Ac-DEVD-AMC

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Ac-DEVD-AMC

Ac-DEVD-AMC | 169332-61-0

Catalog Number A18-0013
Category Fluorescent Enzyme Substrates
Molecular Formula C30H37N5O13
Molecular Weight 675.64
Catalog Number Size Price Quantity

Product Introduction

Ac-DEVD-AMC is a fluorogenic substrate for caspase-3. Caspase activity can be quantified by fluorescent detection of free AMC (7-amino-4-methylcoumarin), which is excited at 340-360 nm and emits at 440-460 nm.

Chemical Information

Synonyms N-Acetyl-Asp-Glu-Val-Asp-7-amido-4-Methylcoumarin; N-acetyl-L-α-aspartyl-L-α-glutamyl-L-valyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-α-asparagine
Purity ≥95%
IUPAC Name (4S)-4-[[(2S)-2-acetamido-3-carboxypropanoyl]amino]-5-[[(2S)-1-[[(2S)-3-carboxy-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CC(=O)O)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C
InChI InChI=1S/C30H37N5O13/c1-13(2)26(35-27(44)18(7-8-22(37)38)33-29(46)19(11-23(39)40)31-15(4)36)30(47)34-20(12-24(41)42)28(45)32-16-5-6-17-14(3)9-25(43)48-21(17)10-16/h5-6,9-10,13,18-20,26H,7-8,11-12H2,1-4H3,(H,31,36)(H,32,45)(H,33,46)(H,34,47)(H,35,44)(H,37,38)(H,39,40)(H,41,42)/t18-,19-,20-,26-/m0/s1
InChI Key ALZSTTDFHZHSCA-RNVDEAKXSA-N
Density 1.423±0.06 g/cm3
Boiling Point 1200.1±65.0 °C at 760 mmHg
  • Product Specification
  • Application
Excitation 340-360 nm
Emission 440-460 nm
Storage Store at -20°C

Ac-DEVD-AMC is a synthetic peptide substrate widely used for studying caspase-3 activity, an enzyme crucial in apoptosis (programmed cell death). Here are some key applications of Ac-DEVD-AMC:

Apoptosis Research: Ac-DEVD-AMC is utilized in apoptosis research to measure caspase-3 activity, which is a key marker of cell apoptosis. When caspase-3 cleaves Ac-DEVD-AMC, it releases the fluorescent compound AMC, allowing researchers to quantify enzyme activity by fluorescence. This helps in understanding the mechanisms of apoptosis in various cell types and disease models.

Drug Screening: In pharmaceutical research, Ac-DEVD-AMC is employed in high-throughput screening assays to identify potential inhibitors or activators of caspase-3. By monitoring changes in fluorescence, researchers can evaluate the efficacy of novel compounds that may modify caspase activity. This is crucial for developing new therapeutic agents for diseases involving dysregulated apoptosis, such as cancer and neurodegenerative disorders.

Cancer Research: Ac-DEVD-AMC aids in studying the role of caspase-3 in cancer cell apoptosis, helping to elucidate how cancer cells evade programmed cell death. Researchers use this substrate to assess the apoptotic response of cancer cells to various treatments, such as chemotherapy and radiation. Understanding caspase-3 activity in cancer cells can lead to the development of more effective cancer therapies.

Neurodegenerative Disease Studies: Caspase-3 is implicated in the neuronal cell death seen in neurodegenerative diseases like Alzheimer’s and Parkinson’s. Ac-DEVD-AMC is used to study caspase-3 activity in neuronal cells and brain tissues affected by these diseases. This application provides insights into the molecular pathways driving neurodegeneration and helps in identifying potential therapeutic targets for these debilitating conditions.

Computed Properties

XLogP3 -1.3
Hydrogen Bond Donor Count 8
Hydrogen Bond Acceptor Count 13
Rotatable Bond Count 17
Exact Mass 675.23878625 g/mol
Monoisotopic Mass 675.23878625 g/mol
Topological Polar Surface Area 284Ų
Heavy Atom Count 48
Formal Charge 0
Complexity 1330
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

Literatures

PMIDPublication DateTitleJournal
25446497 2014-12-05 Isolation and prevention of calcium oxalate-induced apoptotic death and oxidative stress in MDCK cells by diosgenin Chemico-biological interactions
19364322 2009-03-01 A secreted caspase-3-substrate-cleaving activity at low pH belongs to cathepsin B: a study on primary brain cell cultures Biochemistry. Biokhimiia
18393770 2008-03-01 Brain cathepsin B cleaves a caspase substrate Biochemistry. Biokhimiia
17678535 2007-08-01 PepBank--a database of peptides based on sequence text mining and public peptide data sources BMC bioinformatics
16517063 2007-01-08 Bis(2-hydroxybenzylidene)acetone, a potent inducer of the phase 2 response, causes apoptosis in mouse leukemia cells through a p53-independent, caspase-mediated pathway Cancer letters

Patents

Publication NumberTitlePriority Date
EP-3929209-A1 Vasopressin-2 receptor antagonist peptides and uses thereof 2020-06-24
KR-20220158727-A Methods for enriching and expanding tumor-reactive T cells ex vivo and compositions related thereto 2020-02-27
WO-2021127187-A1 Rna nanoparticle for liver cancer treatment 2019-12-20
US-2022372493-A1 Rna nanoparticle for liver cancer treatment 2019-12-20
JP-2023504042-A Methods of generating tumor-reactive T-cell compositions using modulators 2019-11-27
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