Skip to main content

Advertisement

SpringerLink
Log in

Metal Complexes of 1,2,4-Triazole Based Ligand: Synthesis, Structural Elucidation, DFT Calculations, Alpha-Amylase and Alpha-Glucosidase Inhibitory Activity Along with Molecular Docking Studies

  • Research
  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

In search of 1,2,4-triazole-based antidiabetic agents, new mixed-ligand chelates of the type, [M(L)(H2O)3] (where M = Co(II), Ni(II), Cu(II) and Zn(II)), were synthesized using 2-(((3-mercapto-5-(pyridin-3-yl)-4H-1,2,4-triazol-4-yl)imino)methyl)-4-nitrophenol (H2L1) ligand and the corresponding metal acetates in 1:1 molar ratio. FTIR, NMR, mass, UV–Vis, elemental analyses, conductivity measurements, ESR, XRD, TGA, SEM, and EDAX studies were used to determine the nature of bonding, coordination characteristics and the stability of compounds. Spectral and physico-analytical studies suggest that the ligand functioned in a binegative tridentate manner with phenolic-O, azomethine-N and thiol-S as the coordinating sites and an octahedral geometry was proposed for the metal complexes. The quantum computational calculations of the synthesized compounds were executed in the ground state using DFT/B3LYP level with 6-311++G as basis set. In vitro alpha-amylase and alpha-glucosidase inhibitory assay revealed moderate to good results for the synthesized compounds and especially the complex 3 against alpha-amylase and complex 4 against alpha-glucosidase were found to be effective inhibitors. Additionally, the compounds were explored for molecular docking studies against the human pancreatic alpha-amylase (PDB id: 1BSI) and alpha-glucosidase (PDB id: 5ZCC). The molecular docking calculations of complex 3 into 1BSI revealed a binding energy of − 8.6 kcal/mol, whereas that of complex 4 against 5ZCC resulted in a binding energy of − 7.4 kcal/mol respectively, both of which exceeds that of the standard Acarbose.

Graphical Abstract

New Schiff base ligand and its transition metal chelates were synthesized. Furthermore, the synthesized compounds were examined for in vitro alpha-amylase and alpha-glucosidase inhibitory activity.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data Availability

No data was used for the research described in the article.

References

  1. M. Dioguardi, S. Cantore, S. Scacco, C. Quarta, D. Sovereto, F. Spirito, M. Alovisi, G. Troiana, R. Aiuto, D. Garcovich, V. Crincoli, L. Laino, M. Covelli, A. Malcangi, L.L. Muzio, A. Ballini, M. Di Cosola, J. Pers. Med. 12, 235 (2022)

    Article  PubMed  PubMed Central  Google Scholar 

  2. L. Deswal, V. Verma, D. Kumar, Y. Deswal, A. Kumar, R. Kumar, M. Parshad, M. Bhatia, Chem. Pap. 76, 7607 (2022)

    Article  CAS  Google Scholar 

  3. H. Sun, P. Saeedi, S. Karuranga, M. Pinkepank, K. Ogurtsova, B.B. Duncan, C. Stein, A. Chan, C. Basit, J.C. Mbanya, M.E. Pavkov, A. Ramchandran, S.H. Wild, S. James, W.H. Herman, P. Zhang, C. Boomer, S. Kuo, E. Boyko, D.J. Magliano, Diabetes Res. Clin. Pract. 183, 109119 (2022)

    Article  PubMed  Google Scholar 

  4. L. Deswal, V. Verma, D. Kumar, C.P. Kaushik, A. Kumar, Y. Deswal, S. Punia, Arch. Pharm. 353, 2000090 (2020)

    Article  CAS  Google Scholar 

  5. W.S. Azar, R. Njeim, A.H. Fares, N.S. Azar, S.T. Azar, M. El Sayed, A.A. Eid, Rev. Endocr. Metab. Disord. 21, 451 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. A. Kumari, C. Singh, J. Drug Deliv. Ther. 9, 1123 (2019)

    Google Scholar 

  7. Y. Liang, M. Li, Y. Yang, L. Qiao, H. Xu, B. Guo, ACS Nano 16, 3194 (2022)

    Article  CAS  PubMed  Google Scholar 

  8. A. Ito, I. Horie, M. Miwa, A. Sako, T. Niri, Y. Nakashima, R. Shigeno, A. Haraguchi, S. Natsuda, S. Akazawa, A. Kamada, A. Kawakami, N. Abriu, J. Diabetes Investig. 12, 1367 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Y. Deswal, S. Asija, A. Dubey, L. Deswal, D. Kumar, D.K. Jindal, J. Devi, J. Mol. Struct. 1253, 132266 (2022)

    Article  CAS  Google Scholar 

  10. T.C. Farias, H.Y. Kawaguti, M.G.B. Koblitz, Biocat. Agric Biotech. 35, 102054 (2021)

    Article  CAS  Google Scholar 

  11. L. Deswal, V. Verma, J.S. Kirar, D. Kumar, Y. Deswal, A. Kumar, M. Bhatia, Res. Chem. Intermed. 49, 1059 (2023)

    Article  CAS  Google Scholar 

  12. P. Agarwal, S. Asija, Y. Deswal, N. Kumar, J. Indian Chem. Soc. 99, 100556 (2022)

    Article  CAS  Google Scholar 

  13. A.S. Dabhi, N.R. Bhatt, M.J. Shah, J. Clin. Diagnostic Res. 7, 3023 (2013)

    CAS  Google Scholar 

  14. T. Fujisawa, H. Ikegami, K. Inoue, Y. Kawabata, T. Ogihara, Metabolism 54, 387 (2005)

    Article  CAS  PubMed  Google Scholar 

  15. O.M. Ogunyemi, A.G. Gyebi, J.O. Adebayo, J.A. Oguntola, C.O. Olaiya, S.N. Appl, Sci. 2, 1 (2020)

    Article  Google Scholar 

  16. G. Lopes, M. Barbosa, P.B. Andrade, P. Valentao, J. Appl. Phycol. 31, 3143 (2019)

    Article  CAS  Google Scholar 

  17. Y. Deswal, S. Asija, D. Kumar, D.K. Jindal, G. Chandan, V. Panwar, S. Saroya, N. Kumar, Res. Chem. Intermed. 48, 703 (2022)

    Article  CAS  Google Scholar 

  18. W. Zafar, S.H. Sumrra, Z.H. Chohan, Eur. J. Med. Chem. 222, 113602 (2021)

    Article  CAS  PubMed  Google Scholar 

  19. E. Stingaci, M. Zveaghinteva, S. Pogrebnoi, L. Lupascu, V. Valica, L. Uncu, A. Smetanscaia, M. Drumea, A. Petrou, A. Ciric, J. Glamoclija, Bioorg. Med. Chem. Lett. 30, 127368 (2020)

    Article  CAS  PubMed  Google Scholar 

  20. H.A. El-Sherief, B.G. Youssif, S.N.A. Bukhari, A.H. Abdelazeem, M. Abdel-Aziz, H.M. Abdel-Rahman, Eur. J. Med. Chem. 156, 774 (2018)

    Article  CAS  PubMed  Google Scholar 

  21. T.T. Calam, Int. J. Environ. Anal. Chem. 99, 1298 (2019)

    Article  Google Scholar 

  22. B. Kapron, J.J. Luszczki, A. Płazińska, A. Siwek, T. Karcz, A. Grybos, G. Nowak, A. Makuch, K. Walczak, E. Langner, K. Szalast, Eur. J. Pharm. Sci. 129, 42 (2019)

    Article  CAS  PubMed  Google Scholar 

  23. D. Dixit, P.K. Verma, R.K. Marwaha, J. Iran. Chem. Soc. 18, 2535 (2021)

    Article  CAS  Google Scholar 

  24. M.A. Malik, O.A. Dar, P. Gull, M.Y. Wani, A.A. Hashmi, MedChemComm 9, 409 (2018)

    Article  CAS  PubMed  Google Scholar 

  25. N. Kumar, S. Asija, Y. Deswal, S. Saroya, A. Kumar, Res. Chem. Intermed. 48, 5133 (2022)

    Article  CAS  Google Scholar 

  26. N. Kumar, S. Asija, Y. Deswal, S. Saroya, A. Kumar, J. Devi, Phosphorus Sulfur Silicon Relat. Elem. 197, 952 (2022)

    Article  CAS  Google Scholar 

  27. S. Saroya, S. Asija, N. Kumar, Y. Deswal, J. Indian Chem. Soc. 99, 100379 (2022)

    Article  CAS  Google Scholar 

  28. S. Sharma, S. Gupta, A.K. Narula, Indian J. Chem. Sect. A 33A, 1119 (1994)

    Google Scholar 

  29. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 16 Revision B.01 (Gaussian Inc, Wallingford CT, 2010)

    Google Scholar 

  30. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157, 200 (1989)

    Article  CAS  Google Scholar 

  31. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988)

    Article  CAS  Google Scholar 

  32. S. Khokhar, Y. Feng, M.R. Campitelli, R.J. Quinn, J.N. Hooper, M.G. Ekins, R.A. Davis, J. Nat. Prod. 76, 2100 (2013)

    Article  CAS  PubMed  Google Scholar 

  33. E.H. Rydberg, G. Sidhu, H.C. Vo, J. Hewitt, H.C. Côte, Y. Wang, S. Numao, R.T. MacGillivray, C.M. Overall, G.D. Brayer, S.G. Withers, Protein Sci. 8, 635 (1999)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. W. Auiewiriyanukul, W. Saburi, K. Kato, M. Yao, H. Mori, FEBS Lett. 592, 2268 (2018)

    Article  CAS  PubMed  Google Scholar 

  35. P.W. Rose, A. Prlic, C. Bi, W.F. Bluhm, C.H. Christie, S. Dutta, R.K. Green, D.S. Goodsell, J.D. Westbrook, J. Woo, J. Young, C. Zardecki, H.M. Berman, P.E. Bourne, S.K. Burley, Nucleic Acids Res. 43, 345 (2015)

    Article  Google Scholar 

  36. G.M. Sastry, M. Adzhigirey, T. Day, R. Annabhimoju, W. Sherman, J. Comput. Aided Mol. Des. 27, 221 (2013)

    Article  PubMed  Google Scholar 

  37. A. Dubey, A. Marabotti, P.W. Ramteke, A. Facchiano, Future Med. Chem. 8, 841 (2016)

    Article  CAS  PubMed  Google Scholar 

  38. A. Dubey, A. Marabotti, P.W. Ramteke, A. Facchiano, Biochem. Biophys. Res. Commun. 473, 449 (2016)

    Article  CAS  PubMed  Google Scholar 

  39. S. Bharadwaj, A. Dubey, N.K. Kamboj, A.K. Sahoo, S.G. Kang, U. Yadava, Sci. Rep. 11, 10169 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. A. Dubey, S. Dotolo, P.W. Ramteke, A. Facchiano, A. Marabotti, Biomolecules 9, 5 (2019)

    Article  Google Scholar 

  41. B. Kumar, J. Devi, A. Manuja, Res. Chem. Intermed. 49, 2277 (2023)

    Article  Google Scholar 

  42. Z. Xiao, R. Storms, A. Tsang, Anal. Biochem. 351, 146 (2006)

    Article  CAS  PubMed  Google Scholar 

  43. J.B. Xiao, P. Hogger, Curr. Med. Chem. 22, 23 (2015)

    Article  PubMed  Google Scholar 

  44. M.A. Neelakantan, S.S. Marriappan, J. Dharmaraja, T. Jeyakumar, K. Muthuku-maran, Spectrochim. Acta-A: Mol. Biomol Spectrosc. 71, 628 (2008)

    Article  CAS  PubMed  Google Scholar 

  45. V.P. Radha, S. Chitra, S. Jonekirubavathi, I.M. Chung, S.H. Kim, M. Prabakaran, J. Coord. Chem. 73, 1009 (2020)

    Article  CAS  Google Scholar 

  46. S. Saroya, S. Asija, Y. Deswal, N. Kumar, D. Kumar, D.K. Jindal, P. Puri, S. Kumar, Res. Chem. Intermed. 11, 4671 (2022)

    Article  Google Scholar 

  47. V.V. Dhayabaran, T.D. Prakash, R. Renganathan, E. Friehs, D.W. Bahnemann, J. Fluoresc. 27, 135 (2017)

    Article  CAS  PubMed  Google Scholar 

  48. A.A. Olanrewaju, F.S. Fabiyi, C.U. Ibeji, E.G. Kolawole, R. Gupta, J. Mol. Struct. 1211, 128057 (2020)

    Article  CAS  Google Scholar 

  49. B. Kumari, K. Singh, A. Sharma, Chem. Data Coll. 38, 100833 (2022)

    CAS  Google Scholar 

  50. B.U. Gauthama, B. Narayana, B.K. Sarojini, N.K. Suresh, Y. Sangappa, A.K. Kudva, G. Satyanarayana, S.V. Raghu, Microchem. J. 166, 106233 (2021)

    Article  CAS  Google Scholar 

  51. B.J. Okoli, J.S. Modise, Antioxidants 7, 113 (2018)

    Article  PubMed  PubMed Central  Google Scholar 

  52. M. Azam, S.M. Wabaidur, M. Alam, Z. Khan, I.O. Alanazi, S.I. Al-Resayes, I.S. Moon, Transit. Met. Chem. 46, 65 (2021)

    Article  CAS  Google Scholar 

  53. A.K. Singh, O.P. Pandey, S.K. Sengupta, Spectrochim. Acta-A: Mol. Biomol. 113, 393 (2013)

    Article  CAS  Google Scholar 

  54. O.A. El-Gammal, A.A. El-Bindary, F.S. Mohamed, G.N. Rezk, M.A. El-Bindary, J. Mol. Liq. 346, 117850 (2022)

    Article  CAS  Google Scholar 

  55. S. Saroya, S. Asija, Y. Deswal, N. Kumar, A. Kumar, Res. Chem. Intermed. 48, 2949 (2022)

    Article  CAS  Google Scholar 

  56. M. Chaurasia, D. Tomar, S. Chandra, J. Mol. Struct. 1179, 431 (2021)

    Article  Google Scholar 

  57. W.J. Geary, Coord. Chem. Rev. 7, 81 (1971)

    Article  CAS  Google Scholar 

  58. W.H. Mahmoud, R.G. Deghadi, G.G. Mohamed, J. Therm. Anal. Calorim. 127, 2149 (2017)

    Article  CAS  Google Scholar 

  59. B.J. Hathaway, A.A.G. Tomilinson, Coord. Chem. Rev. 5, 1 (1970)

    Article  CAS  Google Scholar 

  60. M.A. Diab, G.G. Mohamed, W.H. Mahmoud, A.Z. ElSonbati, S.M. Morgan, S.Y. Abbas, Appl. Organomet. Chem. 33, 4945 (2019)

    Article  Google Scholar 

  61. W.H. El-Shwiniy, A.G. Ibrahim, S.A. Sadeek, W.A. Zordok, Appl. Organomet. Chem. 35, 6174 (2021)

    Article  Google Scholar 

  62. M.S. Refat, I.M. El-Deen, H.K. Ibrahim, S. El-Ghool, Spectrochim. Acta-A: Mol. Biomol. 65, 1208 (2006)

    Article  Google Scholar 

  63. C.G. Zhan, J.A. Nichols, D.A. Dixon, J. Phys. Chem. A 107, 4184 (2003)

    Article  CAS  Google Scholar 

  64. T.L. Yusuf, S.D. Oladipo, S. Zamisa, H.M. Kumalo, I.A. Lawal, M.M. Lawal, N. Mabuba, ACS Omega 6, 13704 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. P.K. Vishwakarma, J.M. Mir, R.C. Maurya, J. Chem. Sci. 128, 511 (2016)

    Article  CAS  Google Scholar 

  66. M.M. Lawal, T. Govender, G.E. Maguire, H.G. Kruger, B. Honarparvar, Int. J. Quantum Chem. 118, 25497 (2018)

    Article  Google Scholar 

  67. M.M. Lawal, T. Govender, G.E. Maguire, B. Honarparvar, H.G. Kruger, J. Mol. Model. 22, 235 (2016)

    Article  PubMed  Google Scholar 

  68. S.N. Shukla, P. Gaur, M.L. Raidas, B. Chaurasia, J. Mol. Struct. 1202, 127362 (2020)

    Article  CAS  Google Scholar 

  69. J.S. Kirar, S. Khare, N. Tiwari, ChemistrySelect 6, 11557 (2021)

    Article  CAS  Google Scholar 

  70. Y. Deswal, S. Asija, A. Tufail, A. Dubey, L. Deswal, N. Kumar, S. Saroya, J.S. Kirar, N.M. Gupta, Appl. Organomet. Chem. 37, 7050 (2023)

    Article  Google Scholar 

  71. S. Philip, E.G. Jayasree, K. Mohanan, Res. Chem. Intermed. 46, 75 (2020)

    Article  CAS  Google Scholar 

  72. M. Sohrabi, M.R. Binaeizadeh, A. Iraji, B. Larijani, M. Saeedi, M. Mahdavi, RSC Adv. 12, 12011 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

One of the authors (Yogesh Deswal) is highly thankful to Dr. APJ Abdul Kalam Central Instrumentation Laboratory (CIL), GJUS&T, Hisar for providing assistance in characterization of compounds.

Funding

Council of Scientific & Industrial Research (CSIR), New Delhi, India (Ref. No.: 9/752(0087)/2018-EMR-I).

Author information

Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, 125001, India

    Yogesh Deswal, Sonika Asija, Laxmi Deswal, Naresh Kumar & Pinki Barwa

  2. Computational Chemistry and Drug Discovery Division, Quanta Calculus, Greater Noida, Uttar Pradesh, 201310, India

    Aisha Tufail & Amit Dubey

  3. Department of Pharmacology, Saveetha Dental College and Hospital, Saveetha Institute of Medical and Technical Sciences, Chennai, Tamil Nadu, 600077, India

    Amit Dubey

  4. Department of Chemistry, Govt. P. G. College, Guna, Jiwaji University, Gwalior, Madhya Pradesh, 473001, India

    Jagat Singh Kirar & Neeraj Mohan Gupta

  5. Fluorescent Chemistry Lab, Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh, 226031, India

    Neeraj Mohan Gupta

Authors
  1. Yogesh Deswal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sonika Asija
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aisha Tufail
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Amit Dubey
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Laxmi Deswal
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Naresh Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jagat Singh Kirar
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Neeraj Mohan Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Pinki Barwa
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

YD: Writing-original draft, Conceptualization, Methodology, Investigation, Validation, Writing-review & editing, Visualization, Funding acquisition, Data curation. SA: Supervision, Formal analysis, Validation. AT: DFT and molecular docking calculations. AD: DFT and molecular docking calculations. LD: Writing-review & editing, Data curation, Validation. NK: Data curation. JS Kirar: Investigation. NM Gupta: Formal analysis. PB: Investigation.

Corresponding author

Correspondence to Sonika Asija.

Ethics declarations

Competing Interests

The authors declare no competing interests.

Ethical Approval

Not applicable.

Consent for Publication

Not applicable.

Consent to Participate

Not applicable.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2175 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Deswal, Y., Asija, S., Tufail, A. et al. Metal Complexes of 1,2,4-Triazole Based Ligand: Synthesis, Structural Elucidation, DFT Calculations, Alpha-Amylase and Alpha-Glucosidase Inhibitory Activity Along with Molecular Docking Studies. J Inorg Organomet Polym 34, 144–160 (2024). https://doi.org/10.1007/s10904-023-02808-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-023-02808-4

Keywords

Search

Navigation