| Stictamides A-C, MMP12 inhibitors containing 4-amino-3-hydroxy-5-phenylpentanoic acid subunits. | |
| | |
MedLine Citation:
|
PMID: 21500817 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 μM and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism. |
| | |
Authors:
|
Zhibin Liang; Analia Sorribas; Florian J Sulzmaier; Jorge I Jiménez; Xin Wang; Thomas Sauvage; Wesley Y Yoshida; Guangyi Wang; Joe W Ramos; Philip G Williams |
Related Documents
:
|
11288727 - Amino acid sequence of a neurotoxic phospholipase a2 enzyme from common death adder (ac... 18555977 - Antiviral and antiparasite properties of an l-amino acid oxidase from the snake bothrop... 16290077 - Simulations of multi-directional forced unfolding of titin i27. 952967 - Reinterpretation of luminiscence properties of neurotoxins from the venom of middle-asi... 3687967 - Stability of total nutrient admixtures using various intravenous fat emulsions. 17434787 - Beta-oxidation in fatty acid degradation and beyond. |
Publication Detail:
|
Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2011-04-18 |
Journal Detail:
|
Title: The Journal of organic chemistry Volume: 76 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2011 May |
Date Detail:
|
Created Date: 2011-05-13 Completed Date: 2011-09-09 Revised Date: 2012-04-12 |
Medline Journal Info:
|
Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
|
Languages: eng Pagination: 3635-43 Citation Subset: IM |
Affiliation:
|
Departmentsof Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, United States. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Amino Acids
/
chemistry* Cell Line, Tumor Cell Survival / drug effects Humans Matrix Metalloproteinase 12 / antagonists & inhibitors*, chemistry Models, Molecular Neoplasm Invasiveness Peptides / chemistry*, pharmacology* Protease Inhibitors / chemistry*, pharmacology* Protein Conformation |
| Grant Support | |
ID/Acronym/Agency:
|
1R21AG032405/AG/NIA NIH HHS; R01 GM088266-01A1/GM/NIGMS NIH HHS; R01 GM088266-02/GM/NIGMS NIH HHS; R01GM088266/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
|
0/Amino Acids; 0/Peptides; 0/Protease Inhibitors; 72155-51-2/4-amino-3-hydroxy-5-phenylpentanoic acid; EC 3.4.24.65/Matrix Metalloproteinase 12 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Fluorescent sensing of triphosphate nucleotides via anthracene derivatives.
Next Document: Carba-LNA-5MeC/A/G/T modified Oligos Show Nucleobase-specific Modulation of 3'-Exonuclease Activity,...