4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one

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4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one

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
A16-0155 -- $--

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

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

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

PMIDPublication DateTitleJournal
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 NumberTitlePriority 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
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