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A New Isoindoline Based Schiff Base Derivative as Cu(II) Chemosensor: Synthesis, Photophysical, DNA Binding and Molecular Docking Studies

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Abstract

A new chemo sensor 2-(4-methylbenzylideneamino)-isoindoline-1,3-dione (PDB) was synthesized and characterized by UV–Vis., IR, 1H NMR, 13C NMR spectral and elemental analysis. Its photophysical properties in organic solvents with different polarity were studied. The sensitivity of the PDB in different pH solutions was investigated and the results indicated that PDB would be able to act as an efficient “off–on–off” switch for pH. This chemosensor displayed high selectivity towards Cu2+ in the presence of metal ions Ba2+, Cd2+, Co2+, Hg2+, Ni2+, Pb2+, K+ and Zn2+ in DMF/H2O solution. Furthermore DNA binding and molecular docking studies were also carried out to investigate the biological potential of the test compound. The interaction of compound (PDB) with Ct-DNA was examined by absorption, CD spectroscopy, cyclic voltammetry and viscosity measurements. In silico studies revealed that the test compound (PDB) showed good affinity towards the target receptor d (CGCGAATTCGCG)2 with the binding energy of −7.70 kcal/mol.

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References

  1. Robinson NJ, Winge DR (2010) Copper metallochaperones. Annu Rev Biochem 79:537–562

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  2. Liu GL, Feng DQ, Chen T, Li D, Zheng W (2012) DNA-templated formation of silver nanoclusters as a novel light-scattering sensor for label-free copper ionsdetection. J Mater Chem 22:20885–20888

    Article  CAS  Google Scholar 

  3. Liu Y, Liang P, Guo L (2005) Nanometer titanium dioxide immobilized on silica gel as sorbent for preconcentration of metal ions prior to their determination by inductively coupled plasma atomic emission spectrometry. Talanta 68:25–30

    Article  CAS  PubMed  Google Scholar 

  4. Becker JS, Matusch A, Depboylu C, Dobrowolska J, Zoriy MV (2007) Quantitative imaging of selenium, copper, and zinc in thin sections of biological tissues (Slugs-Genus Arion) measured by laser ablation inductively coupled plasma mass spectrometry. Anal Chem 79:6074–6080

    Article  CAS  PubMed  Google Scholar 

  5. Gonzales APS, Firmino MA, Nomure CS, Rocha FRP, Oliveira PV, Gaubeur I (2009) Peat as a natural solid-phase for copper preconcentration and determination in a multicommuted flow system coupled to flame atomic absorption spectrometry. Anal Chim Acta 636:198–204

    Article  CAS  PubMed  Google Scholar 

  6. Wang J, Xiea Y, Wang Z, Song QH (2014) A highly sensitive and selective naked-eye probe for detecting copper ion based on 2,3-modified Bodipy derivatives. Sens Actuators B 194:149–155

    Article  CAS  Google Scholar 

  7. Goswami S, Maity S, Das AK, Maity AC (2013) Single chemosensor for highly selective colorimetric and fluorometric dual sensing of Cu(II) as well as ‘NIRF’ to acetate ion. Tetrahedron Lett 54:6631–6634

    Article  CAS  Google Scholar 

  8. Perez-Ruiz R, Dıaz Y, Goldfuss B, Hertel D, Meerholz K, Griesbeck AG (2009) Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore. Org Biomol Chem 7:3499–3504

    Article  CAS  PubMed  Google Scholar 

  9. Mohamed RR, Fekry AM (2011) Antimicrobial and anticorrosive activity of adsorbents based on chitosan Schiff’s base. Int J Electrochem Sci 6:2488–2508

    CAS  Google Scholar 

  10. De Clercq B, Verpoort F (2003) Atom transfer radical polymerization of vinyl monomers mediated by a new class of neutral and cationic ruthenium alkylidene catalysts containing a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff base ligand. Polym Bull 50:153–160

    Article  Google Scholar 

  11. Wang PH, Keck JG, Lien EJ, Lai MM (1990) Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus. J Med Chem 33(2):608–614

    Article  CAS  PubMed  Google Scholar 

  12. Kumar J, Bhattacharyya PK, Das DK (2015) New duel fluorescent “on–off” and colorimetric sensor for copper (II): Copper (II) binds through N coordination and pi cation interaction to sensor. Spectrochim Acta A 138:99–104

    Article  CAS  Google Scholar 

  13. Shellaiah M, Wu YH, Singh A, Raju MVR, Lin HC (2013) Novel pyrene- and anthracene-based Schiff base derivatives as Cu2+ and Fe3+ fluorescence turn-on sensors and for aggregation induced emissions. J Mater Chem A 1:1310–1318

    Article  CAS  Google Scholar 

  14. Lu F, Gao L, Li H, Ding L, Fang Y (2007) Molecular engineered silica surfaces with an assembled anthracene monolayer as a fluorescent sensor for organic copper(II) salts. Appl Surf Sci 253:4123–4131

    Article  Google Scholar 

  15. Santos JL, Yamasaki PR, Chin CM, Takashi CH, Pavan FR, Leite CQF (2009) Synthesis and in vitro anti Mycobacterium tuberculosis activity of a series of phthalimide derivatives. Bioorg Med Chem 17:3795–3799

    Article  CAS  PubMed  Google Scholar 

  16. Lee NJ, Lee SJ, Kim SH, Kang YS, Moon SB, Sohn H, Kang KT, Theodorakis EA (2004) Synthesis and in vitro antitumor activity of phthalimide-based polymers containing camptothecin. Eur Polym J 40:1291–1296

    Article  CAS  Google Scholar 

  17. Abdel-Aziz AAM (2007) Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modelling study. Eur J Med Chem 42:614–626

    Article  CAS  PubMed  Google Scholar 

  18. Sarkar M, Banthia S, Samanta A (2007) A highly selective ‘off–on’ fluorescence chemosensor for Cr(III). Tetrahedron Lett 47:7575–7578

    Article  Google Scholar 

  19. Sarkar M, Yellampalli R, Bhattacharya B, Kanaparthi R, Samanta A (2007) Ratiometric fluorescence signalling of fluoride ions by an amidophthalimide derivative. J Chem Sci 119:91–97

    Article  CAS  Google Scholar 

  20. Perez-Ruiz R, Griesbeck AG, Sampedro D (2012) Computational study on fluoride recognition by an urea-activated phthalimide chemosensor. Tetrahedron 68:5724–5729

    Article  CAS  Google Scholar 

  21. Zhong W, Yu JS, Liang Y (2003) Chlorobenzylidine-herring sperm DNA interac-tion: binding mode and thermodynamic studies. Spectrochim. Acta A 59:1281–1288

    Article  Google Scholar 

  22. Wang X, Li Y, Gong S, Fu D (2002) A spectroscopic study on the DNA binding behaviour of the anticancer drug dacarbazine. Spectrosc Lett 35:751–756

    Article  CAS  Google Scholar 

  23. Sandstrom K, Warmlander S, Leijon M, Graslund A (2003) 1H NMR studies of selec-tive interactions of norfloxacin with double-stranded DNA. Biochem Biophys Res Commun 304:55–59

    Article  CAS  PubMed  Google Scholar 

  24. Palecek E (2002) Past, present and future of nucleic acids electrochemistry. Talanta 56:809–819

    Article  CAS  PubMed  Google Scholar 

  25. Jangir DK, Charak S, Mehrotra R, Kundu S (2011) FTIR and circular dichroism spectroscopic study of interaction of 5-fluorouracil with DNA. J Photoch Photobiol B105:143–148

    Article  Google Scholar 

  26. Vaidyanathan VG, Nair BU (2003) Oxidative cleavage of DNA by tridentate copper (II) complex. J Inorg Biochem 93:271–276

    Article  CAS  PubMed  Google Scholar 

  27. Huang SY, Zou X (2010) Advances and challenges in protein-ligand docking. Int J Mol Sci 11:3016–3034

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  28. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639–1662

    Article  CAS  Google Scholar 

  29. Mouilleron S, Badet-Denisot MA, Golinelli-Pimpaneau B (2008) Ordering of C-terminal loop and glutaminase domains of glucosamine-6-phosphate synthase promotes sugar ring opening and formation of the ammonia channel. J Mol Biol 377(4):1174–1185

    Article  CAS  PubMed  Google Scholar 

  30. Tanak H, Agar AA, Buyukgungor O (2014) Experimental (XRD, FT-IR and UV–Vis) and theoretical modeling studies of Schiff base (E)-Nا-((5-nitrothiophen-2-yl) methylene)-2-phenoxyaniline. Spectrochim Acta A 118:672–682

    Article  CAS  Google Scholar 

  31. Bojinov VB, Georgiev NI, Bosch P (2009) Design, synthesis of highly photostable yellow–green emitting 1,8-naphthalimides as fluorescent sensors for metal cations and protons. J Fluoresc 19:127–139

    Article  CAS  PubMed  Google Scholar 

  32. Liu SB, Bi CF, Fan YH, Zhao Y, Zhang PF, Luo Q, Zhang D (2011) Synthesis, characterization and crystal structure of a new fluorescent probe based on Schiff base for the detection of Zinc(II). Inorg Chem Commun 14:1297–1301

    Article  CAS  Google Scholar 

  33. Aksuner N, Henden E, Yilmaz I, Cukurovali A (2009) A highly sensitive and selective fluorescent sensor for the determination of copper(II) based on a schiff base. Dyes Pigments 83:211–217

    Article  CAS  Google Scholar 

  34. Icsel C, Yilmaz VT (2014) In vitro DNA binding studies of the sweetening agent saccharin and its copper(II) and zinc(II) complexes. J Photoch Photobiol B 130:115–121

    Article  CAS  Google Scholar 

  35. Zeglis BM, Pierre VC, Barton JK (2007) Metallo-intercalators and metallo-insertors. Chem Commun 28:4565–4579

    Article  Google Scholar 

  36. Hu H, ChenY ZH, Pan Z (2011) Synthesis, crystal structure, and DNA cleavage activity of a dinuclear nickel(II) complex with a macrocyclic ligand. Trans Met Chem 36:395–402

    Article  CAS  Google Scholar 

  37. Ivanov VI, Minchenkova LE, Schyolkina AK, Poletayer AI (1973) Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism. Biopolymers 12:89–110

    Article  CAS  PubMed  Google Scholar 

  38. Chen LM, Liu J, Chen JC, Shi S, Tan CP, Zheng KC, Ji LN (2008) Experimental and theoretical studies on the DNA-binding and spectral properties of water-soluble complex [Ru(MeIm)4(dpq)]2+. J Mol Struct 881:156–166

    Article  CAS  Google Scholar 

  39. Wu H, Yuan J, Bai Y, Pan G, Wang H, Kong J, Fan X, Liu H (2012) Synthesis, structure, DNA-binding properties and antioxidant activity of silver(I) complexes containing V-shaped bis-benzimidazole ligands. Dalton Trans 41:8829–8838

    Article  CAS  PubMed  Google Scholar 

  40. Zhang SS, Niu SY, Qu B, Jie GF, Xu H, Ding CF (2005) Studies on the interaction mechanism between hexakis(imidazole) manganese(II) terephthalate and DNA and preparation of DNA electrochemical sensor. J Inorg Biochem 99:2340–2347

    Article  CAS  PubMed  Google Scholar 

  41. Hirohama T, Kuranuki Y, Ebina E, Sugizaki T, Arii H, Chikira M, Selvi PDB, Palaniandavar M (2005) Copper(II) complexes of 1,10-phenanthroline-derived ligands: studies on DNA binding properties and nuclease activity. J Inorg Biochem 99:1205–1219

    Article  CAS  PubMed  Google Scholar 

  42. Carter MT, Rodriguez M, Bard AJ (1989) Voltammetric studies of the interaction of metal chelates with DNA. 2. tris-chelated complexes of cobalt (III) and iron (II) with 1,10-phenanthroline and 2,2′-bipyridine. J Am Chem Soc 11:8901–8911

    Article  Google Scholar 

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Acknowledgments

The financial support from University Grant Commission (Major Research Project, F.No. 41-238/2012) and Department of Science and Technology, New Delhi (Fast Track Scheme for Young Scientist, SR/FT/CS-002/2009) is gratefully acknowledged. Mr. Nayab is grateful to UGC, New Delhi for the financial support through UGC- BSR Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Jamia Millia Islamia, New Delhi, 110 025, India

    Pattan Sirajuddin Nayab &  Rahisuddin

  2. Department of Biochemistry, Sri Krishnadevraya University, Ananthapuram, 515 003, India

    Madhusudana Pulaganti & Suresh Kumar Chitta

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  1. Pattan Sirajuddin Nayab
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  2. Madhusudana Pulaganti
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Nayab, P.S., Pulaganti, M., Chitta, S.K. et al. A New Isoindoline Based Schiff Base Derivative as Cu(II) Chemosensor: Synthesis, Photophysical, DNA Binding and Molecular Docking Studies. J Fluoresc 25, 1763–1773 (2015). https://doi.org/10.1007/s10895-015-1664-4

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