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Merck

196440

Batimastat

≥98% (HPLC), solid, Matrix metalloproteinase inhibitor, Calbiochem

Synonyme(s) :

Batimastat, (4-N-Hydroxyamino)-2 R-isobutyl-3 S-(thienylthiomethyl)succinyl)-L-phenylalanine-N-methylamide, BB-94, (4-N-Hydroxyamino)-2R-isobutyl-3S-(thienylthiomethyl)succinyl)-L-phenylalanine-N-methylamide, BB-94

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A propos de cet article

Formule empirique (notation de Hill) :
C23H31N3O4S2
Numéro CAS:
130370-60-4
Poids moléculaire :
477.64
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00866533

Principaux documents

Voir toute la documentation
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Nom du produit

Batimastat, Batimastat primarily used in Inhibition.

SMILES string

[s]1c(ccc1)SC[C@@H]([C@@H](CC(C)C)C(=O)N[C@@H](Cc2ccccc2)C(=O)NC)C(=O)NO

InChI

1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1

InChI key

XFILPEOLDIKJHX-QYZOEREBSA-N

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

off-white

solubility

DMSO: 50 mg/mL

shipped in

ambient

Quality Level

100

Catégories apparentées

General description

A Marimastat (Cat. No. 444289) type of peptidyl hydroxamate-based inhibitor that potently inhibits a broad-spectrum of metalloproteinases, including MMP-1, MMP-2, MMP-3/stromelysin, MMP-7/matrilysin, MMP-9, ΔMT1 (MMP-14 without TM domain), ADAM8, and ADAM17/TACE (IC50 = 3, 4, 20, 6, 4, 2.08, 51.3, and 19 nM, respectively), by targeting both the substrate binding site and the active-site Zn2+, while being much less potent toward ACE (Angiotensin Converting Enzyme) or α-secretase (IC50 = 1.6 and 3.3 µM, respectively). Batimastat is widely used in studying the involvement of MMPs in cancinogenesis and non-cancer pathological processes both in cultures in vitro and in animals in vivo. Also available as a 25 mM solution in DMSO (Cat. No. 508408).

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Schlomann, U., et al. 2002. J. Biol. Chem.277, 48210.
Whittaker, M., et al. 1999. Chem. Rev.99, 2735.
Parvathy, S., et al. 1998. Biochemistry37, 1680.
Parvathy, S., et al. 1998. FEBS Lett.431, 63.
Yamamoto, M., et al. 1998. J. Med. Chem.41, 1209.
Moss, M.L., et al. 1997. Nature385, 733.
Eccles, S.A., et al. 1996. Cancer Res.56, 2815.
Brown, P.D. 1995. Advan. Enzyme Regul.35, 293.
Wang, X., et al. 1994. Cancer Res.54, 4726.
Davies, B., et al. 1993. Cancer Res.53, 2087.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Abdulbasit Amin et al.
Molecular metabolism, 73, 101731-101731 (2023-05-01)
The metalloprotease ADAM17 (also called TACE) plays fundamental roles in homeostasis by shedding key signaling molecules from the cell surface. Although its importance for the immune system and epithelial tissues is well-documented, little is known about the role of ADAM17
Ivonne Melano et al.
Microbiology spectrum, 11(5), e0385422-e0385422 (2023-09-15)
Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the etiological agent of the Coronavirus disease-19 (COVID-19) pandemic, utilizes angiotensin-converting enzyme 2 (ACE2) as a receptor for virus infection. However, the expression pattern of ACE2 does not coincide with the tissue tropism
Jana Koch et al.
Cancers, 14(15) (2022-08-13)
Matrix metalloproteinases (MMPs) play a crucial role in tumour initiation, progression, and metastasis, including peritoneal carcinosis (PC) formation. MMPs serve as biomarkers for tumour progression in colorectal cancer (CRC), and MMP overexpression is associated with advanced-stage metastasis and poor survival.
Marina Badenes et al.
Life science alliance, 6(4) (2023-02-01)
The metalloprotease ADAM17 is a sheddase of key molecules, including TNF and epidermal growth factor receptor ligands. ADAM17 exists within an assemblage, the "sheddase complex," containing a rhomboid pseudoprotease (iRhom1 or iRhom2). iRhoms control multiple aspects of ADAM17 biology. The
Eva Maria Wenzel et al.
Nature communications, 15(1), 1277-1277 (2024-02-11)
Overexpression of the transmembrane matrix metalloproteinase MT1-MMP/MMP14 promotes cancer cell invasion. Here we show that MT1-MMP-positive cancer cells turn MT1-MMP-negative cells invasive by transferring a soluble catalytic ectodomain of MT1-MMP. Surprisingly, this effect depends on the presence of TKS4 and

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