Literature DB >> 30204204

Synthesis of protectin D1 analogs: novel pro-resolution and radiotracer agents.

J E Tungen1, M Aursnes, S Ramon, R A Colas, C N Serhan, D E Olberg, S Nuruddin, F Willoch, T V Hansen.   

Abstract

Protectin D1 is a specialized pro-resolving mediator with potent pro-resolving and anti-inflammatory effects in vivo in several human disease models. Herein the preparation of the first synthetic analog of protectin D1, named 22-F-PD1, is presented together with data from in vivo investigations. This analog showed potent pro-resolving and anti-inflammatory properties. These results inspired the preparation of the radiotracer 22-[18F]F-PD1-ME that was used in a positron emission tomography proof of concept study. Altogether, the findings presented contribute to new knowledge on the biomolecular properties of protectin D1 analogs. In addition, an improved formal synthesis of the metabolite 22-OH-PD1 is reported.

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Year:  2018        PMID: 30204204      PMCID: PMC6309860          DOI: 10.1039/c8ob01232f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  32 in total

Review 1.  Treating inflammation and infection in the 21st century: new hints from decoding resolution mediators and mechanisms.

Authors:  Charles N Serhan
Journal:  FASEB J       Date:  2017-01-13       Impact factor: 5.191

Review 2.  Resolution of inflammation: a new therapeutic frontier.

Authors:  James N Fullerton; Derek W Gilroy
Journal:  Nat Rev Drug Discov       Date:  2016-03-29       Impact factor: 84.694

3.  Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator.

Authors:  M Aursnes; J E Tungen; A Vik; J Dalli; T V Hansen
Journal:  Org Biomol Chem       Date:  2013-11-19       Impact factor: 3.876

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

Review 5.  An overview of PET neuroimaging.

Authors:  Ilya Nasrallah; Jacob Dubroff
Journal:  Semin Nucl Med       Date:  2013-11       Impact factor: 4.446

Review 6.  Pro-resolving lipid mediators are leads for resolution physiology.

Authors:  Charles N Serhan
Journal:  Nature       Date:  2014-06-05       Impact factor: 49.962

Review 7.  DHA- and EPA-derived resolvins, protectins, and maresins in airway inflammation.

Authors:  Melody G Duvall; Bruce D Levy
Journal:  Eur J Pharmacol       Date:  2015-11-03       Impact factor: 4.432

8.  Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction.

Authors:  Jørn Eivind Tungen; Marius Aursnes; Jesmond Dalli; Hildur Arnardottir; Charles Nicholas Serhan; Trond Vidar Hansen
Journal:  Chemistry       Date:  2014-09-15       Impact factor: 5.236

9.  Synthesis of the 16S,17S-Epoxyprotectin Intermediate in the Biosynthesis of Protectins by Human Macrophages.

Authors:  Marius Aursnes; Jørn E Tungen; Romain A Colas; Iliyan Vlasakov; Jesmond Dalli; Charles N Serhan; Trond V Hansen
Journal:  J Nat Prod       Date:  2015-11-18       Impact factor: 4.050

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

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  5 in total

1.  A newly synthesized 17-epi-NeuroProtectin D1/17-epi-Protectin D1: Authentication and functional regulation of Inflammation-Resolution.

Authors:  Kajal Hamidzadeh; Jodi Westcott; Nicholas Wourms; Ashley E Shay; Anand Panigrahy; Michael J Martin; Robert Nshimiyimana; Charles N Serhan
Journal:  Biochem Pharmacol       Date:  2022-07-16       Impact factor: 6.100

2.  A new synthetic protectin D1 analog 3-oxa-PD1n-3 DPA reduces neuropathic pain and chronic itch in mice.

Authors:  Jannicke Irina Nesman; Ouyang Chen; Xin Luo; Ru-Rong Ji; Charles N Serhan; Trond Vidar Hansen
Journal:  Org Biomol Chem       Date:  2021-03-09       Impact factor: 3.876

Review 3.  The Protectin Family of Specialized Pro-resolving Mediators: Potent Immunoresolvents Enabling Innovative Approaches to Target Obesity and Diabetes.

Authors:  Trond Vidar Hansen; Anders Vik; Charles N Serhan
Journal:  Front Pharmacol       Date:  2019-01-17       Impact factor: 5.810

4.  Synthesis, Structural Confirmation, and Biosynthesis of 22-OH-PD1n-3 DPA.

Authors:  Jannicke Irina Nesman; Karoline Gangestad Primdahl; Jørn Eivind Tungen; Fransesco Palmas; Jesmond Dalli; Trond Vidar Hansen
Journal:  Molecules       Date:  2019-09-05       Impact factor: 4.927

Review 5.  Specialized Pro-Resolving Mediators Mitigate Cancer-Related Inflammation: Role of Tumor-Associated Macrophages and Therapeutic Opportunities.

Authors:  Margot Lavy; Vanessa Gauttier; Nicolas Poirier; Sophie Barillé-Nion; Christophe Blanquart
Journal:  Front Immunol       Date:  2021-06-30       Impact factor: 7.561

  5 in total

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