A novel phosphotyrosine mimetic 4′-carboxymethyloxy-3′-phosphonophenylalanine (Cpp):: Exploitation in the design of nonpeptide inhibitors of pp60Src SH2 domain

被引：25

作者：

Kawahata, N ^{[1
]}

Yang, MG ^{[1
]}

Luke, GP ^{[1
]}

Shakespeare, WC ^{[1
]}

Sundaramoorthi, R ^{[1
]}

Wang, YH ^{[1
]}

Johnson, D ^{[1
]}

Merry, T ^{[1
]}

Violette, S ^{[1
]}

Guan, W ^{[1
]}

Bartlett, C ^{[1
]}

Smith, J ^{[1
]}

Hatada, M ^{[1
]}

Lu, XD ^{[1
]}

Dalgarno, DC ^{[1
]}

Eyermann, CJ ^{[1
]}

Bohacek, RS ^{[1
]}

Sawyer, TK ^{[1
]}

机构：

[1] ARIAD Pharmaceut Inc, Cambridge, MA 02139 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 17期

关键词：

D O I：

10.1016/S0960-894X(01)00446-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The novel phosphotyrosine (pTyr) mimetic 4 ' -carboxymethyloxy-3 ' -phosphonophenylalanine (Cpp) has been designed and incorporated into a series of nonpeptide inhibitors of the SH2 domain of pp60(c-Src) (Src) tyrosine kinase. A 2,2 Angstrom X-ray crystal structure of la bound to a mutant form of Lek SH2 domain provides insight regarding the structure-activity relationships and supports the design concept of this new pTyr mimetic. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2319 / 2323

页数：5

共 25 条

[1] Ligands for the tyrosine kinase p56lck SH2 domain:: Discovery of potent dipeptide derivatives with monocharged, nonhydrolyzable phosphate replacements [J].

Beaulieu, PL ;

Cameron, DR ;

Ferland, JM ;

Gauthier, J ;

Ghiro, E ;

Gillard, J ;

Gorys, V ;

Poirier, M ;

Rancourt, J ;

Wernic, D ;

Llinas-Brunet, M ;

Betageri, R ;

Cardozo, M ;

Hickey, ER ;

Ingraham, R ;

Jakes, S ;

Kabcenell, A ;

Kirrane, T ;

Lukas, S ;

Patel, U ;

Proudfoot, J ;

Sharma, R ;

Tong, L ;

Moss, N .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (10) :1757-1766

[2] RESORPTION OF DENTIN BY ISOLATED OSTEOCLASTS INVITRO [J].

BOYDE, A ;

ALI, NN ;

JONES, SJ .

BRITISH DENTAL JOURNAL, 1984, 156 (06) :216-220

[3] 4'-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides [J].

Burke, TR ;

Ye, B ;

Akamatsu, M ;

Ford, H ;

Yan, XJ ;

Kole, HK ;

Wolf, G ;

Shoelson, SE ;

Roller, PP .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1021-1027

[4] NONHYDROLYZABLE PHOSPHOTYROSYL MIMETICS FOR THE PREPARATION OF PHOSPHATASE-RESISTANT SH2 DOMAIN INHIBITORS [J].

BURKE, TR ;

SMYTH, MS ;

OTAKA, A ;

NOMIZU, M ;

ROLLER, PP ;

WOLF, G ;

CASE, R ;

SHOELSON, SE .

BIOCHEMISTRY, 1994, 33 (21) :6490-6494

[5] PP60C-SRC ACTIVATION IN HUMAN-COLON CARCINOMA [J].

CARTWRIGHT, CA ;

KAMPS, MP ;

MEISLER, AI ;

PIPAS, JM ;

ECKHART, W .

JOURNAL OF CLINICAL INVESTIGATION, 1989, 83 (06) :2025-2033

[6]

CASTEEL DA, 1991, SYNTHESIS-STUTTGART, P691

[7] Inhibition of Grb2 SH2 domain binding by non-phosphate-containing ligands. 2. 4-(2-malollyl)phenylalanine as a potent phosphotyrosyl mimetic [J].

Gao, Y ;

Luo, J ;

Yao, ZJ ;

Guo, RB ;

Zou, H ;

Kelley, J ;

Voigt, JH ;

Yang, DJ ;

Burke, TR .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :911-920

[8]

GILMER T, 1994, J BIOL CHEM, V269, P31711

[9] PREPARATION OF ENANTIOMERICALLY PURE PROTECTED 4-OXO-ALPHA-AMINO ACIDS AND 3-ARYL-ALPHA-AMINO ACIDS FROM SERINE [J].

JACKSON, RFW ;

WISHART, N ;

WOOD, A ;

JAMES, K ;

WYTHES, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3397-3404

[10] IODINATION OF PHENOLS USING CHLORAMINE-T AND SODIUM-IODIDE [J].

KOMETANI, T ;

WATT, DS ;

JI, T .

TETRAHEDRON LETTERS, 1985, 26 (17) :2043-2046

← 1 2 3 →