130370-60-4 Usage
Description
Batimastat is a potent, broad-spectrum peptidyl hydroxamate-based inhibitor that targets a wide range 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. It inhibits these enzymes 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.
Used in Antineoplastic Applications:
Batimastat is used as an antineoplastic agent for its ability to inhibit matrix metalloproteinases (MMPs) activity, which plays a crucial role in various stages of cancer development, including tumor growth, invasion, and metastasis.
Used in Cancer Research:
Batimastat is used as a research tool for studying the involvement of MMPs in carcinogenesis and non-cancer pathological processes both in cultures in vitro and in animals in vivo.
Used in Neuroinflammation Research:
Batimastat is used as a neuroinflammation inhibitor for attenuating neuroinflammation following focal cerebral ischemia in mice.
Used in Pharmaceutical Development:
Batimastat is used as a lead compound in the development of new drugs targeting MMPs for the treatment of various diseases, including cancer and neuroinflammatory conditions.
Used in Snake Venom Research:
Batimastat is used as an inhibitor of snake venom lethality, specifically for inhibiting the effects of Bothrops asper venom.
Originator
Batimastat,British Biotech
Therapeutic Function
Antineoplastic
Biological Activity
Potent, broad spectrum matrix metalloprotease (MMP) inhibitor (IC 50 values are 3, 4, 4, 6 and 20 nM for MMP -1, -2, -9, -7 and -3 respectively). Exhibits antiproliferative, anti-invasive and antimetastatic activity in human ovarian carcinoma xenografts in vivo .
Biochem/physiol Actions
Cell permeable: yes
Enzyme inhibitor
This potent, broad-spectrum matrix metalloprotease, or MMP, inhibitor (FW = 477.64 g/mol; CAS 130370-60-4; Solubility: 96 mg/mL DMSO, <1 mg/mL H2O), also known by its code name BB-94 and its systematic name (2R,3S)-N4 -hydroxy-N1 -[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl) ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]butanediamide, targets MMP-1 (IC50 = 3 nM), MMP-2 (IC50 = 4 nM), MMP-9 (IC50 = 4 nM), MMP-7 (IC50 = 6 nM) and MMP-3 (IC50 = 22 nM). Matrix metalloproteinases have been implicated in the growth and spread of metastatic tumors, and Batimastat not only prevents colonization of secondary organs by B16-BL6 cells, but limits the growth of solid tumors. Animals receiving BB-94 (30 mg/kg, i.p., once daily for 60 days, followed by 3 times weekly) show a reduction in the median primary tumor weight from 293 mg in the control group to 144 mg in the treated group. BB-94 treatment also reduces the incidence of local and regional invasion. Batimastat also reduces in vivo growth of experimental hemangiomas, most probably by blocking endothelial cell recruitment by the transformed cells or by interfering with cell organization in vascular structures. Target(s): Trimeresurus mucrosquamatus (Taiwan habu) venom metalloproteinases; matrix metalloproteinases; interstitial collagenase, or MMP1; stromelysin, or MMP3; matrilysin, or MMP7; gelatinase A, or or MMP2; gelatinase B, or or MMP9; neutrophil collagenase, or MMP8; atrolysin C, or Crotalus atrox metalloendopeptidase c; membrane-type 1 matrix metalloproteinase, or MMP14; membrane-type 3 matrix metalloproteinase, or MMP-16; ADAM 17 endopeptidase, or tumor necrosis factor-a converting enzyme; TACE (13- 15); a-secretase; ADAM TS-4 endopeptidase, or aggrecanase; macrophage elastase, or MMP12.
References
1) Wang et al. (1994), Matrix metalloproteinase inhibitor BB-94 (batimastat) inhibits human colon tumor growth and spread in a patient-like orthotopic model in nude mice; Cancer Res., 54 4726
2) Davies et al. (1993), A synthetic matrix metalloproteinase inhibitor decreases tumor burden and prolongs survival of mice bearing human ovarian carcinoma zenografts; Cancer Res., 53 2087
3) Lein et al. (2000), Synthetic inhibitor of matrix metalloproteinase (batimastat) reduces prostate cancer growth in an orthotopic rat model; Prostate, 43 77
4) Park et al. (2011), Matrix metalloproteinase inhibitors attenuate neuroinflammation following focal cerebral ischemia in mice; Korean J. Physiol. Pharmacol., 15 115
5) Dubrovskaya et al. (2006), Effects of an inhibitor of alpha-secretase, which metabolizes the amyloid peptide precursor, on memory formation in rats; Neurosci. Behav. Physiol., 36 911
6) Rucavado et al. (2004), Effects of the metalloproteinase inhibitor batimastat in the systemic toxicity induced by Bothrops asper snake venom: understanding the role of metalloproteinases in envenomation; Toxicon, 43 417
Check Digit Verification of cas no
The CAS Registry Mumber 130370-60-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,0,3,7 and 0 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 130370-60:
(8*1)+(7*3)+(6*0)+(5*3)+(4*7)+(3*0)+(2*6)+(1*0)=84
84 % 10 = 4
So 130370-60-4 is a valid CAS Registry Number.
InChI:InChI=1/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
