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7-Amino-4-methylcoumarin

$159

  • Brand : BIOFRON

  • Catalogue Number : BN-O1195

  • Specification : 98%(HPLC)

  • CAS number : 26093-31-2

  • Formula : C10H9NO2

  • Molecular Weight : 175.18

  • PUBCHEM ID : 92249

  • Volume : 5mg

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Catalogue Number

BN-O1195

Analysis Method

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

175.18

Appearance

Powder

Botanical Source

Structure Type

Category

SMILES

CC1=CC(=O)OC2=C1C=CC(=C2)N

Synonyms

Cumarin120/7-amino-4-methylchromen-2-one/T66 BOVJ E1 IZ/7-Amino-4-methyl-2H-1-benzopyran-2-one/H-MCA/7-Amino-4-methylcoumarin (AMC)/COUMARIN 440/C 120/7-NH2-4-CH3-coumarin/7-amino-4-methylcoumarine/7-Amino-4-methylcoumarin/7-Amino-4-methylcoumarin,laser grade/AMC/Coumarin 120/4-methyl-7-amino-coumarin/7-Amino-4-methyl-2H-chromen-2-one/2H-1-Benzopyran-2-one, 7-amino-4-methyl-/7-AMC/Coumarin, 7-amino-4-methyl-

IUPAC Name

Density

1.3±0.1 g/cm3

Solubility

Flash Point

216.9±24.0 °C

Boiling Point

378.3±37.0 °C at 760 mmHg

Melting Point

223-226 °C(lit.)

InChl

InChl Key

GLNDAGDHSLMOKX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:26093-31-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29724067

Abstract

Chromenone-derived natural products include chromones (flavone, isoflavone) and coumarins. Chromenone compounds not only exhibit impressive biological activities, but also are an important resource of experimentally used fluorophores, such as, 7-amino-4-methylcoumarin (AMC). Various chromenone compounds have reported to have weak fluorescence, and this has the potential to interfere with the measurements during AMC fluorogenic assays and result in non-robust assay readouts. Several flavones and isoflavones were found as SIRT1 activators, while fluorogenic sirtuin assays utilized AMC labelled peptides as the substrates. In this study we investigated whether the fluorescent properties of chromenone-derived natural products interrupt the measurement of SIRT1/2 modulated activities. We found that the reported SIRT1 activators: flavones were detected with the SIRT1 activation activity, but isoflavones were not detected with SIRT1 activation activity, and instead that they were found to be fluorogenic compounds. Another chromenone compound, osthole, exhibited a moderate SIRT2 inhibitory activity with an IC50 of 10 μM. In conclusion, the fluorescent properties of these chromenone compounds do affect the measurement of the sirtuin activities of both inhibitors and activators. However, if the possible fluorescence properties are mitigated in the assay readout, these fluorogenic assays enable the screening of activity modulators.

KEYWORDS

AMC; SIRT1 activator; chromenone; fluorescence; fluorogenic assay; isoflavone; osthole; sirtuin.

Title

Exploration of the Fluorescent Properties and the Modulated Activities Against Sirtuin Fluorogenic Assays of Chromenone-Derived Natural Products

Author

Hui Wen 1, Nina Xue 2, Feng Wu 3, Yujun He 4, Gang Zhang 5, Zebin Hu 6, Huaqing Cui 7

Publish date

2018 May 2

PMID

30928100

Abstract

Aminopeptidase B (Ap-B) is a Zn2+-aminopeptidase of the M1 family which is implicated, in conjunction with the nardilysin endoprotease, in the generation of miniglucagon, a peptide involved in the maintenance of glucose homeostasis. Other in vivo physiological roles have been established for this vertebrate enzyme, such as the processing of Arg-extended forms of human insulin and cholecystokinin 9 and the degradation of viral epitopes in the cytoplasm. Among M1 family members, Ap-B is phylogenetically close to leukotriene A4 hydrolase (LTA4H), a bi-functional aminopeptidase also able to transform LTA4 in LTB4 (a lipid mediator of inflammation). As the activities of LTA4H are reported to be inhibited by resveratrol, a polyphenolic molecule from red wine, the effect of this molecule was investigated on the Ap-B activity. Several other active phenolic compounds produced in plants were also tested. Among them, curcumin and mangiferin are the most effective inhibitors. Dixon analysis indicates that curcumin is a non-competitive inhibitor with a Ki value of 46 μmol.L-1. Dixon and Lineweaver-Burk representations with mangiferin show a mixed non-competitive inhibition with Ki’ and Ki values of 194 μmol.L-1 and 105 μmol.L-1, respectively. At 200 μmol.L-1, no significant effect was observed with caffeic, chlorogenic, ferulic, salicylic and sinapic acids as well as with resveratrol. Analyses on the 3D-structure of LTA4H with resveratrol (pdb: 3FTS) and the Ap-B 3D-model allow hypothesis to explain theses results.

KEYWORDS

Aminopeptidase B; Curcumin; Leukotriene A(4) hydrolase; Mangiferin; Resveratrol.

Title

The Effects of Curcumin, Mangiferin, Resveratrol and Other Natural Plant Products on Aminopeptidase B Activity

Author

Sandrine Cadel 1, Cecile Darmon 2, Alexandre Desert 2, Mouna Mahbouli 2, Christophe Piesse 3, Thanos Ghelis 2, Rene Lafont 2, Thierry Foulon 2

Publish date

2019 May 14

PMID

25884115

Abstract

SIRT6, as one of these seven sirtuins, has been shown to have the therapeutic potentials for treating several human diseases. A fluorogenic assay for SIRT6 has been developed to screen their small molecule modulators based on the recent discovery that SIRT6 is a defatty-acylase (removing long chain fatty acyl groups). However, this assay uses a fluorogenic peptide containing 7-amino-4-methylcoumarin (AMC), which becomes the cause of false positive hits from screenings. To overcome this, we have developed an alternative method called a FRET-based assay suitable for screening SIRT6 modulators, which will be reliable and useful in a high-throughput format since no AMC group present in this assay.

KEYWORDS

Deacetylation; Defatty-acylation; FRET assay; Fluorogenic assay; Sirtuin.

Title

A FRET-based Assay for Screening SIRT6 Modulators

Author

Yan Li 1, Ling You 2, Wenfei Huang 2, Jie Liu 3, Hong Zhu 2, Bin He 4

Publish date

2015


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