Skip to main content
SpringerLink
Log in

Synthesis, characterization, DNA-binding and biological studies of novel titanium (IV) complexes

  • Regular Article
  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

A series of novel binuclear titanium (IV) complexes, [Ti(sal)LI–V(OBu)(μ-OBu)]2, was synthesized by the reaction of salicylic acid (H2sal) and substituted indoles (LI = Tryptophol, LII = 5-Methoxyindole, LIII = Indole-5-Carboxaldehyde, LIV = 5-Cyanoindole, LV = 6-Nitroindole) with titanium(IV) tetrabutoxide in predetermined molar ratios under stirring and refluxing conditions in THF solvent. The chemical structure of synthesized complexes was found to be binuclear based on the FTIR, IH (proton) NMR and ESI-Mass (Electron-spray ionization) spectroscopic data. Each titanium metal was surrounded by two bridged butoxy groups and one terminal butoxy group along with bidentate salicylic acid and coordinated substituted indoles. These complexes were investigated for antioxidant potential using DPPH (2,2-diphenyl-1-picrylhydrazyl) assay where they exhibited moderate to good antioxidant activity. Gel electrophoresis method was employed to study the ct-DNA (calf thymus DNA) cleavage efficiency of complexes using an agarose gel. Antimicrobial results stated that most of the complexes were ineffective against selected bacterial and fungal strains. Complexes were investigated for anticancer activity against two selected cancerous cell lines (L6 and L929). From MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay, it has been inferred that complexes 1 and 2 have better anticancer properties than their respective indoles. The DNA binding study of synthesized complexes studied in order to check their efficacy to hinder DNA replication/transcription using electronic absorption and fluorescence spectroscopy revealed them as electrostatic/groove binder. The synthesized complexes were also evaluated for antidiabetic properties using alpha-amylase inhibition assay and complex 5 possessed better alpha-amylase inhibition activity than other complexes.

Graphic abstract

Synopsis: The synthesis, structural characterizationand biological activities of a novel binuclear titanium(IV) complexes [Ti(sal)LI–V(OBu)(μ-OBu)]2 is reported.

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
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14
Figure 15

Similar content being viewed by others

References

  1. Fulton J R, Holland A W, Fox D J and Bergman R G 2002 Formation, reactivity, and properties of nondative late transition metal-oxygen and -nitrogen bonds Acc. Chem. Res. 35 44

    Article  CAS  Google Scholar 

  2. Wolczanski P T 2009 Structure and reactivity studies of transition metals ligated by tBuSi3X (X = O, NH, N, S, and CC) Chem. Commun. 7 740

    Article  Google Scholar 

  3. Buyuktas B S and Aktas O 2006 Complexation of titanium n-butoxide Ti(OBun)4 and zirconium n-butoxide Zr(OBun)4 with some oxime ligands and structural analysis of the complexes Transit. Met. Chem. 31 56

    Article  CAS  Google Scholar 

  4. Mehrotra R C 1990 Chemistry of alkoxide precursors J. Non-Cryst Solids. 121 1

    Article  CAS  Google Scholar 

  5. Sanchez C and Livage J 1990 Sol-gel chemistry of metal alkoxide precursor New J. Chem. 14 513

    CAS  Google Scholar 

  6. Kaushik N K, Kaushik N, Attri P, Kumar N, Kim C H, Verma A K and Choi E H 2013 Biomedical importance of indoles Molecules 18 6620

    Article  CAS  Google Scholar 

  7. Dolle R E and Nelson K H Jr 1999 Comprehensive survey of combinatorial library synthesis J. Comb. Chem. 1 235

    Article  CAS  Google Scholar 

  8. Franzén R G 2000 Recent advances in the preparation of heterocycles on solid support: a review of the literature J. Comb. Chem. 2 195

    Article  Google Scholar 

  9. Dolle R E 2001 Comprehensive survey of combinatorial library synthesis J. Comb. Chem. 3 477

    Article  CAS  Google Scholar 

  10. Chadha N and Silakari O 2017 Indoles as therapeutics of interest in medicinal chemistry: Bird’s eye view Eur. J. Med. Chem. 134 159

    Article  CAS  Google Scholar 

  11. Raj K M and Mruthyunjayaswamy B H M 2017 Synthesis, spectroscopic characterization, electrochemistry and biological activity evaluation of some metal (II) complexes with ONO donor ligands containing indole and coumarin moieties J. Saudi Chem. Soc. 21 S202

    Article  Google Scholar 

  12. Kumar S, Pandya P, Pandav K, Gupta S and Chopra A 2012 Structural studies on ligand-DNA system. A rubst approach in drug design J. Biosci. 37 553

  13. Palchaudhuri R and Hergenrother P 2007 DNA as a target for anticancer compounds: Methods to determine the mode of binding and the mechanism of action Curr. Opin. Biotechnol. 18 497

    Article  CAS  Google Scholar 

  14. Mishra R, Kumar A, Chandra R and Kumar D 2017 A review on theoretical studies of various types of Drug-DNA interaction IJSTS 3 11

    Google Scholar 

  15. Kaushal R, Thakur S and Nehra K 2016 ct-DNA Binding and Antibacterial Activity of Octahedral Titanium (IV) Heteroleptic (Benzoylacetone and Hydroxamic Acids) Complexes Int. J. Med. Chem. 2016 1

    Google Scholar 

  16. Tabassam N, Ali S, Shahzadi S, Shahid M, Abbas M, Khan Q M, Sharma S K and Qanungo K 2013 Synthesis, characterziation, semi-empirical quantum-mechanical study and biological activity of organotin(IV) complexes with 2-ethylanilinocarbonylpropenoic acid Russ. J. Gen. Chem. 83 2423

    Article  CAS  Google Scholar 

  17. Kaushal R, Kumar N, Awasthi P and Nehra K 2013 Syntheses, characterization, and antibacterial study of titanium complexes Turk. J. Chem. 37 936

    Article  CAS  Google Scholar 

  18. Kaur V, Kumar M, Kumar A and Kaur S 2018 Butea monosperma (Lam.) Taub. Bark fractions protect against free radicals and induce apoptosis in MCF-7 breast cancer cells via cell-cycle arrest and ROS-mediated pathway Drug Chem. Toxicol. 1

  19. Sudha P, Smita S Z, Shobha Y B and Ameeta R K 2011 Potent a-amylase inhibitory activity of Indian Ayurvedic medicinal plants BMC Complement Altern. Med. 11 1

    Google Scholar 

  20. Trivedi M K, Branton A, Trivedi D, Shettigar H, Bairwa K and Jana S 2015 Fourier Transform Infrared and Ultraviolet-Visible Spectroscopic Characterization of Biofield Treated Salicylic Acid and Sparfloxacin Nat. Prod. Chem. Res. 3 1

  21. Mehrotra R C and Bohra R 1983 Metal Carboxylates (London UK: Academic Press)

    Google Scholar 

  22. Colthup N B, Daly L H and Wiberley S E 1990 Introduction to Infrared and Raman Spectroscopy 3rd edn. (Boston USA: Academic Press)

    Google Scholar 

  23. Ambreen S, Gupta K, Singh S, Gupta D K, Daniele S, Pandey N D and Pandey A 2013 Synthesis and structural characterization of some titanium butoxides modified with chloroacetic acids Transit. Met. Chem. 38 835

    Article  CAS  Google Scholar 

  24. Lawal A, Shodeinde A S, Amolegbe S A, Elaigwu S E and Yunus-Issa M T 2017 Synthesis, Characterization and Antimicrobial Activity of Mixed Transition Metal Complexes of Salicylic Acid with 1, 10-Phenanthroline J. Appl. Sci. Environ. Manage. 21 568

    CAS  Google Scholar 

  25. Takač M J-M and Topić D V 2004 FT-IR and NMR spectroscopic studies of salicylic acid derivatives. II. Comparison of 2-hydroxy- and 2,4- and 2,5-dihydroxy derivatives Acta Pharm. 54 177

  26. Meng X, Wang X, Duan H, Bu J, Qin D and Zhang Y 2012 Design, synthesis, and characterization of indole derivatives Res. Chem. Intermed. 39 3829

    Article  Google Scholar 

  27. Mandal D, Chakraborty D, Ramkumar V and Chand D K 2016 Group 4 Alkoxide Complexes containing [NNO]-type Scaffold: Synthesis, Structural Characterization and Polymerization Studies RSC Adv. 6 21706

    Article  CAS  Google Scholar 

  28. Tan L F, Liu X H, Chao H and Ji L 2007 Synthesis, DNA-binding and photocleavage studies of ruthenium(II) complex with 2-(30-phenoxyphenyl)imidazo[4,5-f][1,10]phenanthroline J. Inorg. Biochem. 101 56

    Article  CAS  Google Scholar 

  29. Lakshmipraba J, Arunachalam S, Solomon R V, Venuvanalingam P, Riyasdeen A, Dhivya R and Akbarsha M A 2014 Surfactant-copper(II) Schiff base complexes: synthesis, structural investigation, DNA interaction, docking studies, and cytotoxic activity J. Biomol. Struct. Dyn. 33 877

    Article  Google Scholar 

  30. Falcioni M L, Pellei M and Gabbianelli R 2008 Interaction of tributyltin(IV) chloride and a related complex [Bu3Sn(LSM)] with rat leukocytes and erythrocytes: Effect on DNA and on plasma membrane Mutat. Res. 653 57

    Article  CAS  Google Scholar 

  31. Liu J, Zhang T, Lu T, Qu L, Zhou H, Zhang Q and Ji L 2002 D NA-binding and cleavage studies of macrocyclic copper(II) complexes J. Inorg. Biochem. 91 269

    Article  CAS  Google Scholar 

  32. Kundu P and Chattopadhyay N 2017 Interaction of a bioactive pyrazole derivative with calf thymus DNA: Deciphering the mode of binding by multi-spectroscopic and molecular docking investigations J. Photochem. Photobiol. B Biol. 173 485

    Google Scholar 

  33. Chaurasia M, Tomar D and Chandra S 2019 Synthesis, spectroscopic characterization and DNA binding studies of Cu(II) complex of Schiff base containing benzothiazolemoiety J. Taibah. Univ. Sci. 13 1050

    Article  Google Scholar 

  34. Yang C-Z, Liang C-Y, Zhang D and Hu Y-J 2017 Deciphering the interaction of methotrexate with DNA: Spectroscopic and molecular docking study J. Mol. Liq. 248 1

    Article  Google Scholar 

  35. Shaikh Z, Ashiq U, Jamal R A, Mahroof-Tahir M, Shamshad B and Sultan S 2015 Chemistry and antioxidant properties of titanium(IV) complexes Transit. Met. Chem. 40 665

    Article  CAS  Google Scholar 

  36. Waring M 1977 Structural and conformational studies on quinoxaline antibiotics in relation to the molecular basis of their interaction with DNA In Drug Action at the Molecular Level (London: Palgrave Macmillan) pp. 167–189

  37. Pyle A M, Rehmann J P, Meshoyrer R, Kumar C V, Turro N J and Barton J K 1989 Mixed-ligand complexes of Ruthenium (II): factors governing binding to DNA J. Am. Chem. Soc. 111 3051

    Article  CAS  Google Scholar 

  38. Kulkarni A, Patil S A and Badami P S 2009 Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives Eur. J. Med. Chem. 44 2904

    Article  CAS  Google Scholar 

  39. Prashanthi Y, Kiranmai K, Ira, K S K, Chityala V K and Shivaraj 2012 Spectroscopic Characterization and Biological Activity of Mixed Ligand Complexes of Ni(II) with 1,10-Phenanthroline and Heterocyclic Schiff Bases Bioinorg. Chem. Appl. 2012 1

    Article  Google Scholar 

  40. Raman N, Pothiraj K and Baskaran T 2011 DNA-binding, oxidative DNA cleavage, and coordination mode of later 3d transition metal complexes of a Schiff base derived from isatin as antimicrobial agents J. Coord. Chem. 64 3900

    Article  CAS  Google Scholar 

  41. Jelokhani-Niaraki M, Kondejewski L H, Wheaton L C and Hodges R S 2009 Effect of Ring Size on Conformation and Biological Activity of Cyclic Cationic Antimicrobial Peptides J. Med. Chem. 52 2090

    Article  CAS  Google Scholar 

  42. Nejo A A, Kolawole G A and Nejo A O 2010 Synthesis, characterization, antibacterial, and thermal studies of unsymmetrical Schiff-base complexes of cobalt(II) J. Coord. Chem. 63 4398

    Article  CAS  Google Scholar 

  43. Philip J E, Shahid M, Kurup M R P and Velayudhan M P 2017 Metal based biologically active compounds: Design, synthesis, DNA binding and antidiabetic activity of 6-methyl-3-formyl chromone derived hydrazones and their metal (II) complexes J. Photochem. Photobiol. B Biol. 175 178

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Hamirpur, Himachal Pradesh, 177 005, India

    Raj Kaushal & Archana Thakur

  2. Department of Botanical and Environmental Sciences, Guru Nanak Dev University, Amritsar, Punjab, 143005, India

    Astha Bhatia & Saroj Arora

  3. Department of Biotechnology, Deenbandhu Chhotu Ram University of Science and Technology, Murthal (Sonepat), Haryana, 131039, India

    Kiran Nehra

Authors
  1. Raj Kaushal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Archana Thakur
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Astha Bhatia
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Saroj Arora
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kiran Nehra
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Raj Kaushal.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 906 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kaushal, R., Thakur, A., Bhatia, A. et al. Synthesis, characterization, DNA-binding and biological studies of novel titanium (IV) complexes. J Chem Sci 132, 141 (2020). https://doi.org/10.1007/s12039-020-01843-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s12039-020-01843-9

Keywords

Search

Navigation