Literature DB >> 21868240

Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.

Yuji Yoshimitsu1, Shinya Oishi, Jun Miyagaki, Shinsuke Inuki, Hiroaki Ohno, Nobutaka Fujii.   

Abstract

Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKCζ and PKCι) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21868240     DOI： 10.1016/j.bmc.2011.07.061

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  8 in total

1.  Novel sphingosine-containing analogues selectively inhibit sphingosine kinase (SK) isozymes, induce SK1 proteasomal degradation and reduce DNA synthesis in human pulmonary arterial smooth muscle cells.

Authors:  Hoe-Sup Byun; Susan Pyne; Neil Macritchie; Nigel J Pyne; Robert Bittman
Journal:  Medchemcomm       Date:  2013       Impact factor: 3.597

2.  Jaspine B induces nonapoptotic cell death in gastric cancer cells independently of its inhibition of ceramide synthase.

Authors:  Francesca Cingolani; Fabio Simbari; Jose Luis Abad; Mireia Casasampere; Gemma Fabrias; Anthony H Futerman; Josefina Casas
Journal:  J Lipid Res       Date:  2017-06-01       Impact factor: 5.922

3.  Synthesis and biological evaluation of carbocyclic analogues of pachastrissamine.

Authors:  Yongseok Kwon; Jayoung Song; Hoon Bae; Woo-Jung Kim; Joo-Youn Lee; Geun-Hee Han; Sang Kook Lee; Sanghee Kim
Journal:  Mar Drugs       Date:  2015-02-03       Impact factor: 5.118

Review 4.  Mammalian sphingosine kinase (SphK) isoenzymes and isoform expression: challenges for SphK as an oncotarget.

Authors:  Diana Hatoum; Nahal Haddadi; Yiguang Lin; Najah T Nassif; Eileen M McGowan
Journal:  Oncotarget       Date:  2017-05-30

5.  Formulation, Characterization, and In Vitro/In Vivo Efficacy Studies of a Novel Liposomal Drug Delivery System of Amphiphilic Jaspine B for Treatment of Synovial Sarcoma.

Authors:  Sana Khajeh Pour; Sameena Mateen; Srinath Pashikanti; Jared J Barrott; Ali Aghazadeh-Habashi
Journal:  Mar Drugs       Date:  2022-08-10       Impact factor: 6.085

6.  Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block.

Authors:  Volker Martin Schmiedel; Stefano Stefani; Hans-Ulrich Reissig
Journal:  Beilstein J Org Chem       Date:  2013-11-19       Impact factor: 2.883

7.  Pharmacokinetics of Jaspine B and Enhancement of Intestinal Absorption of Jaspine B in the Presence of Bile Acid in Rats.

Authors:  Min-Koo Choi; Jihoon Lee; So Jeong Nam; Yun Ju Kang; Youjin Han; Kwangik Choi; Young A Choi; Mihwa Kwon; Dongjoo Lee; Im-Sook Song
Journal:  Mar Drugs       Date:  2017-09-01       Impact factor: 5.118

Review 8.  Targeting the SphK-S1P-SIPR Pathway as a Potential Therapeutic Approach for COVID-19.

Authors:  Eileen M McGowan; Nahal Haddadi; Najah T Nassif; Yiguang Lin
Journal:  Int J Mol Sci       Date:  2020-09-29       Impact factor: 5.923
  8 in total

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