Roseorubicin A

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Category Antibiotics
Catalog number BBF-02209
CAS 70559-00-1
Molecular Weight 1043.20
Molecular Formula C54H78N2O18

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Description

It is produced by the strain of Actinomyces roseoviolaceus A529. It has anti-gram-positive bacteria and mycobacterium effect, and Roseorubicin A has stronger antibacterial effect than B. It also inhibits leukaemia L1210 with IC50 of 0.04 μg/mL.

Specification

Synonyms BRN 1419073
IUPAC Name 10-[4-(dimethylamino)-5-[4-(dimethylamino)-5-[4-hydroxy-5-[5-(5-hydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione
Canonical SMILES CCC1(CCC2=C(C1OC3CC(C(C(O3)C)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)OC6CCC(C(O6)C)OC7CCC(C(O7)C)O)O)N(C)C)N(C)C)C(=C8C(=C2O)C(=O)C9=C(C8=O)C=CC=C9O)O)O
InChI InChI=1S/C54H78N2O18/c1-11-54(64)20-19-30-43(49(63)45-44(47(30)61)48(62)42-29(46(45)60)13-12-14-34(42)58)53(54)74-40-22-32(56(9)10)50(27(5)68-40)72-39-21-31(55(7)8)51(26(4)67-39)73-41-23-35(59)52(28(6)69-41)71-38-18-16-36(25(3)66-38)70-37-17-15-33(57)24(2)65-37/h12-14,24-28,31-33,35-41,50-53,57-59,61,63-64H,11,15-23H2,1-10H3
InChI Key IWFXKTHFKLCDQJ-UHFFFAOYSA-N

Properties

Appearance Red Powder
Antibiotic Activity Spectrum Gram-positive bacteria; mycobacteria; neoplastics (Tumor)
Melting Point 143-147°C

Reference Reading

1. Electrochemical reduction pathways of anthracycline antibiotics
H Berg, G Horn, W Ihn J Antibiot (Tokyo). 1982 Jul;35(7):800-5. doi: 10.7164/antibiotics.35.800.
The preparative electrochemical reduction of a series of anthracycline antibiotics was performed using the technique of large scale electrolysis and d. c. polarography for recording different reaction pathways. The reduction products were identified by mass spectrometric and chromatographic analyses. Only anthracyclines with sugar residues in the C-10 position chromatographic analyses. Only anthracyclines with sugar residues in the C-10 position (iremycin, roseorubicin A) were reduced reversibly by 2e- to the corresponding hydroquinones. All others with sugar residues in the C-7 position (daunomycin, 5-iminodaunomycin, adriamycin, carminomycin, beta-rhodomycin II, aclacinomycin A, 1-deoxypyrromycin) showed an irreversible behavior because of the reductive splitting of the glycosidic bond after formation of 7-deoxy compounds or -- if the C-11 OH-group was not present -- of dimers, respectively.

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