Actinobolin

Actinobolin

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Actinobolin
Category Antibiotics
Catalog number BBF-00544
CAS 24397-89-5
Molecular Weight 300.31
Molecular Formula C13H20N2O6

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Description

Actinobolin is a broad-spectrum antibiotic isolated from Str. griseoviridus var. atrofaczens. Actinobolin has antibacterial activity, but it can be offset by a variety of amino acids or pyruvate. It has inhibitory effect on Ehrlich ascites tumor, sarcoma 180, etc.

Specification

Related CAS 31327-55-6 (sulfate)
Synonyms 4-(2-Aminopropionamido)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methylisocoumarin
IUPAC Name (2S)-2-amino-N-[(3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydroisochromen-4-yl]propanamide
Canonical SMILES CC1C(C2C(C(CC(=C2C(=O)O1)O)O)O)NC(=O)C(C)N
InChI InChI=1S/C13H20N2O6/c1-4(14)12(19)15-10-5(2)21-13(20)8-6(16)3-7(17)11(18)9(8)10/h4-5,7,9-11,16-18H,3,14H2,1-2H3,(H,15,19)/t4-,5+,7+,9+,10-,11-/m0/s1
InChI Key PQVQBAAWCOTEBG-NSVWQLETSA-N

Properties

Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 592°C at 760 mmHg
Density 1.45 g/cm3

Reference Reading

1. Synthesis and activity of 3-epi-actinobolin
H Adachi, Y Nishimura, S Kondo, T Takeuchi J Antibiot (Tokyo). 1998 Feb;51(2):202-9. doi: 10.7164/antibiotics.51.202.
3-epi-Actinobolin was synthesized by the chemical transformation of actinobolin involving a key step of the reconstruction of fused delta-lacton skeleton via intramolecular acylation reaction. The analogue with low toxicity weakly inhibits Gram-positive and Gram-negative bacteria.
2. Suppression of experimental autoimmune myasthenia gravis with new immunosuppressants: 15-deoxyspergualin and actinobolin
Y Ishigaki, T Sato, D L Song, K Hayashi, T Aoyagi J Neurol Sci. 1992 Oct;112(1-2):209-15. doi: 10.1016/0022-510x(92)90153-c.
In the search for a new drug to treat myasthenia gravis, we studied the efficacy of new immunosuppressants on experimental autoimmune myasthenia gravis (EAMG). 15-Deoxyspergualin (15-DSP), bactobolin and actinobolin were administered to some groups at the time of immunization and to other groups 10 days after. The most effective results were achieved with doses of 2.5 mg/kg daily of 15-DSP and 30 mg/kg daily of actinobolin administered from day 1. In both groups, the body weights of the rats increased as normally as those of controls and signs of myasthenia were mild. Immunoelectron microscopic examination of the neuromuscular junctions in rats treated with 2.5 mg/kg of 15-DSP appeared normal, even in the chronic phase (induced by a booster at week 4). Levels of anti-acetylcholine receptor antibodies were almost completely suppressed. Although the effects of these drugs were more remarkable when administered from day 1 than from day 10, the results suggest that they may prove useful in treating myasthenic patients.
3. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis
Prabhakara R Tharra, Andrey A Mikhaylov, Jiří Švejkar, Marina Gysin, Sven N Hobbie, Jakub Švenda Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202116520. doi: 10.1002/anie.202116520. Epub 2022 Feb 28.
We report a concise synthesis of the naturally occurring protein synthesis inhibitor (+)-actinobolin (1). The densely functionalized and stereochemically complex molecular structure of 1 was assembled from (-)-quinic acid, L-threonine, and L-alanine as the principal components. Our route is based around a convergent strategy that features conjugate addition of an α-amino radical in the key fragment-coupling step. The dramatically simplified synthesis of (+)-actinobolin proceeding in 9 steps with 18 % overall yield has practical implications for analog preparation, as demonstrated herein.

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