Literature DB >> 22128851

(1S, 3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115), a potent γ-aminobutyric acid aminotransferase inactivator for the treatment of cocaine addiction.

Yue Pan1, Madina R Gerasimov, Trine Kvist, Petrine Wellendorph, Karsten K Madsen, Elena Pera, Hyunbeom Lee, Arne Schousboe, Mary Chebib, Hans Bräuner-Osborne, Cheryl M Craft, Jonathan D Brodie, Wynne K Schiffer, Stephen L Dewey, Steven R Miller, Richard B Silverman.   

Abstract

Vigabatrin, a n class="Gene">GABA aminotransferase (GABA-AT) inactivator, is used to treat infantile spasms and refractory complex partial seizures and is in clinical trials to treat addiction. We evaluated a novel GABA-AT inactivator (1S, 3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115, compound 1) and observed that it does not exhibit other GABAergic or off-target activities and is rapidly and completely orally absorbed and eliminated. By use of in vivo microdialysis techniques in freely moving rats and microPET imaging techniques, 1 produced similar inhibition of cocaine-induced increases in extracellular dopamine and in synaptic dopamine in the nucleus accumbens at (1)/(300) to (1)/(600) the dose of vigabatrin. It also blocks expression of cocaine-induced conditioned place preference at a dose (1)/(300) that of vigabatrin. Electroretinographic (ERG) responses in rats treated with 1, at doses 20-40 times higher than those needed to treat addiction in rats, exhibited reductions in ERG responses, which were less than the reductions observed in rats treated with vigabatrin at the same dose needed to treat addiction in rats. In conclusion, 1 can be administered at significantly lower doses than vigabatrin, which suggests a potential new treatment for addiction with a significantly reduced risk of visual field defects.

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Year:  2011        PMID: 22128851      PMCID: PMC3257419          DOI: 10.1021/jm201231w

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


  43 in total

1.  Effects of single and multiple increasing doses of vigabatrin on brain GABA metabolism and correlation with vigabatrin plasma concentration.

Authors:  E M Valdizán; J A Armijo
Journal:  Biochem Pharmacol       Date:  1992-05-28       Impact factor: 5.858

2.  Chronic toxicity studies with vigabatrin, a GABA-transaminase inhibitor.

Authors:  J P Gibson; J T Yarrington; D E Loudy; C G Gerbig; G H Hurst; J W Newberne
Journal:  Toxicol Pathol       Date:  1990       Impact factor: 1.902

3.  Mechanism-based enzyme inactivators.

Authors:  R B Silverman
Journal:  Methods Enzymol       Date:  1995       Impact factor: 1.600

4.  Effects of pharmacologic increases in brain GABA levels on cocaine-induced changes in extracellular dopamine.

Authors:  A E Morgan; S L Dewey
Journal:  Synapse       Date:  1998-01       Impact factor: 2.562

5.  Registry initiated to characterize vision loss associated with vigabatrin therapy.

Authors:  John M Pellock; Edward Faught; Robert C Sergott; W Donald Shields; Gregory A Burkhart; Gregory L Krauss; Rod Foroozan; David L Wesche; Mark A Weinberg
Journal:  Epilepsy Behav       Date:  2011-10-05       Impact factor: 2.937

6.  A novel strategy for the treatment of cocaine addiction.

Authors:  S L Dewey; A E Morgan; C R Ashby; B Horan; S A Kushner; J Logan; N D Volkow; J S Fowler; E L Gardner; J D Brodie
Journal:  Synapse       Date:  1998-10       Impact factor: 2.562

7.  3H-baclofen and 3H-GABA bind to bicuculline-insensitive GABA B sites in rat brain.

Authors:  D R Hill; N G Bowery
Journal:  Nature       Date:  1981-03-12       Impact factor: 49.962

8.  Molecular characterization of four pharmacologically distinct gamma-aminobutyric acid transporters in mouse brain [corrected].

Authors:  Q R Liu; B López-Corcuera; S Mandiyan; H Nelson; N Nelson
Journal:  J Biol Chem       Date:  1993-01-25       Impact factor: 5.157

9.  Reduction of plasma alanine aminotransferase during vigabatrin treatment.

Authors:  G B Foletti; M C Delisle; C Bachmann
Journal:  Epilepsia       Date:  1995-08       Impact factor: 5.864

Review 10.  Basic aspects of GABA-transaminase in neuropsychiatric disorders.

Authors:  F M Sherif; S S Ahmed
Journal:  Clin Biochem       Date:  1995-04       Impact factor: 3.281

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  22 in total

1.  The 2011 E. B. Hershberg award for important discoveries in medicinally active substances: (1S,3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115), a GABA aminotransferase inactivator and new treatment for drug addiction and infantile spasms.

Authors:  Richard B Silverman
Journal:  J Med Chem       Date:  2012-01-10       Impact factor: 7.446

Review 2.  Ornithine aminotransferase versus GABA aminotransferase: implications for the design of new anticancer drugs.

Authors:  Hyunbeom Lee; Jose I Juncosa; Richard B Silverman
Journal:  Med Res Rev       Date:  2014-08-22       Impact factor: 12.944

3.  Design and mechanism of tetrahydrothiophene-based γ-aminobutyric acid aminotransferase inactivators.

Authors:  Hoang V Le; Dustin D Hawker; Rui Wu; Emma Doud; Julia Widom; Ruslan Sanishvili; Dali Liu; Neil L Kelleher; Richard B Silverman
Journal:  J Am Chem Soc       Date:  2015-03-30       Impact factor: 15.419

Review 4.  Pathogenesis and new candidate treatments for infantile spasms and early life epileptic encephalopathies: A view from preclinical studies.

Authors:  Aristea S Galanopoulou; Solomon L Moshé
Journal:  Neurobiol Dis       Date:  2015-05-09       Impact factor: 5.996

5.  Mechanism of Inactivation of GABA Aminotransferase by (E)- and (Z)-(1S,3S)-3-Amino-4-fluoromethylenyl-1-cyclopentanoic Acid.

Authors:  Hyunbeom Lee; Hoang V Le; Rui Wu; Emma Doud; Ruslan Sanishvili; John F Kellie; Phillip D Compton; Boobalan Pachaiyappan; Dali Liu; Neil L Kelleher; Richard B Silverman
Journal:  ACS Chem Biol       Date:  2015-07-06       Impact factor: 5.100

6.  CPP-115, a vigabatrin analogue, decreases spasms in the multiple-hit rat model of infantile spasms.

Authors:  Stephen W Briggs; Wenzhu Mowrey; Charles B Hall; Aristea S Galanopoulou
Journal:  Epilepsia       Date:  2013-10-28       Impact factor: 5.864

7.  Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.

Authors:  Christopher D McCune; Matthew L Beio; Jill M Sturdivant; Roberto de la Salud-Bea; Brendan M Darnell; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2017-09-28       Impact factor: 15.419

8.  S-(N, N-diethylcarbamoyl)glutathione (carbamathione), a disulfiram metabolite and its effect on nucleus accumbens and prefrontal cortex dopamine, GABA, and glutamate: a microdialysis study.

Authors:  Morris D Faiman; Swetha Kaul; Shaheen A Latif; Todd D Williams; Craig E Lunte
Journal:  Neuropharmacology       Date:  2013-07-26       Impact factor: 5.250

9.  Design and Mechanism of (S)-3-Amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic Acid, a Highly Potent γ-Aminobutyric Acid Aminotransferase Inactivator for the Treatment of Addiction.

Authors:  Jose I Juncosa; Kenji Takaya; Hoang V Le; Matthew J Moschitto; Pathum M Weerawarna; Romila Mascarenhas; Dali Liu; Stephen L Dewey; Richard B Silverman
Journal:  J Am Chem Soc       Date:  2018-01-30       Impact factor: 15.419

Review 10.  Neonatal and Infantile Epilepsy: Acquired and Genetic Models.

Authors:  Aristea S Galanopoulou; Solomon L Moshé
Journal:  Cold Spring Harb Perspect Med       Date:  2015-12-04       Impact factor: 6.915

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