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SML0041

Sigma-Aldrich

Batimastat

≥98% (HPLC), powder, matrix metalloproteinase inhibitor

Synonym(s):

BB-94; (2R,3S)-N4-Hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide

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About This Item

Empirical Formula (Hill Notation):
C23H31N3O4S2
CAS Number:
130370-60-4
Molecular Weight:
477.64
MDL number:
MFCD00866533
UNSPSC Code:
12352200
PubChem Substance ID:
329825111
NACRES:
NA.77

product name

Batimastat, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥15 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)[C@H](CSc2cccs2)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

Application

Batimastat has been used to inhibit matrix metalloproteinases (MMPs) activity in various studies.

Biochem/physiol Actions

Batimastat is hydroxamate-type inhibitor of matrix metalloproteinases (MMP). It inhibits the growth and spread of lung tumors, breast cancer regrowth and human colon tumor growth and spread in mouse models. Batimastat reduces MMP-mediated vascular dysfunction and vessel wall damage and enhances the sealing ability and bond strength of dental adhesives.
Batimastat is a potent, broad spectrum matrix metalloprotease (MMP) inhibitor.

Storage Class Code

11 - Combustible Solids

WGK

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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Joseph D Raffetto et al.
Biochemical pharmacology, 75(2), 346-359 (2007-08-07)
Matrix metalloproteinases (MMPs) are a family of proteolytic enzymes that degrade various components of the extracellular matrix (ECM). Members of the MMP family include collagenases, gelatinases, stromelysins, matrilysins and membrane-type MMPs. ProMMPs are cleaved into active forms that promote degradation
Inhibition of Pseudomonas aeruginosa secreted virulence factors reduces lung inflammation in CF mice
Sandri A, et al.
Virulence, 9(1), 1008-1018 (2018)
X Wang et al.
Cancer research, 54(17), 4726-4728 (1994-09-01)
Matrix metalloproteinases have been implicated in the growth and spread of metastatic tumors. This role was investigated in an orthotopic transplant model of human colon cancer in nude mice using the matrix metalloproteinase inhibitor BB-94 (batimastat). Fragments of human colon
Ricardo L Sanz et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 38(3), 518-529 (2017-12-03)
Cell-surface molecules are dynamically regulated at the synapse to assemble and disassemble adhesive contacts that are important for synaptogenesis and for tuning synaptic transmission. Metalloproteinases dynamically regulate cellular behaviors through the processing of cell surface molecules. In the present study
G W Sledge et al.
Journal of the National Cancer Institute, 87(20), 1546-1550 (1995-10-18)
Matrix metalloproteinases (MMPs) are involved in the invasion and metastasis of human cancers by mediating the degradation of extracellular matrix components. Therefore, these enzymes constitute promising targets in the development of anticancer therapies. Batimastat ([(4-N-hydroxyamino)-2R-isobutyl-3S-(thienyl-thiomethyl)succinyl]-L- phenyl-alanine-N-methylamide) is one of a
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