Synthesis and study of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)-phenyl]-propionic acid: a new class of inhibitor for hen egg white lysozyme amyloidogenesis

被引:13
作者
Maity, Sibaprasad [1 ]
Kumar, Ravi [1 ]
Maity, Suman Kumar [1 ]
Jana, Poulami [1 ]
Bera, Santu [1 ]
Haldar, Debasish [1 ]
机构
[1] Indian Inst Sci Educ & Res Kolkata, Dept Chem Sci, Mohanpur 741252, W Bengal, India
关键词
AMYLOID FIBRIL FORMATION; CONGO RED; TAU AGGREGATION; PROTEIN; DISEASE; FLUORESCENCE; DERIVATIVES; SHEET; SPECTROSCOPY; OLIGOMERS;
D O I
10.1039/c2md20236k
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
The compounds capable of blocking the aggregation of amyloidogenic proteins may have therapeutic potentials. We report on the synthesis of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)-phenyl]propionic acid as an HEWL (hen egg white lysozyme) amyloid inhibitor starting from phenylalanine. The compounds arrest the monomers and exhibit anti-aggregating activity. Moreover, the acetyl derivative 1 served as a better inhibitor than the trifluoroacetyl derivative 2 against in vitro amyloid fibrillogenesis of the HEWL model system.
引用
收藏
页码:530 / 536
页数:7
相关论文
共 55 条
[1]   Hydrogen-bonded dimer can mediate supramolecular β-sheet formation and subsequent amyloid-like fibril formation:: a model study [J].
Banerjee, A ;
Maji, SK ;
Drew, MGB ;
Haldar, D ;
Das, AK ;
Banerjee, A .
TETRAHEDRON, 2004, 60 (28) :5935-5944
[2]   Molecular spectroscopic study on the interaction of tetracyclines with serum albumins [J].
Bi, SY ;
Song, DQ ;
Tian, Y ;
Zhou, X ;
Liu, ZY ;
Zhang, HQ .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 61 (04) :629-636
[3]   Polyalanine-based peptides as models for self-associated beta-pleated-sheet complexes [J].
Blondelle, SE ;
Forood, B ;
Houghten, RA ;
PerezPaya, E .
BIOCHEMISTRY, 1997, 36 (27) :8393-8400
[4]   Conformational disease [J].
Carrell, RW ;
Lomas, DA .
LANCET, 1997, 350 (9071) :134-138
[5]   Binding of brilliant red compound to lysozyme: insights into the enzyme toxicity of water-soluble aromatic chemicals [J].
Chen, Fang-Fang ;
Tang, Yi-Nan ;
Wang, Shi-Long ;
Gao, Hong-Wen .
AMINO ACIDS, 2009, 36 (03) :399-407
[6]   INTRAMOLECULAR HYDROGEN-BONDING IN DERIVATIVES OF BETA-ALANINE AND GAMMA-AMINO BUTYRIC-ACID - MODEL STUDIES FOR THE FOLDING OF UNNATURAL POLYPEPTIDE BACKBONES [J].
DADO, GP ;
GELLMAN, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1054-1062
[7]   Aβ oligomers induce neuronal oxidative stress through an N-methyl-D-aspartate receptor-dependent mechanism that is blocked by the Alzheimer drug memantine [J].
De Felice, Fernanda G. ;
Velasco, Pauline T. ;
Lambert, Mary P. ;
Viola, Kirsten ;
Fernandez, Sara J. ;
Ferreira, Sergio T. ;
Klein, William L. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (15) :11590-11601
[8]   Inhibition of Alzheimer's disease β-amyloid aggregation, neurotoxicity, and in vivo deposition by nitrophenols:: implications for Alzheimer's therapy [J].
De Felice, FG ;
Houzel, JC ;
Garcia-Abreu, J ;
Louzada, PRF ;
Afonso, RC ;
Meirelles, MNL ;
Lent, R ;
Neto, VM ;
Ferreira, ST .
FASEB JOURNAL, 2001, 15 (07) :1297-1299
[9]  
DIVRY PAUL, 1927, JOUR NEUROL ET PSYCHIATR, V27, P643
[10]   Principles of protein folding, misfolding and aggregation [J].
Dobson, CM .
SEMINARS IN CELL & DEVELOPMENTAL BIOLOGY, 2004, 15 (01) :3-16