Literature DB >> 31857843

Structural Insights into Interaction Mechanisms of Alternative Piperazine-urea YEATS Domain Binders in MLLT1.

Xiaomin Ni1,2, David Heidenreich1,2, Thomas Christott3, James Bennett3, Moses Moustakim3, Paul E Brennan1,2,3, Oleg Fedorov3, Stefan Knapp1,2, Apirat Chaikuad1,2.   

Abstract

YEATS-domain-containing MLLT1 is an acetyl/acyl-lysine reader domain, which is structurally distinct from well-studied bromodomains and has been strongly associated in development of cancer. Here, we characterized piperazine-urea derivatives as an acetyl/acyl-lysine mimetic moiety for MLLT1. Crystal structures revealed distinct interaction mechanisms of this chemotype compared to the recently described benzimidazole-amide based inhibitors, exploiting different binding pockets within the protein. Thus, the piperazine-urea scaffold offers an alternative strategy for targeting the YEATS domain family.
Copyright © 2019 American Chemical Society.

Entities:  

Year:  2019        PMID： 31857843      PMCID： PMC6912866          DOI： 10.1021/acsmedchemlett.9b00460

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


  35 in total

1.  Discovery of a piperazine urea based compound as a potent, selective, orally bioavailable melanocortin subtype-4 receptor partial agonist.

Authors:  Qingmei Hong; Raman K Bakshi; Brenda L Palucki; Min K Park; Zhixiong Ye; Shuwen He; Patrick G Pollard; Iyassu K Sebhat; Jian Liu; Liangqin Guo; Doreen E Cashen; William J Martin; David H Weinberg; Tanya MacNeil; Rui Tang; Constantin Tamvakopoulos; Qianping Peng; Randy R Miller; Ralph A Stearns; Howard Y Chen; Airu S Chen; Alison M Strack; Tung M Fong; D Euan MacIntyre; Matthew J Wyvratt; Ravi P Nargund
Journal:  Bioorg Med Chem Lett       Date:  2011-03-01       Impact factor: 2.823

2.  MolProbity: More and better reference data for improved all-atom structure validation.

Authors:  Christopher J Williams; Jeffrey J Headd; Nigel W Moriarty; Michael G Prisant; Lizbeth L Videau; Lindsay N Deis; Vishal Verma; Daniel A Keedy; Bradley J Hintze; Vincent B Chen; Swati Jain; Steven M Lewis; W Bryan Arendall; Jack Snoeyink; Paul D Adams; Simon C Lovell; Jane S Richardson; David C Richardson
Journal:  Protein Sci       Date:  2017-11-27       Impact factor: 6.725

3.  Identification of the YEATS domain of GAS41 as a pH-dependent reader of histone succinylation.

Authors:  Yi Wang; Jing Jin; Matthew Wai Heng Chung; Ling Feng; Hongyan Sun; Quan Hao
Journal:  Proc Natl Acad Sci U S A       Date:  2018-02-20       Impact factor: 11.205

4.  AF9 YEATS domain links histone acetylation to DOT1L-mediated H3K79 methylation.

Authors:  Yuanyuan Li; Hong Wen; Yuanxin Xi; Kaori Tanaka; Haibo Wang; Danni Peng; Yongfeng Ren; Qihuang Jin; Sharon Y R Dent; Wei Li; Haitao Li; Xiaobing Shi
Journal:  Cell       Date:  2014-10-23       Impact factor: 41.582

5.  GAS41 Recognizes Diacetylated Histone H3 through a Bivalent Binding Mode.

Authors:  Hyo Je Cho; Hao Li; Brian M Linhares; EunGi Kim; Juliano Ndoj; Hongzhi Miao; Jolanta Grembecka; Tomasz Cierpicki
Journal:  ACS Chem Biol       Date:  2018-08-17       Impact factor: 5.100

6.  Thiadiazolopiperazinyl ureas as inhibitors of fatty acid amide hydrolase.

Authors:  John M Keith; Richard Apodaca; Wei Xiao; Mark Seierstad; Kanaka Pattabiraman; Jiejun Wu; Michael Webb; Mark J Karbarz; Sean Brown; Sandy Wilson; Brian Scott; Chui-Se Tham; Lin Luo; James Palmer; Michelle Wennerholm; Sandra Chaplan; J Guy Breitenbucher
Journal:  Bioorg Med Chem Lett       Date:  2008-07-25       Impact factor: 2.823

7.  Overexpression of YEATS4 contributes to malignant outcomes in gastric carcinoma.

Authors:  Jun Kiuchi; Shuhei Komatsu; Taisuke Imamura; Keiji Nishibeppu; Katsutoshi Shoda; Tomohiro Arita; Toshiyuki Kosuga; Hirotaka Konishi; Atsushi Shiozaki; Takeshi Kubota; Kazuma Okamoto; Hitoshi Fujiwara; Daisuke Ichikawa; Hitoshi Tsuda; Eigo Otsuji
Journal:  Am J Cancer Res       Date:  2018-12-01       Impact factor: 6.166

8.  ENL links histone acetylation to oncogenic gene expression in acute myeloid leukaemia.

Authors:  Liling Wan; Hong Wen; Yuanyuan Li; Jie Lyu; Yuanxin Xi; Takayuki Hoshii; Julia K Joseph; Xiaolu Wang; Yong-Hwee E Loh; Michael A Erb; Amanda L Souza; James E Bradner; Li Shen; Wei Li; Haitao Li; C David Allis; Scott A Armstrong; Xiaobing Shi
Journal:  Nature       Date:  2017-03-01       Impact factor: 49.962

9.  Recognition of histone acetylation by the GAS41 YEATS domain promotes H2A.Z deposition in non-small cell lung cancer.

Authors:  Chih-Chao Hsu; Jiejun Shi; Chao Yuan; Dan Zhao; Shiming Jiang; Jie Lyu; Xiaolu Wang; Haitao Li; Hong Wen; Wei Li; Xiaobing Shi
Journal:  Genes Dev       Date:  2018-02-01       Impact factor: 11.361

10.  Structural insights into the π-π-π stacking mechanism and DNA-binding activity of the YEATS domain.

Authors:  Brianna J Klein; Kendra R Vann; Forest H Andrews; Wesley W Wang; Jibo Zhang; Yi Zhang; Anastasia A Beloglazkina; Wenyi Mi; Yuanyuan Li; Haitao Li; Xiaobing Shi; Andrei G Kutateladze; Brian D Strahl; Wenshe R Liu; Tatiana G Kutateladze
Journal:  Nat Commun       Date:  2018-11-01       Impact factor: 14.919
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  8 in total

Review 1.  Urea-aromatic interactions in biology.

Authors:  Shampa Raghunathan; Tanashree Jaganade; U Deva Priyakumar
Journal:  Biophys Rev       Date:  2020-02-17

2.  Cell-Based Ligand Discovery for the ENL YEATS Domain.

Authors:  Joshua N Asiaban; Natalia Milosevich; Emily Chen; Timothy R Bishop; Justin Wang; Yuxiang Zhang; Christopher J Ackerman; Eric N Hampton; Travis S Young; Mitchell V Hull; Benjamin F Cravatt; Michael A Erb
Journal:  ACS Chem Biol       Date:  2020-03-19       Impact factor: 5.100

Review 3.  Multifaceted roles of YEATS domain-containing proteins and novel links to neurological diseases.

Authors:  Ranchana Yeewa; Pawita Chaiya; Salinee Jantrapirom; Vorasuk Shotelersuk; Luca Lo Piccolo
Journal:  Cell Mol Life Sci       Date:  2022-03-12       Impact factor: 9.261

Review 4.  Structure, function and inhibition of critical protein-protein interactions involving mixed lineage leukemia 1 and its fusion oncoproteins.

Authors:  Xin Li; Yongcheng Song
Journal:  J Hematol Oncol       Date:  2021-04-06       Impact factor: 17.388

5.  A proteolysis-targeting chimera molecule selectively degrades ENL and inhibits malignant gene expression and tumor growth.

Authors:  Xin Li; Yuan Yao; Fangrui Wu; Yongcheng Song
Journal:  J Hematol Oncol       Date:  2022-04-08       Impact factor: 17.388

6.  Discovery of Selective Small-Molecule Inhibitors for the ENL YEATS Domain.

Authors:  Xinyu R Ma; Longxia Xu; Shiqing Xu; Brianna J Klein; Hongkuan Wang; Sukant Das; Kuai Li; Kai S Yang; Sana Sohail; Andrew Chapman; Tatiana G Kutateladze; Xiaobing Shi; Wenshe Ray Liu; Hong Wen
Journal:  J Med Chem       Date:  2021-07-19       Impact factor: 8.039

7.  More Than π-π-π Stacking: Contribution of Amide-π and CH-π Interactions to Crotonyllysine Binding by the AF9 YEATS Domain.

Authors:  Mackenzie W Krone; Christopher R Travis; Ga Young Lee; Hannah J Eckvahl; K N Houk; Marcey L Waters
Journal:  J Am Chem Soc       Date:  2020-09-23       Impact factor: 16.383

8.  Chemical Inhibition of ENL/AF9 YEATS Domains in Acute Leukemia.

Authors:  Leopold Garnar-Wortzel; Timothy R Bishop; Seiya Kitamura; Natalia Milosevich; Joshua N Asiaban; Xiaoyu Zhang; Qinheng Zheng; Emily Chen; Anissa R Ramos; Christopher J Ackerman; Eric N Hampton; Arnab K Chatterjee; Travis S Young; Mitchell V Hull; K Barry Sharpless; Benjamin F Cravatt; Dennis W Wolan; Michael A Erb
Journal:  ACS Cent Sci       Date:  2021-04-30       Impact factor: 14.553
  8 in total

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