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Literature DB >> 23510485

Stereocontrolled total synthesis of the potent anti-inflammatory and pro-resolving lipid mediator resolvin D3 and its aspirin-triggered 17R-epimer.

Jeremy W Winkler¹, Jasim Uddin, Charles N Serhan, Nicos A Petasis.

Abstract

The first total synthesis of stereochemically pure resolvin D3 and aspirin-triggered resolvin D3 is reported. These enzymatic metabolites of docosahexaenoic acid (DHA) have potent anti-inflammatory and pro-resolving actions. The convergent synthetic strategy is based on enantiomerically pure starting materials, and it is highly stereocontrolled.

Entities: Chemical Disease Gene Species

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Year: 2013 PMID： 23510485 PMCID： PMC3696528 DOI： 10.1021/ol400484u

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

27 in total

Review 1. Resolution of inflammation: the beginning programs the end.

Authors: Charles N Serhan; John Savill
Journal: Nat Immunol Date: 2005-12 Impact factor: 25.606

Review 2. Omega-3 fatty acids in inflammation and autoimmune diseases.

Authors: Artemis P Simopoulos
Journal: J Am Coll Nutr Date: 2002-12 Impact factor: 3.169

3. Resolvin D3 and aspirin-triggered resolvin D3 are potent immunoresolvents.

Authors: Jesmond Dalli; Jeremy W Winkler; Romain A Colas; Hildur Arnardottir; Chien-Yee C Cheng; Nan Chiang; Nicos A Petasis; Charles N Serhan
Journal: Chem Biol Date: 2013-02-21

4. Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes.

Authors: Charles N Serhan; Katherine Gotlinger; Song Hong; Yan Lu; Jeffrey Siegelman; Tamara Baer; Rong Yang; Sean P Colgan; Nicos A Petasis
Journal: J Immunol Date: 2006-02-01 Impact factor: 5.422

5. A convergent synthesis of the 11-oxa prostaglandin analogue AL-12182.

Authors: Martin E Fox; Mark Jackson; Ian C Lennon; Raymond McCague
Journal: J Org Chem Date: 2005-02-18 Impact factor: 4.354

6. Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors: K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal: J Am Chem Soc Date: 1986-09-01 Impact factor: 15.419

7. Stereocontrolled total synthesis of neuroprotectin D1 / protectin D1 and its aspirin-triggered stereoisomer.

Authors: Nicos A Petasis; Rong Yang; Jeremy W Winkler; Min Zhu; Jasim Uddin; Nicolas G Bazan; Charles N Serhan
Journal: Tetrahedron Lett Date: 2012-01-14 Impact factor: 2.415

8. Transgenic mice rich in endogenous omega-3 fatty acids are protected from colitis.

Authors: Christian A Hudert; Karsten H Weylandt; Yan Lu; Jingdong Wang; Song Hong; Axel Dignass; Charles N Serhan; Jing X Kang
Journal: Proc Natl Acad Sci U S A Date: 2006-07-17 Impact factor: 11.205

9. Novel docosanoids inhibit brain ischemia-reperfusion-mediated leukocyte infiltration and pro-inflammatory gene expression.

Authors: Victor L Marcheselli; Song Hong; Walter J Lukiw; Xiao Hua Tian; Karsten Gronert; Alberto Musto; Mattie Hardy; Juan M Gimenez; Nan Chiang; Charles N Serhan; Nicolas G Bazan
Journal: J Biol Chem Date: 2003-08-15 Impact factor: 5.157

10. Resolvin D2 is a potent regulator of leukocytes and controls microbial sepsis.

Authors: Matthew Spite; Lucy V Norling; Lisa Summers; Rong Yang; Dianne Cooper; Nicos A Petasis; Roderick J Flower; Mauro Perretti; Charles N Serhan
Journal: Nature Date: 2009-10-29 Impact factor: 49.962

18 in total

1. [(18)F]Fluorobenzoyllysinepentanedioic Acid Carbamates: New Scaffolds for Positron Emission Tomography (PET) Imaging of Prostate-Specific Membrane Antigen (PSMA).

Authors: Xing Yang; Ronnie C Mease; Mrudula Pullambhatla; Ala Lisok; Ying Chen; Catherine A Foss; Yuchuan Wang; Hassan Shallal; Hannah Edelman; Adam T Hoye; Giorgio Attardo; Sridhar Nimmagadda; Martin G Pomper
Journal: J Med Chem Date: 2015-12-16 Impact factor: 7.446

2. Resolvin D3 and aspirin-triggered resolvin D3 are potent immunoresolvents.

Authors: Jesmond Dalli; Jeremy W Winkler; Romain A Colas; Hildur Arnardottir; Chien-Yee C Cheng; Nan Chiang; Nicos A Petasis; Charles N Serhan
Journal: Chem Biol Date: 2013-02-21

Review 3. Metabololipidomic profiling of functional immunoresolvent clusters and eicosanoids in mammalian tissues.

Authors: Paul C Norris; Charles N Serhan
Journal: Biochem Biophys Res Commun Date: 2018-03-15 Impact factor: 3.575

Review 4. New Advances in Targeting the Resolution of Inflammation: Implications for Specialized Pro-Resolving Mediator GPCR Drug Discovery.

Authors: Julia Park; Christopher J Langmead; Darren M Riddy
Journal: ACS Pharmacol Transl Sci Date: 2020-01-20

5. Resolvin D3 and Aspirin-Triggered Resolvin D3 Are Protective for Injured Epithelia.

Authors: Jennifer K Colby; Raja-Elie E Abdulnour; Ho Pan Sham; Jesmond Dalli; Romain A Colas; Jeremy W Winkler; Jason Hellmann; Blenda Wong; Ye Cui; Souheil El-Chemaly; Nicos A Petasis; Matthew Spite; Charles N Serhan; Bruce D Levy
Journal: Am J Pathol Date: 2016-05-10 Impact factor: 4.307

10. First stereoselective total synthesis of 4(S),5(S)-oxido-17(S)-hydroxy-6(E),8(E),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid, the biosynthetic precursor of resolvins D3 and D4.

Authors: Robert Nshimiyimana; Ting Fung Lam; Shubhangi Aggarwal; Charles N Serhan; Nicos A Petasis
Journal: RSC Adv Date: 2022-04-19 Impact factor: 4.036