Literature DB >> 19268584

Design and synthesis of isoform-selective phospholipase D (PLD) inhibitors. Part I: Impact of alternative halogenated privileged structures for PLD1 specificity.

Jana A Lewis1, Sarah A Scott, Robert Lavieri, Jason R Buck, Paige E Selvy, Sydney L Stoops, 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 alternative halogenated piperidinyl benzimidazolone privileged structures, in combination with a key (S)-methyl group, novel PLD inhibitors with low nM potency and unprecedented levels of PLD1 isoform selectivity (approximately 1700-fold) over PLD2 were developed.

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Year:  2009        PMID： 19268584      PMCID： PMC3791604          DOI： 10.1016/j.bmcl.2009.02.057

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


  21 in total

1.  Sch 420789: a novel fungal metabolite with phospholipase D inhibitory activity.

Authors:  M S Puar; E Barrabee; M Hallade; M Patel
Journal:  J Antibiot (Tokyo)       Date:  2000-08       Impact factor: 2.649

2.  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

3.  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 4.  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

5.  Novel polyisoprenyl phosphates block phospholipase D and human neutrophil activation in vitro and murine peritoneal inflammation in vivo.

Authors:  Bruce D Levy; Lorraine Hickey; Andrew J Morris; Mykol Larvie; Raquel Keledjian; Nicos A Petasis; Gerard Bannenberg; Charles N Serhan
Journal:  Br J Pharmacol       Date:  2005-10       Impact factor: 8.739

6.  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

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.  Diethylstilbestrol inhibits phospholipase D activity and degranulation by stimulated human neutrophils.

Authors:  Jen-Sie Tou; Carolina Urbizo
Journal:  Steroids       Date:  2007-10-22       Impact factor: 2.668
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  51 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.  Sustained PKCβII activity confers oncogenic properties in a phospholipase D- and mTOR-dependent manner.

Authors:  Mohamad El Osta; Mengling Liu; Mohamad Adada; Can E Senkal; Jolanta Idkowiak-Baldys; Lina M Obeid; Christopher J Clarke; Yusuf A Hannun
Journal:  FASEB J       Date:  2013-10-11       Impact factor: 5.191

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.  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

Review 5.  Drugs for allosteric sites on receptors.

Authors:  Cody J Wenthur; Patrick R Gentry; Thomas P Mathews; Craig W Lindsley
Journal:  Annu Rev Pharmacol Toxicol       Date:  2013-10-02       Impact factor: 13.820

6.  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.

Authors:  Robert Lavieri; Sarah A Scott; Jana A Lewis; Paige E Selvy; Michelle D Armstrong; H Alex Brown; Craig W Lindsley
Journal:  Bioorg Med Chem Lett       Date:  2009-03-06       Impact factor: 2.823

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.  Human phospholipase D activity transiently regulates pyrimidine biosynthesis in malignant gliomas.

Authors:  Thomas P Mathews; Salisha Hill; Kristie L Rose; Pavlina T Ivanova; Craig W Lindsley; H Alex Brown
Journal:  ACS Chem Biol       Date:  2015-02-17       Impact factor: 5.100

9.  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

10.  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
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