Carbobenzyloxy-Val-Ala-Asp-alpha-fluoromethylketone

Names

[ Name ]:
Carbobenzyloxy-Val-Ala-Asp-alpha-fluoromethylketone

[Synonym ]:
Z-VAD-FMK,Non-methylated
Z-Val-Ala-Asp-FMK
Caspase Inhibitor VI
N-[(Benzyloxy)carbonyl]-L-valyl-N-[(2S)-1-carboxy-4-fluoro-3-oxo-2-butanyl]-L-alaninamide
L-alaninamide,N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-1-(carboxymethyl)-3-fluoro-2-oxopropyl]
(3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoic acid
L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-1-(carboxymethyl)-3-fluoro-2-oxopropyl]-
N-[(benzyloxy)carbonyl]-L-valyl-N-[(2S)-1-carboxy-4-fluoro-3-oxobutan-2-yl]-L-alaninamide

Biological Activity

[Description]:

Z-VAD-FMK (Z-VAD(OH)-FMK) is a well-know pan caspase inhibitor, which does not inhibit ubiquitin carboxy-terminal hydrolase L1 (UCHL1) activity even at concentrations as high as 440 μM[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Apoptosis >> Caspase

[Target]

Caspase

[In Vitro]

Z-VAD-FMK (40 μM) reverses the apoptotic effect exerted by total saponin of Solanum lyratum Thunb (TSSLT) in Hela cells. HeLa cells are pretreated with Z-VAD-FMK (40 μM) for 30 min and exposed to TSSLT (6 μg/mL) for 48 h[2]. Cell Viability Assay[2] Cell Line: HeLa cells Concentration: 40 μM Incubation Time: Prtreated for 30 minutes Result: Prevented TSSLT-induced cell death. More than 80% cell survival was observed.

[References]

[1]. Davies CW, et al. The co-crystal structure of ubiquitin carboxy-terminal hydrolase L1 (UCHL1) with a tripeptide fluoromethyl ketone (Z-VAE(OMe)-FMK). Bioorg Med Chem Lett. 2012 Jun 15;22(12):3900-4.

[2]. Liu HR, et al. Antiproliferative activity of the total saponin of Solanum lyratum Thunb in Hela cells by inducing apoptosis. Pharmazie. 2008 Nov;63(11):836-42.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
758.0±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₈FN₃O₇

[ Molecular Weight ]:
453.461

[ Flash Point ]:
412.2±32.9 °C

[ Exact Mass ]:
453.191132

[ PSA ]:
161.37000

[ LogP ]:
3.04

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.525

Safety Information

[ Hazard Codes ]:
Xi