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Research Article

volume 52 issue 7 (july 2018) : 1043-1047,   Doi: 10.18805/ijar.B-845

In vitro effects of 2, 4-Dichlorophenoxy acetic acid dimethylamine salt and enrofloxacin on BTH 

M
Mustafa Oguzhan Kaya
1Siirt University, Faculty of Veterinary Medicine, Div. Basic Sciences, Dep. of Biochemistry, Siirt, Turkey
Cite article:- Kaya Oguzhan Mustafa (2017). In vitro effects of 2, 4-Dichlorophenoxy acetic acid dimethylamine salt and enrofloxacin on BTH. Indian Journal of Animal Research. 52(7): 1043-1047. doi: 10.18805/ijar.B-845.

ABSTRACT

In this study, the in vitro effects of enrofloxacin, a broad spectrum antibiotic, and 2, 4-Dichlorophenoxy acetic acid dimethylamine salt that, a herbicide, on the bovine testicular hyaluronidase (BTH) were analyzed. BTH was purified using the method of ammonium sulfate precipitation and using affinity gel (Sepharose-4B-L-tyrosine-m-anisidine). Then the inhibiting effects of enrofloxacin and 2, 4-Dichlorophenoxy acetic acid dimethylamine salt on the purified BTH enzyme were identified. IC50 values of these chemical substances were found to be 0.3101 and 0.4276 mM, respectively.

REFERENCES

  1. Arnold, E. K., Beasley, V. R. (1989). The pharmacokinetics of chlorinated phenoxy acid herbicides: A literature review. Veterinary and Human Toxicology, 31: 121–125.
  2. Belem-Gonçalves, S., Tsan, P., Lancelin, J.M., Alves, T.L.M., Salim, V.M., Besson, F. (2006). Interfacial behaviour of bovine testis hyaluronidase. Biochem J., 398: 569–576.
  3. Blair, R. M., Fang, H., Branham, W. S., Hass, B. S., Dial, S. L., Moland, C. L., Tong, W., Shi, L., Perkins, R., Sheehan, D. M. (2000). The estrogen receptor relative binding affinities of 188 natural and Xenochemicals: Structural Diversity of Ligands. Toxicological Sciences, 54: 138–153.
  4. Botzki, A., Rigden, D.J., Braun, S., Nukui, M., Salmen, S., Hoechstetter, J., Bernhardt, G., Dove, S., Jedrzejas, M.J., Buschauer, A. (2004). L-Ascorbic acid 6-hexadecanoate, a potent hyaluronidase inhibitor. X-ray structure and molecular modeling of enzyme-inhibitor complexes. J Biol Chem., 279(44): 45990-45997.
  5. Ceylan, S. (2004). Special Pharmacology (Edition). Uludag University Veterinary Faculty, Bursa, pp. 247-248.
  6. Chain, E. and Duthie, E.S. (1939). A mucolytic enzyme in testis extracts. Nature, 144: 977–978.
  7. Cherr, G. N., Yudin, A. I., Overstreet, J. W. (2001). The dual functions of GPI-anchored PH-20: hyaluronidase and intracellular signaling. Matrix biology, 20: 515–525.
  8. Csoka, T.B., Frost, G.I., Stern, R. (1997). Hyaluronidases in tissue invasion. Invasion and Metastasis, 17: 297–311.
  9. Ecevit, O., Mennan, H., Aksoy, H.M., Akca, Ý. (1999). Agricultural Struggle Drugs and Their Effects on the Environment. O.M.Ü Faculty of Agriculture Course Book, Samsun. pp. 145.
  10. EPA., U. S. (1989). Information about pesticide use and report on the pesticide market. Environmental Protection Agency, 3: 15-20.
  11. Erne, K. (1966). Determination of phenoxy acetic herbicide residues in biological materials. Acta Vet. Scand, 7: 240–256.
  12. Extoxnet. (1996). Pesticide Information Profiles, http://extoxnet.orst.edu/pips/24-D.htm, Date of access: 02.10.2017
  13. Frost, G. I., Csóka, T., Stern, R. (1996). The Hyaluronidases: A Chemical, Biological and Clinical Overview. Trends in Glycoscience and Glycotechnology, 8: 419–434.
  14. Greiling, H. (1957). Spectrophotometric method for the determination of bacterial hyaluron idase. Hoppe-Seyler’s Zeitschrift fur physiologische Chemie, 309: 239–242.
  15. Hoechstetter, J. (2005). Characterisation of bovine testicular hyaluronidase and a hyaluronate lyase from Streptococcus agalactiae. Dissertation, 1–239.
  16. IARC (International Agency for Research on Cancer). (1977). Some fumigants, the herbicides 2,4-D and 2,4,5-T, chlorinated dibenzodioxins and miscellaneous Industrial Chemicals. IARC, 15: 111-138.
  17. Ibrahim, M.A., Bond, G.G., Burke, T.A., Cole, P., Dost, F.N., Enterline, P.E., Gough, M., et al. (1991). Weight of the evidence on the human carcinogenicity of 2,4-D. Environmental Health Perspectives, 96: 213–222.
  18. Kaessler, A., Nourrisson, M.R., Duflos, M., Jose, J. (2008). Indole carboxamides inhibit bovine testes hyaluronidase at pH 7.0 and indole acetamides activate the enzyme at pH 3.5 by different mechanisms. J Enzyme Inhib Med Chem, 23(5): 719-727.
  19. Kaya, M.O., Arslan, O., Guler, O.O. (2014). A new affinity method for purification of bovine testicular hyaluronidase enzyme and an investigation of the effects of some compounds on this enzyme. J Enzyme Inhib Med Chem, 30(4): 524–527.
  20. Keller, T., Skopp, G., Wu, M., Aderjan, R. (1994). Fatal overdose of 2,4-dichlorophenoxyacetic acid (2,4-D). Forensic Science International, 65: 13–18.
  21. Koca, M. (2001). The Investigation of acute toxicitiy of 2,4-dichlorophenoxyacetic acid and related behavioural changes on the lepistes (poecilia reticulata P., 1859). Gazi University, Ankara. pp. 1-57.
  22. Kreil, G. (1995). Hyaluronidases: A group of neglected enzymes. Protein science, 4: 1666–1669.
  23. Kumar, B.S.B., Pandita, S., Sharma, A., Jadhav, V., Soren, S., Mili, B., Ganaie, A.H., Mir, N.A., Kumar, N., Kumar, A.V. (2015). Regulation of postnatal development of testes and its association with puberty and fertility. Agricultural Reviews, 36: 339-344.
  24. Lindguist, N.G., Ulberg, S. (1971). Distribution of the herbicides 2,4,5-T and 2,4-D in pregnanat mice, Accumulation in the yolk sac ephitelium. Experientia, 27: 1439–1441.
  25. Meyer, K., Hobby, G.L., Chaffee, E., Dawson, M.H. (1940). Relationship between ‘Spreading Factor’ and Hyaluronidase. Experimental Biology and Medicine, 44: 294–296. 
  26. Meyer, K. (1971). Hyaluronidases. The Enzymes, 5: 307-320.
  27. Meyer, M.F., Kreil, G., Aschauer, H. (1997). The soluble hyaluronidase from bull testes is a fragment of the membrane-bound PH-20 enzyme. FEBS Letters, 413(2): 385–388.
  28. Olgen, S., Kaessler, A., Nebioglu, D., Jose, J. (2007). New potent indole derivatives as hyaluronidase inhibitors. Chem Biol Drug Des., 70(6): 547-551.
  29. Olgen, S., Kaessler, A., Kýlýç Kurt, Z., Jose, J. (2010). Investigation of aminomethyl indole derivatives as hyaluronidase inhibitors. Z Naturforsch C., 65(7-8): 445-450.
  30. Ozdas, E., Ates, U., Uyanýkgil,Y., Baka, M., Yavasoglu, A., Biçer, S., Ergen, G. (2006). Effect Of 2,4-D (2,4-Dichlorophenoxyacetic Acid) as a Herbicide on rats Testes. Ege Journal of Medicine, 45: 169–174.
  31. Pavan, M., Beninatto, R., Galesso, D., Panfilo, S., Vaccaro, S., Messina, L., Guarise, C. (2016). A new potential spreading factor: Streptomyces koganeiensis hyaluronidase. A comparative study with bovine testes hyaluronidase and recombinant human hyaluronidase of the HA degradation in ECM. Biochim Biophys Acta, 1860(4): 661-668.
  32. Pubchem. (2017). 2,4-Dichlorophenoxy acetic acide dimethyl amine salt, https://pubchem.ncbi.nlm.nih.gov/compound/2_4-    D_dimethylamine_salt, Date of access: 03.12.2017.
  33. Pubchem.(2017).Enrofloxacin,https://pubchem.ncbi.nlm.nih.gov/compound/Enrofloxacin, Date of access: 03.12.2017.
  34. Rigden, D.J., Botzki, A., Nukui, M., Mewbourne, R.B., Lamani, E., Braun, S., Von Angerer, E., Bernhardt, G., Dove, S., Buschauer, A., Jedrzejas, M.J. (2006). Design of new benzoxazole-2-thione-derived inhibitors of Streptococcus pneumoniae hyaluronan lyase: structure of a complex with a 2-phenylindole. Glycobiology, 16(8): 757-65.
  35. Takagaki, K., Nakamura, T., Izumi, J., Saitoh, H., Endo, M., Kojima, K., Kato, I., Majima, M. (1994). Characterization of hydrolysis and transglycosylation by testicular hyaluronidase using ion-spray mass spectrometry. Biochemistry, 33: 6503–6507.
  36. Tanyildizi, S., Bozkurt, T. (2003). The effects of lincomycin-spectinomycin and sulfamethoxazole-trimethoprim on hyaluronidase activities and sperm characteristics of rams. The Journal of Veterinary Medical Science, 65: 775–780.
  37. Wang, Y.S., Jaw, C.G., Chen, Y.L. (1994). Accumulation of 2,4-D and glyphosate in fish and water hyacinth. Water, Air, and Soil Pollution, 74:397–403 
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Indian Journal of Animal Research
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    Research Article

    volume 52 issue 7 (july 2018) : 1043-1047,   Doi: 10.18805/ijar.B-845

    In vitro effects of 2, 4-Dichlorophenoxy acetic acid dimethylamine salt and enrofloxacin on BTH 

    M
    Mustafa Oguzhan Kaya
    1Siirt University, Faculty of Veterinary Medicine, Div. Basic Sciences, Dep. of Biochemistry, Siirt, Turkey
    Cite article:- Kaya Oguzhan Mustafa (2017). In vitro effects of 2, 4-Dichlorophenoxy acetic acid dimethylamine salt and enrofloxacin on BTH. Indian Journal of Animal Research. 52(7): 1043-1047. doi: 10.18805/ijar.B-845.

    ABSTRACT

    In this study, the in vitro effects of enrofloxacin, a broad spectrum antibiotic, and 2, 4-Dichlorophenoxy acetic acid dimethylamine salt that, a herbicide, on the bovine testicular hyaluronidase (BTH) were analyzed. BTH was purified using the method of ammonium sulfate precipitation and using affinity gel (Sepharose-4B-L-tyrosine-m-anisidine). Then the inhibiting effects of enrofloxacin and 2, 4-Dichlorophenoxy acetic acid dimethylamine salt on the purified BTH enzyme were identified. IC50 values of these chemical substances were found to be 0.3101 and 0.4276 mM, respectively.

    REFERENCES

    1. Arnold, E. K., Beasley, V. R. (1989). The pharmacokinetics of chlorinated phenoxy acid herbicides: A literature review. Veterinary and Human Toxicology, 31: 121–125.
    2. Belem-Gonçalves, S., Tsan, P., Lancelin, J.M., Alves, T.L.M., Salim, V.M., Besson, F. (2006). Interfacial behaviour of bovine testis hyaluronidase. Biochem J., 398: 569–576.
    3. Blair, R. M., Fang, H., Branham, W. S., Hass, B. S., Dial, S. L., Moland, C. L., Tong, W., Shi, L., Perkins, R., Sheehan, D. M. (2000). The estrogen receptor relative binding affinities of 188 natural and Xenochemicals: Structural Diversity of Ligands. Toxicological Sciences, 54: 138–153.
    4. Botzki, A., Rigden, D.J., Braun, S., Nukui, M., Salmen, S., Hoechstetter, J., Bernhardt, G., Dove, S., Jedrzejas, M.J., Buschauer, A. (2004). L-Ascorbic acid 6-hexadecanoate, a potent hyaluronidase inhibitor. X-ray structure and molecular modeling of enzyme-inhibitor complexes. J Biol Chem., 279(44): 45990-45997.
    5. Ceylan, S. (2004). Special Pharmacology (Edition). Uludag University Veterinary Faculty, Bursa, pp. 247-248.
    6. Chain, E. and Duthie, E.S. (1939). A mucolytic enzyme in testis extracts. Nature, 144: 977–978.
    7. Cherr, G. N., Yudin, A. I., Overstreet, J. W. (2001). The dual functions of GPI-anchored PH-20: hyaluronidase and intracellular signaling. Matrix biology, 20: 515–525.
    8. Csoka, T.B., Frost, G.I., Stern, R. (1997). Hyaluronidases in tissue invasion. Invasion and Metastasis, 17: 297–311.
    9. Ecevit, O., Mennan, H., Aksoy, H.M., Akca, Ý. (1999). Agricultural Struggle Drugs and Their Effects on the Environment. O.M.Ü Faculty of Agriculture Course Book, Samsun. pp. 145.
    10. EPA., U. S. (1989). Information about pesticide use and report on the pesticide market. Environmental Protection Agency, 3: 15-20.
    11. Erne, K. (1966). Determination of phenoxy acetic herbicide residues in biological materials. Acta Vet. Scand, 7: 240–256.
    12. Extoxnet. (1996). Pesticide Information Profiles, http://extoxnet.orst.edu/pips/24-D.htm, Date of access: 02.10.2017
    13. Frost, G. I., Csóka, T., Stern, R. (1996). The Hyaluronidases: A Chemical, Biological and Clinical Overview. Trends in Glycoscience and Glycotechnology, 8: 419–434.
    14. Greiling, H. (1957). Spectrophotometric method for the determination of bacterial hyaluron idase. Hoppe-Seyler’s Zeitschrift fur physiologische Chemie, 309: 239–242.
    15. Hoechstetter, J. (2005). Characterisation of bovine testicular hyaluronidase and a hyaluronate lyase from Streptococcus agalactiae. Dissertation, 1–239.
    16. IARC (International Agency for Research on Cancer). (1977). Some fumigants, the herbicides 2,4-D and 2,4,5-T, chlorinated dibenzodioxins and miscellaneous Industrial Chemicals. IARC, 15: 111-138.
    17. Ibrahim, M.A., Bond, G.G., Burke, T.A., Cole, P., Dost, F.N., Enterline, P.E., Gough, M., et al. (1991). Weight of the evidence on the human carcinogenicity of 2,4-D. Environmental Health Perspectives, 96: 213–222.
    18. Kaessler, A., Nourrisson, M.R., Duflos, M., Jose, J. (2008). Indole carboxamides inhibit bovine testes hyaluronidase at pH 7.0 and indole acetamides activate the enzyme at pH 3.5 by different mechanisms. J Enzyme Inhib Med Chem, 23(5): 719-727.
    19. Kaya, M.O., Arslan, O., Guler, O.O. (2014). A new affinity method for purification of bovine testicular hyaluronidase enzyme and an investigation of the effects of some compounds on this enzyme. J Enzyme Inhib Med Chem, 30(4): 524–527.
    20. Keller, T., Skopp, G., Wu, M., Aderjan, R. (1994). Fatal overdose of 2,4-dichlorophenoxyacetic acid (2,4-D). Forensic Science International, 65: 13–18.
    21. Koca, M. (2001). The Investigation of acute toxicitiy of 2,4-dichlorophenoxyacetic acid and related behavioural changes on the lepistes (poecilia reticulata P., 1859). Gazi University, Ankara. pp. 1-57.
    22. Kreil, G. (1995). Hyaluronidases: A group of neglected enzymes. Protein science, 4: 1666–1669.
    23. Kumar, B.S.B., Pandita, S., Sharma, A., Jadhav, V., Soren, S., Mili, B., Ganaie, A.H., Mir, N.A., Kumar, N., Kumar, A.V. (2015). Regulation of postnatal development of testes and its association with puberty and fertility. Agricultural Reviews, 36: 339-344.
    24. Lindguist, N.G., Ulberg, S. (1971). Distribution of the herbicides 2,4,5-T and 2,4-D in pregnanat mice, Accumulation in the yolk sac ephitelium. Experientia, 27: 1439–1441.
    25. Meyer, K., Hobby, G.L., Chaffee, E., Dawson, M.H. (1940). Relationship between ‘Spreading Factor’ and Hyaluronidase. Experimental Biology and Medicine, 44: 294–296. 
    26. Meyer, K. (1971). Hyaluronidases. The Enzymes, 5: 307-320.
    27. Meyer, M.F., Kreil, G., Aschauer, H. (1997). The soluble hyaluronidase from bull testes is a fragment of the membrane-bound PH-20 enzyme. FEBS Letters, 413(2): 385–388.
    28. Olgen, S., Kaessler, A., Nebioglu, D., Jose, J. (2007). New potent indole derivatives as hyaluronidase inhibitors. Chem Biol Drug Des., 70(6): 547-551.
    29. Olgen, S., Kaessler, A., Kýlýç Kurt, Z., Jose, J. (2010). Investigation of aminomethyl indole derivatives as hyaluronidase inhibitors. Z Naturforsch C., 65(7-8): 445-450.
    30. Ozdas, E., Ates, U., Uyanýkgil,Y., Baka, M., Yavasoglu, A., Biçer, S., Ergen, G. (2006). Effect Of 2,4-D (2,4-Dichlorophenoxyacetic Acid) as a Herbicide on rats Testes. Ege Journal of Medicine, 45: 169–174.
    31. Pavan, M., Beninatto, R., Galesso, D., Panfilo, S., Vaccaro, S., Messina, L., Guarise, C. (2016). A new potential spreading factor: Streptomyces koganeiensis hyaluronidase. A comparative study with bovine testes hyaluronidase and recombinant human hyaluronidase of the HA degradation in ECM. Biochim Biophys Acta, 1860(4): 661-668.
    32. Pubchem. (2017). 2,4-Dichlorophenoxy acetic acide dimethyl amine salt, https://pubchem.ncbi.nlm.nih.gov/compound/2_4-    D_dimethylamine_salt, Date of access: 03.12.2017.
    33. Pubchem.(2017).Enrofloxacin,https://pubchem.ncbi.nlm.nih.gov/compound/Enrofloxacin, Date of access: 03.12.2017.
    34. Rigden, D.J., Botzki, A., Nukui, M., Mewbourne, R.B., Lamani, E., Braun, S., Von Angerer, E., Bernhardt, G., Dove, S., Buschauer, A., Jedrzejas, M.J. (2006). Design of new benzoxazole-2-thione-derived inhibitors of Streptococcus pneumoniae hyaluronan lyase: structure of a complex with a 2-phenylindole. Glycobiology, 16(8): 757-65.
    35. Takagaki, K., Nakamura, T., Izumi, J., Saitoh, H., Endo, M., Kojima, K., Kato, I., Majima, M. (1994). Characterization of hydrolysis and transglycosylation by testicular hyaluronidase using ion-spray mass spectrometry. Biochemistry, 33: 6503–6507.
    36. Tanyildizi, S., Bozkurt, T. (2003). The effects of lincomycin-spectinomycin and sulfamethoxazole-trimethoprim on hyaluronidase activities and sperm characteristics of rams. The Journal of Veterinary Medical Science, 65: 775–780.
    37. Wang, Y.S., Jaw, C.G., Chen, Y.L. (1994). Accumulation of 2,4-D and glyphosate in fish and water hyacinth. Water, Air, and Soil Pollution, 74:397–403 
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