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Discovery of cell-active phenyl-imidazole Pin1 inhibitors by structure-guided fragment evolution.

Potter A, Oldfield V, Nunns C, Fromont C, Ray S, Northfield CJ, Bryant CJ, Scrace SF, Robinson D, Matossova N, Baker L, Dokurno P, Surgenor AE, Davis B, Richardson CM, Murray JB, Moore JD
Bioorg Med Chem Lett 20 6483-8 (2010)
Related entries: 2xp3, 2xp4, 2xp5, 2xp6, 2xp7, 2xp8, 2xp9, 2xpb, 3odk

Cited: 44 times
EuropePMC logo PMID: 20932746

Abstract

Pin1 is an emerging oncology target strongly implicated in Ras and ErbB2-mediated tumourigenesis. Pin1 isomerizes bonds linking phospho-serine/threonine moieties to proline enabling it to play a key role in proline-directed kinase signalling. Here we report a novel series of Pin1 inhibitors based on a phenyl imidazole acid core that contains sub-μM inhibitors. Compounds have been identified that block prostate cancer cell growth under conditions where Pin1 is essential.

Articles - 2xpa mentioned but not cited (2)

  1. The conserved npl4 protein complex mediates proteasome-dependent membrane-bound transcription factor activation. Hitchcock AL, Krebber H, Frietze S, Lin A, Latterich M, Silver PA. Mol Biol Cell 12 3226-3241 (2001)
  2. Exploring Ligand Stability in Protein Crystal Structures Using Binding Pose Metadynamics. Fusani L, Palmer DS, Somers DO, Wall ID. J Chem Inf Model 60 1528-1539 (2020)


Reviews citing this publication (11)

  1. Comprehensive review in current developments of imidazole-based medicinal chemistry. Zhang L, Peng XM, Damu GL, Geng RX, Zhou CH. Med Res Rev 34 340-437 (2014)
  2. The isomerase PIN1 controls numerous cancer-driving pathways and is a unique drug target. Zhou XZ, Lu KP. Nat Rev Cancer 16 463-478 (2016)
  3. Peptidyl-Proline Isomerases (PPIases): Targets for Natural Products and Natural Product-Inspired Compounds. Dunyak BM, Gestwicki JE. J Med Chem 59 9622-9644 (2016)
  4. Roles of Prolyl Isomerases in RNA-Mediated Gene Expression. Thapar R. Biomolecules 5 974-999 (2015)
  5. Structure and function of the human parvulins Pin1 and Par14/17. Matena A, Rehic E, Hönig D, Kamba B, Bayer P. Biol Chem 399 101-125 (2018)
  6. Function of PIN1 in Cancer Development and Its Inhibitors as Cancer Therapeutics. Yu JH, Im CY, Min SH. Front Cell Dev Biol 8 120 (2020)
  7. Peptidyl-prolyl isomerases: functionality and potential therapeutic targets in cardiovascular disease. Rostam MA, Piva TJ, Rezaei HB, Kamato D, Little PJ, Zheng W, Osman N. Clin Exp Pharmacol Physiol 42 117-124 (2015)
  8. Gears-In-Motion: The Interplay of WW and PPIase Domains in Pin1. Lee YM, Liou YC. Front Oncol 8 469 (2018)
  9. Polyubiquitination inhibition of estrogen receptor alpha and its implications in breast cancer. Tecalco-Cruz AC, Ramírez-Jarquín JO. World J Clin Oncol 9 60-70 (2018)
  10. Roles of peptidyl-prolyl isomerase Pin1 in disease pathogenesis. Li J, Mo C, Guo Y, Zhang B, Feng X, Si Q, Wu X, Zhao Z, Gong L, He D, Shao J. Theranostics 11 3348-3358 (2021)
  11. Targeting Pin1 for Modulation of Cell Motility and Cancer Therapy. Chuang HH, Zhen YY, Tsai YC, Chuang CH, Huang MS, Hsiao M, Yang CJ. Biomedicines 9 359 (2021)

Articles citing this publication (31)

  1. A covalent PIN1 inhibitor selectively targets cancer cells by a dual mechanism of action. Campaner E, Rustighi A, Zannini A, Cristiani A, Piazza S, Ciani Y, Kalid O, Golan G, Baloglu E, Shacham S, Valsasina B, Cucchi U, Pippione AC, Lolli ML, Giabbai B, Storici P, Carloni P, Rossetti G, Benvenuti F, Bello E, D'Incalci M, Cappuzzello E, Rosato A, Del Sal G. Nat Commun 8 15772 (2017)
  2. Pin1 inhibitors: Pitfalls, progress and cellular pharmacology. Moore JD, Potter A. Bioorg Med Chem Lett 23 4283-4291 (2013)
  3. Learning from our mistakes: the 'unknown knowns' in fragment screening. Davis BJ, Erlanson DA. Bioorg Med Chem Lett 23 2844-2852 (2013)
  4. Prolyl isomerase Pin1 acts downstream of miR200c to promote cancer stem-like cell traits in breast cancer. Luo ML, Gong C, Chen CH, Lee DY, Hu H, Huang P, Yao Y, Guo W, Reinhardt F, Wulf G, Lieberman J, Zhou XZ, Song E, Lu KP. Cancer Res 74 3603-3616 (2014)
  5. Targeting Pin1 by inhibitor API-1 regulates microRNA biogenesis and suppresses hepatocellular carcinoma development. Pu W, Li J, Zheng Y, Shen X, Fan X, Zhou JK, He J, Deng Y, Liu X, Wang C, Yang S, Chen Q, Liu L, Zhang G, Wei YQ, Peng Y. Hepatology 68 547-560 (2018)
  6. The prolyl isomerase pin1 regulates mRNA levels of genes with short half-lives by targeting specific RNA binding proteins. Krishnan N, Titus MA, Thapar R. PLoS One 9 e85427 (2014)
  7. Prolyl isomerase Pin1 negatively regulates AMP-activated protein kinase (AMPK) by associating with the CBS domain in the γ subunit. Nakatsu Y, Iwashita M, Sakoda H, Ono H, Nagata K, Matsunaga Y, Fukushima T, Fujishiro M, Kushiyama A, Kamata H, Takahashi S, Katagiri H, Honda H, Kiyonari H, Uchida T, Asano T. J Biol Chem 290 24255-24266 (2015)
  8. Letter Selective targeting of disease-relevant protein binding domains by O-phosphorylated natural product derivatives. Gräber M, Janczyk W, Sperl B, Elumalai N, Kozany C, Hausch F, Holak TA, Berg T. ACS Chem Biol 6 1008-1014 (2011)
  9. Structure-based design of novel human Pin1 inhibitors (III): optimizing affinity beyond the phosphate recognition pocket. Guo C, Hou X, Dong L, Marakovits J, Greasley S, Dagostino E, Ferre R, Johnson MC, Humphries PS, Li H, Paderes GD, Piraino J, Kraynov E, Murray BW. Bioorg Med Chem Lett 24 4187-4191 (2014)
  10. Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors. Zhu L, Jin J, Liu C, Zhang C, Sun Y, Guo Y, Fu D, Chen X, Xu B. Bioorg Med Chem 19 2797-2807 (2011)
  11. DeepFrag: a deep convolutional neural network for fragment-based lead optimization. Green H, Koes DR, Durrant JD. Chem Sci 12 8036-8047 (2021)
  12. Synthesis and biological evaluation of novel human Pin1 inhibitors with benzophenone skeleton. Liu C, Jin J, Chen L, Zhou J, Chen X, Fu D, Song H, Xu B. Bioorg Med Chem 20 2992-2999 (2012)
  13. DeepFrag: An Open-Source Browser App for Deep-Learning Lead Optimization. Green H, Durrant JD. J Chem Inf Model 61 2523-2529 (2021)
  14. A Guide to PIN1 Function and Mutations Across Cancers. El Boustani M, De Stefano L, Caligiuri I, Mouawad N, Granchi C, Canzonieri V, Tuccinardi T, Giordano A, Rizzolio F. Front Pharmacol 9 1477 (2018)
  15. Neighboring phosphoSer-Pro motifs in the undefined domain of IRAK1 impart bivalent advantage for Pin1 binding. Rogals MJ, Greenwood AI, Kwon J, Lu KP, Nicholson LK. FEBS J 283 4528-4548 (2016)
  16. Pin1-based diagnostic and therapeutic strategies for breast cancer. Wang JZ, Liu BG, Zhang Y. Pharmacol Res 93 28-35 (2015)
  17. Synthesis and Pin1 inhibitory activity of thiazole derivatives. Zhao H, Cui G, Jin J, Chen X, Xu B. Bioorg Med Chem 24 5911-5920 (2016)
  18. Aryl hetaryl ketones and thioketones as efficient inhibitors of peptidyl-prolyl cis-trans isomerases. Hediger T, Frank W, Schumann M, Fischer G, Braun M. Chem Biodivers 9 2618-2634 (2012)
  19. Peptidyl prolyl isomerase Pin1-inhibitory activity of D-glutamic and D-aspartic acid derivatives bearing a cyclic aliphatic amine moiety. Nakagawa H, Seike S, Sugimoto M, Ieda N, Kawaguchi M, Suzuki T, Miyata N. Bioorg Med Chem Lett 25 5619-5624 (2015)
  20. Protein-fragment complex structures derived by NMR molecular replacement. Torres F, Ghosh D, Strotz D, Chi CN, Davis B, Orts J. RSC Med Chem 11 591-596 (2020)
  21. Design and Synthesis of Oligopeptidic Parvulin Inhibitors. Relitti N, Prasanth Saraswati A, Carullo G, Papa A, Monti A, Benedetti R, Passaro E, Brogi S, Calderone V, Butini S, Gemma S, Altucci L, Campiani G, Doti N. ChemMedChem 17 e202200050 (2022)
  22. New PIN1 inhibitors identified through a pharmacophore-driven, hierarchical consensus docking strategy. Poli G, Di Stefano M, Estevez JA, Minutolo F, Granchi C, Giordano A, Parisi S, Mauceri M, Canzonieri V, Macchia M, Caligiuri I, Tuccinardi T, Rizzolio F. J Enzyme Inhib Med Chem 37 145-150 (2022)
  23. Pin1 is related with clinical stage of papillary thyroid carcinoma. Jiang L, Chu H, Zheng H. World J Surg Oncol 14 95 (2016)
  24. Ultrafast Fragment Screening Using Photo-Hyperpolarized (CIDNP) NMR. Torres F, Bütikofer M, Stadler GR, Renn A, Kadavath H, Bobrovs R, Jaudzems K, Riek R. J Am Chem Soc 145 12066-12080 (2023)
  25. A Phosphoramidate Strategy Enables Membrane Permeability of a Non-nucleotide Inhibitor of the Prolyl Isomerase Pin1. Schwarz DMC, Williams SK, Dillenburg M, Wagner CR, Gestwicki JE. ACS Med Chem Lett 11 1704-1710 (2020)
  26. Regioselective Synthesis of 2-Aryl-5-cyano-1-(2-hydroxyaryl)-1H-imidazole-4-carboxamides Self-Assisted by a 2-Hydroxyaryl Group. Pedroso de Lima F, Lence E, Suárez de Cepeda P, Correia C, Carvalho MA, González-Bello C, Proença MF. ACS Omega 7 23289-23301 (2022)
  27. A Benchmark Study of Protein-Fragment Complex Structure Calculations with NMR2. Torres F, Stadler G, Kwiatkowski W, Orts J. Int J Mol Sci 24 14329 (2023)
  28. An improved, time-efficient approach to extract accurate distance restraints for NMR2 structure calculation. Pokharna A, Torres F, Kadavath H, Orts J, Riek R. Magn Reson (Gott) 3 137-144 (2022)
  29. Regulation of eukaryotic protein kinases by Pin1, a peptidyl-prolyl isomerase. Chen XR, Igumenova TI. Adv Biol Regul 87 100938 (2023)
  30. Small molecules targeting Pin1 as potent anticancer drugs. Zhang J, Zhou W, Chen Y, Wang Y, Guo Z, Hu W, Li Y, Han X, Si S. Front Pharmacol 14 1073037 (2023)
  31. Structure-Based Design of Novel Benzimidazole Derivatives as Pin1 Inhibitors. Wang S, Guan L, Zang J, Xing K, Zhang J, Liu D, Zhao L. Molecules 24 E1198 (2019)


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