MA144 M1
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| Category | Antibiotics |
| Catalog number | BBF-03638 |
| CAS | 64431-68-1 |
| Molecular Weight | 813.88 |
| Molecular Formula | C42H55NO15 |
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Description
MA144 M1 is originally isolated from Streptomyces galilaeus MA144M1. It has anti-gram-positive bacteria and tumor effects.
Specification
| Synonyms | Antibiotic MA 144M1; 1-Naphthacenecarboxylic acid, 1,2,3,4,6,11-hexahydro-6,11-dioxo-2-ethyl-4-((O-2,3,6-trideoxy-alpha-L-glycero-hexopyranosyl-(1-4)-O-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl-(1,4)-2,3,6-trideoxy-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-2,5,7-trihydroxy-, methyl ester; aclacinomycin M; MA-144M1 |
| IUPAC Name | methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-5-[(2S,5R,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-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)OC6CC(C(C(O6)C)OC7CCC(C(O7)C)O)O)N(C)C)O |
| InChI | InChI=1S/C42H55NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24-25,27-31,35,39-40,44-46,49,51H,8,12-13,15-17H2,1-7H3/t18-,19-,20-,24-,25+,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1 |
| InChI Key | CPUWOKRFRYWIHK-YAPFQWMQSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 901.3°C at 760 mmHg |
| Melting Point | 145-150°C |
| Density | 1.42 g/cm3 |
Reference Reading
1. 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.
2. Radioimmunoassay for aclacinomycin A
Y Matsuzawa, T Kiyosaki, T Oki, T Takeuchi, H Umezawa Gan. 1982 Apr;73(2):229-33.
An antibody against aclacinomycin A (ACM) was produced in a rabbit by immunization with ACM-bovine serum albumin conjugate. The radioimmunoassay (RIA) was based on the competition of unlabeled anthracycline with 3H-labeled ACM for binding sites on a specific antibody. Antibody-bound and free antigen were separated by selective adsorption on dextran-coated charcoal. The antibody reacted equally with ACM and its metabolites, MA144 M1, MA144 S1 and aklavin, and could precisely distinguish aklavinone-related aglycones, adriamycin and daunomycin. RIA was sensitive in the range of 1 approximately 10 pmol per assay. The quantities of ACM and its metabolites in human plasma were practically determined without any pretreatment of physiological samples.
3. New anthracyclinone metabolites from two blocked mutants of Streptomyces galilaeus MA144-M1
H Tobe, A Yoshimoto, T Ishikura, H Naganawa, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1982 Dec;35(12):1641-5. doi: 10.7164/antibiotics.35.1641.
Two blocked mutants of the aclacinomycin-producing Streptomyces galilaeus MA144-M1 produced new anthraquinones and anthracyclinones. The mutant ANR-58 produced compounds 58A, 58B, 58C (7-deoxy-2-hydroxyaklavinone), 58D (2-hydroxyaklavinone) and 58WR. All these compounds have the 2-hydroxyl group. The mutant ANR-665 produced compounds 665A and 665B. The compounds 58A, 58B and 665A have an anthraquinone skeleton.
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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 ╳
