Antibacterial, DNA photocleavage and molecular docking studies of newly prepared Schiff-based macrocyclic complexes
DOI:
https://doi.org/10.15584/ejcem.2024.1.27Keywords:
anti-bacterial, DFT, DNA photocleavage, molecular docking, template methodAbstract
Introduction and aim. At present, several microbial diseases are prominent and of concern worldwide. The intent of this study was to examine the antibacterial potential of newly synthesized tetradentate macrocyclic complexes against different bacte rial strains. The macrocyclic scaffold has gained attention as a biologically active class of supramolecular chemistry due to its unique properties and ability to target various microorganisms. Thus, the goal of the present study was to develop a series of biologically active transition metal-based macrocycles.
Material and methods. All macrocyclic compounds were synthesized by a template method and validated by molar conductiv ity, elemental studies, and spectral and magnetic studies. Antibacterial activities of all metal complexes were evaluated against Escherichia coli (MTCC 739) and Staphylococcus aureus (MTCC 731) bacterial strains by taking ampicillin as a standard reference drug. DNA photocleavage potential was explored using agarose gel electrophoresis.
Results. Results revealed the formation of novel macrocyclic complexes via tetra nitrogen bond trapping of metals. Copper complexes have strong potential against S. aureus bacteria as copper and nickel both show good DNA photocleavage potential.
Conclusion. The findings endorse the biomedical relevance of these macrocyclic scaffolds, suggesting avenues for further exploration in targeted drug delivery and potential clinical applications. The proposed octahedral geometry for the complexes enhances our understanding of their structural aspects. This research contributes substantively to the field, laying the foundation for future investigations in advanced antimicrobial design and application.
Supporting Agencies
Financial assistance from the management of MM (DU) Education Trust is provided to conduct this study.Downloads
References
Jain S, Rana M, Sultana R, Mehandi R, Rahisuddin. Schiff Base Metal Complexes as Antimicrobial and Anticancer Agents. Polycycl Aromat Compd. 2023;43(7):6351-6406. doi: 10.1080/10406638.2022.2117210
Kamboj M, Singh DP, Singh AK, Chaturvedi D. Molecular modeling, in-silico docking and antibacterial studies of novel template wangled macrocyclic complexes involving isatin moiety. J Mol Struct. 2020;1207:127602. doi: 10.1016/j.molstruc.2019.127602
Kaczmarek MT, Zabiszak M, Nowak M, Jastrzab R. Lanthanides: Schiff base complexes, applications in cancer diagnosis, therapy, and antibacterial activity. Coord Chem Rev. 2018;370:42-54. doi: 10.1016/j.ccr.2018.05.012
O’Riley HA, Levina A, Aitken JB, Lay PA. Synthesis, reactivities and anti-cancer properties of ruthenium(II) complexes with a thiaether macrocyclic ligand. Inorganica Chim Acta. 2017;454:128-138. doi: 10.1016/j.ica.2016.07.050
Sangwan V, Singh DP. In-vitro DNA binding and antimicrobial studies of trivalent transition metal ion based macrocyclic complexes. Vietnam J Chem. 2019;57(5):543-551. doi: 10.1002/vjch.201900058
Sangwan V, Singh DP. Synthesis, biological and molecular modeling studies of macrocyclic complexes of trivalent metal ions. Iran Chem Commun. 2017;5(0):345-351.
Mishra P, Sethi P, Sharma N, Sharma J. Macrocyclic scaffold: A boon in advancement of sensor technology- Review. Mater Today Proc. 2022;71(2):370-376. doi: 10.1016/j.matpr.2022.09.448
Sangwan V, Singh DP. Macrocyclic Schiff base complexes as potent antimicrobial agents: Synthesis, characterization and biological studies. Mater Sci Eng C. 2019;105:110119. doi:10.1016/j.msec.2019.110119
Purti M, Pooja S, Anjana K. Emerging applications and host- guest chemistry of synthetic macrocycles. Res J Chem Environ. 2022;26(7):153-167.
Pradhan A, Kumar A. A review: An overview on synthesis of some Schiff bases and there metal complexes with anti-microbial activity. Chem Process Eng Res. 2015;35(Ii):84-87.
Kajal A, Bala S, Kamboj S, Sharma N, Saini V. Schiff Bases: A Versatile Pharmacophore. J Catal. 2013;2013(Mic):1-14. doi: 10.1155/2013/893512
Sharma K, Agarwal S, Gupta S. Antifungal, antibacterial and antifertility activities of biologically active macrocyclic complexes of Tin(II). Int J ChemTech Res. 2013;5(1):456-463.
Zhang Z, Wang H, Wang Q, et al. Anticancer activity and computational modeling of ternary copper (II) complexes with 3-indolecarboxylic acid and 1,10-phenanthroline. Int J Oncol. 2016;49(2):691-699. doi: 10.3892/ijo.2016.3542
Chandra S, Agrawal S. Spectroscopic characterization of Lanthanoid derived from a hexadentate macrocyclic ligand: Study on antifungal capacity of complexes. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2014;124(14):564-570. doi: 10.1016/j.saa.2014.01.042
Ibrahim M, Nabi HU, Muhammad N, et al. Synthesis, Antioxidant, Molecular Docking and DNA Interaction Studies of Metal-Based Imine Derivatives. Molecules. 2023;28(15):5926. doi: 10.3390/molecules28155926
Hazarika B, Singh VP. Macrocyclic supramolecular biomaterials in anti-cancer therapeutics. Chinese Chem Lett. 2023:108220. doi: 10.1016/j.cclet.2023.108220
Khare R, Sethi P. Studies and antibacterial properties Innovare Properties. Int J Pharm Pharm Sci. 2015;7(7):1-8.
Pooja S, Pernita D, Gupta GK, Mostafa Sahar I, Simrat K. Synthesis, characterization, anti-bacterial and DNA nicking activity of new complexes of 1-(2,4-dinitrophenylamino)- 4, 4, 6-trimethyl- 3, 4-dihydropyrimidine-2-(1H)-thione. Res J Chem Environ. 2018;22(11):73-88.
Jana S. Assessment and Benchmarking of Proposed Exchange-Correlation Approximations in Density Functional Theory. http://idr.niser.ac.in:8080/jspui/handle/123456789/200. Accessed April 5, 2023.
Kruse H, Goerigk L, Grimme S. Why the standard B3LYP/6-31G* model chemistry should not be used in DFT calculations of molecular thermochemistry: Understanding and correcting the problem. J Org Chem. 2012;77(23):10824-10834. doi: 10.1021/jo302156p
Ghiggino KP, Scully AD, Leaver IH. Effect of solvent on excited-state intramolecular proton transfer in benzotriazole photostabilizers. J Phys Chem. 1986;90(21):5089-5093.
Tamanna, Fu C, Qadir M, et al. Thiadiazine thione derivatives as anti-leishmanial agents: synthesis, biological evaluation, structure activity relationship, ADMET, molecular docking and molecular dynamics simulation studies. J Biomol Struct Dyn. 2023:1-15 doi: 10.1080/07391102.2023.2245480
Wallace AC, Laskowski RA, Thornton JM. Ligplot: A program to generate schematic diagrams of protein-ligand interactions. Protein Eng Des Sel. 1995;8(2):127-134. doi: 10.1093/protein/8.2.127
Keypour H, Mahmoudabadi M, Shooshtari A, et al. Synthesis and characterization of two new macroacyclic Schiff-base ligands containing piperazine moiety and mononuclear Co(III) and Cu(II) complexes, spectral, X-ray crystal structural, theoretical studies, cytotoxic and antibacterial properties. Polyhedron. 2017;129(3):189-198. doi: 10.1016/j.poly.2017.03.035
Cheng J, Xuan X, Yang X, Zhou J, Cen K. Preparation of a Cu(BTC)-rGO catalyst loaded on a Pt deposited Cu foam cathode to reduce CO2 in a photoelectrochemical cell. RSC Adv. 2018;8(56):32296-32303. doi: 10.1039/c8ra05964k
Gull P, Malik MA, Dar OA, Hashmi AA. Design, synthesis and spectroscopic characterization of metal (II) complexes derived from a tetradentate macrocyclic ligand: Study on antimicrobial and antioxidant capacity of complexes. Microb Pathog. 2017;16(6):882-894. doi: 10.1016/j.micpath.2017.01.036
Sethi P, Khare R, Choudhary R. Complexes of pyrimidine thiones: Mechanochemical synthesis and biological evaluation. Asian J Chem. 2020;32(10):2594-2600. doi: 10.14233/ajchem.2020.22813
Scrocco E, Tomasi J. Electronic Molecular Structure, Reactivity and Intermolecular Forces: An Euristic Interpretation by Means of Electrostatic Molecular Potentials. Advances in Quantum Chemistry. 1978;11:115-193. doi: 10.1016/S0065-3276(08)60236-1
Pearson RG. Quantum mechanical parameters. J Org Chem. 1989;54:1423-1430.
Padmanabhan J, Parthasarathi R, Elango M, Subramanian BS, Krishnamoorthy S. Electron spray. J Phys Chem A. 2007:1358-1358.
Parathasarathi R, Padmanabhan J, Subramaniam V, Sarkar U, Malti B, Chattaraj P. Internet electron. J Mol Des. 2003;2:798-813.
Rathi P, Singh DP. Template engineered biopotent macrocyclic complexes involving furan moiety : Molecular modeling and molecular docking. J Mol Struct. 2015;1093:201-207. doi: 10.1016/j.molstruc.2015.03.045
Rathi P, Singh DP, Surain P. Synthesis, characterization, powder XRD and antimicrobial-antioxidant activity evaluation of trivalent transition metal macrocyclic complexes. Comptes Rendus Chim. 2015;18(4):430-437. doi: 10.1016/j.crci.2014.08.002
Singh DP, Grover V, Rathi P, Jain K. Trivalent transition metal complexes derived from carbohydrazide and dimedone. Arab J Chem. 2017;10:1795-1801. doi: 10.1016/j.arabjc.2013.07.004
Zeynali H, Keypour H, Hosseinzadeh L, Gable RW. The non-templating synthesis of macro-cyclic Schiff base ligands containing pyrrole and homopiperazine and their binuclear nickel(II), cobalt(II) and mononuclear platinum(II) complexes: X-ray single crystal and anticancer studies. J Mol Struct. 2021;1244. doi: 10.1016/j.molstruc.2021.130956
Sangwan V, Singh DP. Template-engineered metal macrocyclic complexes: Synthesis and biological activity. J Chinese Chem Soc. 2020;67(6):1024-1031. doi: 10.1002/jccs.201900290
Rathi P, Singh DP. Investigation of divalent tetraazamacrocyclic complexes as potent antimicrobial and antioxidant agents. Der Pharma Chem. 2014;6(5):203-214.
Rathi P, Singh DP. Spectrochimica Acta Part A : Molecular and Biomolecular Spectroscopy Antimicrobial and antioxidant activity evaluation of Co ( II ), Ni ( II ), Cu ( II ). Spectrochim Acta Part A Mol Biomol Spectrosc. 2015;136:381-387. doi: 10.1016/j.saa.2014.09.044
Kumar S, Sharma V, Pradhan JK, Sharma SK, Singh P, Sharma JK. Structural, optical and antibacterial response of CaO nanoparticles synthesized via direct precipitation technique. Nano Biomed Eng. 2021;13(2):172-178. doi: 10.5101/NBE.V13I2.P172-178
Govindrajan M, Periandy S, Carthigayen K. FMO LUMO. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2012;97:411-422.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2024 European Journal of Clinical and Experimental Medicine
This work is licensed under a Creative Commons Attribution 4.0 International License.
Our open access policy is in accordance with the Budapest Open Access Initiative (BOAI) definition: this means that articles have free availability on the public Internet, permitting any users to read, download, copy, distribute, print, search, or link to the full texts of these articles, crawl them for indexing, pass them as data to software, or use them for any other lawful purpose, without financial, legal, or technical barriers other than those inseparable from having access to the Internet itself.
All articles are published with free open access under the CC-BY Creative Commons attribution license (the current version is CC-BY, version 4.0). If you submit your paper for publication by the Eur J Clin Exp Med, you agree to have the CC-BY license applied to your work. Under this Open Access license, you, as the author, agree that anyone may download and read the paper for free. In addition, the article may be reused and quoted provided that the original published version is cited. This facilitates freedom in re-use and also ensures that Eur J Clin Exp Med content can be mined without barriers for the research needs.
