Matlystatin F
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02312 |
| CAS | 140667-42-1 |
| Molecular Weight | 548.68 |
| Molecular Formula | C27H44N6O6 |
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Description
It is produced by the strain of Actinomadura atramentaria. It's a Type V collagenase inhibitor. It can inhibit type IV collagenase and type I collagenase with ID50 (μmol/L) of 1.82 and 5.1, respectively.
Specification
| Synonyms | Matlystatin F1; Pyrazolo(1,2-a)pyridazin-4-ium,5-carboxy-1-(1-(((hexahydro-2-(2-(2-(hydroyamino)-2-oxoethyl)-1-oxoheptyl)-3-pyridazinyl)carbonyl)amino)-2-methylbutyl)-5,6,7,8-tetrahydro-,hydroxide,inner salt; [(3-{6-[{[1-(5-Carboxy-5,6,7,8-tetrahydropyrazolo[1,2-a]pyridazin-9-ium-1-yl)-2-methylbutyl]imino}(hydroxy)methyl]-1,2-diazinane-1-carbonyl}-1-hydroxyoctylidene)amino]oxidanide |
| IUPAC Name | 1-[2-methyl-1-[[2-[2-[2-(oxidoamino)-2-oxoethyl]heptanoyl]diazinane-3-carbonyl]amino]butyl]-5,6,7,8-tetrahydropyrazolo[1,2-a]pyridazin-4-ium-5-carboxylic acid |
| Canonical SMILES | CCCCCC(CC(=O)N[O-])C(=O)N1C(CCCN1)C(=O)NC(C2=CC=[N+]3N2CCCC3C(=O)O)C(C)CC |
| InChI | InChI=1S/C27H44N6O6/c1-4-6-7-10-19(17-23(34)30-39)26(36)33-21(11-8-14-28-33)25(35)29-24(18(3)5-2)20-13-16-32-22(27(37)38)12-9-15-31(20)32/h13,16,18-19,21-22,24,28H,4-12,14-15,17H2,1-3H3,(H3-,29,30,34,35,37,38,39) |
| InChI Key | XRVWEWLMRRABGU-UHFFFAOYSA-N |
Properties
| Appearance | White Hygroscopic Powder |
| Melting Point | 69-75°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Warhead biosynthesis and the origin of structural diversity in hydroxamate metalloproteinase inhibitors
Franziska Leipoldt, Javier Santos-Aberturas, Dennis P Stegmann, Felix Wolf, Andreas Kulik, Rodney Lacret, Désirée Popadić, Daniela Keinhörster, Norbert Kirchner, Paulina Bekiesch, Harald Gross, Andrew W Truman, Leonard Kaysser Nat Commun. 2017 Dec 6;8(1):1965. doi: 10.1038/s41467-017-01975-6.
Metalloproteinase inhibitors often feature hydroxamate moieties to facilitate the chelation of metal ions in the catalytic center of target enzymes. Actinonin and matlystatins are potent metalloproteinase inhibitors that comprise rare N-hydroxy-2-pentyl-succinamic acid warheads. Here we report the identification and characterization of their biosynthetic pathways. By gene cluster comparison and a combination of precursor feeding studies, heterologous pathway expression and gene deletion experiments we are able to show that the N-hydroxy-alkyl-succinamic acid warhead is generated by an unprecedented variation of the ethylmalonyl-CoA pathway. Moreover, we present evidence that the remarkable structural diversity of matlystatin congeners originates from the activity of a decarboxylase-dehydrogenase enzyme with high similarity to enzymes that form epoxyketones. We further exploit this mechanism to direct the biosynthesis of non-natural matlystatin derivatives. Our work paves the way for follow-up studies on these fascinating pathways and allows the identification of new protease inhibitors by genome mining.
2. Matlystatins, new inhibitors of typeIV collagenases from Actinomadura atramentaria. I. Taxonomy, fermentation, isolation, and physico-chemical properties of matlystatin-group compounds
T Ogita, A Sato, R Enokita, K Suzuki, M Ishii, T Negishi, T Okazaki, K Tamaki, K Tanzawa J Antibiot (Tokyo). 1992 Nov;45(11):1723-32. doi: 10.7164/antibiotics.45.1723.
During the course of a screening for inhibitors of typeIV collagenases, new metabolites, designated matlystatins, have been isolated from an actinomycete strain, which was identified as a strain of Actinomadura atramentaria. Matlystatins were composed of five congeners, which were separated and purified by n-butanol extraction and chromatography.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
