Biotin-VAD-FMK
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Biotin-VAD-FMK

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Biotin-VAD-FMK is a biotin-labeled pan-caspase inhibitor that can be used as a probe for detecting caspases by biotin ligand.

Category
Peptide Inhibitors
Catalog number
BAT-010385
CAS number
1135688-15-1
Molecular Formula
C30H49FN6O8S
Molecular Weight
672.81
Biotin-VAD-FMK
IUPAC Name
methyl (3S)-3-[[(2S)-2-[[(2S)-2-[6-[5-[2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]-3-methylbutanoyl]amino]propanoyl]amino]-5-fluoro-4-oxopentanoate
Synonyms
Biotin-Val-Ala-Asp(OMe)-fluoromethyl ketone; bVAD-fmk; Biotin-VAD(OMe)-FMK
Appearance
Solid
Purity
≥95%
Density
1.202±0.06 g/cm3
Boiling Point
1045.7±65.0 ℃ at 760 mmHg
Sequence
Biotin-Val-Ala-Asp(OMe)-FMK
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C30H49FN6O8S/c1-17(2)26(29(43)33-18(3)28(42)34-19(21(38)15-31)14-25(41)45-4)36-24(40)12-6-5-9-13-32-23(39)11-8-7-10-22-27-20(16-46-22)35-30(44)37-27/h17-20,22,26-27H,5-16H2,1-4H3,(H,32,39)(H,33,43)(H,34,42)(H,36,40)(H2,35,37,44)/t18-,19-,20-,22-,26-,27-/m0/s1
InChI Key
MOQLQMKJGYKHCT-VRKQFSAKSA-N
Canonical SMILES
CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)CCCCCNC(=O)CCCCC1C2C(CS1)NC(=O)N2
1.Caspase-9 mediates photoreceptor death after blunt ocular trauma.
Blanch RJ;Ahmed Z;Thompson AR;Akpan N;Snead DR;Berry M;Troy CM;Scott RA;Logan A Invest Ophthalmol Vis Sci. 2014 Sep 4;55(10):6350-7. doi: 10.1167/iovs.13-13708.
PURPOSE: ;Ocular trauma is common in civilian and military populations. Commotio retinae involves acute disruption of photoreceptor outer segments after blunt ocular trauma, with subsequent photoreceptor apoptosis causing permanent visual impairment. The mechanisms of photoreceptor death in commotio retinae have not previously been described, although caspase-dependent death is important in other nontraumatic retinal degenerations. We assessed the role of caspase-9 as a mediator of photoreceptor death in a rat model of ballistic ocular trauma causing commotio retinae.;METHODS: ;Bilateral commotio retinae was induced in rats by ballistic ocular trauma. Caspase-9 activity was assessed by immunohistochemistry, Western blotting, and bVAD-fmk active caspase capture. Caspase-9 was inhibited by unilateral intravitreal injection of highly specific X-linked inhibitor of apoptosis (IAP) baculoviral IAP repeat 3 (XBIR3) domain linked to the cell transduction peptide penetratin 1 (Pen-1) after ballistic injury, and the affected eyes were compared with control eyes treated with Pen-1 injection alone, and retinal function was assessed by electroretinogram a-wave amplitude and photoreceptor survival by outer nuclear layer thickness.
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