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Beta-Ala-R110-ML

Fluorometric methods based on the peptide substrates labeled with cleavable fluorophores have been widely used for assaying various proteases. The two dominant classes are AMC-based (coumarin dye) and R110-based (rhodamine 110) substrates. AMC substrates are much less sensitive due to their short wavelength, low extinction coefficient and high fluorescent background resulted from the autofluorescence of biological samples. R110-based peptide substrates have a longer excitation and emission wavelength, low background signal, and being highly fluorescent. However, R110-based peptide substrates carries two peptide blocking groups that need to be cleaved from their bis-peptide substrates in order to generate maximal signal. This two-step cleavage severely limits the linear dynamic range of R110-based peptide substrates. N-morpholinecarbonyl-R110 (R110-ML) has been successfully used to overcome both the poor cell penetration and the kinetic limitation of R110-based peptide substrates. R110-ML substrates are as sensitive as R110 substrates for most of protease detections. Beta-Ala-R110-ML is a fluorogenic substrate that might be used for detecting aminopeptidase M substrate, alanyl aminopeptidase and trypsin activities. Beta-Ala-R110-ML may be used for detecting some bacteria in food and other samples by monitoring their alanyl aminopeptidase activities. Compared to Ala-AMC (#13458), Beta-Ala-R110-ML is more sensitive. Its enzymatic product can be readily detected with the common FITC channel or FITC filter set.

Spectrum

References

View all 50 references: Citation Explorer
Design, synthesis and biological evaluation of substituted 3-amino-N-(thiazol-2-yl)pyrazine-2-carboxamides as inhibitors of mycobacterial methionine aminopeptidase 1.
Authors: Juhás, Martin and Pallabothula, Vinod S K and Grabrijan, Katarina and Šimovičová, Martina and Janďourek, Ondřej and Konečná, Klára and Bárta, Pavel and Paterová, Pavla and Gobec, Stanislav and Sosič, Izidor and Zitko, Jan
Journal: Bioorganic chemistry (2022): 105489
A Potent Inhibitor of Aminopeptidase P2 Reduces Reperfusion Injury in Models of Myocardial Infarction and Stroke.
Authors: Lenz, Morgan Rae and Tsai, Shih-Yen and Roessler, Anne E and Wang, Yang and Sethupathi, Periannan and Jones, Walter Keith and Kartje, Gwendolyn L and Simmons, William Howard
Journal: The Journal of pharmacology and experimental therapeutics (2022)
The dual-targeted prolyl aminopeptidase PAP1 is involved in proline accumulation in response to stress and during pollen development.
Authors: Ghifari, Abi S and Teixeira, Pedro F and Kmiec, Beata and Singh, Neha and Glaser, Elzbieta and Murcha, Monika W
Journal: Journal of experimental botany (2022): 78-93
Characterization and heterologous expression of a novel Co2+-dependent leucyl aminopeptidase Amp0279 originating from Lysinibacillus sphaericus.
Authors: Zhao, Puying and Zhang, Meng and Wan, Xiaofu and Geng, Peiling and Xiong, Hairong and Hu, Xiaomin
Journal: Applied microbiology and biotechnology (2022)
Discovery of Selective Inhibitor Leads by Targeting an Allosteric Site in Insulin-Regulated Aminopeptidase.
Authors: Temponeras, Ioannis and Chiniadis, Lykourgos and Papakyriakou, Athanasios and Stratikos, Efstratios
Journal: Pharmaceuticals (Basel, Switzerland) (2021)
Page updated on October 14, 2024

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Catalog Number13205
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Physical properties

Molecular weight

628.56

Solvent

DMSO

Spectral properties

Extinction coefficient (cm -1 M -1)

80000

Excitation (nm)

500

Emission (nm)

522

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C); Minimize light exposure
UNSPSC12171501
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