Literature DB >> 31223453

Discovery of Imidazoisoindole Derivatives as Highly Potent and Orally Active Indoleamine-2,3-dioxygenase Inhibitors.

Wangyang Tu1, Fanglong Yang1, Guoji Xu1, Jiangtao Chi1, Zhiwei Liu1, Wei Peng1, Bing Hu1, Lei Zhang1, Hong Wan1, Nan Yu1, Fangfang Jin1, Qiyue Hu1, Lianshan Zhang2, Feng He1,3, Weikang Tao1,3.   

Abstract

A novel series of imidazoisoindoles were identified as potent indoleamine-2,3-dioxygenase (IDO) inhibitors. Lead optimization toward improving potency and eliminating CYP inhibition resulted in the discovery of lead compound 25, a highly potent IDO inhibitor with favorable pharmacokinetic properties. In the MC38 xenograft model in hPD-1 transgenic mice, 25 in combination with the anti-PD-1 monoclonal antibody (SHR-1210) achieved a synergistic antitumor effect superior to each single agent.

Entities:  

Year:  2019        PMID： 31223453      PMCID： PMC6580535          DOI： 10.1021/acsmedchemlett.9b00114

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  19 in total

1.  Reversal of tumoral immune resistance by inhibition of tryptophan 2,3-dioxygenase.

Authors:  Luc Pilotte; Pierre Larrieu; Vincent Stroobant; Didier Colau; Eduard Dolusic; Raphaël Frédérick; Etienne De Plaen; Catherine Uyttenhove; Johan Wouters; Bernard Masereel; Benoît J Van den Eynde
Journal:  Proc Natl Acad Sci U S A       Date:  2012-01-30       Impact factor: 11.205

Review 2.  Indoleamine 2,3-dioxygenase expression in human cancers: clinical and immunologic perspectives.

Authors:  Jessica Godin-Ethier; Laïla-Aïcha Hanafi; Ciriaco A Piccirillo; Réjean Lapointe
Journal:  Clin Cancer Res       Date:  2011-11-08       Impact factor: 12.531

Review 3.  Challenges in the Discovery of Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors.

Authors:  Ute F Röhrig; Somi Reddy Majjigapu; Pierre Vogel; Vincent Zoete; Olivier Michielin
Journal:  J Med Chem       Date:  2015-05-26       Impact factor: 7.446

4.  An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor.

Authors:  Christiane A Opitz; Ulrike M Litzenburger; Felix Sahm; Martina Ott; Isabel Tritschler; Saskia Trump; Theresa Schumacher; Leonie Jestaedt; Dieter Schrenk; Michael Weller; Manfred Jugold; Gilles J Guillemin; Christine L Miller; Christian Lutz; Bernhard Radlwimmer; Irina Lehmann; Andreas von Deimling; Wolfgang Wick; Michael Platten
Journal:  Nature       Date:  2011-10-05       Impact factor: 49.962

Review 5.  Tryptophan catabolism in cancer: beyond IDO and tryptophan depletion.

Authors:  Michael Platten; Wolfgang Wick; Benoît J Van den Eynde
Journal:  Cancer Res       Date:  2012-10-22       Impact factor: 12.701

Review 6.  Big opportunities for small molecules in immuno-oncology.

Authors:  Jerry L Adams; James Smothers; Roopa Srinivasan; Axel Hoos
Journal:  Nat Rev Drug Discov       Date:  2015-07-31       Impact factor: 84.694

7.  Important Hydrogen Bond Networks in Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Design Revealed by Crystal Structures of Imidazoleisoindole Derivatives with IDO1.

Authors:  Yi-Hui Peng; Shau-Hua Ueng; Chen-Tso Tseng; Ming-Shiu Hung; Jen-Shin Song; Jian-Sung Wu; Fang-Yu Liao; Yu-Shiou Fan; Mine-Hsine Wu; Wen-Chi Hsiao; Ching-Cheng Hsueh; Shu-Yu Lin; Chia-Yi Cheng; Chih-Hsiang Tu; Lung-Chun Lee; Ming-Fu Cheng; Kak-Shan Shia; Chuan Shih; Su-Ying Wu
Journal:  J Med Chem       Date:  2015-12-21       Impact factor: 7.446

Review 8.  Tryptophan-degrading enzymes in tumoral immune resistance.

Authors:  Nicolas van Baren; Benoît J Van den Eynde
Journal:  Front Immunol       Date:  2015-02-03       Impact factor: 7.561

Review 9.  Cancer Immunotherapy by Targeting IDO1/TDO and Their Downstream Effectors.

Authors:  Michael Platten; Nikolaus von Knebel Doeberitz; Iris Oezen; Wolfgang Wick; Katharina Ochs
Journal:  Front Immunol       Date:  2015-01-12       Impact factor: 7.561

10.  Mechanism of tumor rejection with doublets of CTLA-4, PD-1/PD-L1, or IDO blockade involves restored IL-2 production and proliferation of CD8(+) T cells directly within the tumor microenvironment.

Authors:  Stefani Spranger; Holly K Koblish; Brendan Horton; Peggy A Scherle; Robert Newton; Thomas F Gajewski
Journal:  J Immunother Cancer       Date:  2014-02-18       Impact factor: 13.751
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  6 in total

1.  Structure-based optimization of type III indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors.

Authors:  Ute F Röhrig; Somi Reddy Majjigapu; Pierre Vogel; Aline Reynaud; Florence Pojer; Nahzli Dilek; Patrick Reichenbach; Kelly Ascenção; Melita Irving; George Coukos; Olivier Michielin; Vincent Zoete
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756

2.  Discovery of Hydroxyamidine Derivatives as Highly Potent, Selective Indoleamine-2,3-dioxygenase 1 Inhibitors.

Authors:  Fangfang Jin; Qiyue Hu; Hongbo Fei; Hejun Lv; Shenglan Wang; Bin Gui; Junzhen Zhang; Wangyang Tu; Yun Zhang; Lei Zhang; Hong Wan; Limin Zhang; Bin Hu; Fanglong Yang; Chang Bai; Feng He; Lianshan Zhang; Weikang Tao
Journal:  ACS Med Chem Lett       Date:  2021-01-20       Impact factor: 4.345

3.  Carbamate and N-Pyrimidine Mitigate Amide Hydrolysis: Structure-Based Drug Design of Tetrahydroquinoline IDO1 Inhibitors.

Authors:  Derun Li; Yongqi Deng; Abdelghani Achab; Indu Bharathan; Brett Andrew Hopkins; Wensheng Yu; Hongjun Zhang; Sulagna Sanyal; Qinglin Pu; Hua Zhou; Kun Liu; Jongwon Lim; Xavier Fradera; Charles A Lesburg; Alfred Lammens; Theodore A Martinot; Ryan D Cohen; Amy C Doty; Heidi Ferguson; Elliott B Nickbarg; Mangeng Cheng; Peter Spacciapoli; Prasanthi Geda; Xuelei Song; Nadya Smotrov; Pravien Abeywickrema; Christine Andrews; Chad Chamberlin; Omar Mabrouk; Patrick Curran; Matthew Richards; Peter Saradjian; J Richard Miller; Ian Knemeyer; Karin M Otte; Stella Vincent; Nunzio Sciammetta; Alexander Pasternak; David Jonathan Bennett; Yongxin Han
Journal:  ACS Med Chem Lett       Date:  2021-02-26       Impact factor: 4.345

4.  Tryptophan: A Rheostat of Cancer Immune Escape Mediated by Immunosuppressive Enzymes IDO1 and TDO.

Authors:  Minah Kim; Petr Tomek
Journal:  Front Immunol       Date:  2021-02-23       Impact factor: 7.561

Review 5.  Targeting Indoleamine Dioxygenase and Tryptophan Dioxygenase in Cancer Immunotherapy: Clinical Progress and Challenges.

Authors:  Xuerun Peng; Zhipeng Zhao; Liwen Liu; Lan Bai; Rongsheng Tong; Hao Yang; Lei Zhong
Journal:  Drug Des Devel Ther       Date:  2022-08-08       Impact factor: 4.319

6.  Discovery of secondary sulphonamides as IDO1 inhibitors with potent antitumour effects in vivo.

Authors:  Shushan Ge; Haiqing Zhong; Xuewei Ma; Yingbo Zheng; Yi Zou; Fang Wang; Yan Wang; Yue Hu; Yuezhen Li; Wen Liu; Wenjie Guo; Qiang Xu; Yisheng Lai
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051
  6 in total

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