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Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: capturing interactions with Asp48.

Wan ZK, Lee J, Xu W, Erbe DV, Joseph-McCarthy D, Follows BC, Zhang YL
Bioorg Med Chem Lett 16 4941-5 (2006)
Related entries: 2h4k, 2hb1

Cited: 29 times
EuropePMC logo PMID: 16806920

Abstract

A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B.

Articles - 2h4g mentioned but not cited (1)

  1. 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)


Reviews citing this publication (7)

  1. The therapeutic potential of phosphatase inhibitors. Vintonyak VV, Antonchick AP, Rauh D, Waldmann H. Curr Opin Chem Biol 13 272-283 (2009)
  2. Recent and emerging anti-diabetes targets. Mohler ML, He Y, Wu Z, Hwang DJ, Miller DD. Med Res Rev 29 125-195 (2009)
  3. 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)
  4. Bidentate inhibitors of protein tyrosine phosphatases. Low JL, Chai CL, Yao SQ. Antioxid Redox Signal 20 2225-2250 (2014)
  5. Phosphotyrosine isosteres: past, present and future. Cerulli RA, Kritzer JA. Org Biomol Chem 18 583-605 (2020)
  6. Computational Methods in Cooperation with Experimental Approaches to Design Protein Tyrosine Phosphatase 1B Inhibitors in Type 2 Diabetes Drug Design: A Review of the Achievements of This Century. Campos-Almazán MI, Hernández-Campos A, Castillo R, Sierra-Campos E, Valdez-Solana M, Avitia-Domínguez C, Téllez-Valencia A. Pharmaceuticals (Basel) 15 866 (2022)
  7. 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 (21)

  1. 5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases. Maccari R, Paoli P, Ottanà R, Jacomelli M, Ciurleo R, Manao G, Steindl T, Langer T, Vigorita MG, Camici G. Bioorg Med Chem 15 5137-5149 (2007)
  2. Using small molecules to target protein phosphatases. Vintonyak VV, Waldmann H, Rauh D. Bioorg Med Chem 19 2145-2155 (2011)
  3. Highly efficient Suzuki-Miyaura coupling of heterocyclic substrates through rational reaction design. Fleckenstein CA, Plenio H. Chemistry 14 4267-4279 (2008)
  4. Identification of novel PTP1B inhibitors by pharmacophore based virtual screening, scaffold hopping and docking. Balaramnavar VM, Srivastava R, Rahuja N, Gupta S, Rawat AK, Varshney S, Chandasana H, Chhonker YS, Doharey PK, Kumar S, Gautam S, Srivastava SP, Bhatta RS, Saxena JK, Gaikwad AN, Srivastava AK, Saxena AK. Eur J Med Chem 87 578-594 (2014)
  5. Probing acid replacements of thiophene PTP1B inhibitors. Wan ZK, Follows B, Kirincich S, Wilson D, Binnun E, Xu W, Joseph-McCarthy D, Wu J, Smith M, Zhang YL, Tam M, Erbe D, Tam S, Saiah E, Lee J. Bioorg Med Chem Lett 17 2913-2920 (2007)
  6. Exploring conformational search protocols for ligand-based virtual screening and 3-D QSAR modeling. Cappel D, Dixon SL, Sherman W, Duan J. J Comput Aided Mol Des 29 165-182 (2015)
  7. 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)
  8. Prodrug delivery of novel PTP1B inhibitors to enhance insulin signalling. Erbe DV, Klaman LD, Wilson DP, Wan ZK, Kirincich SJ, Will S, Xu X, Kung L, Wang S, Tam S, Lee J, Tobin JF. Diabetes Obes Metab 11 579-588 (2009)
  9. 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)
  10. Illudalic acid as a potential LAR inhibitor: synthesis, SAR, and preliminary studies on the mechanism of action. Ling Q, Huang Y, Zhou Y, Cai Z, Xiong B, Zhang Y, Ma L, Wang X, Li X, Li J, Shen J. Bioorg Med Chem 16 7399-7409 (2008)
  11. Structure-based optimization of protein tyrosine phosphatase-1 B inhibitors: capturing interactions with arginine 24. Wan ZK, Lee J, Hotchandani R, Moretto A, Binnun E, Wilson DP, Kirincich SJ, Follows BC, Ipek M, Xu W, Joseph-McCarthy D, Zhang YL, Tam M, Erbe DV, Tobin JF, Li W, Tam SY, Mansour TS, Wu J. ChemMedChem 3 1525-1529 (2008)
  12. Design, synthesis, in silico and in vitro evaluation of thiophene derivatives: A potent tyrosine phosphatase 1B inhibitor and anticancer activity. Gulipalli KC, Bodige S, Ravula P, Endoori S, Vanaja GR, Suresh Babu G, Narendra Sharath Chandra JN, Seelam N. Bioorg Med Chem Lett 27 3558-3564 (2017)
  13. Knowledge-based characterization of similarity relationships in the human protein-tyrosine phosphatase family for rational inhibitor design. Vidović D, Schürer SC. J Med Chem 52 6649-6659 (2009)
  14. Rationalizing protein-ligand interactions for PTP1B inhibitors using computational methods. Ajmani S, Karanam S, Kulkarni SA. Chem Biol Drug Des 74 582-595 (2009)
  15. Investigation of catalytic loop structure, dynamics, and function relationship of Yersinia protein tyrosine phosphatase by temperature-jump relaxation spectroscopy and X-ray structural determination. Ke S, Ho MC, Zhadin N, Deng H, Callender R. J Phys Chem B 116 6166-6176 (2012)
  16. An enzyme-linked immunosorbent assay to measure insulin receptor dephosphorylation by PTP1B. Zhang YL, Tam M, Kirincich S, Wan ZK, Wilson D, Wu JJ, Lee J, Tobin JF, Erbe DV. Anal Biochem 365 174-184 (2007)
  17. Analysis of structural water and CH···π interactions in HIV-1 protease and PTP1B complexes using a hydrogen bond prediction tool, HBPredicT. Yesudas JP, Sayyed FB, Suresh CH. J Mol Model 17 401-413 (2011)
  18. Discovery of inhibitors targeting protein tyrosine phosphatase 1B using a combined virtual screening approach. Zhao D, Sun L, Zhong S. Mol Divers 26 2159-2174 (2022)
  19. Novel heteroaryl phosphonicdiamides PTPs inhibitors as anti-hyperglycemic agents. Sekhar KC, Syed R, Golla M, Kumar M V J, Yellapu NK, Chippada AR, Chamarthi NR. Daru 22 76 (2014)
  20. QSAR Study on a Series of Protein Tyrosine Phosphatase 1B Inhibitors. Mehta RS, Prajapati HR, Thakkar DV, Brahmkshatriya PS. Int J Biomed Sci 4 266-272 (2008)
  21. Development of trisubstituted thiophene-3-arboxamide selenide derivatives as novel EGFR kinase inhibitors with cytotoxic activity. Makhal PN, Sood A, Shaikh AS, Dayare LN, Khatri DK, Rao Kaki V. RSC Med Chem 14 2677-2698 (2023)


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