Literature DB >> 19299128

Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part II. Identification of the 1,3,8-triazaspiro[4,5]decan-4-one privileged structure that engenders PLD2 selectivity.

Robert Lavieri1, Sarah A Scott, Jana A Lewis, Paige E Selvy, Michelle D Armstrong, H Alex Brown, Craig W Lindsley.   

Abstract

This Letter describes the synthesis and structure-activity relationships (SAR) of isoform-selective PLD inhibitors. By virtue of the installation of a 1,3,8-triazaspiro[4,5]decan-4-one privileged structure, PLD inhibitors with nanomolar potency and an unprecedented 40-fold selectivity for PLD2 over PLD1 were developed. Interestingly, SAR for this diverged from our earlier efforts, and dual PLD1/2 inhibitors were also discovered within this series.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19299128      PMCID： PMC3800051          DOI： 10.1016/j.bmcl.2009.02.125

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  15 in total

1.  Overexpression of phospholipase D1 in human breast cancer tissues.

Authors:  D Y Noh; S J Ahn; R A Lee; I A Park; J H Kim; P G Suh; S H Ryu; K H Lee; J S Han
Journal:  Cancer Lett       Date:  2000-12-20       Impact factor: 8.679

2.  Development of a custom high-throughput preparative liquid chromatography/mass spectrometer platform for the preparative purification and analytical analysis of compound libraries.

Authors:  William Leister; Kimberly Strauss; David Wisnoski; Zhijian Zhao; Craig Lindsley
Journal:  J Comb Chem       Date:  2003 May-Jun

Review 3.  Allosteric modulation of kinases and GPCRs: design principles and structural diversity.

Authors:  Jana A Lewis; Evan P Lebois; Craig W Lindsley
Journal:  Curr Opin Chem Biol       Date:  2008-04-18       Impact factor: 8.822

Review 4.  Application of combinatorial chemistry science on modern drug discovery.

Authors:  J Phillip Kennedy; Lyndsey Williams; Thomas M Bridges; R Nathan Daniels; David Weaver; Craig W Lindsley
Journal:  J Comb Chem       Date:  2008-01-26

5.  Requirement of phospholipase D1 activity in H-RasV12-induced transformation.

Authors:  F Gregory Buchanan; Matt McReynolds; Anthony Couvillon; Yoonseok Kam; Vijaykumar R Holla; Raymond N Dubois; John H Exton
Journal:  Proc Natl Acad Sci U S A       Date:  2005-01-24       Impact factor: 11.205

6.  Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors.

Authors:  Craig W Lindsley; Zhijian Zhao; William H Leister; Ronald G Robinson; Stanley F Barnett; Deborah Defeo-Jones; Raymond E Jones; George D Hartman; Joel R Huff; Hans E Huber; Mark E Duggan
Journal:  Bioorg Med Chem Lett       Date:  2005-02-01       Impact factor: 2.823

7.  Neoplastic transformation and tumorigenesis associated with overexpression of phospholipase D isozymes in cultured murine fibroblasts.

Authors:  D S Min; T K Kwon; W S Park; J S Chang; S K Park; B H Ahn; Z Y Ryoo; Y H Lee; Y S Lee; D J Rhie; S H Yoon; S J Hahn; M S Kim; Y H Jo
Journal:  Carcinogenesis       Date:  2001-10       Impact factor: 4.944

8.  Optimization of halopemide for phospholipase D2 inhibition.

Authors:  Lauren Monovich; Benjamin Mugrage; Elizabeth Quadros; Karen Toscano; Ruben Tommasi; Stacey LaVoie; Eugene Liu; Zhengming Du; Daniel LaSala; William Boyar; Paul Steed
Journal:  Bioorg Med Chem Lett       Date:  2007-01-25       Impact factor: 2.823

9.  Association of a polymorphism of the phospholipase D2 gene with the prevalence of colorectal cancer.

Authors:  Yoshiji Yamada; Nobuyuki Hamajima; Tomoyuki Kato; Hiroji Iwata; Yoshitaka Yamamura; Masayuki Shinoda; Motokazu Suyama; Tetsuya Mitsudomi; Kazuo Tajima; Suzuno Kusakabe; Hitoshi Yoshida; Yoshiko Banno; Yukihiro Akao; Masashi Tanaka; Yoshinori Nozawa
Journal:  J Mol Med (Berl)       Date:  2003-02-11       Impact factor: 4.599

10.  A novel family of phospholipase D homologues that includes phospholipid synthases and putative endonucleases: identification of duplicated repeats and potential active site residues.

Authors:  C P Ponting; I D Kerr
Journal:  Protein Sci       Date:  1996-05       Impact factor: 6.725
View more
  32 in total

1.  Design, synthesis, and biological evaluation of halogenated N-(2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)ethyl)benzamides: discovery of an isoform-selective small molecule phospholipase D2 inhibitor.

Authors:  Robert R Lavieri; Sarah A Scott; Paige E Selvy; Kwangho Kim; Satyawan Jadhav; Ryan D Morrison; J Scott Daniels; H Alex Brown; Craig W Lindsley
Journal:  J Med Chem       Date:  2010-09-23       Impact factor: 7.446

2.  The Role of Phospholipase D in Regulated Exocytosis.

Authors:  Tatiana P Rogasevskaia; Jens R Coorssen
Journal:  J Biol Chem       Date:  2015-10-02       Impact factor: 5.157

Review 3.  Phospholipase D: enzymology, functionality, and chemical modulation.

Authors:  Paige E Selvy; Robert R Lavieri; Craig W Lindsley; H Alex Brown
Journal:  Chem Rev       Date:  2011-09-22       Impact factor: 60.622

4.  Activity-Based DNA-Encoded Library Screening.

Authors:  Wesley G Cochrane; Marie L Malone; Vuong Q Dang; Valerie Cavett; Alexander L Satz; Brian M Paegel
Journal:  ACS Comb Sci       Date:  2019-03-29       Impact factor: 3.784

5.  Label-free detection of G protein-SNARE interactions and screening for small molecule modulators.

Authors:  Christopher A Wells; Katherine M Betke; Craig W Lindsley; Heidi E Hamm
Journal:  ACS Chem Neurosci       Date:  2012-01-18       Impact factor: 4.418

6.  Phospholipases of mineralization competent cells and matrix vesicles: roles in physiological and pathological mineralizations.

Authors:  Saida Mebarek; Abdelkarim Abousalham; David Magne; Le Duy Do; Joanna Bandorowicz-Pikula; Slawomir Pikula; René Buchet
Journal:  Int J Mol Sci       Date:  2013-03-01       Impact factor: 5.923

Review 7.  Targeting phospholipase D with small-molecule inhibitors as a potential therapeutic approach for cancer metastasis.

Authors:  Wenjuan Su; Qin Chen; Michael A Frohman
Journal:  Future Oncol       Date:  2009-11       Impact factor: 3.404

8.  Inhibition of formyl peptide-stimulated phospholipase D activation by Fal-002-2 via blockade of the Arf6, RhoA and protein kinase C signaling pathways in rat neutrophils.

Authors:  Ya-Ru Tsai; Li-Jiau Huang; Hui-Yi Lin; Yun-Jie Hung; Miau-Rong Lee; Sheng-Chu Kuo; Mei-Feng Hsu; Jih-Pyang Wang
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2013-03-23       Impact factor: 3.000

9.  Development of dual PLD1/2 and PLD2 selective inhibitors from a common 1,3,8-Triazaspiro[4.5]decane Core: discovery of Ml298 and Ml299 that decrease invasive migration in U87-MG glioblastoma cells.

Authors:  Matthew C O'Reilly; Sarah A Scott; Kyle A Brown; Thomas H Oguin; Paul G Thomas; J Scott Daniels; Ryan Morrison; H Alex Brown; Craig W Lindsley
Journal:  J Med Chem       Date:  2013-03-13       Impact factor: 7.446

10.  Thematic minireview series on phospholipase D and cancer.

Authors:  Julian Gomez-Cambronero; George M Carman
Journal:  J Biol Chem       Date:  2014-07-02       Impact factor: 5.157
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.