HETERO-BINUCLEAR COMPLEXES OF LANTHANUM (III) USING BRIDGING N,N?-BIS(2-PYRIDYLMETHYL)OXAMIDE AND TERMINAL 1,10-PHENANTHROLINE: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION
Abstract
In the present study, hetero-binuclear La(III) complexes were newly synthesized using well known bridging ligand N,N′-bis(2-pyridylmethyl)oxamide (2PMO, 1) and “complexes as ligands” [Cu(2PMO)] (2) and [Ni(2PMO)] (3). The newly synthesized mononuclear (4) as well as hetero-binuclear complexes (5 and 6) were characterized by analytical and spectroscopic techniques. The newly synthesized complexes were tested for their binding ability towards CT-DNA and chemical nuclease property towards SC pUC 19 DNA. The complexes were tested for antibacterial activities against Gram negative bacteria (E. coli and K. pneumonia) and Gram positive bacteria (B. subtilis and S. aureus), antioxidant activities by DPPH radical scavenging and ferrous-ion chelation methods and cytotoxicity against MCF-7 cell lines by MTT assay. The structure-activity relationship revealed that the newly synthesized hetero-binuclear complexes show potent DNA binding and chemical nuclease activities, antibacterial, antioxidant and cytotoxic activities.
Keywords:
Antibacterial, antioxidant, antitumor, DNA interactions, oxamides, Lanthanum (III) complexesDOI
https://doi.org/10.25004/IJPSDR.2018.100606References
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3. Li XW, Tao L, Li YT, Wu ZY, Yan CW. Bimetallic complexes constructed from asymmetrical N,N′-bis (substituted)-oxamide: Cytotoxicities, and reactivities towards DNA and protein Eur. J. Med. Chem. 2012; 54: 697-708.
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9. Badwaik VB, Aswar AS. Synthesis, Characterization, and Biological Studies of Some Schiff Base Complexes. Russ. J. Coord. Chem. 2007; 33: 755-760.
10. Chohan ZH, Arif M, Akhtar MA, Supuran CT. Metal-Based Antibacterial and Antifungal Agents: Synthesis, Characterization, and In Vitro Biological Evaluation of Co(II), Cu(II), Ni(II), and Zn(II) Complexes With Amino Acid-Derived Compounds. Bioinorg. Chem. Appl. 2006; Article ID 83131: 1-13.
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12. Yao M, Li Y, Hossu M, Joly AG, Liu Z, Liu Z, Chen W. Luminescence of Lanthanide Dimethyl Sulfoxide Compound Solutions. J. Phys. Chem. B. 2011; 115: 9352-9359.
13. Azab HA, Anwar ZM, Ahmed RG. Pyrimidine and Purine Mononucleotides Recognition by Trivalent Lanthanide Complexes with N-Acetyl Amino Acids. J. Chem. Eng. Data. 2010; 55: 459-475.
14. Zhang DW, Yang YJ, Ying SM, Liu YQ. Synthesis Neutral Rare Earth Complexes ofDiethylenetriamine-N, N″-bis(acetyl-o-hydroxybenzoyl hydrazide) -N, N′, N-triacetic Acid as Potential Contrast Enhancement Agents for Magnetic Resonance Imaging. Synth. Reac. Inorg. Met-Org. Nano-Met. Chem. 2013; 43: 217-220.
15. Wang Q, Yang ZY, Qi GF, Qin DD. Crystal structures, DNA-binding studies and antioxidant activities of the Ln(III) complexes with 7-methoxychromone- 3-carbaldehyde-isonicotinoyl hydrazone. Biometals. 2010; 23: 1179-1189.
16. Kostova I, Stefanov T. Synthesis, characterization and cytotoxic/cytostatic activity of La(III) and Dy(III) complexes. J. Trace Elem. Med. Biol. 2010; 24: 7-13.
17. Wang BD, Yang ZY, Wang Q, Caib TK, Crewdson P. Synthesis, characterization, cytotoxic activities, and DNA-binding properties of the La(III) complex with Naringenin Schiff-base. Bioorg. Med. Chem. 2006; 14: 1880–1888.
18. Hussain A, Somyajit K, Banik B, Banerjee S, Nagaraju G, Chakravarty AR, Enhancing the photocytotoxic potential of curcumin on terpyridyl lanthanide(III) complex formation . Dalton Trans. 2013; 42: 182-195.
19. Durgo K, Halec I, Šola I, Franekić J. Cytotoxic and Genotoxic Effects of the Quercetin/Lanthanum Complex on Human Cervical Carcinoma cells in vitro. Arh. Hig. Rada. Toksikol. 2011; 62: 221-227.
20. Marinic´ M, Piantanida I, Rusak G, Zˇinic M. Interactions of quercetin and its lanthane complex with doublestranded DNA/RNA and single stranded RNA: Spectrophotometric sensing of poly G. J. Inorg. Biochem. 2006; 100: 288-298.
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22. Ansari AA, Sharma RK. Synthesis and Characterization of a Biologically Active Lanthanum(III)–Catechin Complex and DNA Binding Spectroscopic Studies. Spect. Lett. 2009; 42: 178-185.
23. Heffeter P, Popovic-Bijelic A, Saiko P, Dornetshuber R, Jungwirth U, Voevodskaya N, Biglino D, Jakupec MA, Elbling L, Micksche M, Szekeres T, Keppler BK, Gräslund A, Berger W, Ribonucleotide Reductase as One Important Target of [Tris(1,10-phenanthroline)lanthanum(III)] Trithiocyanate (KP772). Curr. Canc. Drug Targets. 2009; 9: 1-13.
24. Wang F, Huang W, Zhang Y, Wang M, Sun L, Tang B, Wang W. Determination of Protein by Fluorescence Enhancement of Curcumin in Lanthanum-Curcumin-Sodium Dodecyl Benzene Sulfonate-Protein System J. Fluoresc. 2011; 21: 25-34.
25. Refat MS, Al-Azab FM, Hussein MA, Al-Maydama, Amin RR, Yasmin Jamil MS, Synthesis and in vitro microbial evaluation of La(III), Ce(III), Sm(III) and Y(III) metal complexes of vitamin B6 drug. Spectrochim. Acta Part A. 2014; 127: 196-215.
26. Refat MS, Hussein MA, Al-Maydama, Al-Azab FM, Amin RR, Yasmin Jamil MS, Synthesis, thermal and spectroscopic behaviors of metal-drug complexes: La(III), Ce(III), Sm(III) and Y(III) amoxicillin trihydrate antibiotic drug complexes. Spectrochim Acta Part A. 2014; 128: 427-446.
27. Köse M, Ceyhan G, Atc E, McKee V, Tümer M, Synthesis, structural characterization and photoluminescence properties of a novel La(III) complex. J. Mol. Struc. 2015; 1088: 129-137.
28. Nadia EA, El-Gamel, Thermal studies, structural characterization, and antimicrobial evaluation of coordinated metal complexes containing salen moiety. Monatsh Chem. 2013; 144: 1627-1634.
29. Siddappa K, Sunilkumar BM, Manikprabhu D. La(III) complex involving the O,N-donor environment of quinazoline-4(3H)-one Schiff’s base and their antimicrobial attributes against methicillin-resistant Staphylococcus aureus (MRSA). Spectrochim. Acta Part A. 2014; 130: 634-638.
30. Avaji PG, Badami PS, Patil SA, Synthesis, spectral, thermal, solid state d.c. electrical conductivity and biological studies of lanthanum(III) and thorium(IV) complexes with thiocarbohydrazone. Trans. Met. Chem. 2007; 32: 379-386.
31. Wang BD, Yang ZY, P. Crewdson, Wang DQ, Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxychromone-3-carbaldehyde benzoyl hydrazone. J. Inorg Biochem. 2007; 10: 1492-1504.
32. S. Kobayashi, S. Kanai, Superoxide Scavenging Effects of Some Novel Bis-Ligands and Their Solvated Metal Complexes Prepared by the Reaction of Ligands with Aluminum, Copper and Lanthanum Ions. Molecules. 2013; 18: 6128-6141.
33. Perrin DD, Armarego WLF, Perrin DR, Purification of Laboratory Chemicals, Pergamon Press, Oxford, UK, 1980.
34. Schauer CL, Matwey E, Fowler FW, Lauher JW. Silver Coordination and Hydrogen Bonds: A Study of Competing Forces. Cryst. Eng. 1998; 1: 213-223.
35. Liu B, Wang HM, Yan SP, Liao DZ, Jiang ZH, Huang XY, Wang GL. Crystal structure of the addition compound of N,N′-bi(2-pyridylmethyl)-oxamide and complex of manganese with 1,10-phenanthroline. J. Chem. Cryst. 1999; 29: 623-627.
36. Ouyang Y, Liu B, Wang QL, Liao DZ, Jiang ZH, Yan SP, Three new copper(II)–nickel(II) heterodinuclear complexes with the N,N′-bis(2-pyridyl-ethyl)oxamide dianion. Syntheses, spectra, and magnetic properties. Trans. Met. Chem. 2005; 30: 460-463.
37. Marmur J. A procedure for the isolation of deoxyribonucleic acid from micro-organisms. J. Mol. Biol. 1961; 3: 208-218.
38. McGhee JD, von Hippel PH. Theoretical aspects of DNA protein interactions: cooperative and noncooperative binding of large ligands to a one-dimensional heterogeneous lattice. J. Mol. Biol. 1974; 86: 469-489.
39. LePecq JB, Paoletti C. A fluorescent complex between Ethidium bromide and nucleic acids. Physical-chemical characterization. J. Mol. Biol. 1967; 27: 87-106.
40. Kannan D, Arumugam MN, Synthesis, Characterisation, DNA-Binding Studies and antimicrobial activity of Copper (II) Complex with 1,10 Phenanthroline, L-Tyrosine and Thiosemicarbazide as Ligands. Elixir. Appl. Chem. 2014; 74: 27007-27104.
41. Chetana PR, Srinatha BS, Somashekar MN, Policegoudra RS. Synthesis, spectroscopic characterisation, thermal analysis, DNA interaction and antibacterial activity of copper(I) complexes with N,N′- disubstituted thiourea. J. Mol. Struc. 2016; 1106: 352-365.
42. Bernadou J, Pratviel G, Bennis F, Girardet M, Meunier B. Potassium Monopersulfate and a Water-Soluble Manganese Porphyrin Complex, [ Mn(TMPyP)](OAC)5, as an Efficient Reagent for the Oxidative Cleavage of DNA. Biochemistry. 1989; 28: 7268-7275.
43. Chetana PR, Rao R, Saha S, Policegoudra RS, Vijayan P, Aradhya MS. Oxidative DNA cleavage, cytotoxicity and antimicrobial studies of L-ornithine copper (II) complexes. Polyhedron. 2012; 48: 43-50.
44. Zaidan MRS, Rain AN, Badrul AR, Adlin A, Norazah A, Zakiah I. In vitro screening of five local medicinal plants for antibacterial activity using disc diffusion method. Trop. Biomed. 2005; 22: 165-170.
45. Bauer AW, Kirby WMM, Serris JC, Turck M. Antibiotic susceptibility testing by a standardized single disc method. Am. J. Clin. Path. 1966; 45: 493-496.
46. Chetana PR, Somashekar MN, Srinatha BS, Policegoudra RS, Aradhya SM, Rao R. Synthesis, Crystal Structure, Antioxidant, Antimicrobial, and Mutagenic Activities and DNA Interaction Studies of Ni(II) Schiff Base 4-Methoxy-3-benzyloxybenzaldehyde Thiosemicarbazide complexes. ISRN Inorg. Chem. 2013; Article ID 250791: 11 pages.
47. Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. u.-Technol. 1995; 28: 25-30.
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01-01-2018
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“HETERO-BINUCLEAR COMPLEXES OF LANTHANUM (III) USING BRIDGING N,N?-BIS(2-PYRIDYLMETHYL)OXAMIDE AND TERMINAL 1,10-PHENANTHROLINE: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 6, Jan. 2018, pp. 460-73, https://doi.org/10.25004/IJPSDR.2018.100606.
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How to Cite
“HETERO-BINUCLEAR COMPLEXES OF LANTHANUM (III) USING BRIDGING N,N?-BIS(2-PYRIDYLMETHYL)OXAMIDE AND TERMINAL 1,10-PHENANTHROLINE: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 10, no. 6, Jan. 2018, pp. 460-73, https://doi.org/10.25004/IJPSDR.2018.100606.
