Literature DB >> 17649989

Fine-tuning the amphiphilicity: a crucial parameter in the design of potent alpha-phenyl-N-tert-butylnitrone analogues.

Grégory Durand1, Burkhard Poeggeler, Jutta Böker, Simon Raynal, Ange Polidori, Miguel A Pappolla, Rüdiger Hardeland, Bernard Pucci.   

Abstract

A new series of hydrophilic, lipophilic, and amphiphilic alpha-phenyl-N-tert-butylnitrone (PBN) derivatives were synthesized to explore the relationship between their hydrophilic-lipophilic properties and antioxidant potency. Very potent protective effects of amphiphilic lactobionamide and tris(hydroxymethyl)aminomethane PBN derivatives were observed in mitochondrial preparations, in cell cultures, and in rotifers exposed to unspecific and mitochondria targeted oxidotoxins.

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Year:  2007        PMID: 17649989     DOI: 10.1021/jm0706968

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  9 in total

Review 1.  Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics.

Authors:  Frederick A Villamena; Amlan Das; Kevin M Nash
Journal:  Future Med Chem       Date:  2012-06       Impact factor: 3.808

2.  Reactivities of superoxide and hydroperoxyl radicals with disubstituted cyclic nitrones: a DFT study.

Authors:  Shang-U Kim; Frederick A Villamena
Journal:  J Phys Chem A       Date:  2011-12-12       Impact factor: 2.781

3.  A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan.

Authors:  Burkhard Poeggeler; Kumar Sambamurti; Sandra L Siedlak; George Perry; Mark A Smith; Miguel A Pappolla
Journal:  PLoS One       Date:  2010-04-21       Impact factor: 3.240

4.  Lipophilic beta-cyclodextrin cyclic-nitrone conjugate: synthesis and spin trapping studies.

Authors:  Yongbin Han; Yangping Liu; Antal Rockenbauer; Jay L Zweier; Grégory Durand; Frederick A Villamena
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

5.  Nitrones reverse hyperglycemia-induced endothelial dysfunction in bovine aortic endothelial cells.

Authors:  Colwyn A Headley; David DiSilvestro; Kelsey E Bryant; Craig Hemann; Chun-An Chen; Amlan Das; Ouliana Ziouzenkova; Grégory Durand; Frederick A Villamena
Journal:  Biochem Pharmacol       Date:  2016-01-14       Impact factor: 5.858

6.  Spin trapping and cytoprotective properties of fluorinated amphiphilic carrier conjugates of cyclic versus linear nitrones.

Authors:  Grégory Durand; Robert A Prosak; Yongbin Han; Stéphanie Ortial; Antal Rockenbauer; Bernard Pucci; Frederick A Villamena
Journal:  Chem Res Toxicol       Date:  2009-09       Impact factor: 3.739

7.  N-[2-(2-Methoxyphenyl)benzylidene]-tert-butyl-amine N-oxide.

Authors:  Jin-Long Wu; Yu Liao; Shan-Lin Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-17

8.  Synthesis of N-arylpyridinium salts bearing a nitrone spin trap as potential mitochondria-targeted antioxidants.

Authors:  Linsey Robertson; Richard C Hartley
Journal:  Tetrahedron       Date:  2009-07-04       Impact factor: 2.457

Review 9.  Neuroprotection by radical avoidance: search for suitable agents.

Authors:  Rüdiger Hardeland
Journal:  Molecules       Date:  2009-12-07       Impact factor: 4.411

  9 in total

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