Pharmaceutical Chemistry Journal

, Volume 51, Issue 4, pp 272–276 | Cite as

Biochemical Evaluation of Copper Compounds Derived from O- and N-/O- Donor Ligands

  • Muhammad Nadeem Akhtar
  • Muhammad Shahid
  • Masaaki Sadakiyo
  • Muhammad Ikram
  • Sadia Rehman
  • Irshad Ahmed
Article
First Online:
Received:

Compounds [CuII 2(benz)4(Hbenz)2] (1) and [CuII(ppa)2(H2O)2] n (2), where benz = benzoate and ppa = 3-pyridinepropionic acid, were synthesized and studied for their 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity and the inhibition of enzymes such as acetylcholinesterase (AChE), butyrylcholinesterase (BChE), lipoxygenase (LOX), urease, chymotrypsin and α-glucosidase. The synthesized compounds were also studied by hemolytic method for their cytotoxicity and found to be low-toxicity substances. For AChE inhibition, compound 2 showed IC50 = 31.22 ± 0.45 μM, as compared to compound 1with IC50 = 36.52 ± 0.44 μM. Both compounds showed comparably low activity against BChE and were also active against urease, but compound 1 exhibited selective anti-urease activity. The anti-α-glucosidase activity of both compounds was comparable with that of standard drug used.

Keywords

copper complexes benzoate 3-pyridinepropionic acid antioxidant activity α-enzyme inhibition hemolytic activity 
This is a preview of subscription content, log in to check access.

References

  1. 1.
    (a) R. Sessoli, D. Gatteschi, A. Caneschi, M. A. Novak, Nature, 365, 141 – 143 (1993); (b) P. Horcajada, R. Gref, T. Baati, et al., Chem. Rev., 112, 1232 – 1268 (2012).Google Scholar
  2. 2.
    (a) M. D. Allendorf, C. A. Bauer, R. K. Bhakta, and R. J. T. Houka, Chem. Soc. Rev., 38, 1330 – 1352 (2009); (b) S. Mukhopadhyay, S. K. Mandal, S. Bhaduri, and W. H. Armstrong, Chem. Rev., 104, 3981 – 4026 (2004).Google Scholar
  3. 3.
    (a) S. Rafique, M. Idrees, A. Nasim, et, al., J. Biotech. Mol. Bio. Rev., 5(2), 38 – 45 (2010); (b) D. Chen, V. Milacic, M. Frezza, and Q. P. Dou, Curr. Pharm. Des., 15(7), 777 – 791 (2009).Google Scholar
  4. 4.
    O. M. Yaghi, H. L. Li, C. Davis, et al., Acc. Chem. Res., 31, 474 – 484 (1998).CrossRefGoogle Scholar
  5. 5.
    M. J. Zaworotko, Chem. Soc. Rev., 23, 283 – 288 (1994).CrossRefGoogle Scholar
  6. 6.
    (a) N. Raman, J. Joseph, A. Sakthivel, and R. Jeyamurugan, J. Chil. Chem. Soc., 54, 354 – 357 (2009); (b) J. R. Sorenson, J. Chem. Br., 1110 – 1113 (1984).Google Scholar
  7. 7.
    M. Alkan, H. Yüksek, Ö. G.-Kol, and M. Calapoðlu, Molecules, 13(1), 107 – 121 (2008).Google Scholar
  8. 8.
    (a) S. Nochi, N. Asakawa, and T. Sato, Biol. Pharm. Bull., 18, 1145 – 1147 (1995); (b) W. Tong, E. R. Collantes, Y. Chen, and W. J. Welsh, J. Med. Chem., 39, 380 – 387 (1996).Google Scholar
  9. 9.
    Q. Yu, H. W. Holloway, T. Utsuki, et al., J. Med. Chem., 42, 1855 – 1861 (1999).CrossRefPubMedGoogle Scholar
  10. 10.
    M. Ikram, S.-U. Rehman, S. Rehman, et al. Inorg. Chim. Acta, 390, 210 – 216 (2012).CrossRefGoogle Scholar
  11. 11.
    (a) M. Arfan, M. Ali, H. Ahmad, et al., J. Enz. Inhib. Med. Chem., 25, 296 – 299 (2010); (b) L. Zhang, S. B. Mulrooney, A. F. K. Leung, et al., Biometals, 19, 503 – 511 (2006).Google Scholar
  12. 12.
    J. F. G. Vliegenthart and G. A. Veldink, Free Radicals in Biology, W. A. Pryor (ed.), Academic Press, New York (1982),Vol. 5, pp. 29 – 64.Google Scholar
  13. 13.
    M. J. Nelson, S. Seitz, In Active Oxygen in Biochemistry, J. S. Valentine, C. S. Foote, A. Greenberg, and J. F. Liebman, (eds.), Chapman and Hall, Glasgow (1995), pp. 276 – 312.Google Scholar
  14. 14.
    O. Motabar, Z. D. Shi, E. Goldin, et al., Anal. Biochem., 390, 79 – 84 (2009).CrossRefPubMedPubMedCentralGoogle Scholar
  15. 15.
    (a) N. Yasumatsu, Y. Yoshikawa, Y. Adachi, and H. Sakurai, Bioorg. Med. Chem., 15, 4917 – 4922 (2007); (b) H. Sakurai, A. Katoh, and Y. Yoshikawa, Bull. Chem. Soc. Jpn., 79, 1645 – 1664 (2006).Google Scholar
  16. 16.
    M. N. Akhtar, W. T. A. Harrison, M. Shahid, et al., Transition Met. Chem., 41, 325 – 330 (2016).CrossRefGoogle Scholar
  17. 17.
    (a) T. Kawata, H. Uekusaand, and S. Ohba, Acta Cryst. B, 48, 253 – 261 (1992); (b) Y.-H. Wang, M.-C. Suen, H.-T. Lee, and J.-C. Wang, Polyhedron, 25, 2944 – 2952 (2006).Google Scholar
  18. 18.
    N. Noor, R. A. Sarfraz, S. Y. Ali, and M. Shahid, Food Chem., 143, 362 – 366 (2014).CrossRefPubMedGoogle Scholar
  19. 19.
    G. L. Ellman, K. D. Courtney, V. Andres, and R. M. Featherstone, Biochem. Pharmacol., 7, 88 – 95 (1961).CrossRefPubMedGoogle Scholar
  20. 20.
    A. L. Tappel, Arch. Biochem. Biophys., 44(2), 378 – 395 (1953).CrossRefPubMedGoogle Scholar
  21. 21.
    M. W. Weatherburn, Anal. Chem., 39, 971 – 974 (1967).CrossRefGoogle Scholar
  22. 22.
    A. Lodhi, M. I. Choudhary, M. M. Ahmad, and S. Ahmad, J. Enz. Inhib. Med. Chem., 23(3), 400 – 405 (2008).CrossRefGoogle Scholar
  23. 23.
    P. Chapdelaine, R. Roland, Tremblay, and J. Y. Dube, Clin. Chem., 24, 208 – 211 (1978).Google Scholar
  24. 24.
    W. Zheng, J. Li, Z. Qiu, et al., Toxicol. Appl. Pharmacol., 264, 65 – 72 (2012).CrossRefPubMedGoogle Scholar
  25. 25.
    Q. Yu, H. W. Holloway, T. Utsuki, et al., J. Med. Chem., 42, 1855 – 1861 (1999).CrossRefPubMedGoogle Scholar
  26. 26.
    C. Geula and S. Darvesh, Drugs Today, 40, 711 – 721 (2004).CrossRefPubMedGoogle Scholar
  27. 27.
    B. Ashley, Neurobiol. Aging, 23(6), 1031 – 1038 (2002).CrossRefGoogle Scholar
  28. 28.
    J. Patocka, K. Kuca, D. Jun, Acta Medica, 47(4), 215 – 228 (2004).PubMedGoogle Scholar
  29. 29.
    G. F. Makhaeva, A. Y. Aksinenko, V. B. Sokolov, et al., Bioorg. Med. Chem. Lett., 19(19), 5528 – 5530 (2009).CrossRefPubMedGoogle Scholar
  30. 30.
    N. H. Greig, T. Utsuki, D. K. Ingram, et al., Proc. Natl. Acad. Sci. USA, 102, 17213 – 172218 (2005).CrossRefPubMedPubMedCentralGoogle Scholar
  31. 31.
    N. H. Greig, T. Utsuki, Q. Yu, et al. Curr. Med. Res. Opin., 17, 159 – 165 (2001).CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Muhammad Nadeem Akhtar
    • 1
  • Muhammad Shahid
    • 2
  • Masaaki Sadakiyo
    • 3
  • Muhammad Ikram
    • 4
  • Sadia Rehman
    • 4
  • Irshad Ahmed
    • 5
  1. 1.Department of ChemistryUniversity of AgricultureFaisalabadPakistan
  2. 2.Department of BiochemistryUniversity of AgricultureFaisalabadPakistan
  3. 3.International Institute for Carbon-Neutral Energy Research (I2CNER)Kyushu UniversityFukuokaJapan
  4. 4.Department of ChemistryAbdul Wali Khan UniversityMardanPakistan
  5. 5.Department of PharmacyThe Islamia University of BahawalpurBahawalpurPakistan

Personalised recommendations