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AB146619

Batimastat (BB-94) (DMSO solution), Matrix metalloprotease (MMP) inhibitor

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(2 Publications)

MW 477.6 Da, Purity >98%. Potent, broad-spectrum MMP inhibitor (IC50 values are 3 (MMP-1), 4 (MMP-2), 4 (MMP-9), 6 (MMP-7), 20 nM (MMP-3)). Anticancer activity in vivo.

View Alternative Names

27 kDa interstitial collagenase, 72 kDa gelatinase, 72kD type IV collagenase, 82 kDa matrix metalloproteinase-9, 92 kDa gelatinase, 92 kDa type IV collagenase, BLAST-2, C-type lectin domain family 4, C-type lectin domain family 4 member J, CD 23, CD 23A, CD23 antigen, CHDS6, CLEC 4J, CLG, CLG 3, CLG 4, CLG 4A, CLG 4B, Collagenase 3, Collagenase Type 4 alpha, Collagenase Type 4 beta, Collagenase type IV 92 KD, Collagenase type IV A, EC 3.4.24.35, FCE 2, FCER2A, FCER2_HUMAN, Fc epsilon receptor II, Fc fragment of IgE, Fc fragment of IgE low affinity II receptor for, Fc fragment of IgE receptor II, Fc fragment of IgE, low affinity II, receptor for (CD23), Fc of IgE, Fc of IgE, low affinity II, receptor for (CD23), Fc receptor IgE low affinity II alpha polypeptide, Fc receptor, IgE, low affinity II, alpha polypeptide, isoform CRA_a, Fc-epsilon-RII, FceRII, Fibroblast collagenase, GELB, Gelatinase 92 KD, Gelatinase A, Gelatinase B, Gelatinase alpha, Gelatinase beta, Gelatinase neutrophil, IGEBF, IgE receptor lymphocyte, IgE-binding factor, Immunoglobulin E receptor, Immunoglobulin E receptor, low affinity II, Immunoglobulin E-binding factor, Immunoglobulin epsilon chain, Interstitial collagenase, LEUKOCYTE ANTIGEN CD23, Low Affinity IgE Receptor, Low affinity immunoglobulin epsilon Fc receptor, Low affinity immunoglobulin epsilon Fc receptor membrane bound form, Low affinity immunoglobulin epsilon Fc receptor soluble form, Ly-42, Lymphocyte IgE receptor, Lymphocyte antigen CD23, MANDP1, MANDP2, MGC126102, MGC126103, MGC126104, MGC93219, MMP II, MMP-X1, MMP13_HUMAN, MMP14_HUMAN, MMP1_HUMAN, MMP2_HUMAN, MMP3_HUMAN, MMP7_HUMAN, MMP9_HUMAN, MONA, MPSL1, MT-MMP 1, MT1-MMP, Macrophage gelatinase, Matrilysin, Matrin, Matrix Metalloproteinase 9, Matrix metallopeptidase 1 (interstitial collagenase), Matrix metallopeptidase 13 (collagenase 3), Matrix metallopeptidase 14 (membrane inserted), Matrix metallopeptidase 2 gelatinase A 72kDa gelatinase 72kDa type IV collagenase, Matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase), Matrix metalloprotease 1, Matrix metalloproteinase 2 (gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase), Matrix metalloproteinase 3 preproprotein, Matrix metalloproteinase II, Matrix metalloproteinase-1, Matrix metalloproteinase-13, Matrix metalloproteinase-14, Matrix metalloproteinase-2, Matrix metalloproteinase-3, Matrix metalloproteinase-7, Membrane type 1 metalloprotease, Membrane-type matrix metalloproteinase 1, Membrane-type-1 matrix metalloproteinase, Neutrophil gelatinase, OTTHUMP00000045866, PEX, PUMP 1, Proteoglycanase, Pump-1 protease, SL-1, STMY, STMY1, Stromelisin 1, Stromelysin 1 progelatinase, Stromelysin-1, TBE-1, Transin-1, Type V collagenase, Uterine matrilysin, Uterine metalloproteinase, collagenase, fibroblast, collagenase, interstitial

1 Images
Chemical Structure - Batimastat (BB-94) (DMSO solution), Matrix metalloprotease (MMP) inhibitor (AB146619)
  • Chemical Structure

Lab

Chemical Structure - Batimastat (BB-94) (DMSO solution), Matrix metalloprotease (MMP) inhibitor (AB146619)

2D chemical structure image of ab146619, Batimastat (BB-94) (DMSO solution), Matrix metalloprotease (MMP) inhibitor

Key facts

CAS number

130370-60-4

Purity

>98%

Form

Liquid

form

Molecular weight

477.6 Da

Molecular formula

C<sub>2</sub><sub>3</sub>H<sub>3</sub><sub>1</sub>N<sub>3</sub>O<sub>4</sub>S<sub>2</sub>

PubChem

5362422

Nature

Synthetic

Biochemical name

Batimastat

Biological description

Potent, broad-spectrum MMP inhibitor (IC50 values are 3 (MMP-1), 4 (MMP-2), 4 (MMP-9), 6 (MMP-7), 20 nM (MMP-3)). Anticancer activity in vivo.

Canonical smiles

CC(C)CC(C(CSC1=CC=CS1)C(=O)NO)C(=O)NC(CC2=CC=CC=C2)C(=O)NC

Isomeric smiles

CC(C)C[C@H]([C@H](CSC1=CC=CS1)C(=O)NO)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)NC

InChi

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

InChiKey

XFILPEOLDIKJHX-QYZOEREBSA-N

IUPAC Name

(2S,3R)-N-hydroxy-N'-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide

Product details

Supplied in DMSO (10 mM).

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store in the dark|Store under desiccating conditions|This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The MMP family including MMP14 MMP1 MMP2 MMP3 MMP9 CD23 MMP13 and MMP7 consists of zinc-dependent endopeptidases known as matrix metalloproteinases. MMPs facilitate extracellular matrix (ECM) remodeling by cleaving specific components of the ECM. MMP14 also called MT1-MMP has a mass of approximately 66 kDa and is commonly expressed on the cell surface. It shows high activity in tissues that require constant remodeling such as the skin lungs and digestive tract.
Biological function summary

Each MMP plays distinct roles in processes like cell proliferation migration differentiation angiogenesis and apoptosis. MMP2 and MMP9 for example degrade type IV collagen which is a major component of basement membranes. These enzymes sometimes form complexes in order to regulate their activities more precisely. CD23 though not an MMP acts as an IgE receptor and modulates immune responses adding another layer of complexity to their biological roles.

Pathways

MMPs integrate into essential cellular processes notably the MAPK and PI3K/AKT pathways. These pathways significantly influence cell survival growth and movement. MMP14 activates pro-MMP2 on the cell surface linking it to the proteolytic process. MMP9 can also interact with proteins such as TIMP-1 which inhibits MMP activity to maintain balance in ECM remodeling.

MMPs have strong connections with pathological conditions such as cancer and arthritis. Overexpression of MMPs like MMP9 is often associated with tumor invasion and metastasis. In arthritis MMP13 breaks down cartilage components contributing to joint degradation. MMPs therefore serve as targets for therapeutic interventions with inhibitors like Batimastat and BB-94 in development to curb their excessive activity.

Product protocols

Publications (2)

Recent publications for all applications. Explore the full list and refine your search

The Journal of experimental medicine 217: PubMed32860705

2020

A Fas-4-1BB fusion protein converts a death to a pro-survival signal and enhances T cell therapy.

Applications

Unspecified application

Species

Unspecified reactive species

Shannon K Oda,Kristin G Anderson,Pranali Ravikumar,Patrick Bonson,Nicolas M Garcia,Cody M Jenkins,Summer Zhuang,Andrew W Daman,Edison Y Chiu,Breanna M Bates,Philip D Greenberg

Nature immunology 15:973-81 PubMed25151489

2014

B cell homeostasis and follicle confines are governed by fibroblastic reticular cells.

Applications

Unspecified application

Species

Unspecified reactive species

Viviana Cremasco,Matthew C Woodruff,Lucas Onder,Jovana Cupovic,Janice M Nieves-Bonilla,Frank A Schildberg,Jonathan Chang,Floriana Cremasco,Christopher J Harvey,Kai Wucherpfennig,Burkhard Ludewig,Michael C Carroll,Shannon J Turley
View all publications

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