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Literature DB >> 30511787

Resolving Inflammation: Synthesis, Configurational Assignment, and Biological Evaluations of RvD1_n-3 DPA.

Jørn Eivind Tungen¹, Lisa Gerstmann^1,2, Anders Vik¹, Roberta De Matteis³, Romain Alexandre Colas³, Jesmond Dalli³, Nan Chiang⁴, Charles Nicholas Serhan⁴, Markus Kalesse², Trond Vidar Hansen¹.

Abstract

New drugs that can resolve inflammation without immunosuppressive effects are at the medicinal chemistry frontier. Pro-resolving endogenously formed small molecules, that is, the resolvins, are excellent candidates displaying such bioactions. The first total synthesis of the specialized pro-resolving mediator RvD1n-3 DPA has been achieved using the underutilized sp3 -sp3 Negishi cross coupling reaction and an alkyne hydrosilylation-protodesilylation protocol. Biological evaluations revealed that this novel mediator displays low nanomolar pro-resolving properties and potently activates the human DRV1/GPR32 receptor. As such, this endogenous natural product is a lead compound for the development of novel immunoresolvents.

Entities: CellLine Chemical Disease Gene Species

Keywords: Karstedt's catalyst; natural products; sp3-sp3 cross-coupling; specialized pro-resolving mediators; total synthesis

Mesh：

Substances：

Year: 2018 PMID： 30511787 PMCID： PMC6368681 DOI： 10.1002/chem.201806029

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

39 in total

Review 1. Resolvins and protectins in the termination program of acute inflammation.

Authors: Amiram Ariel; Charles N Serhan
Journal: Trends Immunol Date: 2007-03-06 Impact factor: 16.687

2. Resolvin E1 and protectin D1 activate inflammation-resolution programmes.

Authors: Jan M Schwab; Nan Chiang; Makoto Arita; Charles N Serhan
Journal: Nature Date: 2007-06-14 Impact factor: 49.962

3. The first Negishi cross-coupling reaction of two alkyl centers utilizing a Pd-N-heterocyclic carbene (NHC) catalyst.

Authors: Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal: Org Lett Date: 2005-08-18 Impact factor: 6.005

4. Resolvin D1 and its aspirin-triggered 17R epimer. Stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation.

Authors: Yee-Ping Sun; Sungwhan F Oh; Jasim Uddin; Rong Yang; Katherine Gotlinger; Eric Campbell; Sean P Colgan; Nicos A Petasis; Charles N Serhan
Journal: J Biol Chem Date: 2007-01-23 Impact factor: 5.157

5. The docosatriene protectin D1 is produced by TH2 skewing and promotes human T cell apoptosis via lipid raft clustering.

Authors: Amiram Ariel; Pin-Lan Li; Wei Wang; Wang-Xian Tang; Gabrielle Fredman; Song Hong; Katherine H Gotlinger; Charles N Serhan
Journal: J Biol Chem Date: 2005-10-10 Impact factor: 5.157

6. 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

7. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation.

Authors: Song Hong; Karsten Gronert; Pallavi R Devchand; Rose-Laure Moussignac; Charles N Serhan
Journal: J Biol Chem Date: 2003-02-17 Impact factor: 5.157

8. Neuroprotectin D1: a docosahexaenoic acid-derived docosatriene protects human retinal pigment epithelial cells from oxidative stress.

Authors: Pranab K Mukherjee; Victor L Marcheselli; Charles N Serhan; Nicolas G Bazan
Journal: Proc Natl Acad Sci U S A Date: 2004-05-19 Impact factor: 11.205

9. Maresins: novel macrophage mediators with potent antiinflammatory and proresolving actions.

Authors: Charles N Serhan; Rong Yang; Kimberly Martinod; Kie Kasuga; Padmini S Pillai; Timothy F Porter; Sungwhan F Oh; Matthew Spite
Journal: J Exp Med Date: 2008-12-22 Impact factor: 14.307

10. Resolvins: a family of bioactive products of omega-3 fatty acid transformation circuits initiated by aspirin treatment that counter proinflammation signals.

Authors: Charles N Serhan; Song Hong; Karsten Gronert; Sean P Colgan; Pallavi R Devchand; Gudrun Mirick; Rose-Laure Moussignac
Journal: J Exp Med Date: 2002-10-21 Impact factor: 14.307

7 in total

Review 1. Neutrophil Signaling That Challenges Dogmata of G Protein-Coupled Receptor Regulated Functions.

Authors: Claes Dahlgren; André Holdfeldt; Simon Lind; Jonas Mårtensson; Michael Gabl; Lena Björkman; Martina Sundqvist; Huamei Forsman
Journal: ACS Pharmacol Transl Sci Date: 2020-03-11

2. Stereoselective Synthesis and Structural Confirmation of the Specialized Pro-Resolving Mediator Resolvin E4.

Authors: Amalie Føreid Reinertsen; Karoline Gangestad Primdahl; Ashley Elizabeth Shay; Charles Nicholas Serhan; Trond Vidar Hansen; Marius Aursnes
Journal: J Org Chem Date: 2021-02-03 Impact factor: 4.354

3. Stereoselective synthesis of MaR2_{n-3 DPA}.

Authors: Jeanne Sønderskov; Jørn E Tungen; Francesco Palmas; Jesmond Dalli; Charles N Serhan; Yngve Stenstrøm; Trond Vidar Hansen
Journal: Tetrahedron Lett Date: 2019-12-09 Impact factor: 2.415

4. Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2_{n-3 DPA}.

Authors: Amalie F Reinertsen; Karoline G Primdahl; Roberta De Matteis; Jesmond Dalli; Trond V Hansen
Journal: Chemistry Date: 2021-12-28 Impact factor: 5.020