7-Methoxycoumarin-4-acetic Acid N-Succinimidyl Ester
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7-Methoxycoumarin-4-acetic Acid N-Succinimidyl Ester

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Category
Peptide Synthesis Reagents
Catalog number
BAT-006397
CAS number
359436-89-8
Molecular Formula
C16H13NO7
Molecular Weight
331.28
7-Methoxycoumarin-4-acetic Acid N-Succinimidyl Ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 2-(7-methoxy-2-oxochromen-4-yl)acetate
Synonyms
1-[[(7-methoxy-2-oxo-2H-1-benzopyran-4-yl)acetyl]oxy]-2,5-Pyrrolidinedione; Mca-OsuN-(7-methoxycoumarin-4-acetyloxy)succinimide; 7-Methoxy-4-coumarinylacetic acid N-succinimidyl ester; N-(7-methoxycoumarin-4-acetyloxy)succinimide; Mca-OSu; 2,5-Dioxopyrrolidin-1-yl 2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetate
Appearance
White Solid
Purity
95%
Density
1.490 g/cm3
Melting Point
210-213 °C (dec.)
Boiling Point
527.8 °C at 760 mmHg
Storage
-20 °C under inert atmosphere
Solubility
Soluble in Acetone, Chloroform, DMSO
InChI
InChI=1S/C16H13NO7/c1-22-10-2-3-11-9(6-15(20)23-12(11)8-10)7-16(21)24-17-13(18)4-5-14(17)19/h2-3,6,8H,4-5,7H2,1H3
InChI Key
XYBYCKCNAJSBQE-UHFFFAOYSA-N
Canonical SMILES
COC1=CC2=C(C=C1)C(=CC(=O)O2)CC(=O)ON3C(=O)CCC3=O
1.Assessment of Synthetic Matrix Metalloproteinase Inhibitors by Fluorogenic Substrate Assay.
Lively TJ1, Bosco DB2, Khamis ZI1, Sang QX3,4. Methods Mol Biol. 2016;1406:161-70. doi: 10.1007/978-1-4939-3444-7_13.
Matrix metalloproteinases (MMPs) are a family of metzincin enzymes that act as the principal regulators and remodelers of the extracellular matrix (ECM). While MMPs are involved in many normal biological processes, unregulated MMP activity has been linked to many detrimental diseases, including cancer, neurodegenerative diseases, stroke, and cardiovascular disease. Developed as tools to investigate MMP function and as potential new therapeutics, matrix metalloproteinase inhibitors (MMPIs) have been designed, synthesized, and tested to regulate MMP activity. This chapter focuses on the use of enzyme kinetics to characterize inhibitors of MMPs. MMP activity is measured via fluorescence spectroscopy using a fluorogenic substrate that contains a 7-methoxycoumarin-4-acetic acid N-succinimidyl ester (Mca) fluorophore and a 2,4-dinitrophenyl (Dpa) quencher separated by a scissile bond. MMP inhibitor (MMPI) potency can be determined from the reduction in fluorescent intensity when compared to the absence of the inhibitor.
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