Ac-WEHD-AFC

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Ac-WEHD-AFC

Ac-WEHD-AFC | 210344-99-3

Catalog Number A18-0009
Category Fluorescent Enzyme Substrates
Molecular Formula C38H37F3N8O11
Molecular Weight 838.7
Catalog Number Size Price Quantity
A18-0009 50 mg $498
A18-0009 1 g $1998
A18-0009 -- --

Product Introduction

Ac-WEHD-AFC is a fluorogenic substrate for group I caspases including caspase-1, -4, and -5. Caspase activity can be quantified by fluorescent detection of free AFC (7-amino-4-trifluoromethylcoumarin), which is excited at 400 nm and emits at 505 nm.

Chemical Information

Synonyms Caspase 1 (ICE) Substrate 3f; fluorogenic, Ac-WEHD-AFC; N-Acetyl-L-tryptophyl-L-alpha-glutamyl-L-histidyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-L-alpha-asparagine; N-Acetyl-Trp-Glu-His-Asp-7-amido-4-trifluoromethylcoumarin trifluoroacetate salt
Purity ≥97% by HPLC
IUPAC Name (4S)-4-[[(2S)-2-acetamido-3-(1H-indol-3-yl)propanoyl]amino]-5-[[(2S)-1-[[(2S)-3-carboxy-1-oxo-1-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]propan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCC(=O)O)C(=O)NC(CC3=CN=CN3)C(=O)NC(CC(=O)O)C(=O)NC4=CC5=C(C=C4)C(=CC(=O)O5)C(F)(F)F
InChI InChI=1S/C38H37F3N8O11/c1-18(50)45-27(10-19-15-43-25-5-3-2-4-22(19)25)36(58)47-26(8-9-31(51)52)34(56)48-28(11-21-16-42-17-44-21)37(59)49-29(14-32(53)54)35(57)46-20-6-7-23-24(38(39,40)41)13-33(55)60-30(23)12-20/h2-7,12-13,15-17,26-29,43H,8-11,14H2,1H3,(H,42,44)(H,45,50)(H,46,57)(H,47,58)(H,48,56)(H,49,59)(H,51,52)(H,53,54)/t26-,27-,28-,29-/m0/s1
InChI Key NEGOLAGPKZGIKJ-DZUOILHNSA-N
Density 1.528±0.06 g/cm3(Predicted)
Appearance White to yellow Solid
Boiling Point 1351.5±65.0°C(Predicted)
  • Product Specification
  • Application
  • QC Data
Excitation 400 nm
Emission 505 nm
Storage Store at -20°C

Ac-WEHD-AFC is a highly specialized fluorogenic substrate designed to facilitate the study of group I caspases, specifically caspase-1, -4, and -5. These caspases play crucial roles in the inflammatory response and apoptosis, making them significant targets in the study of numerous diseases. The unique aspect of Ac-WEHD-AFC is its ability to provide a measurable fluorescent signal when cleaved by these caspases. When this substrate is cleaved, it releases 7-amino-4-trifluoromethylcoumarin (AFC), a compound that can be excited at a wavelength of 400 nm and emits fluorescence at 505 nm, allowing researchers to quantify caspase activity with high precision and sensitivity.

The first key application of Ac-WEHD-AFC is in drug discovery, particularly in developing new anti-inflammatory drugs. By enabling precise measurement of caspase activity, researchers can screen potential inhibitors that might reduce unwanted inflammation, a common pathway in a variety of chronic diseases. With continued research, such screening processes could lead to significant breakthroughs in the treatment of conditions like arthritis, asthma, and inflammatory bowel disease by identifying compounds that modulate caspase activity effectively.

Secondly, Ac-WEHD-AFC is instrumental in cancer research, where understanding the mechanisms of apoptosis is crucial. Some cancers evade cell death by manipulating apoptotic pathways, and caspases are central to these processes. Using Ac-WEHD-AFC, scientists can investigate how different cancer cells regulate caspase activity, identify which apoptotic pathways are disrupted, and develop targeted therapies that reactivate these pathways to induce cancer cell death, providing a potential approach to overcome chemoresistance.

Furthermore, Ac-WEHD-AFC is applied in neurodegenerative disease studies. Neurodegenerative diseases, such as Alzheimer’s and Parkinson’s, have been linked to caspase-mediated neuroinflammation and cell death. By using Ac-WEHD-AFC, researchers can explore these pathways in detail, helping to unravel the complex biochemical processes that lead to neuronal damage. This knowledge could aid the discovery of new therapeutic strategies aimed at reducing neuronal loss and preserving cognitive function.

Lastly, Ac-WEHD-AFC is valuable in virology, where caspase activity can influence viral replication and the host’s immune response. Certain viruses exploit caspase pathways to facilitate their replication or evade the immune system. By using Ac-WEHD-AFC in virological studies, researchers can elucidate the interaction between viral components and host cell apoptosis machinery, potentially leading to the development of antiviral drugs that enhance the immune response or prevent viral replication by targeting these pathways.

Computed Properties

XLogP3 0.6
Hydrogen Bond Donor Count 9
Hydrogen Bond Acceptor Count 15
Rotatable Bond Count 18
Exact Mass 838.25338851 g/mol
Monoisotopic Mass 838.25338851 g/mol
Topological Polar Surface Area 291Ų
Heavy Atom Count 60
Formal Charge 0
Complexity 1680
Isotope Atom Count 0
Defined Atom Stereocenter Count 4
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Patents

Publication NumberTitlePriority Date
EP-3884941-A1 Inflammasome inhibitors and use thereof 2020-03-26
US-2019038602-A1 Granzyme b inhibitor formulations and methods for the treatment of burns 2016-02-03
US-10537652-B2 Cyclic urea compounds as granzyme B inhibitors 2014-08-01
US-2017015705-A1 Pyrrole compounds as granzyme b inhibitors 2014-08-01
US-2020062803-A1 Azaindoline compounds as granzyme b inhibitors 2014-08-01
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