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Selective arylsulfonamide inhibitors of ADAM-17: hit optimization and activity in ovarian cancer cell models.
- Source :
-
Journal of medicinal chemistry [J Med Chem] 2013 Oct 24; Vol. 56 (20), pp. 8089-103. Date of Electronic Publication: 2013 Oct 04. - Publication Year :
- 2013
-
Abstract
- Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nM on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.
- Subjects :
- ADAM Proteins chemistry
ADAM Proteins metabolism
ADAM17 Protein
Activated-Leukocyte Cell Adhesion Molecule metabolism
Cell Line, Tumor
Cell Survival drug effects
Crystallography, X-Ray
Dose-Response Relationship, Drug
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Female
Humans
Hydroxamic Acids chemical synthesis
Hydroxamic Acids chemistry
Hydroxamic Acids pharmacology
Models, Chemical
Models, Molecular
Molecular Structure
Ovarian Neoplasms metabolism
Ovarian Neoplasms pathology
Protein Binding
Protein Structure, Tertiary
Sulfonamides chemical synthesis
Sulfonamides chemistry
ADAM Proteins antagonists & inhibitors
Cell Movement drug effects
Enzyme Inhibitors pharmacology
Sulfonamides pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-4804
- Volume :
- 56
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- Journal of medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24044434
- Full Text :
- https://doi.org/10.1021/jm4011753