Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Catalytic Hydrolysis of Phosphate Diesters as DNA Model with Tetranuclear Nickle (II) Complex

  • Sung, Nack-Do (Division of Applied Biology and Chemistry, The Research Center for Transgenic Cloned Pig., Chungnam National University) ;
  • Kim, Tae-Young (Department of Product Development & Registration, Syngenta Korea. Co. Ltd.)
  • Published : 2006.09.30
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Abstract

The novel tetranuclear nickel (II) complex is a high rate accelerator in promoting hydrolysis of phosphate diesters. Nickel-bound bis-nitrophenyl phosphate (BNPP) can be $10^4$ times more reactive than the unbound BNPP. The large rate of enhancements by the complex slightly under basic condition has shown high catalytic activity in phosphate diester cleavage. The bell-shaped pH-rate profile indicated that the nickel-oxide form of the tetranuclear complex or its kinetic equivalent was the active species for cleaving BNPP. The catalytic hydrolysis between tetranuclear nickel (II) complex and phosphate diester proceeds via the formation of bidentate coordination of the anionic phosphate to the Ni (II) atom. This reveals that the complex has the possibility as artificial nuclease.

Keywords

References

  1. Dugas, H. (1996) In Bioorganic Chemistry. (3rd ed.) pp. 388-389, Springer. New York
  2. Cowan, J. A. (2001) Chemical nucleases. Curr. Opin. Chem. Biol. 5, 634- 642 https://doi.org/10.1016/S1367-5931(01)00259-9
  3. Niittymaki, T. and Lonnberg, H. (2006) Artificial ribonucleases. Org. Biomol. Chem. 4, 15-25 https://doi.org/10.1039/b509022a
  4. Wilcox, D. E. (1996) Binuclear metallohydrolases, Chem. Rev. 96, 2435-2458 https://doi.org/10.1021/cr950043b
  5. Chin, J. (1997) Artificial dinuclear phosphoesterases. Curr. Opin. Chem. Biol. 1, 514-521 https://doi.org/10.1016/S1367-5931(97)80046-4
  6. Liu, C., Wang, M., Zhang, T., and Sun, H. (2004) DNA hydrolysis promoted by di-and multi-nuclear metal complexes. Coord. Chem. Rev. 248, 147-168 https://doi.org/10.1016/j.cct.2003.11.002
  7. Yashiro, M., Kaneiwa, H., Onaka, K., and Komiyama, M. (2004) Dinuclear $Zn^{2+}$ complexes in the hydrolysis of the phosphodiester linkage in a diribonucleoside monophosphate diester. Dalton Trans. 605-610
  8. Gupta, T. and Baranwal, B. P. (2006) Synthesis, characterization and phospho-diester bond cleavage studies of the dinuclear, thioacetatocobalt (II) of 3-methylsulfanylpropionic acid complex. Transt. Metal Chem. 31, 123-128 https://doi.org/10.1007/s11243-005-6371-6
  9. Williams, N. H. (2004) Models for biological phosphoryl transfer. Biochem. Biophys. Acta. 279-287
  10. Sung, N. D., Kim, D. W., Kwon, B. M., Kim, T. Y., and Suh, I. H. (2000) Biological activities of some organometallic compounds as artificial nuclease. Kor. J. Pestic. Sci. 4, 32-37
  11. Sung, N. D., Yun, K. S. (2005) The roles of metal ions and water molecules in the hydrolysis of bis(p-nitrophenyl)phosphate as a DNA model catalyzed by dinuclear Ni(II) complex. Agri. Biotech. 48, 115-119
  12. Sung, N. D., Yun, K. S., Kim, J. G., and Suh, I. W. (2000) $\mu$-aqua-pentaaqua-[$\mu$-3,6-bis(6'-methyl-2'-pyridyl)pyridazine] chlorodinickel (II) trichloridetrihydrate, Acta Crystallogr. C 56, e370-e371
  13. Kim, M. J., Lee, J. H., Lee H. J., and Sung, N. D. (1999) The crystal structure of [3,6-bis(6'-methyl-2'-pyridyl) pyridazine]$ZnCl_{2},C_{16}H_{16}N_{4}.\;ZnCl_{2}$. Kor. J. Crystallogrl. 10, 119-124
  14. Choi, K. Y., Sung, N. D., Yun, K. S., Park, Y. S., Kim, J. G., and Suh, I. H. (2001) Bis[3,6-bis(6'-methyl-2'-pyridyl) pyridazine-$k^{2}N^{2},N^{3}$]chlorocopper (II) perchlorate. Acta. Crystallogr. C 57, 47-48
  15. Kwon, B. M., Lee, C. O., Choi, S. U., and Sung, N. D. (2006) Cytotoxic effects of some transition metals, Nickel(II), Copper(II) and Zinc(II) with 3,6-bis(2'-pyridyl) pyridazines complexes. J. Kor. Soc. Appl. Biol. Chem. 49, 21-24
  16. Kim, T. Y. (1999) Synthesis and biological activity of tetranuclear- Nickel(II) complex. M.Sc. Degree Thesis. Graduate School, Chungnam National University, Daejeon, Korea
  17. Sung, N. D., Yun, K. S., Kim, T. Y., Choi, K. Y., Suh, M., Kim, G. J., Suh, I. H. and Chin, J. (2001) Synthesis and characterization of a novel tetranuclear nickel(II) complex: [$Ni_{4}(\mu-OH)_{2}(\mu-dppn)_{4}(\mu-H_{2}O)_{2}](Cl)(ClO_{4})_{5}\;9H_{2}O$, (dppn = 3,6-bis (2'-pyridyl)pyridazine). Inorg. Chem. Comm. 4, 377-380 https://doi.org/10.1016/S1387-7003(01)00195-2
  18. Wahlstrom, E. E. (1979) In Optical Crystallography. (6th ed.) John Wiely and Sons, New York
  19. Sheldrick, G. M. (1990) Phase Annealing in SHELX-90: Direct Methods for Larger Structures, Acta. Crystallogr. A46, 467-473
  20. Sheldrick, G. M. (1997) SHELXL97. Release 97-1. Program for the Refinement of Crystal Structures, University of Gttingen, Germany
  21. Johnson, C. K. (1976) ORTEP-A Fortran Thermal Ellipsoid Plot Program, Technical Report ORNL-5138, Oak Ridge National Lab., USA
  22. Gabe, E. J., Le Page, Y., Charland, J. P., Lee, F. L. and White, P. S. (1989) NRCVAX-an Interactive Program System for Structure Analysis. J. Appl. Crystallogr. 22, 384- 387 https://doi.org/10.1107/S0021889889003201
  23. Sung, N. D. (1994) The transition state analog for metal catalyzed hydrolysis of an ester. Agri. Chem. Biotechnol. 37, 447-450
  24. Sung, N. D. (1998) Hydrolysis of phosphate diesters as nucleic acid model, Agri. Chem. Biotechnol. 41, 611-612
  25. Young, M. J. and Chin. J. (1995) Dinuclear Copper (II) Complex That Hydrolyzes RNA, J. Am. Chem. Soc. 117, 10577-10578 https://doi.org/10.1021/ja00147a022
  26. Wall. M. Hynes, R. C. and Chin, J. (1993) Double Lewis acid activation in phosphate diester cleavage, Angew, Chem. Int. Ed. Engl. 32, 1633-1635 https://doi.org/10.1002/anie.199316331
  27. Linkletter, B. and Chin, J. (1995) Rapid Hydrolysis of RNA with a Cu Complex, Angew. Chem. Int. Ed. Engl. 34, 472- 474 https://doi.org/10.1002/anie.199504721
  28. Zalatan, J. G. and Herschlag, D. (2006) Alkaline phosphatase mono- and diesterase reactions: Comparative transition state analysis. J. Am. Chem. Soc. 128, 1293-1303 https://doi.org/10.1021/ja056528r
  29. Williams, N. H., Cheung, W. and Chin, J. (1998) Reactivity of phosphate diesters doubly coordinated to a dinuclear cobalt (III) complex: Dependence of the reactivity on the basicity of the leaving group. J. Am. Chem. Soc. 120, 8079- 8087 https://doi.org/10.1021/ja980660s
  30. Sung, N. D., Seo, J. S., Rosemary, C. H., Williams, D. and Chin, J. (1998) Structure and reactivity of a dinuclear cobalt (III) complex with peroxide and phosphate diester analogues bridging the metal ions. J. Am. Chem. Soc. 120, 9943-9944 https://doi.org/10.1021/ja9811905