4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one | 25392-41-0
Catalog Number | A16-0155 |
Category | Other Cell Fluorescent Probes |
Molecular Formula | C10H7ClO3 |
Molecular Weight | 210.61 |
Catalog Number | Size | Price | Quantity |
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A16-0155 | -- | $-- |
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Product Introduction
4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one is a thiol-reactive, cell-permeant fluorescent probe that easily passes through cell membranes.
Chemical Information |
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Synonyms | CellHunt Blue CMHC |
IUPAC Name | 4-(chloromethyl)-7-hydroxychromen-2-one |
Canonical SMILES | C1=CC2=C(C=C1O)OC(=O)C=C2CCl |
InChI | InChI=1S/C10H7ClO3/c11-5-6-3-10(13)14-9-4-7(12)1-2-8(6)9/h1-4,12H,5H2 |
InChI Key | TXSLBPGPBNGHRW-UHFFFAOYSA-N |
Appearance | Solid Powder |
- Product Specification
- Application
Excitation | 348 |
Emission | 423 |
4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one, known as CMHC, plays a pivotal role in various biochemical applications. Here are four key applications of CMHC:
Bioconjugation: CMHC finds extensive use in bioconjugation reactions, facilitating the linkage of molecules such as fluorescent labels to proteins or nucleic acids. This process enables the visualization and tracking of these biological entities in microscopic settings or assays. Through the chemical reactivity of the chloromethyl group with biomolecular functional groups, stable covalent bonds are forged.
Pharmaceutical Synthesis: Within the realm of drug development, CMHC emerges as a foundational compound for synthesizing coumarin-based pharmaceuticals with diverse pharmacological activities spanning anticoagulant, anti-inflammatory, and anticancer properties. The adaptability of CMHC in chemical alterations positions it as a cornerstone for crafting novel therapeutic agents with multifaceted potential.
Enzyme Probing: CMHC serves as a valuable tool for delving into enzyme activities, particularly those associated with detoxification processes, like cytochrome P450 enzymes. By acting as a substrate, CMHC aids researchers in unraveling the mechanisms through which enzymes metabolize various compounds. This knowledge forms the bedrock of drug metabolism investigations and informs the design of enzyme inhibitors critical for therapeutic interventions.
Fluorescent Probes: Derivatives of CMHC are harnessed to fabricate fluorescent probes tailored for detecting diverse biological activities and characteristics. These probes find application in cell imaging, flow cytometry, and other diagnostic settings. The hydroxychromenone structure provides a customizable platform for fine-tuning fluorescence properties to match the requirements of varied experimental scenarios, enriching the landscape of biological exploration and analysis.
Computed Properties | |
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Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 3 |
Rotatable Bond Count | 1 |
Exact Mass | 210.0083718 g/mol |
Monoisotopic Mass | 210.0083718 g/mol |
Topological Polar Surface Area | 46.5Ų |
Heavy Atom Count | 14 |
Formal Charge | 0 |
Complexity | 275 |
Isotope Atom Count | 0 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Covalently-Bonded Unit Count | 1 |
Compound Is Canonicalized | Yes |
Literatures
PMID | Publication Date | Title | Journal |
---|---|---|---|
22614805 | 2012-08-01 | TGF-β of lung cancer microenvironment upregulates B7H1 and GITRL expression in dendritic cells and is associated with regulatory T cell generation | Oncology reports |
21559411 | 2011-04-29 | Monitoring the systemic human memory B cell compartment of melanoma patients for anti-tumor IgG antibodies | PloS one |
20580555 | 2010-08-01 | Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II | Bioorganic & medicinal chemistry letters |
19932027 | 2010-01-01 | alpha-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives | Bioorganic & medicinal chemistry |
18251491 | 2008-02-27 | Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships | Journal of medicinal chemistry |
Patents
Publication Number | Title | Priority Date |
---|---|---|
CN-114805432-A | Novel photocatalytic cleavable carboxylic acid protecting group and preparation method of amino acid derivatives thereof | 2022-03-03 |
WO-2022260135-A1 | Method for producing fluorescent probe library using solid-phase extraction and method of measuring enzyme activity using same | 2021-06-09 |
CN-112240879-A | Fluorescent nanomaterial sensors and related methods | 2019-07-17 |
DE-102020208745-A1 | FLUORESCENT NANOMATERIAL SENSORS AND RELATED PROCEDURES | 2019-07-17 |
US-2021015410-A1 | Fluorescent nanomaterial sensors and related methods | 2019-07-17 |
Applications of Fluorescent Probes & Dyes
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