J Med Chem. 2004 Sep 23;47(20):4865-74.

Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: identification of novel substrates with insulin-like activity.

Marti L, Abella A, De La Cruz X, García-Vicente S, Unzeta M, Carpéné C, Palacín M, Testar X, Orozco M, Zorzano A.

Source

Parc Científic de Barcelona and Departament de Bioquímica i Biologia Molecular, Facultat de Biologia, Universitat de Barcelona, Avda. Diagonal 645, E-08028 Barcelona, Spain.

Abstract

We previously reported that substrates of semicarbazide-sensitive amine oxidase in combination with low concentrations of vanadate exert potent insulin-like effects. Here we performed homology modeling of the catalytic domain of mouse SSAO/VAP-1 and searched through chemical databases to identify novel SSAO substrates. The modeling of the catalytic domain revealed that aromatic residues Tyr384, Phe389, and Tyr394 define a pocket of stable size that may participate in the binding of apolar substrates. We identified a number of amines as substrates of human, rat, and mouse SSAO. The compounds PD0119035, 2,3-dimethoxy-benzylamine, and C-naphthalen-1-yl-methylamine showed high affinity as substrates of rat SSAO. C-Naphthalen-1-yl-methylamine was the only substrate that showed high affinity for human SSAO. C-Naphthalen-1-yl-methylamine and 4-aminomethyl-benzenesulfonamide showed the highest capacity to stimulate glucose transport in isolated rat adipocytes. The impact of these findings on the development of new treatments for diabetes is discussed.

PMID:: 15369390; [PubMed - indexed for MEDLINE]

Publication Types, MeSH Terms, Substances

Publication Types

Research Support, Non-U.S. Gov't

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Medical

Diabetes Medicines - MedlinePlus Health Information

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Methylamine but not mafenide mimics insulin-like activity of the semicarbazide-sensitive amine oxidase-substrate benzylamine on glucose tolerance and on human adipocyte metabolism. [Pharmacol Res. 2005]
Methylamine but not mafenide mimics insulin-like activity of the semicarbazide-sensitive amine oxidase-substrate benzylamine on glucose tolerance and on human adipocyte metabolism.
Iglesias-Osma MC, Bour S, Garcia-Barrado MJ, Visentin V, Pastor MF, Testar X, Marti L, Enrique-Tarancon G, Valet P, Moratinos J, et al. Pharmacol Res. 2005 Dec; 52(6):475-84. Epub 2005 Aug 30.
Substrates of semicarbazide-sensitive amine oxidase co-operate with vanadate to stimulate tyrosine phosphorylation of insulin-receptor-substrate proteins, phosphoinositide 3-kinase activity and GLUT4 translocation in adipose cells. [Biochem J. 2000]
Substrates of semicarbazide-sensitive amine oxidase co-operate with vanadate to stimulate tyrosine phosphorylation of insulin-receptor-substrate proteins, phosphoinositide 3-kinase activity and GLUT4 translocation in adipose cells.
Enrique-Tarancón G, Castan I, Morin N, Marti L, Abella A, Camps M, Casamitjana R, Palacín M, Testar X, Degerman E, et al. Biochem J. 2000 Aug 15; 350 Pt 1:171-80.
Semicarbazide-sensitive amine oxidase substrates fail to induce insulin-like effects in fat cells from AOC3 knockout mice. [J Neural Transm. 2007]
Semicarbazide-sensitive amine oxidase substrates fail to induce insulin-like effects in fat cells from AOC3 knockout mice.
Bour S, Prévot D, Guigné C, Stolen C, Jalkanen S, Valet P, Carpéné C. J Neural Transm. 2007; 114(6):829-33. Epub 2007 Apr 4.
Review Semicarbazide-sensitive amine oxidase activity exerts insulin-like effects on glucose metabolism and insulin-signaling pathways in adipose cells. [Biochim Biophys Acta. 2003]
Review Semicarbazide-sensitive amine oxidase activity exerts insulin-like effects on glucose metabolism and insulin-signaling pathways in adipose cells.
Zorzano A, Abella A, Marti L, Carpéné C, Palacín M, Testar X. Biochim Biophys Acta. 2003 Apr 11; 1647(1-2):3-9.
Review Amine oxidase substrates for impaired glucose tolerance correction. [J Physiol Biochem. 2005]
Review Amine oxidase substrates for impaired glucose tolerance correction.
Carpéné C, Bour S, Visentin V, Pellati F, Benvenuti S, Iglesias-Osma MC, García-Barrado MJ, Valet P. J Physiol Biochem. 2005 Jun; 61(2):405-19.

See reviews... See all...

Cited by 4 PubMed Central articles

Implication for functions of the ectopic adipocyte copper amine oxidase (AOC3) from purified enzyme and cell-based kinetic studies. [PLoS One. 2012]
Implication for functions of the ectopic adipocyte copper amine oxidase (AOC3) from purified enzyme and cell-based kinetic studies.
Shen SH, Wertz DL, Klinman JP. PLoS One. 2012; 7(1):e29270. Epub 2012 Jan 4.
Kinetic and structural analysis of substrate specificity in two copper amine oxidases from Hansenula polymorpha. [Biochemistry. 2010]
Kinetic and structural analysis of substrate specificity in two copper amine oxidases from Hansenula polymorpha.
Chang CM, Klema VJ, Johnson BJ, Mure M, Klinman JP, Wilmot CM. Biochemistry. 2010 Mar 23; 49(11):2540-50.
Discovery of a sensitive, selective, and tightly binding fluorogenic substrate of bovine plasma amine oxidase. [J Org Chem. 2009]
Discovery of a sensitive, selective, and tightly binding fluorogenic substrate of bovine plasma amine oxidase.
Ling KQ, Sayre LM. J Org Chem. 2009 Jan 2; 74(1):339-50.

See all...

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.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: ident...
Exploring the binding mode of semicarbazide-sensitive amine oxidase/VAP-1: identification of novel substrates with insulin-like activity.
J Med Chem. 2004 Sep 23 ;47(20):4865-74.

PubMed
Colorectal cancer and solar radiation.
Colorectal cancer and solar radiation.
Cancer Causes Control. 1992 Jan ;3(1):95-9.

PubMed
Leaving methadone maintenance treatment: the role of personality traits and psyc...
Leaving methadone maintenance treatment: the role of personality traits and psychiatric status.
J Psychoactive Drugs. 2004 Jun ;36(2):227-34.

PubMed
Process and product monitoring of recombinant DNA-derived biopharmaceuticals wit...
Process and product monitoring of recombinant DNA-derived biopharmaceuticals with high-performance capillary electrophoresis.
J Capill Electrophor Microchip Technol. 2003 Sep-Dec ;8(5-6):87-99.

PubMed
Oral contraceptives and primary liver cancer among young women.
Oral contraceptives and primary liver cancer among young women.
Cancer Causes Control. 1992 Jan ;3(1):43-8.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: