties. J Antibiot 1979;32:1-12.

Fuente RDL, Sonawane ND, Arumainayagam D, Verkman AS. Small molecules with antimicrobial activity against E. coli and P. aeruginosa identified by high-throughput screening. Br J Pharmacol 2006;149(5):551–9.

Banjara RA, Jadhav SK, Bhoite SA. MIC for determination of antibacterial activity of di-2-ethylaniline phosphate. J Chem Pharm Res 2012;4:648-52.

Gupta MK, Jadhav SK, Bhoite SA. Evaluation of antibacterial activity of phosphate esters by well diffusion method. WJPR 2014;3:420-8.

Sen A, Batra A. Evaluation of antimicrobial activity of different solvent extracts of medicinal plant: Melia Azedarach L. Int J Curr Pharm Res 2012;4:67-73.

Paredes D, Ortiz C, Torres R. Synthesis, characterization and evaluation of antibacterial effect of Ag nanoparticles against Escherichia coli O157:H7 and methicillin resistant Staphylococcus aureus (MRSA). Int J Nanomed 2014;9:1717-29.

Banjara RA, Jadhav SK, Bhoite SA. Antibacterial activity of di-2-ethylaniline phosphate screened by paper disc diffusion method. JAPS 2012;2:230-3.

Kumar AK, Lokanatha Rai KM, Vasanth KG, Mylarappa BN. A facile route for the synthesis of ethyl N-aryl-2,6-dioxo-piperid-3-ene-4-corboxylates and their biological activity. Int J Pharm Pharm Sci 2012;4:564-8.

Reddy CR, Ramana KV, Rani CR, Reddy GCS, Rao VK, Naga Raju C. Synthesis, spectral characterization and anti-microbial activity of 6-Substituted [(2-aminoethyl)amino]-6λ5-dibenzo [d, h][1, 3, 6, 2] oxathiaza-phosphonin-6-ones. Org Commun 2011;4:58-66.

Published

01-08-2015

How to Cite

Gupta, M. K., S. K. Jadhav, and S. A. Bhoite. “IN VITRO ANTIBACTERIAL ACTIVITY OF PHOSPHATE ESTERS SCREENED BY BROTH DILUTION ASSAY METHOD”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, no. 8, Aug. 2015, pp. 267-73, https://journals.innovareacademics.in/index.php/ijpps/article/view/5360.

Issue

Section

Original Article(s)