130370-60-4
130370-60-4 structure
- Name: Batimastat
- Chemical Name: (2S,3R)-N-hydroxy-N'-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide
- CAS Number: 130370-60-4
- Molecular Formula: C23H31N3O4S2
- Molecular Weight: 477.640
- Catalog: Biochemical Inhibitor Proteases MMP inhibitor
- Create Date: 2018-06-08 22:53:51
- Modify Date: 2024-01-02 19:19:05
-
Batimastat is a potent broad spectrum MMP inhibitor with IC50 of 3, 4, 4, 6, and 20 nM for MMP-1, MMP-2, MMP-9, MMP-7 and MMP-3, respectively.
| Name | (2S,3R)-N-hydroxy-N'-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-(2-methylpropyl)-2-(thiophen-2-ylsulfanylmethyl)butanediamide |
|---|---|
| Synonyms |
(2R,3S)-N-Hydroxy-2-isobutyl-N-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-3-[(2-thienylsulfanyl)methyl]succinamide
(2R,3S)-N-hydroxy-N-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide (2S,3R)-5-Methyl-3-(((aS)-a-(methylcarbamoyl)phenethyl)carbamoyl)-2-((2-thienylthio)methyl)hexanohydroxamic Acid (2R,3S)-N-Hydroxy-2-isobutyl-N-[(2S)-1-(methylamino)-1-oxo-3-phenyl-2-propanyl]-3-[(2-thienylsulfanyl)methyl]succinamide BB-94 Butanediamide, N-hydroxy-N-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-, (2R,3S)- Batimastat (BB-94) [2R-[1(S*),2R*,3S*]]-N4-Hydroxy-N1-[2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butane Diamide 1rm8 Batimastat |
| Description | Batimastat is a potent broad spectrum MMP inhibitor with IC50 of 3, 4, 4, 6, and 20 nM for MMP-1, MMP-2, MMP-9, MMP-7 and MMP-3, respectively. |
|---|---|
| Related Catalog | |
| Target |
IC50: 3 nM (MMP-1), 4 nM (MMP-2), 4 nM (MMP-9), 6 nM (MMP-7), 20 nM (MMP-3)[1] |
| In Vitro | Batimastat (BB-94) is a potent matrix metalloproteinase inhibitor, exhibits an unexpected mode of binding. Batimastat inhibits gelatinases A and B with IC50 values of 4 nM and 10 nM, respectively. The IC50 with the structurally similar collagenase Ht-d is 6 nM, which is comparable with values for MMP-1 (3 nM), MMP-8 (10 nM), and MMP-3 (20 nM)[2]. CD30 shedding from the cell line Karpas299 can effectively be blocked by the hydroxamic acidbased metalloproteinase inhibitor Batimastat (BB-94, IC50=230 nM)[3]. |
| In Vivo | Intraperitoneal administration of Batimastat (BB-94) effectively blocks growth of human ovarian carcinoma xenografts and murine melanoma metastasis and delays the growth of primary tumors in an orthotopic model of human breast cancer without cytotoxicity and without affecting mRNA levels[2]. Batimastat (BB-94) is a synthetic matrix metalloproteinase inhibitor that has shown antineoplastic and antiangiogenic activity in various tumor models. Treatment with Batimastat (60 mg/kg i.p. every other day, for a total of eight injections) concomitantly with Cisplatin (4 mg/kg i.v., every 7 days for a total of three injections) completely prevents growth and spread of both xenografts, and all animals are alive and healthy on day 200[4]. Kaplan-Meier analysis of survival (at 48 h) shows that animals treated with Batimastat (BB-94) have increased survival (95.2%) in comparison with controls (75%), and differences are almost statistically significant (p=0.064)[5]. Matrix density is analyzed in saline- or Batimastat (40 mg/kg)-pretreated animals 4 h after E2 administration, the time point at which collagen density is observed to be at its lowest after hormone treatment[6]. |
| Animal Admin | Mice[5] Six-weeks-old female BALB/c mice are used. Mice are treated i.p. with Batimastat (BB-94, 50 mg/kg) 1 h before and 24 h post-infection. Batimastat is suspended at 50 mg/mL in DMSO and stored frozen at -20°C. Prior to use, it is diluted 20-fold in phosphate buffered saline (PBS), and 500 μL are injected into animals. Control mice are injected with 500 μL of 5% DMSO in PBS. Animals are sacrificed 48 h after i.c. challenge. Rats[6] Female Sprague-Dawley rats are administered a single physiological dose of E2 (40 μg/kg in a 0.9% NaCl, 0.4% EtOH vehicle) by intraperitoneal (i.p.) injection at the indicated time intervals prior to tissue collection at necropsy. This in vivo dose level of E2 has been shown to induce changes in uterine wet weight, tissue architecture, and gene expression characteristic of estrogen receptor activation. For all other experiments, animals are i.p. administered a single 40 μg/kg bolus of E2 4 h prior to tissue harvest, while control animals receive vehicle only in all studies. Batimastat is administered i.p. at a dose level (40 mg/kg in a 1× PBS, 0.1% Tween-20 vehicle) shown to be effective at inhibiting MMPs in vivo 4 h prior to E2 or saline control. |
| References |
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Melting Point | 236-238° |
| Molecular Formula | C23H31N3O4S2 |
| Molecular Weight | 477.640 |
| Exact Mass | 477.175598 |
| PSA | 161.07000 |
| LogP | 3.53 |
| Appearance | white to tan |
| Index of Refraction | 1.605 |
| Storage condition | Store at -20°C |
| Water Solubility | DMSO: ≥15mg/mL |
| RIDADR | NONH for all modes of transport |
|---|---|
| HS Code | 29349990 |