Literature DB >> 22820546

Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamides and evaluation of their anti-inflammatory activity.

Padmanabha V Kattamuri1, Rebecca Salmonsen, Catherine McQuain, Sumner Burstein, Hao Sun, Guigen Li.   

Abstract

AIMS: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl)arachidonylamides and evaluate their analgesic and anti-inflammatory potential. MAIN
METHODS: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ(13,14)-PGJ2 (PGJ) are measured by ELISA following LPS (10ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10μM concentrations of the compounds. KEY
FINDINGS: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). SIGNIFICANCE: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.
Copyright © 2012 Elsevier Inc. All rights reserved.

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Year:  2012        PMID: 22820546      PMCID: PMC3516634          DOI: 10.1016/j.lfs.2012.06.040

Source DB:  PubMed          Journal:  Life Sci        ISSN: 0024-3205            Impact factor:   5.037


  27 in total

Review 1.  Inflammatory resolution: new opportunities for drug discovery.

Authors:  Derek W Gilroy; Toby Lawrence; Mauro Perretti; Adriano G Rossi
Journal:  Nat Rev Drug Discov       Date:  2004-05       Impact factor: 84.694

2.  N-arachidonoyl glycine induces macrophage apoptosis via GPR18.

Authors:  Rina Takenouchi; Kazuhiko Inoue; Yuki Kambe; Atsuro Miyata
Journal:  Biochem Biophys Res Commun       Date:  2012-01-11       Impact factor: 3.575

3.  Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.

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4.  Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.

Authors:  T Sheskin; L Hanus; J Slager; Z Vogel; R Mechoulam
Journal:  J Med Chem       Date:  1997-02-28       Impact factor: 7.446

5.  Potent anandamide analogs: the effect of changing the length and branching of the end pentyl chain.

Authors:  W J Ryan; W K Banner; J L Wiley; B R Martin; R K Razdan
Journal:  J Med Chem       Date:  1997-10-24       Impact factor: 7.446

6.  Molecular characterization of a peripheral receptor for cannabinoids.

Authors:  S Munro; K L Thomas; M Abu-Shaar
Journal:  Nature       Date:  1993-09-02       Impact factor: 49.962

7.  (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability.

Authors:  V Abadji; S Lin; G Taha; G Griffin; L A Stevenson; R G Pertwee; A Makriyannis
Journal:  J Med Chem       Date:  1994-06-10       Impact factor: 7.446

8.  Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent.

Authors:  E Fride; R Mechoulam
Journal:  Eur J Pharmacol       Date:  1993-02-09       Impact factor: 4.432

9.  Development of novel tail-modified anandamide analogs.

Authors:  Fenmei Yao; Chen Li; Subramanian K Vadivel; Anna L Bowman; Alexandros Makriyannis
Journal:  Bioorg Med Chem Lett       Date:  2008-07-31       Impact factor: 2.823

Review 10.  Recent advances in the synthesis of endocannabinoid related ligands.

Authors:  R K Razdan; A Mahadevan
Journal:  Chem Phys Lipids       Date:  2002-12-31       Impact factor: 3.329

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