Development of antibacterial conjugates using sulfamethoxazole with monocyclic terpenes: A systematic medicinal chemistry based computational approach

Computer Methods and Programs in Biomedicine

Volumn 140, Issue , 2017, Pages 185-194

  Swain, Shasank S ^a   Paidesetty, Sudhir K ^a   Padhy, Rabindra N ^a  

^a SIKSHA O ANUSANDHAN DEEMED TO BE UNIVERSITY   (India)

Author keywords

Dihydropteroate synthase; Molecular docking; Monoterpene conjugates; PASS prediction; Sulfamethoxazole; Toxicity assessment

Indexed keywords

BACTERIOLOGY; BIOCHEMISTRY; CELL CULTURE; COMPUTATIONAL CHEMISTRY; ESCHERICHIA COLI; MOLECULAR MODELING; PHENOLS; RAT CONTROL; TOXICITY; TUBES (COMPONENTS);

DIHYDROPTEROATE SYNTHASE; MOLECULAR DOCKING; MONOTERPENE CONJUGATES; SULFAMETHOXAZOLE; TOXICITY ASSESSMENT;

MONOTERPENES;

ANTIINFECTIVE AGENT; DIHYDROPTEROATE SYNTHASE; EUGENOL; MYRISTIC ACID; MYRISTIN; SAFROLE; SULFAMETHOXAZOLE; TERPENE DERIVATIVE; THYMOL; UNCLASSIFIED DRUG; TERPENE;

ACUTE TOXICITY; ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS ANTHRACIS; CONTROLLED STUDY; DRUG CONJUGATION; DRUG SYNTHESIS; ESCHERICHIA COLI; MEDICINAL CHEMISTRY; MOLECULAR DOCKING; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; SEQUENCE ALIGNMENT; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PNEUMONIAE; TOXICITY TESTING; AMINO ACID SEQUENCE; BACTERIUM; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECTS; ENZYMOLOGY; MICROBIAL SENSITIVITY TEST; MULTIDRUG RESISTANCE; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; BACTERIA; CHEMISTRY, PHARMACEUTICAL; COMPUTER SIMULATION; DIHYDROPTEROATE SYNTHASE; DRUG RESISTANCE, MULTIPLE, BACTERIAL; MICROBIAL SENSITIVITY TESTS; SEQUENCE HOMOLOGY, AMINO ACID; SULFAMETHOXAZOLE; TERPENES;

EID: 85007309215     PISSN: 01692607     EISSN: 18727565     Source Type: Journal    
DOI: 10.1016/j.cmpb.2016.12.013     Document Type: Article

References (40)

1. [1] Chambers, H.F., Deleo, F.R., Waves of resistance: Staphylococcus aureus in the antibiotic era. Nat. Rev. Microbiol. 7 (2009), 629–641.
2. [2] Dubey, D., Rath, S., Sahu, M.C., Patnaik, L., Debata, N.K., Padhy, R.N., Surveillance of infection status of drug resistant Staphylococcus aureus in an Indian teaching hospital. Asian Pac. J. Trop. Dis. 3 (2013), 133–142.
3. [3] Adwan, K., Jarrar, N., Abu-Hijl eh, A., Adwan, G., Awwad, E., Salameh, Y., Molecular analysis and susceptibility patterns of methicillin-resistant Staphylococcus aureus strains causing community- and health care-associated infections in the northern region of Palestine. Am. J. Infect. Control. 41 (2013), 195–198.
4. [4] Sydnor, E.R.M., Perl, T.M., Hospital epidemiology and infection control in acute-care settings. Clin. Microbiol. Rev. 24 (2011), 141–173.
5. [5] Canton, R., Morosini, M.I., Emergence and spread of antibiotic resistance following exposure to antibiotics. FEMS Microbiol. Revs. 35 (2011), 977–991.
6. [6] Anonymous2013, http://www.aplaceformom.com/blog/2013-10-22-common-elderly-infections/ (assessed on December 2015).
7. [7] Al-Badr, A., Al-Shaikh, G., Recurrent urinary tract infection management in women. Sultan Qaboos Uni. Med. J. 13 (2013), 359–367.
8. [8] Berger, T., Kassirer, M., Aran, A.A., Injectional anthrax [sbnd] new presentation of an old disease. Euro. Surveill., 19, 2014 pii: 20877 http://dx.doi.org/10.2807/1560-7917.ES2014.19.32.20877.
9. [9] Watt, J.P., Wolfson, L.J., O'Brien, K.L., Henkle, E., Deloria-Knoll, M., McCall, N., et al. Burden of disease caused by Haemophilus influenzae type b in children younger than 5years: global estimates. Lancet 374 (2009), 903–911.
10. [10] Davies, J., Davies, D., Origins and evolution of antibiotic resistance. Microbiol. Mol. Biol. Rev. 74 (2010), 417–433.
11. [11] Lee, C.-R., Cho, I.H., Jeong, B.C, Lee, S.H., Strategies to minimize antibiotic resistance. Int. J. Environ. Res. Publ. Heal. 10 (2013), 4274–4305.
12. [12] Dubey, D., Padhy, R.N., Prevalence of inducible clindamycin resistance among Enterococcus faecalis isolates from a teaching hospital in India. Asian Pac. J. Trop. Dis. 5 (2015), S127–S132.
13. [13] Dubey, D., Rath, S., Sahu, M.C., Nayak, N., Debata, N.K., Padhy, R.N., Status of multidrug resistance in Tubercle bacillus and phytochemicals for the control. J. Publ. Healt. 21 (2013), 115–119.
14. [14] Sun, H., Zhang, C., Xiang, L., Pi, R., Guo, Z., Zheng, C., et al. Characterization of mutations in streptomycin-resistant Mycobacterium tuberculosis isolates in Sichuan, China and the association between Beijing-lineage and dual-mutation in gid B. Tuberculosis, 2015, 10.1016/j.tube.2015. 09.004.
15. [15] World Health Organization, WHO report 2011: global tuberculosis control. Available at http://www.who/htm/tb/2011.16, (2011) (accessed 20 December 2015).
16. [16] Fair, R.J., Tor, Y., Antibiotics and bacterial resistance in the 21st century. Perspect. Medicin. Chem. 6 (2014), 25–64.
17. [17] Palomino, J.C., Martin, A., Drug resistance mechanisms in Mycobacterium tuberculosis. Antibiotics 3 (2014), 317–340.
18. [18] Gibreel, A., SkoÈld, O., Sulfonamide resistance in clinical isolates of Campylobacter jejuni: mutational changes in the chromosomal dihydropteroate synthase. Antimicrob. Agent. Chemother. 43 (1999), 2156–2160.
19. [19] Ma, L., Kovacs, J.A., Rapid detection of mutations in the human-derived Pneumocystis carinii dihydropteroate synthase gene associated with sulfa resistance. Antimicrob. Agent. Chemother. 45 (2001), 776–780.
20. [20] Buwembo, W., Aery, S., Rwenyonyi, C.M., Swedberg, G., Kironde, F., Point mutations in the folP gene partly explain sulfonamide resistance of Streptococcus mutans. Int. J. Microbiol., 2013, 367021, 10.1155/2013/367021.
21. [21] Juhász, E., Pongrácz, J., Iván, M., Kristóf, K., Antibiotic susceptibility of sulfamethoxazole-trimethoprim resistant Stenotrophomonas maltophilia strains isolated at a tertiary care centre in Hungary. Acta Microbiol. Immunol. Hung. 62 (2015), 295–305.
22. [22] Ye, Q., Wu, Q., Hu, H., Zhang, J., Huang, H., Prevalence, antimicrobial resistance and genetic diversity of Yersinia enterocolitica isolated from retail frozen foods in China. FEMS Microbiol. Lett., 2015, 362, 10.1093/femsle/fnv197 pii: fnv197.
23. [23] Mishra, M.P., Sarangi, R., Padhy, R.N., Prevalence of multidrug resistant uropathogenic bacteria in pediatric patients of a tertiary care hospital in eastern India. J. Infect. Publ. Healt., 2016, 10.1016/j.jiph.2015.10.002.
24. [24] Swain, S.S., Padhy, R.N., In vitro antibacterial efficacy of plants used by an Indian aborigine tribe against pathogenic bacteria isolated from clinical samples. J. Taibah. Univ. Med. Sci. 10 (2015), 379–390.
25. [25] Wang, M.W., Hao, X., Chen, K., Biological screening of natural products and drug innovation in China. Philos. Trans. R. Soc. Lond. B Biol. Sci. 362 (2007), 1093–1105.
26. [26] Sahoo, J., Mekap, S.K., Paidesetty, S.K., Synthesis, spectral characterization of some new 3-heteroaryl azo 4-hydroxy coumarin derivatives and their antimicrobial evaluation. J. Taibah Univ. Sci. 9 (2015), 187–195.
27. [27] Swain, S.S., Sahu, M.C., Padhy, R.N., In silico attempt for adduct agent(s) against malaria: combination of chloroquine with alkaloids of Adhatoda vasica. Comp. Method. Program. Biomed. 122 (2015), 16–25.
28. [28] Anand, A.V.K., Dasary, K., Lavania, A., Synthesis of potential phytochemicals: pyrrolylindolinones and quinoxaline derivatives using PEG as an environmentally benign solvent. S. Khemani, L.D., Srivastava, M.M., Srivastava, S., (eds.) Chemistry of Phytopotentials: Health Energy Environmental Perspective, 2012, Springer Inc., 335–337, 10.1007/978-3-642-23394-4 70.
29. [29] Kumar, S., Kumar, R., Dwivedi, A., Pandey, A.K., In vitro antioxidant, antibacterial and cytotoxic activity and in vivo effect of Syngonium podophyllum and Eichhornia crassipes leaf extracts on ionized induced oxidative stress and hepatic markers. Biomed. Res. Int., 2014, 459452, 10.1155/2014/459452.
30. [30] Khurana, N., Ishar, M.P.S., Gajbhiye, A., Goel, R.K., PASS assisted prediction and pharmacological evaluation of novel nicotinic analogs for nootropic activity in mice. Eur. J. Pharmacol. 662 (2011), 22–30.
31. [31] Racané, L., Kraljević-Pavelić, S., Ratkaj, I., Stepanić, V., Pavelić, K., Tralić-Kulenović, V., Karminski-Zamola, G., Synthesis and antiproliferative evaluation of some new amidino-substituted bis-benzothiazolyl-pyridines and pyrazine. Eur. J. Med. Chem. 55 (2015), 108–116.
32. [32] CLSI. Performance standards for antimicrobial susceptibility testing. CLSI Approved Standard M100eS23, 2013, Clinical and Laboratory Standards Institute, Wayne, PA.
33. [33] Organization for Economic Co-operation and Development. Guidance Document on Acute Oral Toxicity Testing 420 [R]. 2000, OECD, Paris.
34. [34] Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J., Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46 (2001), 3–26.
35. [35] Hughes, J.P., Rees, S., Kalindjian, S.B., Philpott, K.L., Principles of early drug discovery. Br. J. Pharmacol. 162 (2011), 1239–1249.
36. [36] Grant, M.A., Protein structure prediction in structure-based ligand design and virtual screening. Comb. Chem. High Throughput Screen. 12 (2009), 940–960.
37. [37] Ma, X.H., Shi, Z., Tan, C., Jiang, Y., Go, M.L., Low, B.C., Chen, Y.Z., In silico approaches to multi-target drug discovery: computer aided multi-target drug design, multi-target virtual screening. Pharm. Res. 27 (2010), 739–749.
38. [38] Tam, V.H., Nikolaou, M., A novel approach to pharmacodynamics assessment of antimicrobial agents: new insights to dosing regimen design. PLoS Comput. Biol., 7, 2011, e1001043, 10.1371/ journal.pcbi.1001043.
39. [39] Tropsha, A., Bajorath, J., Computational methods for drug discovery and design. J. Med. Chem., 59, 2016, 1.
40. [40] Jayaraman, P., Sakharkar, K.R., Lim, C., Siddiqi, M.I., Dhillon, S.K., Sakharkar, M.K., Novel phytochemical–antibiotic conjugates as multitarget inhibitors of Pseudomononas aeruginosa GyrB/ParE and DHFR. Drug Des. Devel. Ther. 7 (2013), 449–475.