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Ct-DNA binding and antimicrobial studies of MnII and FeII macrocyclic complexes

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Abstract

The designing of efficient macrocyclic complexes for the alteration in nucleic acids and understanding is still in debate. Herein, to study the deoxyribonucleic acid (DNA) interaction with MN5-complexes, two macrocyclic complexes, A (MnII) and B (FeII), have been synthesized and characterized using multiple analytical techniques. The electronic absorption, fluorescence, and electrochemical methods were utilized to examine the binding ability of both complexes with calf thymus-DNA (ct-DNA). The spectral results were found to be in good agreement with the interaction of both complexes with ct-DNA, as also supported by the remarkable decrease in both anodic peak current (ipa) and cathodic peak current (ipc) during cyclic voltammetric analysis in the presence of ct-DNA. The spectral investigations clearly indicated the higher binding affinity of complex A as compared to complex B towards ct-DNA. Additionally, both complexes were also found to be potential antibacterial agents.

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References

  1. Qi, Z., Schalley, A.C.: Exploring macrocycles in functional supramolecular gels: from stimuli responsiveness to systems chemistry. Acc. Chem. Res. 47(7), 2222–2233 (2014). https://doi.org/10.1021/ar500193z

    Article  CAS  PubMed  Google Scholar 

  2. Chen, Y.F., Liu, M., Mao, J.W., Song, H.T., Zhou, H., Pan, Z.Q.: Synthesis and structure of a macrocyclic dinuclear Zn(II) complex together with DNA-binding and kinetic studies. J. Coord. Chem. 65, 3413–3423 (2012). https://doi.org/10.1080/00958972.2012.717690

    Article  CAS  Google Scholar 

  3. He, Y., Wang, X., Zhou, H., Pan, Z., Li, J., Huang, Q.: DNA cleavage activities and mechanism of a novel heterodinuclear macrocyclic complex. Inorg. Chem. Commun. 13, 314–318 (2010). https://doi.org/10.1016/j.inoche.2009.12.013

    Article  CAS  Google Scholar 

  4. Cheng, Q., Pan, Z., Zhou, H., Chen, J.: New tetranuclear macrocyclic complex: crystal structure, magnetic property and DNA cleavage activity. Inorg. Chem. Commun. 14, 929–933 (2011). https://doi.org/10.1016/j.inoche.2011.03.034

    Article  CAS  Google Scholar 

  5. Cordero, M.R., Cigüela, N., Llovera, L., González, T., Briceño, A., Landaeta, V.R., Pastrán, J.: Synthesis, structural elucidation and DNA binding profile of Zn(II) bis-benzimidazole complexes. Inorg. Chem. Commun. 91, 124–128 (2018). https://doi.org/10.1016/j.inoche.2018.03.019

    Article  CAS  Google Scholar 

  6. Shakir, M., Sadiqa, K., Farha, F., Abdul, M.A., Saud, I.A.R.: Synthesis, spectroscopic characterization, DNA interaction and antibacterial study of metal complexes of tetraazamacrocyclic Schiff base. Spectrochim. Acta A 93, 354–362 (2012). https://doi.org/10.1016/j.saa.2012.03.025

    Article  CAS  Google Scholar 

  7. Kumar, A., Vashistha, V.K., Das, D.K.: Recent development on metal phthalocyanines based materials for energy conversion and storage applications. Coord. Chem. Rev. (2020). https://doi.org/10.1016/j.ccr.2020.213678

    Article  Google Scholar 

  8. Imran, M., Kondratyuk, T., Bélanger-Gariepy, F.: New ternary platinum(II) dithiocarbamates: synthesis, characterization, anticancer, DNA binding and DNA denaturing studies. Inorg. Chem. Commun. 103, 12–20 (2019). https://doi.org/10.1016/j.inoche.2019.02.007

    Article  CAS  Google Scholar 

  9. Sandra, O.R., Torrejon, C., Cuadrado, I., Molina, R.H., Hortelano, S., Braun, A.E., de las Heras, B.: Synthesis and cytotoxic activity of metallic complexes of lawsone. Bioorg. Med. Chem. 21(9), 2471–2477 (2013). https://doi.org/10.1016/j.bmc.2013.03.002

    Article  CAS  Google Scholar 

  10. Anatol, L., Bisang, C., Obrecht, D.: Advances in macrocyclic peptide-based antibiotics. Bioorg. Med. Chem. 26(10), 2850–2858 (2018). https://doi.org/10.1016/j.bmc.2017.08.006

    Article  CAS  Google Scholar 

  11. Vetterli, S.U., Moehle, K., Robinson, A.J.: Synthesis and antimicrobial activity against Pseudomonas aeruginosa of macrocyclic β-hairpin peptidomimetic antibiotics containing N-methylated amino acids. Bioorg. Med. Chem. 24(24), 6332–6339 (2016). https://doi.org/10.1016/j.bmc.2016.05.027

    Article  CAS  PubMed  Google Scholar 

  12. Chandrasekar, T., Pravin, N.: Raman, biosensitive metal chelates from curcumin analogues: DNA unwinding and anti-microbial evaluation. Inorg. Chem. Commun. 43, 45–50 (2014). https://doi.org/10.1016/j.inoche.2014.02.019

    Article  CAS  Google Scholar 

  13. Aiyelabola, T.O., Otto, D.P., Jordaan, J.H., Akinkunmi, E.O., Olawuni, I.: Synthesis, characterization, antimicrobial and DNA binding studies of a tetradentate N2O2 amino acid Schiff base and its coordination compounds. Adv. Biol. Chem. 11(1), 30–51 (2021). https://doi.org/10.4236/abc.2021.111004

    Article  CAS  Google Scholar 

  14. Abreu, F.D., de F. Paulo, T., Gehlen, M.H., Ando, R.A., Lopes, L.G.F., Gondim, A.C.S., Mayron, A., Vasconcelos, E.H., Sousa, T.E.H.S., de Carvalho, I.M.M.: Aryl-substituted ruthenium(II) complexes: a strategy for enhanced photocleavage and efficient DNA binding. Inorg. Chem. 56(15), 9084–9096 (2017). https://doi.org/10.1021/acs.inorgchem.7b01108

    Article  CAS  PubMed  Google Scholar 

  15. Pari, M., Kumar, P., Jilani, B.S., Mruthyunjayachari, C.D., Reddy, K.R.V.: Synthesis and characterization of tetra-ganciclovir cobalt(II) phthalocyanine for electroanalytical applications of AA/DA/UA. Heliyon 5(7), e01946 (2019). https://doi.org/10.1016/j.heliyon.2019.e01946

    Article  Google Scholar 

  16. Xiang, Y.Z., Zhou, L.H., Jiang, N., Lin, H.H., Yu, X.Q.: Synthesis of a novel linear polymer of a macrocyclic polyamine copper(II) complex and its interaction with plasmid DNA. J. Enzym. Inhib. Med. Chem. 24(2), 315–319 (2009)

    Article  CAS  Google Scholar 

  17. Kumar, A., Vashistha, V.K., Tevatia, P., Singh, R.: Electrochemical studies of DNA interaction and antimicrobial activities of MnII, FeIII, CoII and NiII Schiff base tetraazamacrocyclic complexes. Spectrochim. Acta A 176, 123–133 (2017). https://doi.org/10.1016/j.saa.2016.12.011

    Article  CAS  Google Scholar 

  18. Gavey, E.L., Pilkington, M.: Coordination complexes of 15-membered pentadentate aza, oxoaza and thiaaza Schiff base macrocycles “Old Complexes Offer New Attractions.” Coord. Chem. Rev. 296, 125–152 (2015). https://doi.org/10.1016/j.ccr.2015.03.017

    Article  CAS  Google Scholar 

  19. Dees, A., Zahl, A., Puchta, R., van Eikema Hommes, N.J., Heinemann, F.W., Ivanović-Burmazović, I.: Water exchange on seven-coordinate Mn(II) complexes with macrocyclic pentadentate ligands: insight in the mechanism of Mn(II) SOD mimetics. Inorg. Chem. 46(7), 2459–2470 (2007). https://doi.org/10.1021/ic061852o

    Article  CAS  PubMed  Google Scholar 

  20. Michael, G.B.D., Othman, A.H.B., McFall, G.S., Mcllroy, P.D.A., Nelson, S.M.: Seven-co-ordination in metal complexes of quinquedentate macrocyclic ligands. Part 5. Synthesis and properties of pentagonal-bipyramidal and pentagonal-pyramidal manganese(II) complexes and crystal and molecular structure of {2,15-dimethyl-3,7,10,14,20-penta-azabicyclo [14.3.1]eicosa-1(20),2,14,16,18-pentaene}bis(isothiocyanato)manganese(II). J. Chem. Soc. Dalton Trans. 5, 438–446 (1977). https://doi.org/10.1039/DT9770000438

    Article  Google Scholar 

  21. Kumar, A., Tevatia, P., Agarwal, M., Singh, R.: Synthesis, spectral, electrochemical and antibacterial studies of tetraaza macrocyclic complexes of Mn(II) and Co(II). Int. J. Pharm. Chem. 5, 149–157 (2015)

    CAS  Google Scholar 

  22. Muslu, H., Golcu, A., Tumer, M., Ozsoz, M.: Electrochemical investigation and DNA-binding studies of pefloxacin–metal (II/III) complexes. J. Coord. Chem. 64(19), 3393–3407 (2011). https://doi.org/10.1080/00958972.2011.610103

    Article  Google Scholar 

  23. Gandhi, S.R., Kumar, D.S., Tajudeen, S.S., Sheriff, A.K.I.: Studies on synthetic, structural characterization, thermal, DNA cleavage, antimicrobial and catalytic activity of tetradentate (N4) Schiff base and its transition transition metal complexes. Asian J. Chem. 29(5), 1076–1084 (2017)

    Article  CAS  Google Scholar 

  24. Shetty, D., Jeong, J.M., Ju, C.H., Kim, Y.J., Lee, J.Y., Lee, Y.S., Lee, D.S., Chung, J.K., Lee, M.C.: Synthesis and evaluation of macrocyclic amino acid derivatives for tumor imaging by gallium-68 positron emission tomography. Bioorg. Med. Chem. 18(21), 7338–7347 (2010). https://doi.org/10.1016/j.bmc.2010.09.022

    Article  CAS  PubMed  Google Scholar 

  25. Kumar, A., Vashistha, V.K.: Design and synthesis of CoIIHMTAA-14/16 macrocycles and their nano-composites for oxygen reduction electrocatalysis. RSC Adv. 9(23), 13243–13248 (2019). https://doi.org/10.1039/C9RA02169H

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Vashistha, V.K., Kumar, A., Sweety, Singh, R.: Synthesis, electrochemical and antimicrobial studies of Me6-dibenzotetraazamacrocyclic complexes of Ni(II) and Cu(II) metal ions. Russ. J. Electrochem. 55(3), 161–167 (2019). https://doi.org/10.1134/S1023193519020113

    Article  Google Scholar 

  27. Raman, N., Jeyamurugan, R., Sakthivel, A., Mitu, L.: Novel metal-based pharmacologically dynamic agents of transition metal(II) complexes: designing, synthesis, structural elucidation, DNA binding and photo-induced DNA cleavage activity. Spectrachim. Acta A 75, 88–97 (2010). https://doi.org/10.1016/j.saa.2009.09.047

    Article  CAS  Google Scholar 

  28. Arthi, P., Haleel, A., Srinivasan, P., Prabhu, D., Arulvasu, C., Kalilur Rahiman, A.: Antibacterial, DNA interaction and cytotoxic activities of pendant-armed polyamine macrocyclic dinuclear nickel(II) and copper(II) complexes. Spectrochim. Acta A 129, 400–414 (2014). https://doi.org/10.1016/j.saa.2014.03.058

    Article  CAS  Google Scholar 

  29. Liu, J., Zhang, T., Lu, T., Qu, L., Zhou, H., Zhang, Q., Ji, L.: DNA-binding and cleavage studies of macrocyclic copper(II) complexes. J. Inorg. Biochem. 91(1), 269–276 (2002). https://doi.org/10.1016/S0162-0134(02)00441-5

    Article  CAS  PubMed  Google Scholar 

  30. Mathur, N., Bargotya, S.: DNA–binding and cleavage studies of macrocyclic metal complexes containing heteroatomic ligands. Chem. Sci. Trans. 5(1), 117–124 (2016). https://doi.org/10.7598/cst2016.1161

    Article  CAS  Google Scholar 

  31. Patel, M., Chhasatia, M., Parmar, P.: Antibacterial and DNA interaction studies of zinc(II) complexes with quinolone family member, ciprofloxacin. Eur. J. Med. Chem. 45(2), 439–446 (2010). https://doi.org/10.1016/j.ejmech.2009.10.024

    Article  CAS  PubMed  Google Scholar 

  32. Lamani, D.S., Badiger, S.G., Reddy, K.R.V., Naik, H.S.B.: Macrocyclic complexes: synthesis, characterization, antitumor and DNA binding studies. Nucleos. Nucleot. Nucl. Acids 37(9), 498–517 (2018). https://doi.org/10.1080/15257770.2018.1498515

    Article  CAS  Google Scholar 

  33. Mewis, R.E., Archibald, S.J.: Biomedical applications of macrocyclic ligand complexes. Coord. Chem. Rev. 254(15–16), 1686–1712 (2010). https://doi.org/10.1016/j.ccr.2010.02.025

    Article  CAS  Google Scholar 

  34. Khan, S.I., Ahmad, S., Khan, I.A., Badshah, A., Rauf, M.K., Putejo, J.A., Siddiq, M.N., Kausar, S., Altaf, A.A.: Mononuclear copper (i) complexes of triphenylphosphine and N,N′-disubstituted thioureas as potential DNA binding chemotherapeutics. New J. Chem. 45(20), 8925–8935 (2021). https://doi.org/10.1039/D0NJ06182D

    Article  CAS  Google Scholar 

  35. Lal, B., Kanwal, A., Altaf, A.A., Badshah, A., Asghar, F., Akhter, S., Ullah, S., Khan, S.I., Tahir, M.N.: Synthesis, crystal structure, spectral and electrochemical characterization, DNA binding and free radical scavenging studies of ferrocene-based thioureas. J. Coord. Chem. 72(14), 2376–2392 (2019). https://doi.org/10.1080/00958972.2019.1651846

    Article  CAS  Google Scholar 

  36. Altaf, A.A., Hashmat, U., Yousaf, M., Lal, B., Ullah, S., Holder, A.A., Badshah, A.: Synthesis and characterization of azo-guanidine based alcoholic media naked eye DNA sensor. R. Soc. Open Sci. 3(11), 160351 (2016). https://doi.org/10.1098/rsos.160351

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Altaf, A.A., Khan, N., Lal, B., Badshah, A.: Synthesis, characterization and DNA-intercalation studies of two ferrocene-based Fe–Sn heterobimetallic compounds, and crystal structure of trimethyltin (p-ferrocenyl) benzoate. J. Coord. Chem. 70(20), 3523–3540 (2017). https://doi.org/10.1080/00958972.2017.1384547

    Article  CAS  Google Scholar 

  38. Cheng, Q., Pan, Z., Zhou, H., Chen, J.: New tetranuclear macrocyclic complex: crystal structure, magnetic property and DNA cleavage activity. Inorg. Chem. Commun. 14(6), 929–933 (2011). https://doi.org/10.1016/j.inoche.2011.03.034

    Article  CAS  Google Scholar 

  39. Wang, M.Q., Zhang, J., Zhang, Y., Zhang, D.W., Liu, Q., Liu, J.L., Lin, H.H., Yu, X.Q.: Metal-free cleavage efficiency toward DNA by a novel PNA analog-bridged macrocyclic polyamine. Bioorg. Med. Chem. Lett. 21(19), 5866–5869 (2011). https://doi.org/10.1016/j.bmcl.2011.07.097

    Article  CAS  PubMed  Google Scholar 

  40. Kumar, A., Sharma, P., Kumari, P., Kalal, B.L.: Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4 (3H)-ones. Bioorg. Med. Chem. Lett. 21(14), 4353–4357 (2011). https://doi.org/10.1016/j.bmcl.2011.05.031

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We are grateful to GLA University, Mathura, SAIF Panjab University Chandigarh, and Beijing University of Chemical Technology, China for infrastructural support and completion of this work.

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Authors and Affiliations

  1. Department of Chemistry, GLA University, Mathura, 281406, India

    Anuj Kumar, Vinod Kumar Vashistha & Dipak Kumar Das

  2. Institute for Advanced Study, Shenzhen University, Shenzhen, 518060, Guangdong, China

    Ghulam Yasin

  3. Department of Chemistry, Pittsburg State University, Pittsburg, KS, 66762, USA

    Ram K. Gupta

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  1. Anuj Kumar
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Kumar, A., Vashistha, V.K., Das, D.K. et al. Ct-DNA binding and antimicrobial studies of MnII and FeII macrocyclic complexes. J Incl Phenom Macrocycl Chem 102, 683–692 (2022). https://doi.org/10.1007/s10847-022-01150-5

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