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A novel phosphotyrosine mimetic 4'-carboxymethyloxy-3'-phosphonophenylalanine (Cpp): exploitation in the design of nonpeptide inhibitors of pp60(Src) SH2 domain.

Kawahata N, Yang MG, Luke GP, Shakespeare WC, Sundaramoorthi R, Wang Y, Johnson D, Merry T, Violette S, Guan W, Bartlett C, Smith J, Hatada M, Lu X, Dalgarno DC, Eyermann CJ, Bohacek RS, Sawyer TK
Bioorg Med Chem Lett 11 2319-23 (2001)
Cited: 11 times
EuropePMC logo PMID: 11527723

Abstract

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 A X-ray crystal structure of 1a bound to a mutant form of Lck SH2 domain provides insight regarding the structure-activity relationships and supports the design concept of this new pTyr mimetic.

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  1. Post-Translational Modifications of Cytochrome c in Cell Life and Disease. Guerra-Castellano A, Márquez I, Pérez-Mejías G, Díaz-Quintana A, De la Rosa MA, Díaz-Moreno I. Int J Mol Sci 21 E8483 (2020)

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  1. Exploring protein phosphorylation by combining computational approaches and biochemical methods. Pérez-Mejías G, Velázquez-Cruz A, Guerra-Castellano A, Baños-Jaime B, Díaz-Quintana A, González-Arzola K, Ángel De la Rosa M, Díaz-Moreno I. Comput Struct Biotechnol J 18 1852-1863 (2020)
  2. SAR of carbon-linked, 2-substituted purines: synthesis and characterization of AP23451 as a novel bone-targeted inhibitor of Src tyrosine kinase with in vivo anti-resorptive activity. Shakespeare WC, Wang Y, Bohacek R, Keenan T, Sundaramoorthi R, Metcalf C, Dilauro A, Roeloffzen S, Liu S, Saltmarsh J, Paramanathan G, Dalgarno D, Narula S, Pradeepan S, van Schravendijk MR, Keats J, Ram M, Liou S, Adams S, Wardwell S, Bogus J, Iuliucci J, Weigele M, Xing L, Boyce B, Sawyer TK. Chem Biol Drug Des 71 97-105 (2008)
  3. Structure-based design of novel nonpeptide inhibitors of the Src SH2 domain:phosphotyrosine mimetics exploiting multifunctional group replacement chemistry. Sundaramoorthi R, Kawahata N, Yang MG, Shakespeare WC, Metcalf CA, Wang Y, Merry T, Eyermann CJ, Bohacek RS, Narula S, Dalgarno DC, Sawyer TK. Biopolymers 71 717-729 (2003)
  4. Proton dissociation properties of arylphosphonates: Determination of accurate Hammett equation parameters. Dargó G, Bölcskei A, Grün A, Béni S, Szántó Z, Lopata A, Keglevich G, Balogh GT, Balogh GT. J Pharm Biomed Anal 143 101-109 (2017)
  5. Synthesis and evaluation of phosphopeptides containing iminodiacetate groups as binding ligands of the Src SH2 domain. Ye G, Schuler AD, Ahmadibeni Y, Morgan JR, Faruqui A, Huang K, Sun G, Zebala JA, Parang K. Bioorg Chem 37 133-142 (2009)
  6. Novel aminomethylindole derivatives as inhibitors of pp60c-Src tyrosine kinase: synthesis and biological activity. Işgör YG, Kiliç Z, Olgen S. Chem Biol Drug Des 72 599-604 (2008)


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