Literature DB >> 27429541

An Expedient Synthesis of Fluorescent Labeled Ceramide-1-phosphate Analogues.

I A Boldyrev1, R E Brown2, J G Molotkovsky1.   

Abstract

A synthesis for fluorescent analogs of ceramide-1-phosphate bearing 9-anthrylvinyl or 4,4-difluoro-3a,4a-diaza-s-indacene-8-yl (Me4-BODIPY) fluorophore at co-position of fatty acid residue was carried out. The key stage of the synthesis is hydrolysis of corresponding sphingomyelins catalyzed by phospholipase D from Streptomyces chromofuscus; the enzymatic yield has been raised to 50-70% by appliance of organic solvent in the incubation medium.

Entities:  

Keywords:  BODIPY; anthrylvinyl; ceramide-1-phosphate; fluorescent lipid probes; phospholipase D; synthesis

Year:  2013        PMID： 27429541      PMCID： PMC4943763          DOI： 10.1134/S106816201305004X

Source DB:  PubMed          Journal:  Russ J Bioorg Chem        ISSN： 1068-1620            Impact factor:   0.796


  20 in total

1.  Localisation of BODIPY-labelled phosphatidylcholines in lipid bilayers.

Authors:  Radek Sachl; Ivan Boldyrev; Lennart B A Johansson
Journal:  Phys Chem Chem Phys       Date:  2010-04-14       Impact factor: 3.676

Review 2.  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

3.  Stimulation of DNA synthesis by natural ceramide 1-phosphate.

Authors:  A Gomez-Muñoz; L M Frago; L Alvarez; I Varela-Nieto
Journal:  Biochem J       Date:  1997-07-15       Impact factor: 3.857

4.  Effects of ceramide-1-phosphate on cultured cells: dependence on dodecane in the vehicle.

Authors:  Loïc Tauzin; Christine Graf; Mei Sun; Philipp Rovina; Nicolas Bouveyron; Markus Jaritz; Anthony Winiski; Nicole Hartmann; Frank Staedtler; Andreas Billich; Thomas Baumruker; Mei Zhang; Frédéric Bornancin
Journal:  J Lipid Res       Date:  2006-10-03       Impact factor: 5.922

5.  Methanolysis of sphingomyelin. Toward an epimerization-free methodology for the preparation of D-erythro-sphingosylphosphocholine.

Authors:  R Bittman; C A Verbicky
Journal:  J Lipid Res       Date:  2000-12       Impact factor: 5.922

6.  Quantitative measurement of sn-1,2-diacylglycerols present in platelets, hepatocytes, and ras- and sis-transformed normal rat kidney cells.

Authors:  J Preiss; C R Loomis; W R Bishop; R Stein; J E Niedel; R M Bell
Journal:  J Biol Chem       Date:  1986-07-05       Impact factor: 5.157

Review 7.  An update on sphingosine-1-phosphate and other sphingolipid mediators.

Authors:  Henrik Fyrst; Julie D Saba
Journal:  Nat Chem Biol       Date:  2010-07       Impact factor: 15.040

8.  Synaptic vesicle ceramide kinase. A calcium-stimulated lipid kinase that co-purifies with brain synaptic vesicles.

Authors:  S M Bajjalieh; T F Martin; E Floor
Journal:  J Biol Chem       Date:  1989-08-25       Impact factor: 5.157

9.  An efficient, one-pot synthesis of various ceramide 1-phosphates from sphingosine 1-phosphate.

Authors:  Peter Nussbaumer; Valentin Hornillos; Michael Ghobrial; Thomas Ullrich
Journal:  Chem Phys Lipids       Date:  2007-11-09       Impact factor: 3.329

Review 10.  Phospholipase D mechanism using Streptomyces PLD.

Authors:  Yoshiko Uesugi; Tadashi Hatanaka
Journal:  Biochim Biophys Acta       Date:  2009-02-04
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  3 in total

1.  Arabidopsis accelerated cell death 11, ACD11, is a ceramide-1-phosphate transfer protein and intermediary regulator of phytoceramide levels.

Authors:  Dhirendra K Simanshu; Xiuhong Zhai; David Munch; Daniel Hofius; Jonathan E Markham; Jacek Bielawski; Alicja Bielawska; Lucy Malinina; Julian G Molotkovsky; John W Mundy; Dinshaw J Patel; Rhoderick E Brown
Journal:  Cell Rep       Date:  2014-01-09       Impact factor: 9.423

2.  Phosphatidylserine Stimulates Ceramide 1-Phosphate (C1P) Intermembrane Transfer by C1P Transfer Proteins.

Authors:  Xiuhong Zhai; Yong-Guang Gao; Shrawan K Mishra; Dhirendra K Simanshu; Ivan A Boldyrev; Linda M Benson; H Robert Bergen; Lucy Malinina; John Mundy; Julian G Molotkovsky; Dinshaw J Patel; Rhoderick E Brown
Journal:  J Biol Chem       Date:  2016-12-23       Impact factor: 5.157

3.  Ceramide-1-phosphate transfer protein (CPTP) regulation by phosphoinositides.

Authors:  Yong-Guang Gao; Xiuhong Zhai; Ivan A Boldyrev; Julian G Molotkovsky; Dinshaw J Patel; Lucy Malinina; Rhoderick E Brown
Journal:  J Biol Chem       Date:  2021-03-26       Impact factor: 5.157
  3 in total

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