Ditrisarubicin C
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| Category | Antibiotics |
| Catalog number | BBF-01169 |
| CAS | 87385-18-0 |
| Molecular Weight | 1165.29 |
| Molecular Formula | C60H80N2O21 |
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Description
It is produced by the strain of Streptomyces MG 344-hF49. It has anti-gram-positive bacterial activity and is toxic to L-1210 cells.
Specification
| Synonyms | Cytorhodin A,2F,3F-didehydro-4C,4F-dideoxy-2C,3B-epoxy-4C,4F-dioxo-, (2CS,3BS)-; Cytorhoidin D |
| IUPAC Name | (7S,9R,10R)-7-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[[(1R,3R,5S,8S,10S,12S,14S)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]oxy]-6-methyloxan-2-yl]oxy-10-[(2S,4S,5S,6S)-4-(dimethylamino)-6-methyl-5-[(2S,6S)-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxyoxan-2-yl]oxy-9-ethyl-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CCC1(CC(C2=C(C1OC3CC(C(C(O3)C)OC4CCC(C(O4)C)OC5C=CC(=O)C(O5)C)N(C)C)C(=C6C(=C2O)C(=O)C7=C(C6=O)C=CC=C7O)O)OC8CC(C(C(O8)C)OC9CC1C(C(O9)C)OC2C(O1)CC(=O)C(O2)C)N(C)C)O |
| InChI | InChI=1S/C60H80N2O21/c1-12-60(70)24-40(79-43-20-32(61(8)9)56(29(6)73-43)81-45-23-38-57(30(7)75-45)83-59-39(77-38)22-36(65)26(3)76-59)47-50(54(69)48-49(53(47)68)52(67)46-31(51(48)66)14-13-15-35(46)64)58(60)82-44-21-33(62(10)11)55(28(5)74-44)80-42-19-17-37(27(4)72-42)78-41-18-16-34(63)25(2)71-41/h13-16,18,25-30,32-33,37-45,55-59,64,68-70H,12,17,19-24H2,1-11H3/t25-,26-,27-,28-,29-,30-,32-,33-,37?,38-,39-,40-,41-,42-,43-,44-,45-,55+,56+,57+,58+,59-,60+/m0/s1 |
| InChI Key | SGOOJJACKKMDRV-NCSOINJOSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | gram-posotive becteria; Neoplastics (Tumor) |
| Melting Point | 173-176 °C (dec.) |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. [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.
2. Experimental studies of new anthracyclines: aclacinomycin, THP-adriamycin and ditrisarubicins
K Umezawa, S Kunimoto, T Takeuchi Biomed Pharmacother. 1987;41(5):206-13.
Aclacinomycin is a member of naturally occurring anthracyclines having three sugar moieties in the molecule. It showed antitumour activity on various mouse and rat tumours. Combination therapy with AraC etc. gave remarkable clinical results on acute myeloid leukaemia. Aclacinomycin strongly inhibits RNA synthesis of the tumour cells. It has lower cardiac toxicity than adriamycin and no mutagenicity. THP-Adriamycin is a derivative of adriamycin designed from the structure of baumycins. It showed stronger effects than adriamycin in inhibiting many mouse tumours such as L1210 and P388 leukaemia, B16 melanoma and colon 38 adenocarcinoma. THP-Adriamycin is rapidly taken up by both adriamycin-sensitive and resistant leukaemic cells. Its level of cardiac toxicity is as low as that of aclacinomycin. Ditrisarubicins are new naturally occurring anthracyclines isolated from Streptomyces having six sugar moieties in the molecule. Ditrisarubicin has a potent cytostatic and antitumour activities on adriamycin resistant mouse leukaemia. Its binding constant to DNA is extremely high compared with other anthracyclines.
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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 ╳
