Promising antioxidant and anticancer (human breast cancer) oxidovanadium(IV) complex of chlorogenic acid. Synthesis, characterization and spectroscopic examination on the transport mechanism with bovine serum albumin

被引:81
作者
Naso, Luciana G. [1 ]
Valcarcel, Maria [2 ]
Roura-Ferrer, Meritxell [2 ]
Kortazar, Danel [2 ]
Salado, Clarisa [2 ]
Lezama, Luis [3 ]
Rojo, Teofilo [3 ]
Gonzalez-Baro, Ana C. [1 ]
Williams, Patricia A. M. [1 ]
Ferrer, Evelina G. [1 ]
机构
[1] Univ Nacl La Plata, Fac Ciencias Exactas, Dept Quim, Ctr Quim Inorgan,CEQUINOR,CONICET,UNLP, RA-1900 La Plata, Buenos Aires, Argentina
[2] INNOPROT, Derio, Spain
[3] Univ Basque Country, Fac Ciencias & Tecnol, Dept Quim Inorgan, E-48080 Bilbao, Spain
关键词
Albumin interaction; Anticancer activity; Antioxidant activity; Chlorogenic acid; Oxidovanadium(IV); IN-VITRO; BIS(4,7-DIMETHYL-1,10-PHENANTHROLINE) SULFATOOXOVANADIUM(IV); OXOVANADIUM(IV) COMPLEXES; ANTITUMOR-ACTIVITY; CAFFEIC ACID; VANADIUM; APOPTOSIS; CELLS; FLUORESCENCE; INHIBITION;
D O I
10.1016/j.jinorgbio.2014.02.013
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new chlorogenate oxidovanadium complex (Na[VO(chlorog)(H2O)(3)]center dot 4H(2)O) was synthesized by using Schlenk methodology in the course of a reaction at inert atmosphere in which deprotonated chlorogenic acid ligand binds to oxidovanadium(IV) in a reaction experiment controlled via EPR technique and based in a species distribution diagram. The compound was characterized by FTIR, EPR, UV-visible and diffuse reflectance spectroscopies and thermogravimetric, differential thermal and elemental analyses. The ligand and the complex were tested for their antioxidant effects on DPPH center dot (1,1-diphenyl-2-picrylhydrazyl radical), ABTS(center dot+) (radical cation of 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt), O-2(center dot-), OH center dot and ROO center dot radicals and their cytotoxic activity on different cancer cell lines (SKBR3,T47D and MDAMB231) and primary human mammary epithelial cells. The complex behaved as good antioxidant agent with strongest inhibitory effects on O-2(center dot-), OH center dot and ROO center dot radicals and exhibited selective cytotoxicity against SKBR3 cancer cell line. Albumin interaction experiments denoted high affinity toward the complex and its calculated binding constant was indicative of a strong binding to the protein. Based on this study, it is hypothesized that Na[VO(chlorog)(H2O)(3)]center dot 4H(2)O would be a promising candidate for further evaluation as an antioxidant and anticancer agent. (C) 2014 Elsevier Inc. All rights reserved.
引用
收藏
页码:86 / 99
页数:14
相关论文
共 65 条
  • [1] Stability constants for aluminum(III) complexes with the 1,2-dihydroxyaryl ligands caffeic acid, chlorogenic acid, DHB, and DASA in aqueous solution
    Adams, ML
    O'Sullivan, B
    Downard, AJ
    Powell, KJ
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2002, 47 (02) : 289 - 296
  • [2] Oxovanadium(IV) complexes of quinic acid.: Synthesis, characterization and potentiometric study
    Allegretti, Y
    Ferrer, EG
    Baró, ACG
    Williams, PAM
    [J]. POLYHEDRON, 2000, 19 (26-27) : 2613 - 2619
  • [3] [Anonymous], 1981, Biol. Magn. Reson., DOI DOI 10.1007/978-1-4613-3201-52
  • [4] Vanadium in the detection, prevention and treatment of cancer: The in vivo evidence
    Bishayee, Anupam
    Waghray, Abhijeet
    Patel, Mehool A.
    Chatterjee, Malay
    [J]. CANCER LETTERS, 2010, 294 (01) : 1 - 12
  • [5] Chlorogenic acid, a polyphenol from Prunus domestica (Mirabelle), with coupled anxiolytic and antioxidant effects
    Bouayed, Jaouad
    Rammal, Hassan
    Dicko, Amadou
    Younos, Chafique
    Soulimani, Rachid
    [J]. JOURNAL OF THE NEUROLOGICAL SCIENCES, 2007, 262 (1-2) : 77 - 84
  • [6] EXAMINATION OF THE SECONDARY STRUCTURE OF PROTEINS BY DECONVOLVED FTIR SPECTRA
    BYLER, DM
    SUSI, H
    [J]. BIOPOLYMERS, 1986, 25 (03) : 469 - 487
  • [7] Effect of Zinc (II) on the interactions of bovine serum albumin with flavonols bearing different number of hydroxyl substituent on B-ring
    Cao, Shuhong
    Jiang, Xinyu
    Chen, Jingwen
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2010, 104 (02) : 146 - 152
  • [8] Clifford MN, 1999, J SCI FOOD AGR, V79, P362, DOI 10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO
  • [9] 2-D
  • [10] Complexation of Lead(II) by Chlorogenic Acid: Experimental and Theoretical Study
    Cornard, Jean-Paul
    Lapouge, Christine
    Dangleterre, Laetitia
    Allet-Bodelot, Cyrille
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (48) : 12475 - 12484