Cosmomycin C
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| Category | Antibiotics |
| Catalog number | BBF-03037 |
| CAS | 55945-22-7 |
| Molecular Weight | 1173.34 |
| Molecular Formula | C60H88N2O21 |
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Description
It is an anthracycline antibiotic produced by the strain of Streptomyces cyaneus (A-447). It has anti-tumor and gram-positive bacteria activity. It can inhibit the growth of P388 murine lymphocytic leukemia cells.
Specification
| Synonyms | Antibiotic A-447B; (3''S)-3''-Hydroxycytorhodin A; 3B-Hydroxycytorhodin A; A-447B; β-Rhodomycin S2; 5,12-Naphthacenedione, 8-ethyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-10-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-[(2S,5S,6S)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy]-7-[[2,3,6-trideoxy-3-(dimethylamino)-4-O-[(2S,5S,6S)-tetrahydro-6-methyl-5-[[(2S,5S,6S)-tetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl]oxy]-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]oxy]-,(7R,8R,10S)- |
| IUPAC Name | (7S,9R,10R)-7-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-[(2S,4S,5S,6S)-4-(dimethylamino)-5-[(2S,5S,6S)-5-[(2S,5S,6S)-5-hydroxy-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(CC(C2=C(C1OC3CC(C(C(O3)C)OC4CCC(C(O4)C)OC5CCC(C(O5)C)O)N(C)C)C(=C6C(=C2O)C(=O)C7=C(C6=O)C=CC=C7O)O)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1CCC(C(O1)C)O)O)N(C)C)O |
| InChI | InChI=1S/C60H88N2O21/c1-12-60(71)25-40(79-44-22-33(61(8)9)57(30(6)75-44)82-46-24-38(66)58(31(7)77-46)81-42-20-17-36(64)27(3)73-42)48-51(55(70)49-50(54(48)69)53(68)47-32(52(49)67)14-13-15-37(47)65)59(60)83-45-23-34(62(10)11)56(29(5)76-45)80-43-21-18-39(28(4)74-43)78-41-19-16-35(63)26(2)72-41/h13-15,26-31,33-36,38-46,56-59,63-66,69-71H,12,16-25H2,1-11H3/t26-,27-,28-,29-,30-,31-,33-,34-,35-,36-,38-,39-,40-,41-,42-,43-,44-,45-,46-,56+,57+,58+,59+,60+/m0/s1 |
| InChI Key | JRCMJKKALYUURJ-OVYBONNASA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Melting Point | 180-183°C |
| Density | 1.39 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Field desorption tandem mass spectrometry of anthracycline antibiotics, cosmomycin A, B, A', B', C and D
K Hirayama, S Akashi, T Ando, I Horino, Y Etoh, H Morioka, H Shibai, A Murai Biomed Environ Mass Spectrom. 1987 Jul;14(7):305-12. doi: 10.1002/bms.1200140703.
Field desorption mass spectrometry was applied to a series of underivatized anthracycline, cosmomycins, to obtain fragment ions which were mass analysed using the linked scan technique without using collision activated dissociation. The daughter spectra of the various protonated compounds contain sugar sequence information which is in the mass spectra. The mass spectrometric data make it clear that field desorption tandem mass spectrometry can become a valuable additional technique for the structural analysis of anthracyclines.
2. Cosmomycin C inhibits signal transducer and activator of transcription 3 (STAT3) pathways in MDA-MB-468 breast cancer cell
Jihoon Kim, Yu-Jin Lee, Dae-Seop Shin, Sun-Hee Jeon, Kwang-Hee Son, Dong Cho Han, Seung-Nam Jung, Tae-Kwang Oh, Byoung-Mog Kwon Bioorg Med Chem. 2011 Dec 15;19(24):7582-9. doi: 10.1016/j.bmc.2011.10.025. Epub 2011 Oct 17.
The signal transducer and activator of transcription 3 (STAT3) is constitutively activated in cancer cells. Therefore, blocking the aberrant activity of STAT3 in tumor cells is a validated therapeutic strategy. To discover novel inhibitors of STAT3 activity, we screened against microbial natural products using a dual-luciferase assay. Using the microbial metabolome library, we identified cosmomycin C (CosC), which was isolated from the mycelium extract of Streptomyces sp. KCTC19769, as a STAT3 pathway inhibitor. CosC inhibited STAT3 (Tyr705) phosphorylation and subsequent nuclear translocation in MDA-MB-468 breast cancer cells. CosC-mediated inhibition of STAT3 signaling pathway was confirmed by suppressed expression of STAT3 downstream target proteins including cyclin D1, Bcl-xL, survivin, Mcl-1, and VEGF in CosC-treated MDA-MB-468 cells. Flow cytometry showed that CosC caused accumulation in the G(0)-G(1) phase of the cell cycle and induced apoptosis via PARP cleavage and caspase-3 activation. Based on these findings, CosC may be a potential candidate for modulation of STAT3 pathway.
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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 ╳
