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Vanoxonin

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Vanoxonin
Category Antibiotics
Catalog number BBF-02743
CAS 86933-99-5
Molecular Weight 427.40
Molecular Formula C18H25N3O9

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
Appearance Colorless Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Melting Point 105-109°C
Density 1.459 g/cm3
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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