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FT-Raman, FT-IR, NMR structural characterization and antimicrobial activities of 1,6-bis(benzimidazol-2-yl)-3,4-dithiahexane ligand and its Hg(II) halide complexes

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Abstract

1,6-Bis(benzimidaz-2-yl)-3,4-dithiahexane ligand (L) and its mercury halide complexes were prepared and characterised. The elemental analysis, molecular conductivity, FT-Raman, FT-IR (mid, far), 1H, 13C NMR and geometry optimization in MOPAC using MNDOd parameter on CACHE, prove the existence of neutral, mononuclear and the distorted tetrahedral [Hg(L)X2] complexes. In all the three complexes, the ligand acts as a chelating bidentate, through two of the bridging sulphur atoms and together with the monodentate coordination of the two anionic halide ligands to the metal centre forming a possible 4-coordinate compounds. The antimicrobial activities of free ligand, its hydrochlorinated salt, mercury halides and the complexes are evaluated using disk diffusion method in dimethyl sulfoxide (DMSO) as well as the minimal inhibitory concentration (MIC) dilution method, against 10 bacteria. The obtained results from disk diffusion method are assessed in side-by-side comparison with those of Penicillin-g, Ampicillin, Cefotaxime, Vancomycin, Oflaxacin and Tetracyclin well-known antibacterial agents. The results from dilution procedure are compared with Gentamycin as antibacterial and Nystatin as antifungal. The antifungal activities are reported on five yeast cultures namely Candida albicans, Kluyveromyces fragilis, Rhodotorula rubra, Debaryomyces hansenii and Hanseniaspora guilliermondii, and the results are referenced with Nystatin, Ketaconazole and Clotrimazole, commercial antifungal agents. In most cases, the compounds show broad-spectrum (Gram+ & Gram bacteria) activities that are comparatively, slightly less active or equipotent to the antibiotic and antifungal agents in the comparison tests.

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References

  1. Rosenberg B (1980) Metal Ions in Biol Syst 1:1

    CAS  Google Scholar 

  2. Corey EJ, Mehrotra MM, Khan AU (1987) Science 236:68

    Article  CAS  Google Scholar 

  3. Sadler PI (1991) Adv Inorg Chem 36:1

    Article  CAS  Google Scholar 

  4. Bertini I, Gray HB, Lippard SJ, Valentine JS (1994) Bioinorganic chemistry. University Science Books, Sausalito

    Google Scholar 

  5. Patrick GL (2005) An introduction to medicinal chemistry, 3th edn. Oxford University Press

  6. Giovagnini L, Marzano C, Bettio F, Fregona D (2005) J Inorg Biochem 99:39

    Article  CAS  Google Scholar 

  7. Ma Y, Day CS, Bierbach U (2005) J Inorg Biochem 99:2013

    Article  CAS  Google Scholar 

  8. Budakoti A, Abid M, Azam A (2006) Eur J Med Chem 41:63

    Article  CAS  Google Scholar 

  9. Agh-Atabay NM, Dulger B, Gucin F (2005) Eur J Med Chem 40:1096

    Article  CAS  Google Scholar 

  10. Tavman A, Agh-Atabay NM, Neshat A, Gucin F, Dulger B, Haciu D (2006) Trans Met Chem 31:194

    Article  CAS  Google Scholar 

  11. Agh-Atabay NM, Dulger B, Gucin F (2003) Eur J Med Chem 38:875

    Article  CAS  Google Scholar 

  12. Devereux M, Mc Cann M, Shea DO, Kelly R, Egan D, Deegan C, Kavanagh K, McKee V, Finn G (2004) J Inorg Biochem 98:1023

    Article  CAS  Google Scholar 

  13. Aghatabay NM, Neshat A, Karabiyik T, Somer M, Haciu D, Dulger B (2007) Eur J Med Chem 42:205

    Article  CAS  Google Scholar 

  14. Monthilal KK, Karunakaran C, Rajendran A, Murugesan R (2004) J Inorg Biochem 98:322

    Article  CAS  Google Scholar 

  15. Irving H, Williams PJR (1953) J Chem Soc 3192

  16. (a) Pearson RG (1963) J Am Chem Soc 85:3353; (b) Parr RG, Pearson RG (1983) J Am Chem Soc 105:7512

  17. Addison AW, Burke PJ (1981) Heterocycl Chem 18:803

    Article  CAS  Google Scholar 

  18. Agh-Atababy NM, Baykal A, Somer M (2004) Trans Met Chem 29:59

    Google Scholar 

  19. Performance standards for antimicrobial disk susceptibility tests (1993) Approved standard NCCLS publication M2-A5, Villanova, pp 1–32

  20. Collins CH, Lyre PM, Grange JM (1989) Microbiological methods, 6th ed. Butterworth Co. Ltd., London

    Google Scholar 

  21. Jones RN, Barry AL, Gaven TL, Washington JA (1984) In: Lennette EH, Balows A, Shadomy WJ (eds) Manual of clinical microbiology, 4th edn. American Society for Microbiology, Washington, pp 972–977

  22. Aghatabay NM, Somer M, Senel M, Dulger B, Gucin F (2007) Eur J Med Chem 42:1069

    Article  CAS  Google Scholar 

  23. Yee KK, Barrow RF, Rogstad A (1974) J Chem Soc Faraday II 68:1105

    Google Scholar 

  24. Hopkins AG, Brown CW (1975) J Chem Phys 62:1598

    Article  CAS  Google Scholar 

  25. Nakamoto K (1997) Infrared and Raman spectra of inorganic and coordination compounds, Part B, 5th edn. Wiley, p 200

  26. Nakamoto K (1997) Infrared and Raman spectra of inorganic and coordination compounds, Part B, 5th edn. Wiley, p 199

  27. Müller A, Jaegermann W, Enemark JH (1982) Coord Chem Rev 46:245

    Article  Google Scholar 

  28. Chakrabarty PK, Bhattacharya S, Pierpont CG, Chakrabarty R (1992) Inorg Chem 31:3573

    Article  CAS  Google Scholar 

  29. Guilard R, Ratti C, Tabard A, Richard P, Dubios D, Kadish KM (1990) Inorg Chem 29:2532

    Article  CAS  Google Scholar 

  30. Müller A, Jostes R, Jaegermann W, Bhattacharyya RG (1980) Inorg Chim Acta 41:259

    Article  Google Scholar 

  31. Müller A (1980) Analytical applications of FT-IR to molecular band biological systems. D Reidel, Dordrecht, p 257

    Google Scholar 

  32. Pearson RG (1968) J Chem Edu 45:581

    Article  CAS  Google Scholar 

  33. Frost RL, Edwards HGM, Duong L, Kloprogge JT, Martens WN (2002) Analyst 127:293

    Article  CAS  Google Scholar 

  34. Relf J, Cooney RP, Henneike HF (1972) Organomet Chem 39:75

    Article  CAS  Google Scholar 

  35. Smith JH, Brill TB (1976) Inorg Chim Acta 18:225

    Article  CAS  Google Scholar 

  36. Waters DN, Short EL, Thartwat M, Morris DFC (1973) J Mol Struct 17:389

    Article  CAS  Google Scholar 

  37. Givan A, Loewenschuss A (1976) J Chem Phys 64:1967, ibid 65:1851

    Google Scholar 

  38. Loewenschuss A, Ron A, Schneep O (1969) J Chem Phys 50:2502

    Article  CAS  Google Scholar 

  39. Givan A, Loewenschuss A (1978) J Chem Phys 68:2228

    Article  CAS  Google Scholar 

  40. Nakashima S, Mishima H, Mitsuishi A (1973) Raman Spectrsc 1:325

    Article  CAS  Google Scholar 

  41. Adams DM, Hopper MA (1971) Austr J Chem 24:885

    Article  CAS  Google Scholar 

  42. Demiray AF (1977) Dissertation TU Clausthal Germany

  43. Nyquist RA, Kagel RO (1971) Infrared spectra of inorganic compounds. Academic Press, New York, pp 423, 457, 475

  44. Wells TNC, Scully P, Paravicini G, Proudfoot AEI, Payton MA (1995) Biochem 34:7896

    Article  CAS  Google Scholar 

  45. McCutcheon AR, Ellis SM, Hancock REW, Towers GHN (1992) J Ethnopharmacol 37:213

    Article  CAS  Google Scholar 

Download references

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Correspondence to Naz Mohammed Aghatabay.

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Aghatabay, N.M., Tulu, M., Mahmiani, Y. et al. FT-Raman, FT-IR, NMR structural characterization and antimicrobial activities of 1,6-bis(benzimidazol-2-yl)-3,4-dithiahexane ligand and its Hg(II) halide complexes. Struct Chem 19, 71–80 (2008). https://doi.org/10.1007/s11224-007-9253-z

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  • DOI: https://doi.org/10.1007/s11224-007-9253-z

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