Aclarubicin

ChEBI: An anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity.

It is produced by fermentation and produces Streptomyces galilacus. First prepare an aqueous solution containing the following substances: 1% potato flour, 1% glucose, 1.5% Prorich, 0.1% KH2PO4, 0.1% KH2PO4, 0.1% MgSO4 7H2O, 0.3% NaCl, 0.15% compound Minerals and 0.05% silicone (KM75), the Ph value of the aqueous solution is 7.0. The composition of the composite minerals is: 2.8g CuSO4?5H2O, 0.4g FeSO4?7H2O, 3.2g MnCl2?4H2O and 0.8g ZnSO4?7H2O dissolved in 500ml water. 100ml of the above aqueous solution was sterilized in a 500ml shaker bottle with Streptomyces galilaeus MA 144-M1 strain at 120°C for 15 minutes. In a reciprocating shaker, culture was carried out at 28°C for 48 hours to obtain seed liquid. The above 10L disinfectant was put into a 20L stainless steel fermentation tank and inoculated with 200ml of seed liquid. Under stirring (240r/min) and aeration (5L/min) and 28°C, fermentation was carried out for 32h. Adjust to Ph=4.5, mix with diatomaceous earth adsorbent, and filter. The filtrate and filter cake of the fermentation broth are treated separately. The filter cake was suspended in acetone (3L/kg wet cake), stirred for 2 hours and filtered, and the filter cake was extracted with acetone once more. The extract thus obtained was concentrated under reduced pressure to 1/10 volume. The filtrate of the fermentation broth was adjusted to Ph=6.8, extracted twice with 1/3 volume of ethyl acetate, and the extract was concentrated to 1/10 volume under reduced pressure. The obtained 20 g oily substance and 20 g silicic acid were mixed, and chromatographed with a silicic acid column, first eluting with 1:1 phenyl-acetone, and the eluate was discarded. Then it was eluted with benzene-acetone-methanol at 1:3:0 and 1:3:0.3, collected, and concentrated under reduced pressure to dryness. The remaining 11.5 g of crude product was dissolved in a small amount of ethyl acetate, and then subjected to silicic acid column chromatography as above, and the first 1:1 and 2:1 benzene-acetone eluent was discarded. Aclamycin B was eluted with 1:3 and 1:5 phenyl-acetone, and then arubicin was eluted with 1:5:0.5 and 1:5:1 phenyl-acetone-methanol. The eluate was dried with anhydrous sodium sulfate and concentrated to dryness under reduced pressure to obtain 4.8 g of arubicin (Aclarithromycin A) and 3.5 g of aclarithromycin B crude products. 2.0g crude arubicin was dissolved in a small amount of chloroform, and 30g silica gel was used for column chromatography. The impurities were first eluted with chloroform and a chloroform solution containing 1.5% methanol, and then a chloroform solution containing 2% methanol Bixin eluted. The eluate was concentrated to dryness under reduced pressure to obtain 53 mg of arubicin as a yellow powder with a melting point of 129-135°C.

Antitumor antibiotics, mainly used for lung cancer, breast cancer, digestive tract cancer, acute leukemia, etc.

Molecular Weight:811.9
XLogP3:3.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:16
Rotatable Bond Count:10
Exact Mass:811.34151998
Monoisotopic Mass:811.34151998
Topological Polar Surface Area:217
Heavy Atom Count:58
Complexity:1530
Undefined Atom Stereocenter Count:13
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes