Oximidine III

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Category Antibiotics
Catalog number BBF-02329
CAS
Molecular Weight 424.45
Molecular Formula C23H24N2O6

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Description

It is produced by the strain of Pseudomonas sp. QN05727. It's an anti-tumor antibiotic. It can selectively inhibit the growth of 3Y1 in rat fibroblasts with degeneration of various tumor genes. It inhibits v-H-ras-3Y1, v-src-3Y1 cells and the normal 3Y1 cells with IC50 (nmol/L) of 14, 4.5 and 140, respectively. It stops RAS-or SRC-denatured cells at G1 phase of the cell cycle and increases p21WAF1 expression.

Specification

IUPAC Name (Z,4E)-N-[(Z)-3-[(4S,6S,8R,9Z,11E)-17-hydroxy-2-oxo-3,7-dioxatricyclo[11.4.0.06,8]heptadeca-1(13),9,11,14,16-pentaen-4-yl]prop-1-enyl]-4-methoxyiminobut-2-enamide
Canonical SMILES CON=CC=CC(=O)NC=CCC1CC2C(O2)C=CC=CC3=C(C(=CC=C3)O)C(=O)O1
InChI InChI=1S/C23H24N2O6/c1-29-25-14-6-12-21(27)24-13-5-9-17-15-20-19(31-20)11-3-2-7-16-8-4-10-18(26)22(16)23(28)30-17/h2-8,10-14,17,19-20,26H,9,15H2,1H3,(H,24,27)/b7-2+,11-3-,12-6-,13-5-,25-14+/t17-,19+,20-/m0/s1
InChI Key AHOWOFTYCJCPEK-VYBMSKHHSA-N

Properties

Appearance Colorless Powder
Antibiotic Activity Spectrum Neoplastics (Tumor)
Melting Point 87-89°C
Solubility Soluble in Methanol

Reference Reading

1. Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950
Robert S Coleman, Pei-Hua Liu Org Lett. 2004 Feb 19;6(4):577-80. doi: 10.1021/ol036381d.
[reaction: see text] A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)- and (Z)-vinyl iodides with a protected maleimide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.
2. Oximidine III, a new antitumor antibiotic against transformed cells from Pseudomonas sp. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activity
Yoichi Hayakawa, Taijiro Tomikawa, Kazuo Shin-ya, Nakako Arao, Koji Nagai, Ken-ichi Suzuki J Antibiot (Tokyo). 2003 Nov;56(11):899-904. doi: 10.7164/antibiotics.56.899.
Our screening for antitumor antibiotics against transformed cells resulted in the isolation of a new active metabolite, oximidine III, from Pseudomonas sp. QN05727. This substance selectively inhibited the growth of rat 3Y1 fibroblasts transformed with various oncogenes. In ras- or src-transformed cells, oximidine III arrested the cell cycle at G1 phase and increased the expression of p21WAF1.
3. Oximidine III, a new antitumor antibiotic against transformed cells from Pseudomonas sp. II. Structure elucidation
Yoichi Hayakawa, Taijiro Tomikawa, Kazuo Shin-ya, Nakako Arao, Koji Nagai, Ken-ichi Suzuki, Kazuo Furihata J Antibiot (Tokyo). 2003 Nov;56(11):905-8. doi: 10.7164/antibiotics.56.905.
The structure of oximidine III, a new antitumor antibiotic against transformed cells from Pseudomonas sp. QN05727, was determined to be a benzolactone enamide containing an O-methyloxime moiety as shown in Fig. 1 by NMR spectral analysis including a variety of two-dimensional techniques.

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