Akrobomycin
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| Category | Antibiotics |
| Catalog number | BBF-00395 |
| CAS | 89156-94-5 |
| Molecular Weight | 481.49 |
| Molecular Formula | C26H27NO8 |
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Description
It is produced by the strain of Actinomadura reseoviolacea 129-AVI. It has anti-gram-negative bacteria, ringworm and tumor activity.
Specification
| Synonyms | 9,10-Anhydro-13-deoxocarminomycin; 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-ethyl-9,10-dihydro-1,6,11-trihydroxy-, (S)-; DTXSID601008673; LS-94000; 3-Ethyl-5,10,12-trihydroxy-6,11-dioxo-1,2,6,11-tetrahydrotetracen-1-yl 3-amino-2,3,6-trideoxyhexopyranoside; Akrobomycin; Rubomycin Q1 |
| IUPAC Name | 7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-9-ethyl-4,6,11-trihydroxy-7,8-dihydrotetracene-5,12-dione |
| Canonical SMILES | CCC1=CC2=C(C(C1)OC3CC(C(C(O3)C)O)N)C(=C4C(=C2O)C(=O)C5=C(C4=O)C(=CC=C5)O)O |
| InChI | InChI=1S/C26H27NO8/c1-3-11-7-13-19(16(8-11)35-17-9-14(27)22(29)10(2)34-17)26(33)21-20(24(13)31)23(30)12-5-4-6-15(28)18(12)25(21)32/h4-7,10,14,16-17,22,28-29,31,33H,3,8-9,27H2,1-2H3 |
| InChI Key | KURBZXMNPPHYKQ-UHFFFAOYSA-N |
Properties
| Appearance | Red Purple Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria; fungi; neoplastics (Tumor) |
| Boiling Point | 690.8 °C at 760 mmHg |
| Melting Point | 143-148 °C |
| Density | 1.530 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Are reduction potentials of antifungal agents relevant to activity?
P Kovacic, P F Kiser, B A Feinberg Pharm Res. 1990 Mar;7(3):283-8. doi: 10.1023/a:1015834431140.
Cyclic voltammetry data were obtained for several categories of fungicidal agents including quinones (akrobomycin, podosporin A), iminium ions and precursors (pyridazines, 15-azahomosterol, griseofulvin-4'-oxime), and metal derivatives of chelators (pyridine-2-aldehyde thiosemicarbazones). The reductions usually occurred in the range of -0.7 to +0.3 V. Reduction potentials provide information on the feasibility of electron transfer in vivo. Catalytic production of oxidative stress from redox cycling is a possible mode of action. Alternatively, there may be interference with normal electron transport chains.
2. [New anthracycline antibiotics and derivatives]
K Tatsuta Gan To Kagaku Ryoho. 1984 Dec;11(12 Pt 2):2640-52.
Studies of anthracycline antibiotics which have been carried out for the purpose of finding compounds useful in the treatment of cancer are described. Synthetic development of derivatives and analogs which have stronger activities and lower characteristic toxicities than parent antitumor antibiotics such as daunomycin, adriamycin, etc., have been illustrated namely: (1) syntheses of 4'-O-derivatives such as 4'-O-tetrahydropyranyl-adriamycin; (2) syntheses of N-alkyl derivatives such as 3'-deamino-3'-morpholino-adriamycin; and (3) syntheses of 11-deoxy-adriamycin. Notably, 4'-O-tetrahydropyranyl-adriamycin having a (2" R)-configuration has been confirmed to have stronger activity and lower toxicity than adriamycin by Phase II study. New, naturally occurring anthracycline antibiotics (decilorubicin, arugomycin, ditrisarubicin, etc.) have also been reviewed.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
