Skip to main content
SpringerLink
Log in

Synthesis, characterization, and studies on DNA binding of a new Mg(II) complex with N1,N8-bis(1-methyl-4-nitropyrrole-2-carbonyl)triethylenetetramine

  • Published:
Biochemistry (Moscow) Aims and scope Submit manuscript

Abstract

A new Mg(II) complex of MgL(NO3)2 (here L = N1,N8-bis(1-methyl-4-nitropyrrole-2-carbonyl)triethylenetetramine) has been synthesized and characterized. The interactions between the Mg(II) complex and calf thymus DNA has been investigated using UV spectra, fluorescent spectra, viscosity, thermal denaturation, and molecular modeling. The cleavage reaction on plasmid DNA has been monitored by agarose gel electrophoresis. The experimental results show that the mode of binding of the complex to DNA is non-classical electrostatic action and the complex can cleave pBR322 DNA.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

CCC:

supercoiled DNA form

DFT:

density functional theory

DMF:

dimethylformamide

DMSO:

dimethyl sulfoxide

HRMS:

high resolution mass spectrum

OC:

open circular DNA form

TMS:

tetramethyl silicon

References

  1. Erkkila, K. E., Odom, D. T., and Barton, J. K. (1999) Chem. Rev., 99, 2777–2796.

    Article  PubMed  CAS  Google Scholar 

  2. Vester, B., and Wengel, J. (2004) Biochemistry, 43, 13233–13241.

    Article  PubMed  CAS  Google Scholar 

  3. Pinskaya, M., Romanova, E., Volkov, E., Deprez, E., Leh, H., Brochon, J. C., Mouscadet, J. F., and Gottikh, M. (2004) Biochemistry, 43, 8735–8743.

    Article  PubMed  CAS  Google Scholar 

  4. Cassidy, S. A., Strekowski, L., Wilson, W. D., and Fox, K. R. (1994) Biochemistry, 33, 15338–15347.

    Article  PubMed  CAS  Google Scholar 

  5. Thuong, N. T., and Helene, C. (1993) Angew. Chem. Int. Ed. Engl., 32, 666–690.

    Article  Google Scholar 

  6. Kumar, V. A., and Ganesh, K. N. (2005) Acc. Chem. Res., 38, 404–412.

    Article  PubMed  CAS  Google Scholar 

  7. Bentin, T., and Nielsen, P. E. (1996) Biochemistry, 35, 8863–8869.

    Article  PubMed  CAS  Google Scholar 

  8. Nicolaou, K. C., Ajito, K., Komatus, H., Smith, B. M., Li, T. H., Egan, M. G., and Gomez-Paloma, L. (1995) Angew. Chem. Int. Ed. Engl., 34, 576–578.

    Article  CAS  Google Scholar 

  9. White, S., Szewczyk, J. W., Turner, J. M., Baird, E. E., and Dervan, P. B. (1998) Nature, 391, 468–471.

    Article  PubMed  CAS  Google Scholar 

  10. Kielkopf, C. L., White, S. E., Szewczyk, J. W., Turner, J. M., Baird, E. E., and Dervan, P. B. (1998) Science, 282, 111–115.

    Article  PubMed  CAS  Google Scholar 

  11. Pyle, A. M., Rehmann, J. P., Meshoyrer, R., Kumar, C. V., Turro, N. J., and Barton, J. K. (1989) J. Am. Chem. Soc., 111, 3051–3058.

    Article  CAS  Google Scholar 

  12. Satyanarayana, S., Dabrowiak, J. C., and Chaires, J. B. (1992) Biochemistry, 31, 9319–9324.

    Article  PubMed  CAS  Google Scholar 

  13. Melander, C., Burnett, R., and Gottesfeld, J. M. (2004) J. Biotechnol., 112, 195–220.

    Article  PubMed  CAS  Google Scholar 

  14. Wade, W. S., Mrksich, M. M., and Dervan, P. B. (1992) J. Am. Chem. Soc., 114, 8783–8794.

    Article  CAS  Google Scholar 

  15. Trauger, J. W., Baird, E. E., and Dervan, P. B. (1996) Nature, 382, 559–561.

    Article  PubMed  CAS  Google Scholar 

  16. White, S., Baird, E. E., and Dervan, P. B. (1997) Chem. Biol., 4, 569–578.

    Article  PubMed  CAS  Google Scholar 

  17. Dickinson, L. A., Burnett, R., Melander, C., Edelson, B. S., Arora, P. S., Dervan, P. B., and Gottesfeldl, J. M. (2004) Chem. Biol., 11, 1583–1594.

    Article  PubMed  CAS  Google Scholar 

  18. Dickinson, L. A., Trauger, J. W., Baird, E. E., Ghazal, P., Dervan, P. B., and Gottesfeld, J. M. (1999) Biochemistry, 38, 10801–10807.

    Article  PubMed  CAS  Google Scholar 

  19. Yang, P., Ren, R., Guo, M. L., and Song, A. X. (2004) J. Biol. Inorg. Chem., 9, 495–506.

    Article  PubMed  CAS  Google Scholar 

  20. Liu, Y. M., Wenning, L. R., Lynch, M., and Reineke, T. M. (2004) J. Am. Chem. Soc., 126, 7422–7423.

    Article  PubMed  CAS  Google Scholar 

  21. Liu, Y. M., and Reineke, T. M. (2005) J. Am. Chem. Soc., 127, 3004–3015.

    Article  PubMed  CAS  Google Scholar 

  22. Tweedle, M. F., and Wilson, L. J. (1976) J. Am. Chem. Soc., 98, 4824–4834.

    Article  CAS  Google Scholar 

  23. Greenman, D. L., Morrissey, R. L., Blakemore, W., Crowell, J., Siitonen, P., Felton, P., Allen, R., and Cronin, G. (1996) Fundament. Appl. Toxicol., 29, 185–193.

    Article  CAS  Google Scholar 

  24. Doyle, F. M., and Liu, Z. (2003) J. Colloid Interface Sci., 258, 396–403.

    Article  PubMed  CAS  Google Scholar 

  25. Zhou, C. Y., Zhao, J., Wu, Y. B., Yin, C. X., and Yang, P. (2007) J. Inorg. Biochem., 101, 10–18.

    Article  PubMed  CAS  Google Scholar 

  26. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2003) GAUSSIAN03 (Revision A.1), Gaussian, Inc., Pittsburgh, PA.

    Google Scholar 

  27. Becke, A. D. (1988) Phys. Rev. A, 38, 3098–3100.

    Article  PubMed  CAS  Google Scholar 

  28. Lee, C., Yang, W., and Parr, R. G. (1988) Phys. Rev. B, 37, 785–789.

    Article  CAS  Google Scholar 

  29. Stevens, P. J., Devlin, J. F., Chabalowski, J. F., and Frisch, M. J. (1994) J. Phys. Chem., 98, 11623–11627.

    Article  Google Scholar 

  30. Waring, M. J. (1977) in Drug Action at the Molecular Level (Roberts, G. C. K., ed.) Maemillar, London.

    Google Scholar 

  31. Waring, M. J. (1965) J. Mol. Biol., 13, 269–282.

    Article  PubMed  CAS  Google Scholar 

  32. Chaires, J. B., Dattagupta, N., and Crothers, D. M. (1982) Biochemistry, 21, 3933–3940.

    Article  PubMed  CAS  Google Scholar 

  33. Wakelin, L. P. G., Atwell, G. J., Rewcastle, G. W., and Denny, W. A. (1987) J. Med. Chem., 30, 855–861.

    Article  PubMed  CAS  Google Scholar 

  34. Li, Q. S., Yang, P., Wang, H. F., and Guo, M. L. (1996) J. Inorg. Biochem., 64, 181–195.

    Article  PubMed  CAS  Google Scholar 

  35. Shi, S., Liu, J., Li, J., Zheng, K. C., Huang, X. M., Tan, C. P., Chen, L. M., and Ji, L. N. (2006) J. Inorg. Biochem., 100, 385–395.

    Article  PubMed  CAS  Google Scholar 

  36. Lepecq, J. B., and Paoletti, C. (1967) J. Mol. Biol., 27, 87–106.

    Article  PubMed  CAS  Google Scholar 

  37. Zhou, C. Y., Xi, X. L., and Yang, P. (2007) Biochemistry (Moscow), 72, 37–43.

    Article  CAS  Google Scholar 

  38. Li, F. H., Zhao, G. H., Wu, H. X., Lin, H., Wu, X. X., Zhu, S. R., and Lin, H. K. (2006) J. Inorg. Biochem., 100, 36–43.

    Article  PubMed  CAS  Google Scholar 

  39. Li, Y. Q., White, J., David, S., Gary, S., and Michael, S. (2001) Biotechnol. Progr., 17, 348–354.

    Article  CAS  Google Scholar 

  40. Zeynep, D., Ralph, P., Jan, A. R. S., Sukunath, N., and Clemens, R. (2004) J. Am. Chem. Soc., 126, 4762–4763.

    Article  Google Scholar 

  41. Thierry, D. J. (2006) Photochem. Photobiol. B: Biol., 82, 45–52.

    Article  Google Scholar 

  42. Silvestri, A., Barone, G., Ruisi, G., Giudice, M. T. L., and Tumminello, S. (2004) J. Inorg. Biochem., 98, 589–594.

    Article  PubMed  CAS  Google Scholar 

  43. Foloppel, M. P., Rault, S., Thurston, D. E., Jenkins, T. C., and Robbal, M. (1996) Eur. J. Med. Chem., 31, 407–410.

    Article  Google Scholar 

  44. Selvakumar, B., Rajendiran, V., Maheswari, P. U., Evans, H. S., and Palaniandavar, M. (2006) J. Inorg. Biochem., 100, 316–330.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Changzhi University, Shanxi, Changzhi, 046011, PR China

    Cheng-Yong Zhou

  2. Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan, Shanxi, 030006, PR China

    Yan-Bo Wu & Pin Yang

Authors
  1. Cheng-Yong Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yan-Bo Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pin Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cheng-Yong Zhou.

Additional information

Published in Russian in Biokhimiya, 2008, Vol. 73, No. 3, pp. 303–310.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM07-200, February 3, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhou, CY., Wu, YB. & Yang, P. Synthesis, characterization, and studies on DNA binding of a new Mg(II) complex with N1,N8-bis(1-methyl-4-nitropyrrole-2-carbonyl)triethylenetetramine. Biochemistry Moscow 73, 245–251 (2008). https://doi.org/10.1134/S0006297908030024

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0006297908030024

Key words

Search

Navigation