WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406273
CAS#: 50935-04-1 (free base)
Description: Carubicin is an anthracycline antineoplastic antibiotic isolated from the bacterium Actinomadura carminata. Carubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis.
MedKoo Cat#: 406273
Name: Carubicin
CAS#: 50935-04-1 (free base)
Chemical Formula: C26H27NO10
Exact Mass: 513.1635
Molecular Weight: 513.49
Elemental Analysis: C, 60.81; H, 5.30; N, 2.73; O, 31.16
Related CAS #: 52794-97-5 (HCl) 50935-04-1 (free base)
Synonym: Antibiotic R 588A; Carminomicin I; Carminomycin I; Carubicin; carminomycin; Demethyldaunomycin; Karminomitsin; karminomycin; CMM.
IUPAC/Chemical Name: (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,6,8,11-tetrahydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChi Key: XREUEWVEMYWFFA-CSKJXFQVSA-N
InChi Code: 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
SMILES Code: O=C1C2=C(O)C([C@@H](O[C@@H]3O[C@@H](C)[C@@H](O)[C@@H](N)C3)C[C@](O)(C(C)=O)C4)=C4C(O)=C2C(C5=C1C(O)=CC=C5)=O
Appearance: Red solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: soluble in DMSO, not soluble in water.
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| In vitro activity: | CA (Carubicin) induced apoptosis in CCRCC (clear cell renal cell carcinoma) cells by a mechanism independent of p53 or hypoxia-inducible factor 2. 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. |
| In vivo activity: | TBD |
The following data is based on the product molecular weight 513.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Woldemichael GM, Turbyville TJ, Linehan WM, McMahon JB. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells. Cancer Res. 2011 Jan 1;71(1):134-42. doi: 10.1158/0008-5472.CAN-10-0757. PMID: 21199801; PMCID: PMC3074515. |
| In vitro protocol: | 1. Woldemichael GM, Turbyville TJ, Linehan WM, McMahon JB. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells. Cancer Res. 2011 Jan 1;71(1):134-42. doi: 10.1158/0008-5472.CAN-10-0757. PMID: 21199801; PMCID: PMC3074515. |
| In vivo protocol: | TBD |
1: Woldemichael GM, Turbyville TJ, Linehan WM, McMahon JB. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells. Cancer Res. 2011 Jan 1;71(1):134-42. doi: 10.1158/0008-5472.CAN-10-0757. PubMed PMID: 21199801; PubMed Central PMCID: PMC3074515.
2: Tevyashova AN, Shtil AA, Olsufyeva EN, Simonova VS, Samusenko AV, Preobrazhenskaya MN. Carminomycin, 14-hydroxycarminomycin and its novel carbohydrate derivatives potently kill human tumor cells and their multidrug resistant variants. J Antibiot (Tokyo). 2004 Feb;57(2):143-50. PubMed PMID: 15112963.
3: Toshchevikova AIu, Pisarev OA. [Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger]. Prikl Biokhim Mikrobiol. 2002 Mar-Apr;38(2):128-31. Russian. PubMed PMID: 11962206.
4: Andersson BS, Eksborg S, Vidal RF, Sundberg M, Carlberg M. Anthraquinone-induced cell injury: acute toxicity of carminomycin, epirubicin, idarubicin and mitoxantrone in isolated cardiomyocytes. Toxicology. 1999 Jul 1;135(1):11-20. PubMed PMID: 10454220.
5: Leont'eva OV, Trenin AS, Bukhman VM, Dudnik IuV. [The cytotoxicity of mevalonate, lovastatin and carminomycin with respect to MOLT-4 human malignant T-lymphoblasts in vitro]. Antibiot Khimioter. 1999;44(2):13-8. Russian. PubMed PMID: 10202552.
6: Csorvási A, Kövér KE, Menyhárt MM, Sztaricskai F, Dobrynin YV, Nikolaeva TG. Synthesis of phosphoramide mustard analogues of daunomycin and carminomycin. Arch Pharm (Weinheim). 1998 Sep;331(9):265-8. PubMed PMID: 9793480.
7: Scotti C, Hutchinson CR. Immobilization and properties of carminomycin 4-O-methyltranferase, the enzyme which catalyzes the final step in the biosynthesis of daunorubicin in Streptomyces peucetius. Biotechnol Bioeng. 1995 Oct 20;48(2):133-40. PubMed PMID: 18623469.
8: Madduri K, Torti F, Colombo AL, Hutchinson CR. Cloning and sequencing of a gene encoding carminomycin 4-O-methyltransferase from Streptomyces peucetius and its expression in Escherichia coli. J Bacteriol. 1993 Jun;175(12):3900-4. PubMed PMID: 8509343; PubMed Central PMCID: PMC204808.
