Abstract
The neutral mononuclear Ln(III) complexes (Ln = La, Sm) with 7-methoxychrom-one-3-carbaldehyde-isonicotinoyl hydrazone ligand (L) have been synthesized, characterized and investigated their interactions with calf-thymus DNA. The results show that the binding affinity of the La(III) complex is stronger than that of the Sm(III) complex and that of the ligand (L). Furthermore, the antioxidant activities of the ligand (L) and its Ln(III) complexes (Ln = La, Sm) were studied in detail.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bai GY, Wang KZ, Duan ZM, Gao LH (2004) Luminescent pH sensing and DNA binding properties of a novel ruthenium(II) complex. J Inorg Biochem 98:1017–1022. doi:10.1016/j.jinorgbio.2004.02.021
Barton JK, Danishefsky A, Goldberg J (1984) Tris(phenanthroline)ruthenium(II): stereoselectivity in binding to DNA. J Am Chem Soc 106:2172–2176. doi:10.1021/ja00319a043
Bektasoglu B, Celik SE, Ozyurek M, Guclu K, Apak R (2006) Novel hydroxyl radical scavenging antioxidant activity assay for water-soluble antioxidants using a modified CUPRAC method. Biochem Biophys Res Commun 345:1194–1200. doi:10.1016/j.bbrc.2006.05.038
Belicchi-Ferrari M, Bisceglie F, Pelosi G, Tarasconi P (2008) Heterocyclic substituted thiosemicarbazones and their Cu(II) complexes: synthesis, characterization and studies of substituent effects on coordination and DNA binding. Polyhedron 27:1361–1367. doi:10.1016/j.poly.2007.12.034
Bi SY, Qiao CY, Song DQ, Tian Y, Gao DJ, Sun Y, Zhang HQ (2006) Study of interactions of flavonoids with DNA using acridine orange as a fluorescence probe. Sens Actuators B Chem 119:199–208. doi:10.1016/j.snb.2005.12.014
Bors W, Saran M (1987) Radical scavenging by flavonoid antioxidants. Free Radic Res Commun 2:289–294. doi:10.3109/10715768709065294
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 111:8901–8911. doi:10.1021/ja00206a020
Chen YT, Zheng RL, Jia ZJ, Ju Y (1990) Flavonoids as superoxide scavengers and antioxidants. Free Radic Biol Med 9:19–21. doi:10.1016/0891-5849(90)90110-5
Cohen G, Eisenberg H (1969) Viscosity and sedimentation study of sonicated DNA-proflavine complexes. Biopolymers 8:45–49. doi:10.1002/bip.1969.360080105
Dalton SR, Glazier S, Leung B, Win S, Megatulski C, Burgmayer SJN (2008) DNA binding by Ru(II)-bis(bipyridine)-pteridinyl complexes. J Biol Inorg Chem 13:1133–1148. doi:10.1007/s00775-008-0399-y
Dhara K, Ratha J, Manassero M, Wang XY, Gao S, Banerjee P (2006) Synthesis, crystal structure, magnetic property and oxidative DNA cleavage activity of an octanuclear copper(II) complex showing water–perchlorate helical network. J Inorg Biochem 101:95–103. doi:10.1016/j.jinorgbio.2006.08.010
Efink MR, Ghiron CA (1981) Fluorescence quenching studies with proteins. Anal Biochem 114:199–227. doi:10.1016/0003-2697(81)90474-7
Fiorentino A, D′Abrosca B, Pacifico S, Iacovino R, Mastellone C, Blasio BD, Distachyasin PM (2006) Distachyasin: a new antioxidant metabolite from the leaves of Carex distachya. Bioorg Med Chem Lett 16:6096–6101. doi:10.1016/j.bmcl.2006.08.106
Firdaus F, Fatma K, Azam M, Khan SN, Khan AU, Shakir M (2008) Template synthesis and physicochemical studies of 14-membered hexaazmacrocyclic complexes with Co(II), Ni(II), Cu(II) and Zn(II): a comparative spectroscopic approach on DNA binding with Cu(II) and Ni(II) complexes. Transit Metab Chem 33:467–473. doi:10.1007/s11243-008-9066-y
Gao EJ, Wang KH, Gu XF, Yu Y, Sun YG, Zhang WZ, Yin HX, Wu Q, Zhu MC, Yan XM (2007) A novel binuclear palladium complex with benzothiazole-2-thiolate: synthesis, crystal structure and interaction with DNA. J Inorg Biochem 101:1404–1409. doi:10.1016/j.jinorgbio.2007.06.007
Hogberg T, Vora M, Drake S, Mitscher LA, Chu DTW (1984) Structure–activity relationships among DNA-gyrase inhibitors. Synthesis and antimicrobial evaluation of chromones and coumarins related to oxolinic acid. Acta Chem Scand B 38:359–366. doi:10.3891/acta.chem.scand.38b-0359
Husain SR, Cillard J, Cillard P (1987) Hydroxyl radical scavenging activity of flavonoids. Phytochemistry 26:2489–2491. doi:10.1016/S0031-9422(00)83860-1
Kong DM, Wang J, Zhu LN, Jin YW, Li XZ, Shen HX, Mi HF (2008) Oxidative DNA cleavage by Schiff base tetraazamacrocyclic oxamido nickel(II) complexes. J Inorg Biochem 102:824–832. doi:10.1016/j.jinorgbio.2007.12.002
Kostopanagiotou G, Pandazi AK, Andreadou I, Markantonis SL, Niokou D, Teloudis A, Costopanagiotou C, Arkadopoulos N, Smyrniotis V (2006) Effects of mannitol in the prevention of lipid peroxidation during liver resection with hepatic vascular exclusion. J Clin Anesth 18:570–574. doi:10.1016/j.jclinane.2006.03.014
Kumar RS, Arunachalam S (2007) DNA binding and antimicrobial studies of some polyethyleneimine-copper(II) complex samples containing 1,10-phenanthroline and l-theronine as co-ligands. Polyhedron 26:3255–3262. doi:10.1016/j.poly.2007.03.001
Kumar CV, Asuncion EH (1993) DNA binding studies and site selective fluorescence sensitization of an anthryl probe. J Am Chem Soc 115:8547–8553. doi:10.1021/ja00072a004
Laskowski H, Minczykowski A, Wysocki H (1995) Mortality and clinical course of patients with acute myocardial infarction treated with streptokinase and antioxidants: mannitol and ascorbic acid. Int J Cardiol 48:235–237. doi:10.1016/0167-5273(94)02252-E
Liu F, Meadows A, McMillin DR (1993) DNA-binding studies of Cu(bcp)2+ and Cu(dmp)2+: DNA elongation without intercalation of Cu(bcp)2+. J Am Chem Soc 115:6699–6704. doi:10.1021/ja00068a029
Marinic M, Piantanida I, Rusak G, Zinic M (2006) Interactions of quercetin and its lanthane complex with double stranded DNA/RNA and single stranded RNA: spectrophotometric sensing of poly G. J Inorg Biochem 100:288–298. doi:10.1016/j.jinorgbio.2005.11.013
Marmur J (1961) A procedure for the isolation of deoxyribonucleic acid from micro-organisms. J Mol Biol 3:208–218
Melidou M, Riganakos K, Galaris D (2005) Protection against nuclear DNA damage offered by flavonoids in cells exposed to hydrogen peroxide: the role of iron chelation. Free Radic Biol Med 39:1591–1600. doi:10.1016/j.freeradbiomed.2005.08.009
Nagababu P, Satyanarayana S (2007) DNA binding and cleavage properties of certain ethylenediamine cobalt(III) complexes of modified 1,10-phenanthrolines. Polyhedron 26:1686–1692. doi:10.1016/j.poly.2006.12.027
Nakamoto K (1986) Infrared and Raman spectra of inorganic and coordination compounds, 4th edn. Wiley, New York
Negre-Salvayre A, Salvayre R (1992) Quercetin prevents the cytotoxicity of oxidized LDL on lymphoid cell lines. Free Radic Biol Med 12:101–106
Psomas G (2008) Mononuclear metal complexes with ciprofloxacin: synthesis, characterization and DNA-binding properties. J Inorg Biochem 102:1798–1881. doi:10.1016/j.jinorgbio.2008.05.012
Qi HM, Zhang QB, Zhao TT, Hu RG, Zhang K, Lia Z (2006) In vitro antioxidant activity of acetylated and benzoylated derivatives of polysaccharide extracted from Ulva pertusa (Chlorophyta). Bioorg Med Chem Lett 16:2441–2445. doi:10.1016/j.bmcl.2006.01.076
Rao R, Patra AK, Chetana PR (2008) Synthesis, structure, DNA binding and oxidative cleavage activity of ternary (l-leucine/isoleucine) copper(II) complexes of heterocyclic bases. Polyhedron 27:1343–1352. doi:10.1016/j.poly.2007.12.026
Robak J, Gryglewski RJ (1988) Flavonoids are scavengers of superoxide anions. Biochem Pharmacol 37:837–841. doi:10.1016/0006-2952(88)90169-4
Selim M, Chowdhury SR, Mukherjea KK (2007) DNA binding and nuclease activity of a one-dimensional heterometallic nitrosyl complex. Int J Biol Macromol 41:579–583. doi:10.1016/j.ijbiomac.2007.07.016
Sharma SD, Rajor HK, Chopra S, Sharma RK (2005) Studies on structure activity relationship of some dihydroxy-4-methylcoumarin antioxidants based on their interaction with Fe(III) and ADP. Biometals 18:143–154. doi:10.1007/s10534-004-4256-3
Shi S, Liu J, Li J, Zheng KC, Huang XM, Tan CP, Chen LM, Ji LN (2006) Synthesis, characterization and DNA-binding of novel chiral complexes Δ- and Λ-[Ru(bpy)2L]2+ (L = o-mopip and p-mopip). J Inorg Biochem 100:385–395. doi:10.1016/j.jinorgbio.2005.12.005
Suh D, Chaires JB (1995) Criteria for the mode of binding of DNA binding agents. Bioorg Med Chem 3:723–728. doi:10.1016/0968-0896(95)00053-J
Sun YT, Bi SY, Song DQ, Qiao CY, Mu D, Zhang HQ (2008) Study on the interaction mechanism between DNA and the main active components in Scutellaria baicalensis Georgi. Sens Actuators B Chem 129:799–810. doi:10.1016/j.snb.2007.09.082
Tan LF, Chao H (2007) DNA-binding and photocleavage studies of mixed polypyridyl ruthenium(II) complexes with calf thymus DNA. Inorg Chim Acta 360:2016–2022. doi:10.1016/j.ica.2006.10.016
Tan LF, Chao H, Li H, Liu YJ, Sun B, Wei W, Ji LN (2005) Synthesis, characterization, DNA-binding and photocleavage studies of [Ru(bpy)2(PPIP)]2+ and [Ru(phen)2(PPIP)]2+. J Inorg Biochem 99:513–520. doi:10.1016/j.jinorgbio.2004.10.028
Tan LF, Liu XH, Chao H, Ji LN (2007) Synthesis, DNA-binding and photocleavage studies of ruthenium(II) complex with 2-(3′-phenoxyphenyl)imidazo[4,5-f][1,10] phenanthroline. J Inorg Biochem 101:56–63. doi:10.1016/j.jinorgbio.2006.08.006
Tysoe SA, Kopelman R, Schelzig D (1999) Flipping the molecular light switch off: formation of DNA-bound heterobimetallic complexes using Ru(bpy)2tpphz2+ and transition metal ions. Inorg Chem 38:5196–5197. doi:10.1021/ic9901315
Valentao P, Fernandes E, Carvalho F, Andrade PB, Seabra RM, Bastos ML (2002) Antioxidant activity of hypericum androsaemum infusion: scavenging activity against superoxide radical, hydroxyl radical and hypochlorous acid. Biol Pharm Bull 25:1320–1323. doi:10.1248/bpb.25.1320
Walenzyk T, Carola C, Buchholzb H, Koniga B (2005) Chromone derivatives which bind to human hair. Tetrahedron 61:7366–7377. doi:10.1016/j.tet.2005.05.081
Walle T (2007) Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? Semin Cancer Biol 17:354–362. doi:10.1016/j.semcancer.2007.05.002
Wang BD, Yang ZY (2008) Synthesis, characterization, DNA-binding properties of the Ln(III) complexes with 6-hydroxy chromone-3-carbaldehyde-(4′-hydroxy) benzoyl hydrazone. J Fluoresc 18:547–553. doi:10.1007/s10895-007-0298-6
Wang BD, Yang ZY, Wang Q, Cai TK, Crewdson P (2006) Synthesis, characterization, cytotoxic activities, and DNA-binding properties of the La(III) complex with naringenin Schiff-base. Bioorg Med Chem 14:1880–1888. doi:10.1016/j.bmc.2005.10.031
Wang BD, Yang ZY, Crewdson P, Wang DQ (2007) Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxy-chromone-3-carbaldehyde benzoyl hydrazone. J Inorg Biochem 101:1492–1504. doi:10.1016/j.jinorgbio.2007.04.007
Winterbourn CC (1979) Comparison of superoxide with other reducing agents in the biological production of hydroxyl radicals. Biochem J 182:625–628
Winterbourn CC (1981) Hydroxyl radical production in body fluids. Roles of metal ions, ascorbate and superoxide. Biochem J 198:125–131
Xu H, Zheng KC, Lin LJ, Li H, Gao Y, Ji LN (2004) Effects of the substitution positions of Br group in intercalative ligand on the DNA-binding behaviors of Ru(II) polypyridyl complexes. J Inorg Biochem 98:87–97. doi:10.1016/j.jinorgbio.2003.09.002
Zhou CY, Zhao J, Wu YB, Yin CX, Yang P (2007) Synthesis, characterization and studies on DNA-binding of a new Cu(II) complex with N1, N8-bis(l-methyl-4-nitropyrrole-2-carbonyl)triethylenetetramine. J Inorg Biochem 101:10–18. doi:10.1016/j.jinorgbio.2006.07.011
Acknowledgments
This work is supported by the National Natural Science Foundation of China (20475023) and Gansu NSF(0710RJZA012).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wang, Q., Yang, ZY., Qi, GF. et al. Crystal structures, DNA-binding studies and antioxidant activities of the Ln(III) complexes with 7-methoxychromone-3-carbaldehyde-isonicotinoyl hydrazone. Biometals 22, 927–940 (2009). https://doi.org/10.1007/s10534-009-9245-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10534-009-9245-0