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Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.

Han Y, Belley M, Bayly CI, Colucci J, Dufresne C, Giroux A, Lau CK, Leblanc Y, McKay D, Therien M, Wilson MC, Skorey K, Chan CC, Scapin G, Kennedy BP
Bioorg Med Chem Lett 18 3200-5 (2008)
Cited: 27 times
EuropePMC logo PMID: 18477508

Abstract

A series of quinoline/naphthalene-difluoromethylphosphonates were prepared and were found to be potent PTP1B inhibitors. Most of these compounds bearing polar functionalities or large lipophilic residues did not show appreciable oral bioavailability in rodents while small and less polar analogs displayed moderate to good oral bioavailability. The title compound was found to have the best overall potency and pharmacokinetic profile and was found to be efficacious in animal models of diabetes and cancer.

Articles - 3cwe mentioned but not cited (6)

  1. Identification and characterization of fragment binding sites for allosteric ligand design using the site identification by ligand competitive saturation hotspots approach (SILCS-Hotspots). MacKerell AD, Jo S, Lakkaraju SK, Lind C, Yu W. Biochim Biophys Acta Gen Subj 1864 129519 (2020)
  2. An expanded allosteric network in PTP1B by multitemperature crystallography, fragment screening, and covalent tethering. Keedy DA, Hill ZB, Biel JT, Kang E, Rettenmaier TJ, Brandão-Neto J, Pearce NM, von Delft F, Wells JA, Fraser JS. Elife 7 (2018)
  3. Evaluation of the Antidiabetic Activity and Chemical Composition of Geranium collinum Root Extracts-Computational and Experimental Investigations. Numonov S, Edirs S, Bobakulov K, Qureshi MN, Bozorov K, Sharopov F, Setzer WN, Zhao H, Habasi M, Sharofova M, Aisa HA. Molecules 22 (2017)
  4. Serendipitous discovery of light-induced (In Situ) formation of an Azo-bridged dimeric sulfonated naphthol as a potent PTP1B inhibitor. Bongard RD, Lepley M, Thakur K, Talipov MR, Nayak J, Lipinski RAJ, Bohl C, Sweeney N, Ramchandran R, Rathore R, Sem DS. BMC Biochem. 18 10 (2017)
  5. research-article Native dynamics and allosteric responses in PTP1B probed by high-resolution HDX-MS. Woods VA, Abzalimov RR, Keedy DA. bioRxiv 2023.07.12.548582 (2023)
  6. Unified access to up-to-date residue-level annotations from UniProtKB and other biological databases for PDB data. Choudhary P, Anyango S, Berrisford J, Tolchard J, Varadi M, Velankar S. Sci Data 10 204 (2023)


Reviews citing this publication (5)

  1. Targeting protein tyrosine phosphatases for anticancer drug discovery. Scott LM, Lawrence HR, Sebti SM, Lawrence NJ, Wu J. Curr. Pharm. Des. 16 1843-1862 (2010)
  2. Benzotriazole: An overview on its versatile biological behavior. Briguglio I, Piras S, Corona P, Gavini E, Nieddu M, Boatto G, Carta A. Eur J Med Chem 97 612-648 (2015)
  3. Modulation of VEGF receptor 2 signaling by protein phosphatases. Corti F, Simons M. Pharmacol. Res. 115 107-123 (2017)
  4. Bidentate inhibitors of protein tyrosine phosphatases. Low JL, Chai CL, Yao SQ. Antioxid. Redox Signal. 20 2225-2250 (2014)
  5. The development of protein tyrosine phosphatase1B inhibitors defined by binding sites in crystalline complexes. Zhang Y, Du Y. Future Med Chem 10 2345-2367 (2018)

Articles citing this publication (16)

  1. PTP1B regulates Eph receptor function and trafficking. Nievergall E, Janes PW, Stegmayer C, Vail ME, Haj FG, Teng SW, Neel BG, Bastiaens PI, Lackmann M. J. Cell Biol. 191 1189-1203 (2010)
  2. Protein tyrosine phosphatase 1B is a key regulator of IFNAR1 endocytosis and a target for antiviral therapies. Carbone CJ, Zheng H, Bhattacharya S, Lewis JR, Reiter AM, Henthorn P, Zhang ZY, Baker DP, Ukkiramapandian R, Bence KK, Fuchs SY. Proc. Natl. Acad. Sci. U.S.A. 109 19226-19231 (2012)
  3. Fragment-based discovery of selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase PtpA. Rawls KA, Lang PT, Takeuchi J, Imamura S, Baguley TD, Grundner C, Alber T, Ellman JA. Bioorg. Med. Chem. Lett. 19 6851-6854 (2009)
  4. Discovery of potent, selective and orally bioavailable triaryl-sulfonamide based PTP1B inhibitors. Patel D, Jain M, Shah SR, Bahekar R, Jadav P, Joharapurkar A, Dhanesha N, Shaikh M, Sairam KV, Kapadnis P. Bioorg. Med. Chem. Lett. 22 1111-1117 (2012)
  5. Using small molecules to target protein phosphatases. Vintonyak VV, Waldmann H, Rauh D. Bioorg. Med. Chem. 19 2145-2155 (2011)
  6. 5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors. Ottanà R, Maccari R, Ciurleo R, Paoli P, Jacomelli M, Manao G, Camici G, Laggner C, Langer T. Bioorg. Med. Chem. 17 1928-1937 (2009)
  7. Discovery of orally active, potent, and selective benzotriazole-based PTP1B inhibitors. Patel D, Jain M, Shah SR, Bahekar R, Jadav P, Darji B, Siriki Y, Bandyopadhyay D, Joharapurkar A, Kshirsagar S, Patel H, Shaikh M, Sairam KV, Patel P. ChemMedChem 6 1011-1016 (2011)
  8. The discovery of a novel and selective inhibitor of PTP1B over TCPTP: 3D QSAR pharmacophore modeling, virtual screening, synthesis, and biological evaluation. Ma Y, Jin YY, Wang YL, Wang RL, Lu XH, Kong DX, Xu WR. Chem Biol Drug Des 83 697-709 (2014)
  9. Design and synthesis of nonpeptidic, small molecule inhibitors for the Mycobacterium tuberculosis protein tyrosine phosphatase PtpB. Rawls KA, Grundner C, Ellman JA. Org. Biomol. Chem. 8 4066-4070 (2010)
  10. Copper-Mediated Introduction of the CF2 PO(OEt)2 Motif: Scope and Limitations. Ivanova MV, Bayle A, Besset T, Pannecoucke X, Poisson T. Chemistry 23 17318-17338 (2017)
  11. Nitrate in the active site of protein tyrosine phosphatase 1B is a putative mimetic of the transition state. Kenny PW, Newman J, Peat TS. Acta Crystallogr. D Biol. Crystallogr. 70 565-571 (2014)
  12. Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases. Wagner S, Accorsi M, Rademann J. Chemistry 23 15387-15395 (2017)
  13. Computational Insight into Protein Tyrosine Phosphatase 1B Inhibition: A Case Study of the Combined Ligand- and Structure-Based Approach. Zhang X, Jiang H, Li W, Wang J, Cheng M. Comput Math Methods Med 2017 4245613 (2017)
  14. Regio-controllable [2+2] benzannulation with two adjacent C(sp3)-H bonds. Yang JM, Lin YK, Sheng T, Hu L, Cai XP, Yu JQ. Science 380 639-644 (2023)
  15. Synthesis, structure-activity relationship and docking studies of substituted aryl thiazolyl phenylsulfonamides as potential protein tyrosine phosphatase 1B inhibitors. Varshney K, Gupta S, Rahuja N, Rawat AK, Singh N, Tamarkar AK, Srivastava AK, Saxena AK. ChemMedChem 7 1185-1190 (2012)
  16. Theoretical studies on the interaction of biphenyl inhibitors with Mycobacterium tuberculosis protein tyrosine phosphatase MptpB. Dong L, Shi J, Liu Y. J Mol Model 18 3847-3856 (2012)


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