Mimosamycin
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| Category | Antibiotics |
| Catalog number | BBF-01942 |
| CAS | 59493-94-6 |
| Molecular Weight | 233.22 |
| Molecular Formula | C12H11NO4 |
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Description
Mimosamycin is an antibiotic produced by Str. lavendulae No. 314. It has activity against mycobacteria and streptomyces resistant strains.
Specification
| Synonyms | 7-Methoxy-2,6-dimethyl-3,5,8(2H)-isoquinolinetrione |
| IUPAC Name | 7-methoxy-2,6-dimethylisoquinoline-3,5,8-trione |
| Canonical SMILES | CC1=C(C(=O)C2=CN(C(=O)C=C2C1=O)C)OC |
| InChI | InChI=1S/C12H11NO4/c1-6-10(15)7-4-9(14)13(2)5-8(7)11(16)12(6)17-3/h4-5H,1-3H3 |
| InChI Key | BXQZTMMXFKFJIY-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 416.5°C at 760 mmHg |
| Melting Point | 227-231°C |
| Density | 1.35 g/cm3 |
Reference Reading
1. Chemistry of renieramycins. Part 4.synthesis of a simple natural marine product, 6-hydroxy-7-methoxyisoquinolinemethanol
Naoki Saito, Chieko Tanaka, Tomoo Satomi, Chigusa Oyama, Akinori Kubo Chem Pharm Bull (Tokyo). 2004 Feb;52(2):282-6. doi: 10.1248/cpb.52.282.
6-Hydroxy-7-methoxyisoquinolinemethanol (15) and mimosamycin (1) were recently isolated from a marine sponge, Haliclona sp. The former was prepared in ten steps from vanillin (22) in 26% overall yield using an isopropyl for phenol protection.
2. Antifilarial activity of marine sponge Haliclona oculata against experimental Brugia malayi infection
Jyoti Gupta, Sweta Misra, Sunil Kumar Mishra, Shishir Srivastava, M N Srivastava, Vijai Lakshmi, Shailja Misra-Bhattacharya Exp Parasitol. 2012 Apr;130(4):449-55. doi: 10.1016/j.exppara.2012.01.009. Epub 2012 Jan 25.
The present study incorporates the findings on in vitro and in vivo antifilarial activity in the marine sponge, Haliclona oculata using an experimental rodent infection of human lymphatic filarial parasite, Brugia malayi. The in vitro antifilarial action was determined on both adult female worms as well as microfilariae using two parameters viz. adverse effect on motility and inhibition in MTT reduction by the treated adult parasite over control worm. The antifilarial activity could be located in the methanol extract and one of its four fractions (chloroform). Bioactivity guided fractionation of chloroform fraction led to localization of in vitro activity in one of its eight chromatographic fractions. Methanol extract, chloroform fraction and one of the chromatographic fractions revealed IC(50) values of 5.00, 1.80, and 1.62μg/ml, respectively when adult B. malayi were exposed to these test samples for 72h at 37°C. Under similar exposure conditions, the IC(50) values for microfilariae were 1.88, 1.72 and 1.19μg/ml, respectively. The active test samples were found to be safe revealing >10 selectivity indices (SI) on the basis of cytotoxicity to Vero cells (monkey kidney cells) and therefore selected for in vivo evaluation against primary (adult B. malayi intraperitoneal transplanted jird) and secondary (subcutaneous infective larvae induced mastomys) screens. In primary jird model, the three test samples at 100mg/kg for five consecutive days by subcutaneous route demonstrated significant macrofilaricidal efficacy to the tune of 51.3%, 64% and 70.7% by methanol extract, chloroform and chromatographic fraction, respectively. The three samples demonstrated 45-50% macrofilaricidal activity with moderate embryostatic effect in secondary model at 5×500, 5×250 and 5×125mg/kg by oral route. Chromatographic fraction possessing highest antifilarial action was primarily found to be a mixture of four alkaloids Mimosamycin, Xestospongin-C, Xestospongin-D and Araguspongin-C in addition to few minor compounds.
3. Jorunnamycins A-C, new stabilized renieramycin-type bistetrahydroisoquinolines isolated from the Thai nudibranch Jorunna funebris
Kornvika Charupant, Khanit Suwanborirux, Surattana Amnuoypol, Emi Saito, Akinori Kubo, Naoki Saito Chem Pharm Bull (Tokyo). 2007 Jan;55(1):81-6. doi: 10.1248/cpb.55.81.
Jorunnamycins A-C (1a-c), three stabilized renieramycin-type bistetrahydroisoquinolines, were isolated from the mantles, the visceral organs, and the egg ribbons of the Thai nudibranch Jorunna funebris that was pretreated with potassium cyanide (KCN), along with five known compounds, renieramycins M (2m), N (2n), O (2o), and Q (2q) and mimosamycin (3). The structures of 1a-c were elucidated from spectroscopic data and by chemical conversion of renieramycin M (2m) into 1c via 1a. The chemical stability and the oxidative degradation generating simple isoquinoline alkaloids of a carbinolamine analog 1d, which was easily prepared by reacting 1c with silver nitrate in aqueous acetonitrile, are discussed. The results of cytotoxicity studies are also presented.
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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 ╳
