Mca-PLA-Nva-Dap(Dnp)-AR-NH2

Catalog Number	A18-0036
Category	Fluorescent Enzyme Substrates
Molecular Formula	C49H68N14O15
Molecular Weight	1093.1

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Product Introduction

Mca-PLA-Nva-Dap(Dnp)-AR-NH2 is a synthetic peptide-based fluorogenic probe that features a 7-methoxycoumarin (Mca) chromophore and a dinitrophenyl (Dnp) quencher. This compound is designed to participate in fluorescence resonance energy transfer (FRET) assays, where the proximity of the Mca donor and Dnp acceptor allows for quenching of fluorescence until enzymatic cleavage occurs. The peptide sequence and reactive functionalities enable its use in protease activity assays and biochemical studies where monitoring peptide cleavage is essential.

Chemical Information
Product Specification
Application
Computed Properties

Chemical Information

Synonyms	Matrix Metalloproteinase-2 Fluorogenic Substrate; MMP-2 Fluorogenic Substrate; 1-[(7-methoxy-2-oxo-2H-1-benzopyran-4-yl)acetyl]-L-prolyl-L-leucyl-L-alanyl-L-norvalyl-3-[(2,4-dinitrophenyl)amino]-L-alanyl-L-alanyl-L-argininamide
Purity	≥95%
IUPAC Name	(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(2,4-dinitroanilino)-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]-1-[2-(7-methoxy-2-oxochromen-4-yl)acetyl]pyrrolidine-2-carboxamide
SMILES	CCCC(C(=O)NC(CNC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])C(=O)NC(C)C(=O)NC(CCCN=C(N)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C2CCCN2C(=O)CC3=CC(=O)OC4=C3C=CC(=C4)OC
InChI	InChI=1S/C49H68N14O15/c1-7-10-34(45(69)60-36(24-54-32-16-13-29(62(73)74)22-38(32)63(75)76)47(71)56-26(4)43(67)57-33(42(50)66)11-8-17-53-49(51)52)58-44(68)27(5)55-46(70)35(19-25(2)3)59-48(72)37-12-9-18-61(37)40(64)20-28-21-41(65)78-39-23-30(77-6)14-15-31(28)39/h13-16,21-23,25-27,33-37,54H,7-12,17-20,24H2,1-6H3,(H2,50,66)(H,55,70)(H,56,71)(H,57,67)(H,58,68)(H,59,72)(H,60,69)(H4,51,52,53)/t26-,27-,33-,34-,35-,36-,37-/m0/s1
InChIKey	YFZQNMDPUINDHE-QEFIOWGDSA-N

Product Specification

Storage

Store at -20°C

Application

Mca-PLA-Nva-Dap(Dnp)-AR-NH2 is a synthetic peptide substrate specifically designed for the analysis of matrix metalloproteinase-2 (MMP-2) activity. This fluorogenic substrate contains several key amino acids linked to a fluorescent moiety, 7-methoxycoumarin-4-acetyl (Mca), which is released upon cleavage by MMP-2. The substrate’s ability to release Mca makes it highly useful for quantifying enzyme activity, as the generation of fluorescence correlates directly with the enzymatic cleavage event. This marked change in fluorescence provides a sensitive means to measure proteolytic activity, making it a useful tool in biochemistry and molecular biology for studying MMP-2 behavior under various experimental conditions.

The first key application of Mca-PLA-Nva-Dap(Dnp)-AR-NH2 is in the research and development of cancer therapies. MMP-2 is often upregulated in cancerous tissues, where it aids in tumor invasion and metastasis by degrading components of the extracellular matrix. By utilizing this substrate, researchers can screen for inhibitors of MMP-2, potentially identifying compounds that could limit cancer progression. This application is crucial as it helps in understanding and targeting the mechanisms of cancer metastasis, providing avenues for developing new therapeutic drugs.

Another important application of this substrate is in the study of cardiovascular diseases. MMP-2 is implicated in the remodeling of blood vessels and the breakdown of structural proteins in the vascular system. By measuring MMP-2 activity with this substrate, researchers can investigate the enzyme’s role in conditions such as atherosclerosis and aneurysms. Understanding how MMP-2 contributes to these diseases can lead to better diagnostic markers and therapeutic interventions, thereby improving patient outcomes.

Furthermore, Mca-PLA-Nva-Dap(Dnp)-AR-NH2 is used in neurological research to study its role in neurodegenerative diseases. MMP-2 activity is associated with the breakdown of the blood-brain barrier and extracellular matrix alterations in the brain. Employing this substrate allows scientists to quantify MMP-2 activity changes in diseases like Alzheimer’s, providing insights into disease progression and potential therapeutic targets. This application is vital for developing interventions that could mitigate the detrimental effects of excessive proteolytic activity in the nervous system.

Lastly, the substrate is also applied in basic biochemical research to unveil the general mechanisms of protease activity. By using Mca-PLA-Nva-Dap(Dnp)-AR-NH2, researchers can explore the kinetic properties of MMP-2, such as substrate specificity, inhibitor interactions, and pH or temperature dependencies. This foundational research is essential for understanding the physiological roles of MMP-2 and designing experiments that require specific modulation of its activity, thereby contributing to the broader field of enzymology and proteomics.

Computed Properties

XLogP3	1.3
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	27
Exact Mass	1092.49885752 g/mol
Monoisotopic Mass	1092.49885752 g/mol
Topological Polar Surface Area	442Å²
Heavy Atom Count	78
Formal Charge	0
Complexity	2250
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes