Rare earth complexes with 3-carbaldehyde chromone-(benzoyl) hydrazone: Synthesis, characterization, DNA binding studies and antioxidant activity

Journal of Fluorescence

Volumn 20, Issue 1, 2010, Pages 329-342

  Li, Yong ^a   Yang, Zheng Yin ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

3 carbaldehyde chromone (benzoyl) hydrazone; Antioxidant activity; DNA binding properties; Fluorescence spectra; Rare earth complexes

Indexed keywords

ANTIOXIDANT ACTIVITIES; CHROMONES; DNA-BINDING PROPERTIES; FLUORESCENCE SPECTRA; HYDRAZONES; RARE EARTH COMPLEX;

ABSORPTION SPECTROSCOPY; BINDING ENERGY; DNA; EXPERIMENTS; FLUORESCENCE; GENES; LIGANDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PLANTS (BOTANY); RARE EARTHS; VISCOSITY MEASUREMENT;

COMPLEXATION;

3 CARBALDEHYDE CHROMONE (BENZOYL) HYDRAZONE; 3-CARBALDEHYDE CHROMONE-(BENZOYL) HYDRAZONE; ANTINEOPLASTIC AGENT; CHROMONE DERIVATIVE; DNA; HYDRAZONE DERIVATIVE; HYDROXYL RADICAL; LANTHANIDE; LIGAND; ORGANOMETALLIC COMPOUND; SCAVENGER; SUPEROXIDE;

ABSORPTION; ANIMAL; ARTICLE; CATTLE; CHEMISTRY; ELECTRON; METABOLISM; MOLECULAR PROBE; SPECTROSCOPY; SYNTHESIS; VISCOSITY;

ABSORPTION; ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CHROMONES; DNA; ELECTRONS; FREE RADICAL SCAVENGERS; HYDRAZONES; HYDROXYL RADICAL; LIGANDS; METALS, RARE EARTH; MOLECULAR PROBES; ORGANOMETALLIC COMPOUNDS; SPECTRUM ANALYSIS; SUPEROXIDES; VISCOSITY;

EID: 77951022842     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-009-0561-0     Document Type: Article

References (51)

1. LR Kelland 2005 Overcoming the immortality of tumour cells by telomere and telomerase based cancer therapeutics-current status and future prospects Eur J Cancer 41 7 971 979 10.1016/j.ejca.2004.11.024 1:CAS:528:DC%2BD2MXjs1Crtbg%3D 15862745 (Pubitemid 40602848)
2. V Uma M Kanthimath T Weyhermuller BU Nair 2005 Oxidative DNA cleavage mediated by a new copper (II) terpyridine complex: crystal structure and DNA binding studies JInorgChem 99 12 2299 2307 1:CAS:528:DC%2BD2MXht1Omu7fM (Pubitemid 41727920)
3. KE Erkkila DT Odom JK Barton 1999 Recognition and reaction of metallointercalators with DNA Chem Rev 99 9 2777 2795 10.1021/cr9804341 1:CAS:528:DyaK1MXksl2ls7w%3D 11749500
4. DL Arockiasamy S Radhika R Parthasarathi BU Nair 2009 Synthesis and DNA-binding studies of two ruthenium(II) complexes of an intercalating ligand Eur J MedChem 44 5 2044 2051
5. BD Wang ZY Yang P Crewdson DQ Wang 2007 Synthesis, crystal structure and DNA-binding studies of the Ln(III) complex with 6-hydroxychromone-3-carbaldehyde benzoyl hydrazone J Inorg Biochem 101 10 1492 1504 10.1016/j.jinorgbio.2007.04. 007 1:CAS:528:DC%2BD2sXhtVWht7nK 17692381 (Pubitemid 47362354)
6. CV Kumar JK Barton NJ Turro 1985 Photophysics of ruthenium complexes bound to double helical DNA J Am Chem Soc 107 19 5518 5523 10.1021/ja00305a032 1:CAS:528:DyaL2MXltF2hsLw%3D
7. H Xu KC Zheng Y Chen YZ Li LJ Lin H Li PX Zhang LN Ji 2003 Effects of ligand planarity on the interaction of polypyridyl Ru(II) complexes with DNA Dalton Trans 3 11 2260 2268 10.1039/b300353a
8. S Mahadvan M Palaniandavar 1997 Spectroscopic and voltammetric studies of copper(II) complexes of bis(pyrid-2-yl)-di/trithia ligands bound to calf thymus DNA Inorg Chim Acta 254 2 291 302 10.1016/S0020-1693(96)05175-4 1:CAS:528:DyaK2sXhsFWrtbw%3D (Pubitemid 127350396)
9. H Xu KC Zheng H Deng LJ Lin QL Zhang LN Ji 2003 Effects of the ancillary ligands of polypyridyl ruthenium(III) complexes on the DNA-binding behaviors New J Chem 27 8 1255 1263 10.1039/b212826h 1:CAS:528:DC%2BD3sXls1CqtL4%3D (Pubitemid 37046902)
10. M Asadi E Safaei B Ranjbar L Hasani 2004 Thermodynamic and spectroscopic study on the binding of cationic Zn(II) and Co(II) tetrapyridinoporphyrazines to calf thymus DNA: the role of the central metal in binding parameters New J Chem 28 10 1227 1234 10.1039/b404068f 1:CAS:528:DC%2BD2cXotVOnt7Y%3D (Pubitemid 39457456)
11. CC Bisi O Carugo 1989 Studies on fluorescent lanthanide complexes. New complexes of lanthanides(III) with coumarinic-3-carboxylic acid Inorg Chim Acta 159 2 157 161 10.1016/S0020-1693(00)80560-5
12. YX Ci YZ Li WB Chang 1991 Fluorescence reaction of terbium(III) with nucleic acids in the presence of phenanthroline Anal Chim Acta 248 2 589 594 10.1016/S0003-2670(00)84680-2 1:CAS:528:DyaK3MXlsFChtb4%3D
13. DA Horne PB Dervan 1990 Recognition of mixed-sequence duplex DNA by alternate-strand triple-helix formation J Am Chem Soc 112 6 2435 2437 10.1021/ja00162a063 1:CAS:528:DyaK3cXhtlCltrw%3D (Pubitemid 20144461)
14. HE Moser PB Dervan 1987 Sequence-specific cleavage of double helical DNA by triple helix formation Science 238 4827 645 650 10.1126/science.3118463 1:CAS:528:DyaL1cXltVKitA%3D%3D 3118463
15. VY Sosnovskikh 2003 Synthesis and reactions of halogen-containing chromones Russ Chem Rev 72 6 489 516 10.1070/RC2003v072n06ABEH000770 1:CAS:528:DC%2BD3sXosVKns74%3D (Pubitemid 44339500)
16. G Athanasellis G Melagraki A Afantitis K Makridima OI Markopoulou 2006 A simple synthesis of functionalized 2-amino-3-cyano-4-chromones by application of the N-hydroxybenzotriazole methodology Arkivoc 10 28 34 (Pubitemid 43276524)
17. G Singh R Singh NK Girdhar MPS Ishar 2002 A versatile route to 2-alkyl-/aryl-amino-3-formyl- and hetero-annelated-chromones, through a facile nucleophilic substitution at C2 in 2-(N-methylanilino)-3-formylchromones Tetrahedron 58 12 2471 2480 10.1016/S0040-4020(02)00128-X 1:CAS:528: DC%2BD38XhslGqtrw%3D (Pubitemid 34215055)
18. LZ Piao HR Park YK Park SK Lee JH Park MK Park 2002 Mushroom tyrosinase inhibition activity of some chromones Chem Pharm Bull 50 3 309 311 10.1248/cpb.50.309 1:CAS:528:DC%2BD38Xks12ksbc%3D 11911191 (Pubitemid 41685629)
19. YZ Cai Q Luo M Sun H Corke 2004 Antioxidant activity and phenolic compounds of 112 traditional Chinese medicinal plants associated with anticancer Life Sci 74 17 2157 2184 10.1016/j.lfs.2003.09.047 1:CAS:528: DC%2BD2cXht1yqtLY%3D 14969719 (Pubitemid 38210440)
20. KE Heim AR Tagliaferro DJ Bobilya 2002 Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships J Nutr Biochem 13 10 572 584 10.1016/S0955-2863(02)00208-5 1:CAS:528:DC%2BD38XotVeqs7s%3D 12550068 (Pubitemid 35246546)
21. GM Howe KC Wu WR Bauer SJ Lippard 1976 Binding of platinum and palladium metallointercalation reagents and antitumor drugs to closed and open DNAs Biochem 15 19 4339 4346 10.1021/bi00664a031
22. MR Eftink CA Ghiron 1981 Fluorescence quenching studies with proteins Anal Biochem 114 2 199 227 10.1016/0003-2697(81)90474-7 1:CAS:528: DyaL3MXkvFeitLs%3D 7030122
23. CV Kumar RS Turner EH Asuncion 1993 Groove binding of a styrylcyanine dye to the DNA double helix: the salt effect J Photochem Photobiol A: Chem 74 2-3 231 238 10.1016/1010-6030(93)80121-O 1:CAS:528:DyaK3sXms1Gktr0%3D
24. 2 studied by NMR Biochem 33 17 5031 5040 10.1021/bi00183a005 1:CAS:528: DyaK2cXis1equrk%3D (Pubitemid 24150967)
25. Y Xiong XF He XH Zou JZ Wu XM Chen LN Ji RH Li JY Zhou KB Yu 1999 Interaction of polypyridyl ruthenium(II) complexes containing non-planar ligands with DNA J Chem Soc, Dalton Trans: Inorg Chem 1 19 24 10.1039/a806170j
26. CC Winterbourn 1979 Comparison of superoxide with other reducing agents in the biological production of hydroxyl radicals Biochem J 182 2 625 628 1:CAS:528:DyaL3cXltlOmtw%3D%3D 41521
27. CC Winterbourn 1981 Hydroxyl radical production in body fluids. Roles of metal ions, ascorbate and superoxide Biochem J 198 1 125 131 1:CAS:528:DyaL3MXmtFKntro%3D 6275837
28. A Nohara T Umetani Y Sanno 1973 Facile synthesis of chromone-3- carboxaldehyde, chromone-3-carboxylic acid, and 3-hydroxymethylchromone Tetrahedron Lett 14 22 1995 1998 10.1016/S0040-4039(01)96102-7
29. WJ Geary 1971 Use of conductivity measurements in organic solvents for the characterization of coordination compounds Coord Chem Rev 7 1 81 122 10.1016/S0010-8545(00)80009-0 1:CAS:528:DyaE3MXlsVCgsrg%3D
30. 2-Schiff- base ligands incorporating pyrazole: synthesis, characterisation and reactivity toward S-donors, N-donors, copper and tin acceptors Polyhedron 18 23 3041 3050 10.1016/S0277-5387(99)00230-2 1:CAS:528:DyaK1MXnsVGnt7k%3D
31. KK Narang VP Singh 1993 Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with acetylacetone bis-benzoylhydrazone and acetylacetone bis-isonicotinoylhydrazone Transition Met Chem 18 3 287 290 10.1007/BF00207948 1:CAS:528:DyaK3sXltVOqsrY%3D
32. BD Wang ZY Yang DW Zhang Y Wang 2006 Synthesis, structure, infrared and fluorescence spectra of new rare earth complexes with 6-hydroxy chromone-3-carbaldehyde benzoyl hydrazone Spectrochim acta Part A 63 1 213 219 10.1016/j.saa.2005.05.007 (Pubitemid 41774108)
33. JM Lehn 1990 Perspectives in supramolecular chemistry: from molecular recognition to molecular information processing and self organization Angew Chem Int Ed Engl 29 11 1304 1319 10.1002/anie.199013041
34. III ion luminescence and efficient energy transfer between lanthanide chelates within the polymeric structure in aqueous solutions J Chem Soc, Perkin Trans 2 5 995 999
35. SL Wu YL Wu YS Yang 1992 Rare earth(iii) complexes with indole-derived acetylacetones II. luminescent intensity for europium(iii) and terbium(iii) complexes J Alloys Compd 180 2 399 402 10.1016/0925-8388(92)90408-2 1:CAS:528:DyaK38Xksl2jtbw%3D
36. S Sato M Wada 1970 Relations between intramolecular energy transfer efficiencies and triplet state energies in rare Earth β-diketone chelates Bull Chem Soc Jpn 43 7 1955 1962 10.1246/bcsj.43.1955 1:CAS:528: DyaE3cXkvVags7Y%3D
37. WN Wua N Tang L Yan 2008 Rare earth complexes with a novel ligand N-(naphthalen-2-yl)-N-phenyl-2-(quinolin-8-yloxy)acetamide: preparation and spectroscopic studies Spectrochim Acta Part A 71 4 1461 1465 10.1016/j.saa.2008.05.001
38. Y Tang KZ Tang WS Liu MY Tan 2008 Assembly, crystal structure, and luminescent properties of three-dimensional (10,3)-a netted rare earth coordination polymers Sci China, Ser B 51 7 614 622 10.1007/s11426-008-0042-3 1:CAS:528:DC%2BD1cXnsFalsLg%3D
39. M Latva H Takalo VM Mukkala C Matachescu JC Rodríguez-Ubis J Kankare 1997 Correlation between the lowest triplet state energy level of the ligand and lanthanide(III) luminescence quantum yield J Lumin 75 2 149 169 10.1016/S0022-2313(97)00113-0 1:CAS:528:DyaK2sXlvVKktLY%3D (Pubitemid 127403587)
40. F Gao H Chao F Zhou YX Yuan B Peng LN Ji 2006 DNA interactions of a functionalized ruthenium(II) mixed-polypyridyl complex [Ru(bpy)2 ppd]2+ J Inorg Biochem 100 9 1487 1494 10.1016/j.jinorgbio.2006.04.008 1:CAS:528: DC%2BD28Xot1Wrs78%3D 16766033 (Pubitemid 44209186)
41. AM Pyle JP Rehmann R Meshoyrer CV Kumar NJ Turro JK Barton 1989 Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA J Am Chem Soc 111 8 3051 3058 10.1021/ja00190a046 1:CAS:528:DyaL1MXitVOqur0%3D
42. WD Wilson L Ratmeyer M Zhao L Strekowski D Boykin 1993 The search for structure-specific nucleic acid-interactive drugs: effects of compound structure on RNA versus DNA interaction strength Biochem 32 15 4098 4104 10.1021/bi00066a035 1:CAS:528:DyaK3sXltlSqsro%3D (Pubitemid 23127004)
43. H Xu KC Zheng LJ Lin H Li Y Gao LN Ji 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 1 87 97 10.1016/j.jinorgbio. 2003.09.002 1:CAS:528:DC%2BD3sXpsVSqtrc%3D 14659637 (Pubitemid 37495014)
44. JB Le-Pecq C Paoletti 1967 A fluorescent complex between ethidium bromide and nucleic acids J Mol Biol 27 1 87 106 10.1016/0022-2836(67)90353-1 1:CAS:528:DyaF2sXksFSns7c%3D
45. M Lee AL Rhodes MD Wyatt S Forrow JA Hartley 1993 GC base sequence recognition by oligo(imidazolecarboxamide) and C-terminus-modified analogues of distamycin deduced from circular dichroism, proton nuclear magnetic resonance, and methidiumpropylethylenediaminetetraacetate-iron(II) footprinting studies Biochem 32 16 4237 4245 10.1021/bi00067a011 1:CAS:528:DyaK3sXitVCks7k%3D (Pubitemid 23137729)
46. LS Lerman 1961 Structural considerations in the interaction of deoxyribonucleic acid and acridines J Mol Biol 3 18 30 10.1016/S0022-2836(61) 80004-1 1:CAS:528:DyaF3MXntVyqsw%3D%3D 13761054
47. S Satyanarayana JC Dabrowiak JB Chaires 1993 Tris(phenanthroline) ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding Biochem 32 10 2573 2584 10.1021/bi00061a015 1:CAS:528:DyaK3sXht1Sgu7c%3D
48. 2+ with DNA: effects of the ancillary ligands on the DNA-binding behaviors Inorg Chem 40 19 5045 5050 10.1021/ic001124f 1:CAS:528:DC%2BD3MXls12qtLs%3D 11531457 (Pubitemid 32825905)
49. JG Liu BH Ye H Li QX Zhen LN Ji YH Fu 1999 Polypyridyl ruthenium(II) complexes containing intramolecular hydrogen-bond ligand: syntheses, characterization, and DNA-binding properties J Inorg Biochem 76 3-4 265 271 10.1016/S0162-0134(99)00154-3 1:CAS:528:DC%2BD3cXhtFSltQ%3D%3D
50. Q Wang ZY Yang GF Qi DD Qin 2009 Synthesis, crystal structure, antioxidant activities and DNA-binding studies of the Ln(III) complexes with 7-methoxychromone-3-carbaldehyde-(4'-hydroxy) benzoyl hydrazone Eur J Med Chem 44 6 2425 2433 10.1016/j.ejmech.2008.10.023 1:CAS:528:DC%2BD1MXkslyjtb8%3D 19038478
51. PH Proctor ES Reynolds 1984 Free radicals and disease in man Physiol Chem Phys Med NMR 16 3 175 195 1:CAS:528:DyaL2MXktlKktA%3D%3D 6393156