Pelagiomicin A

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Pelagiomicin A
Category Antibiotics
Catalog number BBF-02672
CAS 173485-80-8
Molecular Weight 399.40
Molecular Formula C20H21N3O6
Purity 95%

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Description

It is produced by the strain of Pelagiobacter variabilis. It has strong activity against gram-positive bacteria and gram-negative bacteria, but no activity against candida albicans. It's cytotoxic to HeLa cells, BALB3T3 and BALB3T3/H-ras cultured in vivo with IC50 (μg/mL) of 0.04, 0.2 and 0.07, respectively. In vivo it has weak inhibitory effect on leukemia P388.

Specification

Synonyms Antibiotic 2088A; 3-Hydroxy-L-valine(6-carboxy-4-methoxy-1-phenazinyl)methylester; L-Valine, 3-hydroxy-, (6-carboxy-4-methoxy-1-phenazinyl)methyl ester; (S)-6-(((2-amino-3-hydroxy-3-methylbutanoyl)oxy)methyl)-9-methoxyphenazine-1-carboxylic acid
IUPAC Name 6-[[(2S)-2-amino-3-hydroxy-3-methylbutanoyl]oxymethyl]-9-methoxyphenazine-1-carboxylic acid
Canonical SMILES CC(C)(C(C(=O)OCC1=CC=C(C2=NC3=C(C=CC=C3N=C12)C(=O)O)OC)N)O
InChI InChI=1S/C20H21N3O6/c1-20(2,27)17(21)19(26)29-9-10-7-8-13(28-3)16-14(10)22-12-6-4-5-11(18(24)25)15(12)23-16/h4-8,17,27H,9,21H2,1-3H3,(H,24,25)/t17-/m1/s1
InChI Key SFUOAUKIPVZJLK-QGZVFWFLSA-N

Properties

Appearance Red-orange Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor)
Boiling Point 684.7°C at 760 mmHg
Melting Point 130°C (dec.)
Density 1.403 g/cm3
Solubility Soluble in Chloroform, Ethanol

Reference Reading

1. New anticancer antibiotics pelagiomicins, produced by a new marine bacterium Pelagiobacter variabilis
N Imamura, M Nishijima, T Takadera, K Adachi, M Sakai, H Sano J Antibiot (Tokyo). 1997 Jan;50(1):8-12. doi: 10.7164/antibiotics.50.8.
In the course of our screening for new anticancer compounds produced by marine bacteria, we found that a new genus marine bacterium Pelagiobacter variabilis produced new phenazine antibiotics, pelagiomicins A, B and C. Those compounds were labile in water and alcohols. The absolute structure of the main component, pelagiomicin A, and the structures of the minor ones were determined from the spectroscopic data and by synthesis. Pelagiomicin A exhibits activity against Gram-positive and -negative bacteria and antitumor activity in vitro and in vivo.

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