Carminomycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antineoplastic |
| Catalog number | BBF-00702 |
| CAS | 39472-31-6 |
| Molecular Weight | 513.49 |
| Molecular Formula | C26H27NO10 |
| Purity | ≥95% |
Online Inquiry
Description
It is produced by the strain of Actinomadura carminata. Intravenous injection of 2 to 4 times of yangerythromycin (1.3-2.25mg) in mice could inhibit the growth of bronchial carcinoma, transplanted gastric cancer, lymphoid leukemia L-1210 and lymphosarcoma, but had poor effect on sarcoma-180 and lymphangiopathy, and had no effect on Eilinite ascites carcinoma.
Specification
| Related CAS | 52794-97-5 (hydrochloride) |
| Synonyms | Carubicin; Carminomicin; NSC 180024; KARMINOMYCIN; O-Demethyldaunomycin; (1S,3S)-3-acetyl-3,5,10,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside |
| Storage | Store at -20°C |
| IUPAC Name | (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C(=O)C)O)N)O |
| InChI | InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1 |
| InChI Key | XREUEWVEMYWFFA-CSKJXFQVSA-N |
Properties
| Appearance | Dark Red to Black Solid |
| Application | An antitumor antibiotic. |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 750.6 °C at 760 mmHg |
| Melting Point | 191-192 °C |
| Density | 1.63 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Ethanol |
Reference Reading
1. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells
Girma M Woldemichael, Thomas J Turbyville, W Marston Linehan, James B McMahon Cancer Res. 2011 Jan 1;71(1):134-42. doi: 10.1158/0008-5472.CAN-10-0757.
Clear cell renal cell carcinoma (CCRCC) evolves due to mutations in the Von Hippel-Lindau (VHL) tumor suppressor gene. Although the loss of VHL enables survival and proliferation of CCRCC cells, it is also expected to introduce vulnerabilities that may be exploited for therapeutics discovery. To this end, we developed a high-throughput screen to identify small molecules derived from plants, microorganisms, and marine organisms to which CCRCC cells are sensitive. Screening over 8,000 compounds using this approach, we report here the identification of the microbially derived compound carminomycin I (CA) as an effective inhibitor of VHL-defective (VHL(-/-)) CCRCC cell proliferation. CA also induced apoptosis in CCRCC cells by a mechanism independent of p53 or hypoxia-inducible factor 2. We found that P-glycoprotein (P-gp) sequestered CA within the Golgi complex. Interestingly, Golgi sequestration was critical for the antiproliferative effects of CA and P-gp inhibitors abrogated this activity. Furthermore, CA induced cleavage of the Golgi protein p115 and the translocation of its C-terminal fragment to the nucleus. Finally, examination of the activity of the VHL-interacting Golgi protein, endoplasmic reticulum-Golgi intermediate compartment, ERGIC-53 showed that VHL could mediate protection from CA in CCRCC cells. Our natural product-based screening approach has revealed the P-gp-mediated localization of anticancer compounds within the Golgi in CCRCC cells as a potential strategy of targeting VHL-deficient CCRCC cells.
2. Anthraquinone-induced cell injury: acute toxicity of carminomycin, epirubicin, idarubicin and mitoxantrone in isolated cardiomyocytes
B S Andersson, S Eksborg, R F Vidal, M Sundberg, M Carlberg Toxicology. 1999 Jul 1;135(1):11-20. doi: 10.1016/s0300-483x(99)00041-4.
Acute toxic effects of the antineoplastic anthraquinones carminomycin, epirubicin, idarubicin and mitoxantrone were studied in primary cultures of cardiomyocytes, which were isolated from adult rats. Both time- and concentration-dependent changes of cell structure and viability (trypan blue exclusion) following incubation of myocytes with subclinical, clinical and toxic concentrations of the anthraquinones were examined by light microscopy. The area under the decay curve of viable and rod-shaped myocytes was used to express cytotoxicity of the drugs. Mitoxantrone was found to reduce cell viability and number of rod-shaped cells to the greatest extent, followed by carminomycin, idarubicin and epirubicin. A significantly lower accumulation in cardiomyocytes was obtained with epirubicin and idarubicin compared with carminomycin. An inhibitory effect on oxygen consumption by the cells occurred already at 0.1 microM with epirubicin, whereas inhibition caused by other anthraquinones was less pronounced. Our data indicate a weak association of net accumulation and the toxicity parameter IC50 for carminomycin and idarubicin. In contrast to these results, a more significant correlation of cytotoxicity and anthraquinone lipophilicity was found, which suggests that the lipophilic character of a particular anthraquinone may be an important factor in drug-induced acute cardiotoxicity.
3. Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants
Anna N Tevyashova, Alexander A Shtil, Eugenia N Olsufyeva, Valeria S Simonova, Alexei V Samusenko, Maria N Preobrazhenskaya J Antibiot (Tokyo). 2004 Feb;57(2):143-50. doi: 10.7164/antibiotics.57.143.
The new hydrophilic derivatives of 14-hydroxycarminomycin were obtained using 13-dimethyl ketal of 14-bromocarminomycin (6) as the starting compound. The reductive alkylation of 6 with melibiose or D-galactose followed by hydrolysis of the corresponding intermediate bromoketals 9 and 11 produced 3'-N-[-alpha-D-(galactopyranosyl-(1 --> 6)-O-D-1-desoxyglucit-1-yl]-14-hydroxycarminomycin (10) and 3'-N-(1-desoxy-D-galactit-1-yl)-14-hydroxycarminomycin (12), respectively. These novel derivatives 10 and 12 were less toxic than carminomycin or 14-hydroxycarminomycin for leukemia (K562) and breast carcinoma (MCF-7) cells. Importantly, carminomycin, 14-hydroxycarminomycin and compounds 10 and 12 were similarly active for wild type cells and their multidrug resistant (MDR) sublines, K562i/S9 and MCF-7Dox.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
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 ╳
