CAS 142880-36-2|GM 6001
| Common Name | GM 6001 | ||
|---|---|---|---|
| CAS Number | 142880-36-2 | Molecular Weight | 388.461 |
| Density | 1.228±0.06 g/cm3 | Boiling Point | / |
| Molecular Formula | C20H28N4O4 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | / |
Names
| Name | (R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide |
|---|---|
| Synonym | More Synonyms |
GM 6001 BiologicalActivity
| Description | Ilomastat (Galardin; GM6001) is a broad spectrum matrix metalloprotease (MMP) inhibitor, with Ki of 0.4 nM, 0.5 nM, 27 nM, 3.7 nM, 0.1 nM, 0.2 nM, 3.6 nM, 13.4 nM, 0.36 nM for MMP-1/2/3/7/8/9/12/14/26, respectively. |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>MMPResearch Areas >>Cancer |
| Target | Ki: 0.4 nM (MMP-1), 0.5 nM (MMP-2), 27 nM (MMP-3), 3.7 nM (MMP-7), 0.1 nM (MMP-8), 0.2 nM (MMP-9), 3.6 nM (MMP-12), 13.4 nM (MMP-14), 0.36 nM (MMP-26) |
| In Vitro | Ilomastat (GM6001) inhibits human skin fibroblast collagenase with Ki of 0.4 nM when assayed with a synthetic thio ester substrate at pH 6.5, with 50-fold selectivity over two bacterial enzymes, thermolysin and Pseudomonas aeruginosa elastase[1]. Ilomastat (0.1 nM-10 nM) inhibits gelatinase A and gelatinase B produced by T-cells, and thus inhibits T-cell homing[4]. |
| In Vivo | Ilomastat (GM6001) (400 μg/mL) prevents corneal ulceration after severe alkali injury[2]. Ilomastat (GM6001) significantly inhibits intimal hyperplasia and intimalcollagen content, and it increases lumen area in stented arteries without effects on proliferation rates in rabbit model after stenting[3]. |
| Animal Admin | To assess the effects of MMP inhibition, animals are given daily injections of either vehicle (“placebo group”) or Ilomastat (GM6001) (100 mg/kg per day as subcutaneous suspension), beginning one day before the second injury until seven days after the procedure. Ilomastat (GM6001) is a nonspecific hydroxamic acid-based MMPI with potent inhibitory activity against collagenase, gelatinases and stromelysin. Animals are euthanized at either 1 week or 10 weeks after the second injury. For biochemical studies, iliac artery tissue is removed under general anesthetic, followed by a fatal intracardiac injection of thiopentol. For histomorphometric studies, iliac arteries are perfusion-fixed in 10% buffered formalin for 20 min at a perfusion pressure of 80 mm Hg. |
| References | [1]. Grobelny D, et al. Inhibition of human skin fibroblast collagenase, thermolysin, and Pseudomonas aeruginosa elastase by peptide hydroxamic acids. Biochemistry. 1992 Aug 11;31(31):7152-4. [2]. Schultz GS, et al. Treatment of alkali-injured rabbit corneas with a synthetic inhibitor of matrix metalloproteinases. Invest Ophthalmol Vis Sci. 1992 Nov;33(12):3325-31. [3]. Li C, et al. Arterial repair after stenting and the effects of GM6001, a matrix metalloproteinase inhibitor. J Am Coll Cardiol. 2002 Jun 5;39(11):1852-8. [4]. Leppert D, et al. T cell gelatinases mediate basement membrane transmigration in vitro. J Immunol. 1995 May 1;154(9):4379-89. |
Chemical & Physical Properties
| Density | 1.228±0.06 g/cm3 |
|---|---|
| Molecular Formula | C20H28N4O4 |
| Molecular Weight | 388.461 |
| Exact Mass | 388.211060 |
| PSA | 123.32000 |
| LogP | 0.83 |
| Appearance of Characters | Off-white solid |
| Index of Refraction | 1.590 |
| InChIKey | NITYDPDXAAFEIT-DYVFJYSZSA-N |
| SMILES | CNC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(CC(=O)NO)CC(C)C |
| Storage condition | 2-8°C |
| Water Solubility | Practically insoluble (0.062 g/L) (25 ºC) |
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| Safety Phrases | 22-24/25 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| HS Code | 29339900 |
Articles1
More Articles| Inhibition of human skin fibroblast collagenase, thermolysin, and Pseudomonas aeruginosa elastase by peptide hydroxamic acids. Biochemistry 31 , 7152, (1992) The hydroxamic acid HONHCOCH2CH(i-Bu)CO-L-Trp-NHMe, isomer 6A (GM 6001), inhibits human skin fibroblast collagenase with Ki of 0.4 nM using the synthetic thiol ester substrate Ac-Pro-Leu-Gly-SCH(i-Bu)... |
Synonyms
| Ilomastat |
| (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide |
| (S-(R*,S*))-N4-Hydroxy-N{1}-(1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)butanediamide |
| GM6001 |
| (2R)-N4-(hydroxy)-N1-((1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)butanediamide |
| Butanediamide, N-hydroxy-N-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)-, (2R)- |
| (2R)-N-Hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-isobutylsuccinamide |
| (2R)-N-Hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxo-2-propanyl]-2-isobutylsuccinamide |
| Galardin |
