Leuseramycin
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| Category | Antibiotics |
| Catalog number | BBF-02260 |
| CAS | 73537-10-7 |
| Molecular Weight | 851.12 |
| Molecular Formula | C47H78O13 |
| Purity | 95% |
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Description
It is produced by the strain of Str. hygroscopicus TM-531. It's a polyether antibiotic. It has anti-gram-positive bacteria, plant pathogenic bacteria and some protozoa effects.
Specification
| Synonyms | (2R,4S,8R,E)-8-((2R,2'S,4'S,5R,5'S,7S,7'S,8S,9S,9'R,10'S)-9-hydroxy-2'-((2S,3S,5S,6S)-6-hydroxy-3,5,6-trimethyltetrahydro-2H-pyran-2-yl)-9'-(((2R,5R,6R)-5-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2,4',8,10'-tetramethyl-1,1',6,6'-tetraoxa[2,7'-bispiro[4.5]decan]-7-yl)-2,4,6-trimethyl-5-oxonon-6-enoic acid; 30-Deoxydianemycin; Antibiotic TM-531; TM-531 |
| IUPAC Name | (E,2R,4S,8R)-8-[(2R,5R,7S,8S,9S)-7-hydroxy-2-[(2S,4S,5S,7S,9R,10S)-2-[(2S,3S,5S,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-9-[(2R,5R,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid |
| Canonical SMILES | CC1CC(C(OC1C2CC(C3(O2)C(C(CC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C=C(C)C(=O)C(C)CC(C)C(=O)O)C)O)C)OC6CCC(C(O6)C)OC)C)C)(C)O)C |
| InChI | InChI=1S/C47H78O13/c1-24(40(49)25(2)19-28(5)43(50)51)18-26(3)41-31(8)34(48)23-46(59-41)17-16-44(11,60-46)38-22-36(55-39-15-14-35(53-13)33(10)54-39)32(9)47(57-38)30(7)21-37(56-47)42-27(4)20-29(6)45(12,52)58-42/h18,25-39,41-42,48,52H,14-17,19-23H2,1-13H3,(H,50,51)/b24-18+/t25-,26+,27-,28+,29-,30-,31-,32-,33+,34-,35+,36+,37-,38-,39-,41-,42-,44+,45-,46+,47-/m0/s1 |
| InChI Key | ALQNAINCHNBUOD-YWQQLZDRSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Parasites |
| Boiling Point | 881.7°C at 760 mmHg |
| Melting Point | 88-91°C |
| Density | 1.18 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Studies on the ionophorous antibiotics. XXIV. Leuseramycin, a new polyether antibiotic produced by Streptomyces hygroscopicus
T Mizutani, M Yamagishi, H Hara, A Kawashima, S Omura, M Ozeki J Antibiot (Tokyo). 1980 Feb;33(2):137-43. doi: 10.7164/antibiotics.33.137.
A new antibiotic leuseramycin has been isolated from the cultured mycelium of the strain of Streptomyces hygroscopicus TM-531. Physicochemical data, in particular those of 1H- and 13C-NMR spectra, revealed that leuseramycin is closely related to dianemycin in its structure, the former having a methyl group in place of the hydroxymethyl group at C-30. It is active against Gram-positive bacteria, some phytopathogenic fungi and some protozoa.
2. Circumvention of multidrug resistance in human carcinoma KB cells by polyether antibiotics
M Kawada, S Sumi, K Umezawa, S Inouye, T Sawa, H Seto J Antibiot (Tokyo). 1992 Apr;45(4):556-62. doi: 10.7164/antibiotics.45.556.
We examined the effect of various polyether antibiotics on colchicine resistance in multidrug-resistant KB-C4 cells which exhibit about 4,000-fold resistance to colchicine. As a result, 4 out of 14 polyether antibiotics were found to reverse colchicine resistance. Among them, laidlomycin was the most potent. It potentiated colchicine cytotoxicity on KB-C4 cells about 700-fold at 1 microgram/ml. Degree of potentiation was calculated by dividing of the IC50 value of colchicine in the absence of a polyether antibiotic by the IC50 value of colchicine in the presence of the polyether antibiotic. Monensin, dianemycin, and leuseramycin at 3 micrograms/ml also potentiated the cytotoxicity, about 100-fold. We previously reported that inostamycin is a potent chemosensitizer in KB-C4 cells. Although lysocellin has a structure very similar to that of inostamycin, it didn't reverse colchicine resistance. It slightly increased [3H]vinblastine accumulation in KB-C4 cells and weakly inhibited the [3H]vinblastine binding to KB-C4 plasma membranes.
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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 ╳
