Bioorg Med Chem. 2007 Aug 1;15(15):5198-206. Epub 2007 May 22.

Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthioamphetamine derivatives: insights from molecular modeling studies.

Fierro A, Osorio-Olivares M, Cassels BK, Edmondson DE, Sepúlveda-Boza S, Reyes-Parada M.

Source

Faculty of Chemistry and Biology, University of Santiago de Chile, Alameda, Santiago, Chile.

Abstract

Four enantiomerically pure (S)-4-alkylthioamphetamine derivatives were evaluated as monoamine oxidase (MAO) inhibitors using the human and rat isoforms of the enzyme. Molecular dockings were performed in order to gain insights regarding the binding mode of these inhibitors. All compounds were potent and selective MAO-A inhibitors although different rank orders of potencies were observed against the enzymes from different species. This behavior can be rationalized on the basis of different binding modes to each enzyme, as determined in silico. These findings further support the concept that MAO inhibitory activity of novel compounds, determined with enzymes from diverse mammalian species, should be considered with caution if human MAO is the final target to be addressed.

PMID:: 17521909; [PubMed - indexed for MEDLINE]
PMCID:: PMC1949415

Free PMC Article

Images from this publication.See all images (6) Free text

Publication Types, MeSH Terms, Substances, Grant Support

Publication Types

MeSH Terms

Substances

Grant Support

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Chemical Information

BindingDB

Supplemental Content

Save items

Related citations in PubMed

Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors. [Bioorg Med Chem. 2009]
Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors.
Gökhan-Kelekçi N, Simşek OO, Ercan A, Yelekçi K, Sahin ZS, Işik S, Uçar G, Bilgin AA. Bioorg Med Chem. 2009 Sep 15; 17(18):6761-72. Epub 2009 Jul 23.
2-Arylthiomorpholine derivatives as potent and selective monoamine oxidase B inhibitors. [Bioorg Med Chem. 2010]
2-Arylthiomorpholine derivatives as potent and selective monoamine oxidase B inhibitors.
Lühr S, Vilches-Herrera M, Fierro A, Ramsay RR, Edmondson DE, Reyes-Parada M, Cassels BK, Iturriaga-Vásquez P. Bioorg Med Chem. 2010 Feb 15; 18(4):1388-95. Epub 2010 Jan 15.
Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors. [Bioorg Med Chem. 2010]
Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors.
Shi L, Yang Y, Li ZL, Zhu ZW, Liu CH, Zhu HL. Bioorg Med Chem. 2010 Feb 15; 18(4):1659-64. Epub 2010 Jan 4.
Review Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors. [Curr Med Chem. 2006]
Review Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors.
Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Granese A, Befani O, Turini P, Cirilli R, La Torre F, et al. Curr Med Chem. 2006; 13(12):1411-28.
Review Function of endogenous monoamine oxidase inhibitors (tribulin). [J Neural Transm Suppl. 1998]
Review Function of endogenous monoamine oxidase inhibitors (tribulin).
Glover V. J Neural Transm Suppl. 1998; 52:307-13.

See reviews... See all...

Cited by 1 PubMed Central article

High-level expression and purification of rat monoamine oxidase A (MAO A) in Pichia pastoris: comparison with human MAO A. [Protein Expr Purif. 2010]
High-level expression and purification of rat monoamine oxidase A (MAO A) in Pichia pastoris: comparison with human MAO A.
Wang J, Edmondson DE. Protein Expr Purif. 2010 Apr; 70(2):211-7. Epub 2009 Oct 31.

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
BioAssay
PubChem BioAssay experiments on the biological activities of small molecules that cite the current articles. The depositors of BioAssay data provide these references.
References for this PMC Article
Citation referenced in PubMed article. Only valid for PubMed citations that are also in PMC.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Free in PMC
Free full text articles in PMC
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthi...
Human and rat monoamine oxidase-A are differentially inhibited by (S)-4-alkylthioamphetamine derivatives: insights from molecular modeling studies.
Bioorg Med Chem. 2007 Aug 1 ;15(15):5198-206. Epub 2007 May 22 .

PubMed
One year pre-post intervention follow-up of psychological, immune, endocrine and...
One year pre-post intervention follow-up of psychological, immune, endocrine and blood pressure outcomes of mindfulness-based stress reduction (MBSR) in breast and prostate cancer outpatients.
Brain Behav Immun. 2007 Nov ;21(8):1038-49. Epub 2007 May 22 .

PubMed
The Meningitis Vaccine Project.
The Meningitis Vaccine Project.
Vaccine. 2007 Sep 3 ;25 Suppl 1:A97-100. Epub 2007 May 7 .

PubMed
Acute ischemic stroke: overview of major experimental rodent models, pathophysio...
Acute ischemic stroke: overview of major experimental rodent models, pathophysiology, and therapy of focal cerebral ischemia.
Pharmacol Biochem Behav. 2007 May ;87(1):179-97. Epub 2007 May 4 .

PubMed
Comparison of endoscopic ultrasonography and magnetic resonance cholangiopancrea...
Comparison of endoscopic ultrasonography and magnetic resonance cholangiopancreatography in the diagnosis of pancreatobiliary diseases: a prospective study.
Am J Gastroenterol. 2007 Aug ;102(8):1632-9. Epub 2007 May 23 .

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: