Vol. 22 No. 1 (2023): Mapana Journal of Sciences
Research Articles

CT-DNA interaction, Fluorescence binding and Microbial activity of Schiff base metal complexes derived from 4-bromobenzaldehyde and 2-amino-6-methylbenzothiazole

PDF
  • Senthamilselvan,
  • Palanimurugan,
  • Sithi Asma,
  • Cyril
Senthamilselvan
Raja Doraisingam Government Arts College, Sivagangai.
Bio
Palanimurugan
Raja Doraisingam Government Arts College, Sivagangai.
Bio
Sithi Asma
Raja Doraisingam Government Arts College, Sivagangai.
Bio
Cyril
Raja Doraisingam Government Arts College, Sivagangai.
Bio
DOI: https://doi.org/10.12723/mjs.64.8

Published 2022-12-06

Keywords

  • 2-amino-6-methylbenzothiazole based ligand,
  • metal complexes,
  • CT-DNA binding,
  • Fluorescence,
  • anti microbial study

Copyright (c) 2022

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Abstract

Bidentate ligand (L) was synthesized by knoevenagel reaction using 4-bromobenzaldehyde and 2-amino-6-methylbenzothiazole. The ligand has been confirmed from the analytical technique such as UV-Vis, FTIR, NMR, Mass and EPR spectral. The synthesized metal complexes were characterized from the spectra and physico-chemical techniques. These studies showed that the stoichiometric composition of ML2 type complexes. Absorption study implies that the compounds posses the octahedral geometry and their chelates are electrolytic and monomeric in nature. Absorption and gel electrophoreses experiments set up accepted the effective interaction with CT-DNA molecules. It was extended to Fluorescence emission study of binding. The anti bacterial and anti fungi studies were carried out by disc diffusion method. From the MIC values, metal complexes were controlling larger than Schiff base.

PDF

References

  1. Jeyamurugan R, Raman N, Synthesis, Characterization, Electrochemical Behaviour,
  2. DNA Binding and Cleavage tudies of ubstituted β-Diketimine Copper(II) and Zinc(II)
  3. Complexes, IJIRSET. 4(2) (2015) 477- 485.
  4. Dupureur C M, Barton J K, Structural Studies of Λ- and Δ-[Ru(phen)2dppz]2+ Bound to
  5. d(GTCGAC)2: Characterization of Enantioselective Intercalation. Inorg. Chem., 36
  6. (1997) 33-43 .
  7. Nair R B,Teng E S, Kirkland S L and Murphy C J, Synthes.is and DNA-Binding
  8. Properties of [Ru(NH(3))(4)dppz](2+). Inorg. Chem., 37 (1998) 139-141. L. Mishra, K.
  9. Bindu and L. C. Nathan, Indian.J. chem., 41A (2002) 2533.
  10. Nordan B, Lincoln P, Akerman B and Tuite E, In Metal Ions in Biological systems:
  11. Probing of Nucleic Acids by Metal Ion Complexes of Small Molecule, edited by A. Sigel
  12. and H. Sigel (Marcel Decker, Newyork), 33 (1996) 177.
  13. Gellert M, et al., Cold Spring HarberSymps. Quant. Biol., 43 (1979) 35.
  14. Foley F M ,Keene F R and Collins J G ,The DNA binding of the ΔΔ-, ΔΛ- and ΛΛ-
  15. stereoisomers of [{Ru(Me2bpy)2}2(μ-bpm)]4+ J.Chem. Soc. Dalton Trans, 21 (2001)
  16. -2974.
  17. Fitzgerald J A, Rauter H and Farrell N ,Approaches to Selective DNA Binding in
  18. Polyfunctional Dinuclear Platinum Chemistry. The Synthesis of a Trifunctional
  19. Compound and Its Interaction with the Mononucleotide 5‘-Guanosine Monophosphate,
  20. Inorg. Chem., 40 (2001) 6324-6327.
  21. Todd J A ,Rendina L M,Synthesis and DNA-Binding Properties of Cationic 2,2‘:6‘,2‘ ‘-
  22. Terpyridineplatinum(II) Complexes Containing 1,2- and 1,7-Dicarba-closo-dodecaborane
  23. Inorg. Chem.,41(2001) 3331-3333.
  24. Zhang C X ,Lippard S J ,New metal complexes as potential therapeutics, Curr. Op.
  25. Chem. Biol., 7 (2003) 481-489.
  26. Smith, J A. Collins, J G. Patterson B Tand Keene F R, Total enantioselectivity in the
  27. DNA binding of the dinuclear ruthenium(ii) complex [{Ru(Me2bpy)2}2(μ-bpm)]4+
  28. {bpm = 2,2′-bipyrimidine Me2bpy = , ′-dimethyl-2,2′-bipyridine},, J. Chem. Soc.
  29. Dalton Trans, 9 (2004) 1277-1283.
  30. Sortino, S, Condorelli G, Complexes between fluoroquinolones and calf thymus DNA:
  31. binding mode and photochemical reactivity, New J. Chem., 26 (2002) 250-258.
  32. Cusumano M , Di-Pietron M L, Giannetto A and Romano F, Influence of DNA on the
  33. Rate of Ligand Substitution in Platinum(II) Terpyridine Complexes, Inorg.Chem., 39
  34. (2000) 50-55 .
  35. Szacilowski K, Macyk W, Darzewiecka-Matuszek A, Brindell M and Stochel
  36. G,Bioinorganic Photochemistry: Frontiers and Mechanisms Chem. Rev., 105 (2005)
  37. -2694 .
  38. Alvarez M G, Alzuet G, Borras J , Macias B and Castineriras A, Oxidative Cleavage of
  39. DNA by a New Ferromagnetic Linear Trinuclear Copper(II) Complex in the Presence of
  40. H2O2/Sodium Ascorbate, Inorg. Chem., 42 (2003) 2992-2998.
  41. Ren R, Yang P, Zheng W and Hua Z A , imple Copper(II)−l-Histidine System for
  42. Efficient Hydrolytic Cleavage of DNA. Inorg. Chem., 39 (2000) 5454-5463.
  43. Reddy P A N, Nethaji M and Chakravarthy A R, Hydrolytic Cleavage of DNA by
  44. Ternary Amino Acid Schiff Base Copper(II) Complexes Having Planar Heterocyclic
  45. Ligands, Inorg. Chem., (2004) 1440-1446.
  46. Raman N, Pravin N, DNA fastening and ripping actions of novel Knoevenagel
  47. condensed dicarboxylic acid complexes in antitumor journey, Eur. J. Med. Chem. 80
  48. (2014) 57- 70.
  49. Bosseggia E , Gatos M , Lucatello L , Mancin F , Moro S, Palumbo M , Sissi C, Tecilla
  50. P , Tonellato U and Zegotto G, Toward Efficient Zn(II)-Based Artificial Nucleases.
  51. Chem. Soc., 126 (2004) 4543-4549 .
  52. Pathak R B, Thana B and Bahel S C, Antibacterial Antifungal agents, 8 (1980) 12.
  53. Chohan Z H, Rauf A, Synth. React. Inorg. Met. Org. Chem., 26 (1996) 591.
  54. Geary W, Geary W J. The Use of Conductivity Measurements in Organic Solvents for the
  55. Characterisation of Coordination Compounds. Coordination Chemistry. Chem.Rev.,7
  56. (1971) 81-122.
  57. Heim K E, Tagliaferro A R and Bobilya D J ,Nutr J, Flavonoid antioxidants: chemistry,
  58. metabolism and structure-activity relationships Biochem, 13 (2002) 572-584.
  59. Bakir S R, Al-hamdani A A, and Jarad A, Synthesis and Characterization of Mixed
  60. Ligands of Dithizone and Schiff Base Complexes with Selected Metal Ions.Journal for
  61. Pure Sciences, 9 (2013) 82 -94.
  62. Srivastava S D, Sen, J P, Synthesis and Biological Evaluation of 2- Amino benzo thiazole
  63. Derivatives.Indian Journal of Chemistry. 47B,10 (2008)1583-1586.
  64. Speier G , Csihony J ,Whalen A M and Pierpont C G, Studies on Aerobic Reactions of
  65. Ammonia/3,5-Di-tert-butylcatechol Schiff-Base Condensation Products with Copper,
  66. Copper(I), and Copper(II). trong Copper(II)−Radical Ferromagnetic Exchange and
  67. Observations on a Unique N−N Coupling Reaction Inorg. Chem., 35 (1 6) 351 -3524.
  68. Sasma P K, Patra A K, Nethaji M , Chakravarty A R, DNA Cleavage by New
  69. Oxovanadium(IV) Complexes of N- alicylidene α-Amino Acids and Phenanthroline
  70. Bases in the Photodynamic Therapy Window ., Inorg. Chem., 45 (2007) 11112-11121.
  71. Abdel-Rahman L H, El-Khatib R M, Nassr, L A E, Abu- Dief A M, Lashin F E,
  72. Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA
  73. interaction of few high spin Fe (II) Schiff base amino acid complexes, Spectrochim.Acta
  74. Part A. 111 (2013) 266 – 276.
  75. Gaber M H, Ghamry A E, Fathalla S K, Mansour M A, Synthesis, spectroscopic,
  76. thermal and molecular modeling studies of Zn2 +, Cd2 + andUO22 + complexes of
  77. Schiff bases containing triazole moiety. Antimicrobial, anticancer,antioxidant and DNA
  78. binding studies, Mater. Sci. Eng. C. 83, 78-89.
  79. Emara A A A, Spectrochim. Acta A. Structural, spectral and biological studies of
  80. binuclear tetradentate metal complexes of N3O Schiff base ligand synthesized from 4,6-
  81. diacetylresorcinol and diethylenetriamine 77 (2010) 117–125 .
  82. Anna K. F. Mårtensson, Maria Abrahamsson, Eimer M. Tuite, Per Lincoln.
  83. Diastereomeric Crowding Effects in the Competitive DNA Intercalation of
  84. Ru(phenanthroline)2dipyridophenazine2+ Enantiomers. Inorganic Chemistry , 58 (14)
  85. (2019) , 9452-9459.
  86. Vhanale B T , Deshmukh N J, Shinde A T, Synthesis, characterization, spectroscopic
  87. studies and biological evaluation of Schiff bases derived from 1–hydroxy-2-
  88. acetonapthanone, Heliyon, 5 (2019) e02774.
  89. Utecht-Jarzyńska G, Michalak A, Banaś J, Mlostoń G, Jasiński M, Trapping of
  90. trifluoroacetonitrile imines with mercapto acetaldehyde and mercapto carboxylic acids:
  91. An access to fluorinated 1,3,4-thiadiazine derivatives via (3+3)-annulation, J. Fluor.
  92. Chem.222–223 (2019) 8-14.
  93. Freeman F , Properties and reactions of Ylidene malononitriles, Chem. Rev. 80 (1980)
  94. - 350.
  95. Raman N, Joseph J, Sakthivel A, Jeyamurugan R, Synthesis, structural, characterization
  96. and antimicrobial studies of novel schiff base Copper(II) Complexes, J. Chil. Chem. Soc.
  97. (4) (2009) 354-357.
  98. Ramesh R, Maheshwaran S, Synthesis, spectra, dioxygen affinity and antifungal activity
  99. of Ru(III)Schiff base complexes, J. Inorg. Biochem. 96 (2003) 457-462.
  100. Al – Mohammed N. N, Alias Y, Abdullah Z, Shakir R M, Taha E M, Hamid A A,
  101. Synthesis and antibacterial evaluation of some novel imidazole and benzimidazole
  102. sulfonamides, Molecules, 26 (2013) 11978- 11995.
  103. Shukla S N, Gaur P, Lal Raidas M , Chaurasia B, Tailored synthesis of unsymmetrical
  104. tetradentate ONNO schiff base complexes of Fe(IIl), Co(II) and Ni(II): Spectroscopic
  105. characterization, DFT optimization, oxygenbinding study, antibacterial and anticorrosion
  106. activity, J. Mol. Stru. 1202 (2020) 127362- 127371.
  107. Saddam Hossain M D, Zahid A A S M, Zakaria C M, Anti-pathogenic Activity of Cu(II)
  108. Complexes Incorporating Schiff Bases,American Journal of Heterocyclic
  109. Chem5(1)(2019) 11-23.
  110. Raman N, Mahalakshmi R , Bio active mixed ligand complexes of Cu(II), Ni(II) and
  111. Zn(II): Synthesis, spectral, XRD, DNA binding and cleavage properties, Inorganic
  112. Chemistry Communications 40 (2014) 157–163.
  113. Hossain S , Camellia F K, Uddin N , Banu L A and Haque M , Synthesis,
  114. Characterization and Antimicrobial Activity of Metal Complexes of N-(4-
  115. methoxybenzylidene) Isonicotinohydrazone Schiff Base, 6 (2019) 1-8 .
  116. Tyagi P , Tyag M, Agrawal S , Chandra S, Ojha H, Pathak M , Synthesis,
  117. characterization of 1,2,4-triazole Schiff base derived 3d-metal complexes: Induces
  118. cytotoxicity in HepG2, MCF-7 cell line, BSA binding fluorescence and DFT study.
  119. Tyagi P, Chandra S, Saraswat B S, Ni(II) and Zn(II) complexes of 2-((thiophen-2-
  120. ylmethylene)amino) benzamide: Synthesis, spectroscopic characterization, thermal, DFT
  121. and anticancer activities, Biomolecular Spectroscopy 134 (2015) 200–209.