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Literature DB >> 19908915

Caged ceramide 1-phosphate analogues: synthesis and properties.

Ravi S Lankalapalli¹, Alberto Ouro, Lide Arana, Antonio Gómez-Muñoz, Robert Bittman.

Abstract

Sphingolipid phosphate analogues bearing 7-(diethylamino)coumarin (DECM) and 4-bromo-5-hydroxy-2-nitrobenzhydryl (BHNB) groups in a photolabile ester bond were synthesized. The ability of the "caged" ceramide 1-phosphate analogues to release the bioactive parent molecule upon irradiation at 400-500 nm was demonstrated by stimulation of macrophage cell proliferation.

Entities: CellLine Chemical Disease Gene Species

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Year: 2009 PMID： 19908915 PMCID： PMC2782442 DOI： 10.1021/jo902076w

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

34 in total

1. Synthesis and use of caged sphingolipids.

Authors: R H Scott; J Pollock; A Ayar; N M Thatcher; U Zehavi
Journal: Methods Enzymol Date: 2000 Impact factor: 1.600

2. Rapid photolytic release of adenosine 5'-triphosphate from a protected analogue: utilization by the Na:K pump of human red blood cell ghosts.

Authors: J H Kaplan; B Forbush; J F Hoffman
Journal: Biochemistry Date: 1978-05-16 Impact factor: 3.162

3. Synthesis of the glycosphingolipid beta-galactosyl ceramide and analogues via olefin cross metathesis.

Authors: Anand Narain Rai; Amit Basu
Journal: J Org Chem Date: 2005-09-30 Impact factor: 4.354

4. 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

5. Synthesis of borondipyrromethene (BODIPY)-labeled sphingosine derivatives by cross-metathesis reaction.

Authors: Carsten Peters; Andreas Billich; Michael Ghobrial; Klemens Högenauer; Thomas Ullrich; Peter Nussbaumer
Journal: J Org Chem Date: 2007-01-24 Impact factor: 4.354

6. A concise synthesis of a promising protein kinase C inhibitor: D-erythro-sphingosine.

Authors: Van-Thoai Pham; Jae-Eun Joo; Yong-Shou Tian; Chang-Young Oh; Won-Hun Ham
Journal: Arch Pharm Res Date: 2007-01 Impact factor: 4.946

7. Resonance Raman characterization of different forms of ground-state 8-bromo-7-hydroxyquinoline caged acetate in aqueous solutions.

Authors: Hui-Ying An; Chensheng Ma; Jameil L Nganga; Yue Zhu; Timothy M Dore; David Lee Phillips
Journal: J Phys Chem A Date: 2009-03-26 Impact factor: 2.781

8. Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation.

Authors: M Jarrett Davis; Christopher H Kragor; Khalilah G Reddie; Hunter C Wilson; Yue Zhu; Timothy M Dore
Journal: J Org Chem Date: 2009-02-20 Impact factor: 4.354

Review 9. Metabolism and biological functions of two phosphorylated sphingolipids, sphingosine 1-phosphate and ceramide 1-phosphate.

Authors: Akio Kihara; Susumu Mitsutake; Yukiko Mizutani; Yasuyuki Igarashi
Journal: Prog Lipid Res Date: 2007-03-14 Impact factor: 16.195

10. Diels-Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the anti-HIV agent siamenol.

Authors: Michael R Naffziger; Bradley O Ashburn; Johanna R Perkins; Rich G Carter
Journal: J Org Chem Date: 2007-06-29 Impact factor: 4.354

11 in total

Review 1. 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

2. Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies.

Authors: Young Ah Kim; Jenna Day; Carol Ann Lirette; Willard J Costain; Linda J Johnston; Robert Bittman
Journal: Chem Phys Lipids Date: 2015-07-19 Impact factor: 3.329

Review 3. Egg yolk lipids: separation, characterization, and utilization.

Authors: Edirisingha Dewage Nalaka Sandun Abeyrathne; Ki-Chang Nam; Xi Huang; Dong Uk Ahn
Journal: Food Sci Biotechnol Date: 2022-08-10 Impact factor: 3.231

Review 4. Ceramide and ceramide 1-phosphate in health and disease.

Authors: Lide Arana; Patricia Gangoiti; Alberto Ouro; Miguel Trueba; Antonio Gómez-Muñoz
Journal: Lipids Health Dis Date: 2010-02-05 Impact factor: 3.876

5. Ceramide 1-phosphate stimulates glucose uptake in macrophages.

Authors: Alberto Ouro; Lide Arana; Patricia Gangoiti; Io-Guané Rivera; Marta Ordoñez; Miguel Trueba; Ravi S Lankalapalli; Robert Bittman; Antonio Gomez-Muñoz
Journal: Cell Signal Date: 2013-01-16 Impact factor: 4.315

6. Photouncaging of ceramides promotes reorganization of liquid-ordered domains in supported lipid bilayers.

Authors: Daniel M Carter Ramirez; Spencer P Pitre; Young Ah Kim; Robert Bittman; Linda J Johnston
Journal: Langmuir Date: 2013-02-25 Impact factor: 3.882

7. Lipid Phase Separation and Protein-Ganglioside Clustering in Supported Bilayers Are Induced by Photorelease of Ceramide.

Authors: Daniel M Carter Ramirez; Young Ah Kim; Robert Bittman; Linda J Johnston
Journal: Soft Matter Date: 2013-05-21 Impact factor: 3.679