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7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

Substrate of matrix metalloproteinases assay CAS# 140430-53-1

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7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide: 5mg	$334	In Stock
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Quality Control of 7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

Quality Control & MSDS

Purity: >98%

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Chemical Properties of 7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

Cas No.	140430-53-1	SDF	Download SDF
PubChem ID	56832348	Appearance	Powder
Formula	C49H68N14O15	M.Wt	1093.15
Type of Compound	N/A	Storage	Desiccate at -20°C
Synonyms	MCA-PRO-LEU-ALA-NVA-DAP(DNP)-ALA-ARG-NH2
Solubility	Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name	(2S)-N-[(2S)-1-[[2-[[(2S)-1-[[(2S)-2-amino-3-[[(2S)-1-[[(2S)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-(2,4-dinitrophenyl)-3-oxopropyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]-1-[2-(7-methoxy-2-oxochromen-4-yl)acetyl]pyrrolidine-2-carboxamide
SMILES	CC(C)CC(C(=O)NC(C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])C(C(=O)NC(C)C(=O)NC(CCCN=C(N)N)C(=O)N)N)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C2CCCN2C(=O)CC3=CC(=O)OC4=C3C=CC(=C4)OC
Standard InChIKey	OHJYDZUSNOGPHT-DDHXSUAISA-N
Standard InChI	InChI=1S/C49H68N14O15/c1-24(2)17-33(59-47(71)35-10-8-16-61(35)39(65)19-27-20-40(66)78-37-22-29(77-6)12-14-30(27)37)45(69)55-23-38(64)57-34(18-25(3)4)46(70)60-42(31-13-11-28(62(73)74)21-36(31)63(75)76)41(50)48(72)56-26(5)44(68)58-32(43(51)67)9-7-15-54-49(52)53/h11-14,20-22,24-26,32-35,41-42H,7-10,15-19,23,50H2,1-6H3,(H2,51,67)(H,55,69)(H,56,72)(H,57,64)(H,58,68)(H,59,71)(H,60,70)(H4,52,53,54)/t26-,32-,33-,34-,35-,41-,42?/m0/s1
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

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Background on 7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

We have retained the Pro-Leu-Gly-Lcu sequence, but labelled the N-terminus with the highly fluorescent (7-methoxycoumarin-4-yl) acetyl (Mea) group. The quenching Dnp group has been inserted with the novel N3-Dnp-t_-2.3-diaminopropionic acid (Dpa) in the P2’ position1, as the matrix metalloproteinases favour aromatic side chains at P2’2, 3.
In the unquenched peptide Mca-Pro-Leu, the fluorescence has an excitation maximum at 328 nm and the emission is centered around 393 nm. When the fluorescence emissions were compared at a concentration of 1 ,µM, Mca-Pro-Leu was 130 times more fluorescent than Mca-Pro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2.
3.3 CIeavuge of Mea-Pro-Leu-Gus)-Lrlt-Dpu-AMca-Pro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2, is the most sensitive substrate so far described for continuous assays of the matrix metalloproteinases. Not only are the values of Kcut/Km, higher than those reported previously. but the cleavage product is more readily detectable, as the Mea group is both more fluorescent than tryptophan and more efficiently quenched by the Dnp group. With the exception of collegenase, continuous assays can be made with the new substrate at enzyme concentrations similar to those required in assays with their preferred macromolecular substrates. Mca-Pro- Leu-Gly-Leu-Dpa-Ala-Arg-NH2 is suitable therefore for the assessment of total matrix metalloproteinase activity in crude preparations. Further work to develop peptides that are specifically cleaved by the individual enzymes will permit their measurement under these conditions3.

Reference:
1.   Schectcr, I, and Beryer. A. (lYG7) Biochem. Biophyt;. Rcs, Commun. 27, 157-161
2.   Nctzcl-Arnctt, s.. Mallya. SK., Nugasc. H.. Birkedal-Hansen, H. and Van Wurt. H.E. (1991) Anal. Biochcm. 195. 86-92.
3.   Netzel-Arnctt, S., Fields. G., Birkedal-Hunscn. H. and Vai Wart. H.E. (1991) J. Biol. Chem. 266. 6747-6755
4.   C.G.Knight, F. Willenbrock and G. Murphy. A novel coumarin-labelled peptide for sensitive continuous assays of the matrix metalloproteinases. FEDS. Volume 296, number 3, 263-266

Keywords:

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7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

Catalog No. BCC1086----Order now to get a substantial discount!

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Quality Control of 7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

Quality Control & MSDS

Number of papers citing our products

Chemical structure

3D structure

Chemical Properties of 7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide

7-Methoxycoumarin-4-acetyl-P-L-G-L-β-(2,4-dinitrophenylamino)A-R amide Dilution Calculator

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