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SML1292

Sigma-Aldrich

TAPI-0

≥95% (HPLC)

Synonym(s):

N-(R)-(2-(Hydroxyaminocarbonyl)Methyl)-4-Methylpentanoyl-L-Naphthylalanyl-L-Alanine amide, TNF-α Processing Inhibitor-0, TNF-α Protease Inhibitor-0

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About This Item

Empirical Formula (Hill Notation):
C24H32N4O5
CAS Number:
163958-73-4
Molecular Weight:
456.53
MDL number:
MFCD02684279
UNSPSC Code:
12352200
PubChem Substance ID:
329825768
NACRES:
NA.77

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

NC([C@@](C)([H])NC([C@]([H])(CC1=CC=CC2=C1C=CC=C2)NC([C@@](CC(C)C)([H])CC(NO)=O)=O)=O)=O

InChI

1S/C24H32N4O5/c1-14(2)11-18(13-21(29)28-33)23(31)27-20(24(32)26-15(3)22(25)30)12-17-9-6-8-16-7-4-5-10-19(16)17/h4-10,14-15,18,20,33H,11-13H2,1-3H3,(H2,25,30)(H,26,32)(H,27,31)(H,28,29)/t15-,18+,20-/m0/s1

InChI key

WSJJYJNVFYARGB-CVAIRZPRSA-N

Biochem/physiol Actions

TAPI-0 inhibit peptide deformylase (PDF) activity and retard the growth Chlamydia trachomatis, which is an obligate intracellular bacterium responsible for a number of human diseases.
TAPI-0 is a metalloproteinase inhibitor with selectivity for TACE (TNF-α converting enzyme/ADAM17; IC50 = 100 nM). TAPI-0 also inhibits of collagenase and gelatinase. Although not specific for TACE, TAPI-0 is extensively used to block TACE-mediated TNF-α shedding.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Metalloprotease inhibitors GM6001 and TAPI-0 inhibit the obligate intracellular human pathogen Chlamydia trachomatis by targeting peptide deformylase of the bacterium.
Balakrishnan A, et al.
The Journal of Biological Chemistry, 281(24), 16691-16699 (2006)

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