Vanoxonin
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| Category | Antibiotics |
| Catalog number | BBF-02743 |
| CAS | 86933-99-5 |
| Molecular Weight | 427.40 |
| Molecular Formula | C18H25N3O9 |
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Description
Vanoxonin is produced by the strain of Saccharopolyspora hirsuta. It can inhibit thymidylate synthase (IC50 = 0.7μg/mL). And the MIC of the complex against L-1210 and Ehrlich ascites cancer cells was 25 μg/mL.
Specification
| Synonyms | Antibiotic MG 245CF2A; N(sup 5)-Acetyl-N(sup 2)-(N-(2,3-dihydroxybenzoyl)-L-threonyl)-N(sup 5)-hydroxy-L-ornithine; (S)-2-((2S,3R)-2-(2,3-dihydroxybenzamido)-3-hydroxybutanamido)-5-(N-hydroxyacetamido)pentanoic acid |
| IUPAC Name | (2S)-5-[acetyl(hydroxy)amino]-2-[[(2S,3R)-2-[(2,3-dihydroxybenzoyl)amino]-3-hydroxybutanoyl]amino]pentanoic acid |
| Canonical SMILES | CC(C(C(=O)NC(CCCN(C(=O)C)O)C(=O)O)NC(=O)C1=C(C(=CC=C1)O)O)O |
| InChI | InChI=1S/C18H25N3O9/c1-9(22)14(20-16(26)11-5-3-7-13(24)15(11)25)17(27)19-12(18(28)29)6-4-8-21(30)10(2)23/h3,5,7,9,12,14,22,24-25,30H,4,6,8H2,1-2H3,(H,19,27)(H,20,26)(H,28,29)/t9-,12+,14+/m1/s1 |
| InChI Key | KCWDMHXDGAWLOA-LQJRIPTKSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 105-109°C |
| Density | 1.459 g/cm3 |
Reference Reading
1. Vanoxonin, a new inhibitor of thymidylate synthetase. II. Structure determination and total synthesis
F Kanai, K Isshiki, Y Umezawa, H Morishima, H Naganawa, T Takita, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1985 Jan;38(1):31-8. doi: 10.7164/antibiotics.38.31.
Acid hydrolysis of vanoxonin yielded one mol each of 2,3-dihydroxybenzoic acid, L-threonine, L-N omega-hydroxyornithine. Presence of acetyl group in vanoxonin was suggested by the 1H NMR. Periodate oxidation of vanoxonin liberated one mol of acetic acid suggesting that the acetyl group bound to the omega-nitrogen of N omega-hydroxyornithine. The sequence of three components was determined to be L-N-(2,3-dihydroxybenzoyl)threonyl-L-(N omega-acetyl-N omega-hydroxy)ornithine by mass spectrometric analysis. This structure was confirmed by the total synthesis of vanoxonin.
2. Vanoxonin, a new inhibitor of thymidylate synthetase. III. Inhibition of thymidylate synthetase by vanoxonin-vanadium complex
F Kanai, T Kaneko, H Morishima, K Isshiki, T Takita, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1985 Jan;38(1):39-50. doi: 10.7164/antibiotics.38.39.
Quinquevalent vanadium complex with two mol of vanoxonin ligated by the two catechols was shown to be the active structure for inhibition of thymidylate synthetase. The catechol group of vanoxonin as the essential moiety for the inhibition of enzyme was further confirmed by studies of structure-activity relationships using the enzyme obtained from Ehrlich ascites carcinoma cells of mice. Vanoxonin-vanadium complex showed competitive inhibition with respect to deoxyuridylic acid but uncompetitive to 5,10-methylenetetrahydrofolate.
3. Vanoxonin, a new inhibitor of thymidylate synthetase
F Kanai, T Sawa, M Hamada, H Naganawa, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1983 Jun;36(6):656-60. doi: 10.7164/antibiotics.36.656.
Vanoxonin, a new inhibitor of thymidylate synthetase, was found in cultured broths of the strain MG245-CF2 classified as Saccharopolyspora hirsuta. Vanoxonin, C18H25N3O9, was obtained as colorless powder. Vanoxonin forms a vanadium complex which exhibits a strong inhibition against thymidylate synthetase. The concentration for 50% inhibition of the enzyme (IC50) was 0.7 micrograms/ml.
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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 ╳
