Matlystatin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02310 |
| CAS | 140638-25-1 |
| 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 3.64 and 28, respectively.
Specification
| Synonyms | Matlystatin D1; Pyrazolo(1,2-a)pyridazin-4-ium,8-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-(8-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 | 3-[2-methyl-1-[[2-[2-[2-(oxidoamino)-2-oxoethyl]heptanoyl]diazinane-3-carbonyl]amino]butyl]-5,6,7,8-tetrahydropyrazolo[1,2-a]pyridazin-9-ium-5-carboxylic acid |
| Canonical SMILES | CCCCCC(CC(=O)N[O-])C(=O)N1C(CCCN1)C(=O)NC(C2=CC=[N+]3N2C(CCC3)C(=O)O)C(C)CC |
| InChI | InChI=1S/C27H44N6O6/c1-4-6-7-10-19(17-23(34)30-39)26(36)32-21(11-8-14-28-32)25(35)29-24(18(3)5-2)20-13-16-31-15-9-12-22(27(37)38)33(20)31/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 | ZWXPBQLKZALQOQ-UHFFFAOYSA-N |
Properties
| Appearance | White Hygroscopic Powder |
| Melting Point | 122-126°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
2. 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.
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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 ╳
