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Isothiazolidinone inhibitors of PTP1B containing imidazoles and imidazolines.

Douty B, Wayland B, Ala PJ, Bower MJ, Pruitt J, Bostrom L, Wei M, Klabe R, Gonneville L, Wynn R, Burn TC, Liu PC, Combs AP, Yue EW
Bioorg Med Chem Lett 18 66-71 (2008)
Related entries: 2veu, 2vew, 2vex, 2vey

Cited: 30 times
EuropePMC logo PMID: 18037290

Abstract

The structure-based design and synthesis of isothiazolidinone (IZD) inhibitors of PTP1B containing imidazoles and imidazolines and their modification to interact with the B site of PTP1B are described here. The X-ray crystal structures of 3I and 4I complexed with PTP1B were solved and revealed the inhibitors are interacting extensively with the B site of the enzyme.

Articles - 2vev mentioned but not cited (4)

  1. Hypoglycemic effect and mechanism of honokiol on type 2 diabetic mice. Sun J, Fu X, Liu Y, Wang Y, Huo B, Guo Y, Gao X, Li W, Hu X. Drug Des Devel Ther 9 6327-6342 (2015)
  2. Isothiazolidinone (IZD) as a phosphoryl mimetic in inhibitors of the Yersinia pestis protein tyrosine phosphatase YopH. Kim SE, Bahta M, Lountos GT, Ulrich RG, Burke TR, Waugh DS. Acta Crystallogr. D Biol. Crystallogr. 67 639-645 (2011)
  3. 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)
  4. Suggestion of suitable animal models for in vivo studies of protein tyrosine phosphatase 1b (PTP1B) inhibitors using computational approaches. Nguyen XT, Le L. 3 380 (2014)


Reviews citing this publication (5)

  1. Protein tyrosine phosphatase 1B inhibitors: a molecular level legitimate approach for the management of diabetes mellitus. Thareja S, Aggarwal S, Bhardwaj TR, Kumar M. Med Res Rev 32 459-517 (2012)
  2. PTP1B inhibitors for type 2 diabetes treatment: a patent review (2011 - 2014). Tamrakar AK, Maurya CK, Rai AK. Expert Opin Ther Pat 24 1101-1115 (2014)
  3. Bidentate inhibitors of protein tyrosine phosphatases. Low JL, Chai CL, Yao SQ. Antioxid. Redox Signal. 20 2225-2250 (2014)
  4. PTP1b Inhibition, A Promising Approach for the Treatment of Diabetes Type II. Eleftheriou P, Geronikaki A, Petrou A. Curr Top Med Chem 19 246-263 (2019)
  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)

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  1. New Frontiers in Druggability. Kozakov D, Hall DR, Napoleon RL, Yueh C, Whitty A, Vajda S. J Med Chem 58 9063-9088 (2015)
  2. A re-examination of the difluoromethylenesulfonic acid group as a phosphotyrosine mimic for PTP1B inhibition. Hussain M, Ahmed V, Hill B, Ahmed Z, Taylor SD. Bioorg Med Chem 16 6764-6777 (2008)
  3. Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors. Liu QC, Guo TT, Zhang L, Yu Y, Wang P, Yang JF, Li YX. Eur J Med Chem 63 511-522 (2013)
  4. 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)
  5. 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)
  6. Molecular mechanism of T-cell protein tyrosine phosphatase (TCPTP) activation by mitoxantrone. Ylilauri M, Mattila E, Nurminen EM, Käpylä J, Niinivehmas SP, Määttä JA, Pentikäinen U, Ivaska J, Pentikäinen OT. Biochim. Biophys. Acta 1834 1988-1997 (2013)
  7. Design and synthesis of 2-substituted benzoxazoles as novel PTP1B inhibitors. Chandrasekharappa AP, Badiger SE, Dubey PK, Panigrahi SK, Manukonda SR. Bioorg. Med. Chem. Lett. 23 2579-2584 (2013)
  8. Design and synthesis of new potent PTP1B inhibitors with the skeleton of 2-substituted imino-3-substituted-5-heteroarylidene-1,3-thiazolidine-4-one: Part I. Meng G, Zheng M, Wang M, Tong J, Ge W, Zhang J, Zheng A, Li J, Gao L, Li J. Eur J Med Chem 122 756-769 (2016)
  9. Discovery and evaluation of the hybrid of bromophenol and saccharide as potent and selective protein tyrosine phosphatase 1B inhibitors. Zhang R, Yu R, Xu Q, Li X, Luo J, Jiang B, Wang L, Guo S, Wu N, Shi D. Eur J Med Chem 134 24-33 (2017)
  10. Discovery of novel, potent, selective and cellular active ADC type PTP1B inhibitors via fragment-docking-oriented de novel design. Du Y, Ling H, Zhang M, Shen J, Li Q. Bioorg. Med. Chem. 23 4891-4898 (2015)
  11. Prediction of enzyme inhibition and mode of inhibitory action based on calculation of distances between hydrogen bond donor/acceptor groups of the molecule and docking analysis: An application on the discovery of novel effective PTP1B inhibitors. Eleftheriou P, Petrou A, Geronikaki A, Liaras K, Dirnali S, Anna M. SAR QSAR Environ Res 26 557-576 (2015)
  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. Design and synthesis of imidazolidine-2,4-dione derivatives as selective inhibitors by targeting protein tyrosine phosphatase-1B over T-cell protein tyrosine phosphatase. Ma Y, Sun SX, Cheng XC, Wang SQ, Dong WL, Wang RL, Xu WR. Chem Biol Drug Des 82 595-602 (2013)
  14. Docking Assisted Prediction and Biological Evaluation of Sideritis L. Components with PTP1b Inhibitory Action and Probable Anti-Diabetic Properties. Eleftheriou P, Therianou E, Lazari D, Dirnali S, Micha A. Curr Top Med Chem 19 383-392 (2019)
  15. Structure of the Trypanosoma cruzi protein tyrosine phosphatase TcPTP1, a potential therapeutic target for Chagas' disease. Lountos GT, Tropea JE, Waugh DS. Mol Biochem Parasitol 187 1-8 (2013)
  16. A small molecule inhibitor of PTP1B and PTPN2 enhances T cell anti-tumor immunity. Liang S, Tran E, Du X, Dong J, Sudholz H, Chen H, Qu Z, Huntington ND, Babon JJ, Kershaw NJ, Zhang ZY, Baell JB, Wiede F, Tiganis T. Nat Commun 14 4524 (2023)
  17. Combined Ligand- and Receptor-Based Virtual Screening Methodology to Identify Structurally Diverse Protein Tyrosine Phosphatase 1B Inhibitors. Gimeno A, Ardid-Ruiz A, Ojeda-Montes MJ, Tomás-Hernández S, Cereto-Massagué A, Beltrán-Debón R, Mulero M, Valls C, Aragonès G, Suárez M, Pujadas G, Garcia-Vallvé S. ChemMedChem 13 1939-1948 (2018)
  18. Discovery of 4-[(5-arylidene-4-oxothiazolidin-3-yl)methyl]benzoic acid derivatives active as novel potent allosteric inhibitors of protein tyrosine phosphatase 1B: In silico studies and in vitro evaluation as insulinomimetic and anti-inflammatory agents. Ottanà R, Paoli P, Naß A, Lori G, Cardile V, Adornato I, Rotondo A, Graziano ACE, Wolber G, Maccari R. Eur J Med Chem 127 840-858 (2017)
  19. Novel Mixed-Type Inhibitors of Protein Tyrosine Phosphatase 1B. Kinetic and Computational Studies. Sarabia-Sánchez MJ, Trejo-Soto PJ, Velázquez-López JM, Carvente-García C, Castillo R, Hernández-Campos A, Avitia-Domínguez C, Enríquez-Mendiola D, Sierra-Campos E, Valdez-Solana M, Salas-Pacheco JM, Téllez-Valencia A. Molecules 22 (2017)
  20. One bis-indole alkaloid-voacamine from Voacanga africana Stapf: biological activity evaluation of PTP1B in vitro utilizing enzymology method based on SPRi expriment. Wang YQ, Li HX, Liu XC, Zhao JS, Liu RQ, Huai WY, Ding WJ, Zhang TE, Deng Y. Nat. Prod. Res. 33 3459-3463 (2019)
  21. 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)


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