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SML0041

Sigma-Aldrich

Batimastat

≥98% (HPLC)

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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
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

Quality Level

100

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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S100A4 elevation empowers expression of metastasis effector molecules in human breast cancer
Ismail TM, et al.
Cancer Research, 77(3), 780-789 (2017)
Ursula Mirastschijski et al.
Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society, 18(2), 223-234 (2010-04-23)
The ability to regulate wound contraction is critical for wound healing as well as for pathological contractures. Matrix metalloproteinases (MMPs) have been demonstrated to be obligatory for normal wound healing. This study examined the effect that the broad-spectrum MMP inhibitor
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
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)
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