Synthesis and Cav2.2 binding data for non-peptide mimetics of ω-conotoxin GVIA based on a 5-amino-anthranilamide core

被引：6

作者：

Duggan, Peter J. ^{[2
]}

Faber, Jonathan M. ^{[1
]}

Graham, Janease E. ^{[2
]}

Lewis, Richard J. ^{[3
]}

Lumsden, Natalie G. ^{[3
]}

Tuck, Kellie L. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[2] CSIRO, Clayton, Vic 3169, Australia

[3] Univ Queensland, Inst Mol Biosci, St Lucia, Qld 4072, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2008年 / 61卷 / 01期

关键词：

D O I：

10.1071/CH07327

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient method has been developed for the synthesis of two anthranilamide-based non-peptide mimetics of omega-conotoxin GVIA. These anthranilamide derivatives aim to mimic the K2, R17, and Y13 residues of the peptide. The synthetic route described enables the rapid synthesis of anthranilamide analogues with identical alkyl chain lengths. The target compounds show affinity to rat N-type voltage gated calcium channels (Ca(v)2.2) with EC50 values of 42 and 75 mu M.

引用

页码：11 / 15

页数：5

共 30 条

[1]

Adams DJ, 1999, DRUG DEVELOP RES, V46, P219

[2] Synthesis and biological evaluation of nonpeptide mimetics of co-conotoxin GVIA [J].

Baell, JB ;

Duggan, PJ ;

Forsyth, SA ;

Lewis, RJ ;

Lok, YP ;

Schroeder, CI .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4025-4037

[3] Design and synthesis of type-III mimetics of ω-conotoxin GVIA [J].

Baell, JB ;

Forsyth, SA ;

Gable, RW ;

Norton, RS ;

Mulder, RJ .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2001, 15 (12) :1119-1136

[4] Synthesis and biological evaluation of anthranilamide-based non-peptide mimetics of ω-conotoxin GVIA [J].

Baell, Jonathan B. ;

Duggan, Peter J. ;

Forsyth, Stewart A. ;

Lewis, Richard J. ;

Lok, Y. Phei ;

Schroeder, Christina I. ;

Shepherd, Nicholas E. .

TETRAHEDRON, 2006, 62 (31) :7284-7292

[5] Pharmacotherapeutic potential of omega-conotoxin MVIIA (SNX-111), an N-type neuronal calcium channel blocker found in the venom of Conus magus [J].

Bowersox, SS ;

Luther, R .

TOXICON, 1998, 36 (11) :1651-1658

[6]

BOWERSOX SS, 1994, DRUG NEWS PERSPECT, V7, P261

[7] Contulakin-G, an O-glycosylated invertebrate neurotensin [J].

Craig, AG ;

Norberg, T ;

Griffin, D ;

Hoeger, C ;

Akhtar, M ;

Schmidt, K ;

Low, W ;

Dykert, J ;

Richelson, E ;

Navarro, V ;

Mazella, J ;

Watkins, M ;

Hillyard, D ;

Imperial, J ;

Cruz, LJ ;

Olivera, BM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (20) :13752-13759

[8]

CRUZ LJ, 1986, J BIOL CHEM, V261, P6230

[9]

CRUZ LJ, 1987, J BIOL CHEM, V262, P15821

[10]

CRUZ LJ, 1995, HDB CLIN TOXICOLOGY

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