Aklavin
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| Category | Antibiotics |
| Catalog number | BBF-00394 |
| CAS | 60504-57-6 |
| Molecular Weight | 569.60 |
| Molecular Formula | C30H35NO10 |
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Description
It is produced by the strain of Streptomyces galilaeus. It has the activity of resisting gram positive bacterium, negative bacterium, candida and ringworm.
Specification
| Related CAS | 66676-88-8 (free base) 65059-09-8 (hydrochloride) |
| Synonyms | Aclacinomycin T; 1-Deoxypyrromycin; Aclacinomycin; Doxypyrromycin; NSC 100290; CHEBI:74351; 1-Naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexapyranosyl)oxy)-, methyl ester, (1R-(1-alpha,2-beta,4-beta))-; aklavine |
| IUPAC Name | methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| Canonical SMILES | CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)O)N(C)C)O |
| InChI | InChI=1S/C30H35NO10/c1-6-30(38)12-19(41-20-11-17(31(3)4)25(33)13(2)40-20)22-15(24(30)29(37)39-5)10-16-23(28(22)36)27(35)21-14(26(16)34)8-7-9-18(21)32/h7-10,13,17,19-20,24-25,32-33,36,38H,6,11-12H2,1-5H3/t13-,17-,19-,20-,24-,25+,30+/m0/s1 |
| InChI Key | LJZPVWKMAYDYAS-QKKPTTNWSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 633.1 °C (Predicted) |
| Melting Point | 197 °C |
| Density | 1.289 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Identification of a new Z-DNA inducer using SYBR green 1 as a DNA conformation sensor
Jeong Hwan Hur, Ae-Ree Lee, Wanki Yoo, Joon-Hwa Lee, Kyeong Kyu Kim FEBS Lett. 2019 Sep;593(18):2628-2636. doi: 10.1002/1873-3468.13513. Epub 2019 Jul 10.
Z-DNA, which is left-handed double-stranded DNA, is involved in various cellular processes. However, its biological roles have not been fully evaluated due to the lack of tools available that can control the precise conformational change to Z-DNA in vitro and in vivo. Therefore, the need for identifying new Z-DNA inducers is high. We developed an assay system to monitor the conformational change in DNA utilizing the fluorescence of SYBR green I integrated into a double-stranded oligonucleotide. By applying this assay to screen for compounds that induce the B-DNA to Z-DNA transition, we identified the natural compound aklavin as a novel Z-DNA inducer.
2. Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24
M L Dickens, W R Strohl J Bacteriol. 1996 Jun;178(11):3389-95. doi: 10.1128/jb.178.11.3389-3395.1996.
DNA sequence analysis of a region of the Streptomyces sp. strain C5 daunomycin biosynthesis gene cluster, located between the daunomycin polyketide biosynthesis gene cluster and a dnrI (transcriptional activator) homolog, revealed the presence of a gene encoding a P-450-like enzyme with a deduced Mr of 46,096. Expression of this gene, named herein doxA, in Streptomyces lividans TY24 resulted in in vivo bioconversion of daunomycin to doxorubicin. DoxA showed specificity for only daunomycin and 13-dihydrodaunomycin, both of which were converted to doxorubicin. Daunomycinone (daunomycin aglycone), carminomycin, 13-dihydrocarminomycin, idarubicin, and aklavin were not apparent substrates for DoxA. In vector controls or in vectors in which doxA was poorly expressed, S. lividans catalyzed the reduction of daunomycin and other 13-oxo-anthracyclines and -anthracyclinones to their 13-dihydro homologs.
3. Sensitive enzyme immunoassay for the quantification of aclacinomycin A using beta-D-galactosidase as a label
M Sohda, K Fujiwara, H Saikusa, T Kitagawa, N Nakamura, K Hara, H Tone Cancer Chemother Pharmacol. 1985;14(1):53-8. doi: 10.1007/BF00552726.
A sensitive enzyme immunoassay method (EIA) for an anticancer drug, aclacinomycin A (ACM), has been developed. With a double-antibody technique, ACM at a concentration as low as 100 pg/tube can be detected. An antibody to ACM was obtained by immunizing rabbits with an antigen prepared by coupling ACM with mercaptosuccinylated bovine serum albumin via N-maleoyl aminobutyric acid (MABA) as a coupling agent. Enzyme labeling of ACM was performed with beta-D-galactosidase (beta-Gal; EC 3.2.1.23) via m-maleoyl benzoic acid (MBA). The standard curve of the assay was linear on a logit-log plot over a concentration range of 30 pg to 10 ng. The antibody detected ACM and its metabolites, MA144 M1 (M1), MA144 N1 (N1), MA144 S1 (S1), and aklavin (T1) equally well, but was only minimally reactive with aklavinone (D1) and 7-deoxyaklavinone (C1), thus suggesting that this EIA can detect the total amounts of ACM and its biologically active glycosides among metabolites of ACM. This EIA is practically free from interference by any other anticancer drugs. Using this assay, serum levels of ACM equivalents can be determined accurately after administration of the drug to rats at a single dose of 10 mg/kg. Since ACM is now undergoing clinical trial, the EIA of the drug will be a valuable tool in clinical pharmacological studies.
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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 ╳
