Feldamycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01706 |
| CAS | 61230-27-1 |
| Molecular Weight | 407.42 |
| Molecular Formula | C17H25N7O5 |
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Description
Feldamycin is a nitrogen-containing heterocyclic antibiotic produced by Streptomyces ficellus. In vitro it shows anti-Gram-positive and negative bacteria activity, but the treatment of bacterial infection in mice is invalid.
Specification
| IUPAC Name | 3-[[1-carboxy-2-(1H-imidazol-5-yl)ethyl]amino]-2-[[3-(1H-imidazol-5-yl)-2-(methylamino)propanoyl]amino]butanoic acid |
| Canonical SMILES | CC(C(C(=O)O)NC(=O)C(CC1=CN=CN1)NC)NC(CC2=CN=CN2)C(=O)O |
| InChI | InChI=1S/C17H25N7O5/c1-9(23-13(16(26)27)4-11-6-20-8-22-11)14(17(28)29)24-15(25)12(18-2)3-10-5-19-7-21-10/h5-9,12-14,18,23H,3-4H2,1-2H3,(H,19,21)(H,20,22)(H,24,25)(H,26,27)(H,28,29) |
| InChI Key | LUOBEJSTJAVJPL-UHFFFAOYSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 853°C at 760 mmHg |
| Density | 1.443 g/cm3 |
| Solubility | Soluble in Methanol, Water, Ethanol |
Reference Reading
1. Synthesis, stereochemistry, and biological properties of the depigmenting agents, melanostatin, feldamycin and analogs
K Imae, H Kamachi, H Yamashita, T Okita, S Okuyama, T Tsuno, T Yamasaki, Y Sawada, M Ohbayashi, T Naito, et al. J Antibiot (Tokyo). 1991 Jan;44(1):76-85. doi: 10.7164/antibiotics.44.76.
Syntheses of melanostatin and feldamycin have been completed from L-serine and L-threonine, respectively, and the configuration of unknown asymmetric carbons determined. Feldamycin analogs have also been prepared and the L-tryptophyl analog was the most potent in the depigmentation of Streptomyces bikiniensis and B16 melanoma cells.
2. A new screening method for melanin biosynthesis inhibitors using Streptomyces bikiniensis
K Tomita, N Oda, M Ohbayashi, H Kamei, T Miyaki, T Oki J Antibiot (Tokyo). 1990 Dec;43(12):1601-5. doi: 10.7164/antibiotics.43.1601.
A novel screening method for melanin biosynthesis inhibitors using Streptomyces bikiniensis NRRL B-1049 as the indicator organism has been developed. Several known compounds, including tyrosinase inhibitors, were found to inhibit melanin production of S. bikiniensis on agar plates. This screening method was applied to fermentation broths of actinomycetes and several cultures with melanin biosynthesis inhibitory activity were found.
3. Inhibition of melanogenesis by BMY-28565, a novel compound depressing tyrosinase activity in B16 melanoma cells
M Terao, K Tomita, T Oki, L Tabe, M Gianni, E Garattini Biochem Pharmacol. 1992 Jan 22;43(2):183-9. doi: 10.1016/0006-2952(92)90276-o.
The mechanism of a novel melanin synthesis inhibitor, BMY-28565, was studied using mouse B16 melanoma cells. This compound was active in depressing the intracellular accumulation of melanin with an IC50 of 5 microM. At dose levels causing no cytotoxicity, the melanolytic effect of this compound was correlated strongly with depression of the enzymatic activity of tyrosinase (monophenol oxygenase, EC 1.14.18.1), the key enzyme in the melanin synthesis pathway. Transcription of the tyrosinase gene was not inhibited by BMY-28565, as determined by RNA blotting analysis. BMY-28565 and three other active derivatives of this compound caused increased glycosylation of proteins in B16 melanoma cells, as assessed by radioactive mannose incorporation. It is, thus, suggested that the mechanism of inhibition of tyrosinase might be related to modifications of the sugar moiety of this enzyme or of a protein(s) that is essential for the expression of its enzymatic activity.
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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 ╳
