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10'-Desmethoxystreptonigrin

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10'-Desmethoxystreptonigrin
Category Antibiotics
Catalog number BBF-01834
CAS 136803-89-9
Molecular Weight 476.44
Molecular Formula C24H20N4O7
Purity >95% by HPLC

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

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

It is a close analogue of streptonigrin produced by selected streptomyces species. It is a moderately potent inhibitor of farnesylation of RAS P21 protein, 3-fold more active than streptonigrin. It has potent and broad spectrum antibacterial and antitumour activity.

  • Specification
  • Properties
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Synonyms 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3-methoxyphenyl)-3-methyl-; 10-Desmethoxystreptonigrin
Storage Store at -20°C
IUPAC Name 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3-methoxyphenyl)-3-methylpyridine-2-carboxylic acid
Canonical SMILES CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=CC=C4)OC)O
InChI InChI=1S/C24H20N4O7/c1-9-14(10-5-4-6-13(34-2)20(10)29)15(25)19(28-17(9)24(32)33)12-8-7-11-18(27-12)22(31)16(26)23(35-3)21(11)30/h4-8,29H,25-26H2,1-3H3,(H,32,33)
InChI Key ULSNCNUVHUNMCF-UHFFFAOYSA-N
Source Streptomyces sp.
Appearance Red Brown Solid
Antibiotic Activity Spectrum Neoplastics (Tumor); Bacteria
Boiling Point 683.6°C at 760 mmHg
Density 1.55 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water
1. 10'-Desmethoxystreptonigrin, a novel analog of streptonigrin
J M Clark, P B Fernandes, A R Crosswell, T W Doyle, M Bulgar, W C Liu, L Dean, S Huang, V Manne, M Barbacid J Antibiot (Tokyo) . 1992 Apr;45(4):454-7. doi: 10.7164/antibiotics.45.454.
10'-Desmethoxystreptonigrin, a novel analog of streptonigrin produced by Streptomyces albus, was discovered in a screen for inhibitors of farnesylation of RAS p21 protein. The compound was isolated from the fermentation broth and its structure determined. It is markedly cytotoxic to several human tumor cell lines and also exhibits potent broad-spectrum antibacterial activity.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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