Synthesis of butyl-isobutyl-phthalate and its interaction with α-glucosidase in vitro

被引：38

作者：

Liu, Ming ^{[1
]}

Zhang, Wei ^{[2
]}

Qiu, Lin ^{[3
]}

Lin, Xiukun ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China

[2] So Res Inst, Birmingham, AL 35205 USA

[3] Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Nutr Sci, Shanghai 200031, Peoples R China

来源：

JOURNAL OF BIOCHEMISTRY | 2011年 / 149卷 / 01期

关键词：

butyl-isobutyl-phthalate; alpha-glucosidase; interaction; docking simulation; BETA-GLUCOSIDASE; METAL-IONS; FLUORESCENCE; INHIBITORS; BINDING; ACID; THERMODYNAMICS; ASSOCIATION; DERIVATIVES; MIGLITOL;

D O I：

10.1093/jb/mvq110

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：

Butyl-isobutyl-phthalate (BIP), isolated from the rhizoid of Laminaria japonica, is a potential alpha-glucosidase inhibitor for Type II diabetes treatment. In the present study, a synthetic route was established as a useful approach to obtain enough BIP. Fluorescence analysis, circular dichroism spectra and molecular docking methods were employed to elucidate the underlying molecular mechanisms of BIP inhibition on alpha-glucosidase. The results revealed that BIP could be synthesized in two steps and the synthesized BIP bound with alpha-glucosidase and induced conformational changes of the enzyme. The interaction between BIP and alpha-glucosidase was driven by both hydrophobic forces and hydrogen bond. The docking results indicated that the benzene ring and the isopropyl group of the BIP could fit into the hydrophobic pocket composed of Phe177, Phe157, Leu176, Leu218, Ala278 and the propyl group fitted into another nearby hydrophobic pocket formed by Trp154, Pro240, Leu174 and Ala162, respectively. This study provides useful information for the understanding of the BIP-alpha-glucosidase interaction and development of new alpha-glucosidase inhibitors.

引用

页码：27 / 33

页数：7

共 34 条

[1] Binding mode analyses and pharmacophore model development for sulfonamide chalcone derivatives, a new class of α-glucosidase inhibitors [J].

Bharatham, Kavitha ;

Bharatham, Nagakumar ;

Park, Ki Hun ;

Lee, Keun Woo .

JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2008, 26 (08) :1202-1212

[2] α-Glucosidase Inhibition and the In Vivo Hypoglycemic Effect of Butyl-isobutyl-phthalate derived from the Laminaria japonica Rhizoid [J].

Bu, Tong ;

Liu, Ming ;

Zheng, Lanhong ;

Guo, Yuewei ;

Lin, Xiukun .

PHYTOTHERAPY RESEARCH, 2010, 24 (11) :1588-1591

[3] FLUORESCENCE AND LOCATION OF TRYPTOPHAN RESIDUES IN PROTEIN MOLECULES [J].

BURSTEIN, EA ;

VEDENKINA, NS ;

IVKOVA, MN .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1973, 18 (04) :263-279

[4]

Campbell LK, 2000, ANN PHARMACOTHER, V34, P1291

[5]

CHIPMAN DM, 1967, J BIOL CHEM, V242, P4388

[6] α- and β-Glucosidase inhibitors:: chemical structure and biological activity [J].

de Melo, Eduardo Borges ;

Gomes, Adriane da Silveira ;

Carvalho, Ivone .

TETRAHEDRON, 2006, 62 (44) :10277-10302

[7] α-glucosidase inhibition of natural curcuminoids and curcumin analogs [J].

Du, ZY ;

Liu, RR ;

Shao, WY ;

Mao, XP ;

Ma, L ;

Gu, LQ ;

Huang, ZS ;

Chan, ASC .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (02) :213-218

[8] FLUORESCENCE QUENCHING STUDIES WITH PROTEINS [J].

EFTINK, MR ;

GHIRON, CA .

ANALYTICAL BIOCHEMISTRY, 1981, 114 (02) :199-227

[9] Phenolic compounds, antioxidant activity and in vitro inhibitory potential against key enzymes relevant for hyperglycemia and hypertension of commonly used medicinal plants, herbs and spices in Latin America [J].

Galvez Ranilla, Lena ;

Kwon, Young-In ;

Apostolidis, Emmanouil ;

Shetty, Kalidas .

BIORESOURCE TECHNOLOGY, 2010, 101 (12) :4676-4689

[10] Adsorption study of metal ions onto crosslinked seaweed Laminaria japonica [J].

Ghimire, Kedar Nath ;

Inoue, Katsutoshi ;

Ohto, Keisuke ;

Hayashida, Takehiro .

BIORESOURCE TECHNOLOGY, 2008, 99 (01) :32-37

← 1 2 3 4 →