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ChemicalBook--->CAS DataBase List--->201608-14-2

201608-14-2

201608-14-2 Structure

201608-14-2 Structure
IdentificationBack Directory
[Name]

AC-DEVD-AFC
[CAS]

201608-14-2
[Synonyms]

AC-DEVD-AFC
AC-DEVD-AFC?, >98%
AC-DEVD-AFC USP/EP/BP
AC-ASP-GLU-VAL-ASP-AFC
CASPASE-3 SUBSTRATE (AFC)
M.W. 729.62 C30H34F3N5O13
CASPASE-3 FLUOROGENIC SUBSTRATE
CASPASE-3 SUBSTRATE VII, FLUOROGENIC
FLUOROGENIC CASPASE 3 SUBSTRATE AC-DEVD-AFC
CASPASE 3 (APOPAIN) SUBSTRATE 1F, FLUOROGENIC
AC-ASP-GLU-VAL-ASP-7-AMINO-4-TRIFLUORO-METHYLCOUMARIN
Ac-Asp-Glu-Val-Asp -7-amino-4-trrifluoromethylcoumarin
N-ACETYL-ASP-GLU-VAL-ASP 7-AMIDO-4-TRIFLUOROMETHYLCOUMARIN
N-ACETYL-ASP-GLU-VAL-ASP-(7-AMINO-4-TRIFLUOROMETHYLCOUMARIN)
N-ACETYL-ASP-GLU-VAL-ASP-7-AMINO-4-TRIFLUOROMETHYLCOUMARIN AFC
Ac-DEVD-AFC,N-Acetyl-Asp-Glu-Val-Asp-7-amido-4-trifluoromethylcoumarin, >98%
L-α-Asparagine, N-acetyl-L-α-aspartyl-L-α-glutamyl-L-valyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-
[Molecular Formula]

C30H34F3N5O13
[MDL Number]

MFCD01310970
[MOL File]

201608-14-2.mol
[Molecular Weight]

729.61
Chemical PropertiesBack Directory
[Boiling point ]

1152.7±65.0 °C(Predicted)
[density ]

1.495±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C
[solubility ]

H2O: 1 mg/mL
[form ]

powder
[pka]

4.09±0.10(Predicted)
[color ]

white
[Water Solubility ]

H2O: 1mg/mL
Safety DataBack Directory
[WGK Germany ]

3
Hazard InformationBack Directory
[Uses]

A fluorogenic substrate for caspase-3
[Uses]

Ac-DEVD-AFC is a fluorogenic substrate for caspase-3 (CPP32) and related cysteine proteases, which emits a blue to green shift in fluorescence. It also acts as a substrate for granzyme B-processed caspase-6, caspase-7, caspase-8, and caspase-10. It is known that Ac-DEVD-AFC has a greater Stokes'' shift than Ac-DEVD-AMC once it has been cleaved. Since caspase-3 is an effector caspase, it is involved in the cleavage of many substrates which promote apoptosis. This indicator excites light at 400 nm and emits light at 505 nm. In addition, Ac-DEVD-AFC is modeled after Asp216 on caspase-3, the PARP cleavage site. Ac-DEVD-AFC is an essential indicator used to monitor the cellular effects of caspase-3.
[Biological Activity]

ac-devd-afc is a fluorogenic substrate for activated caspase-3 (cpp32) with km value of 9.7 μm, and related cysteine proteases [1][2].apoptosis is a process of programmed cell death that occurs in multicellular organisms. caspase are a family of protease enzymes playing essential roles in programmed cell death (including apoptosis, pyroptosis and necroptosis) and inflammation. caspase activation is a major event in apoptosis. caspase-3 cleaves and activates caspases 6 and 7, and is processed and activated by caspases 8, 9, and 10 [1][2][3].ac-devd-afc (n-acetyl-asp-glu-val-asp-7-amido-4-trifluoromethylcoumarin) is a fluorogenic substrate for activated caspase-3 and related caspases. during apoptosis, activated caspase-3 cleaves poly (adp-ribose) polymerase, which it specifically targets at the amino sequence asp-glu-val-asp (devd). sequence is based on parp cleavage at asp216 for caspase-3 [1][2]. caspase activity can be quantified by fluorescent detection of free afc (7-amino-4-trifluoromethylcoumarin) at excitation 400 nm and emission 505 nm [2].
[Biochem/physiol Actions]

A fluorogenic substrate for caspase 3, a protease that is rapidly activated when cells are exposed to apoptotic conditions and that cleaves poly(ADP-ribose) polymerase. The 7-amido-4-trifluoromethylcoumarin derivative has better membrane permeability than the 7-amido-4-methylcoumarin derivative (A1086).
[References]

[1]. lazebnik ya1, kaufmann sh, desnoyers s, et al. cleavage of poly(adp-ribose) polymerase by a proteinase with properties like ice. nature. 1994 sep 22;371(6495):346-7.
[2]. xiang, j.,chao, d.t., and korsmeyer, s.j. bax-induced cell death may not require interleukin 1β-converting enzyme-like proteases. proceedings of the national academy of sciences of the united states of america 93, 14559-14563 (1996).
Spectrum DetailBack Directory
[Spectrum Detail]

AC-DEVD-AFC(201608-14-2)1HNMR
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