WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H406273
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.
Hodoodo Cat#: H406273
Name: Carubicin
CAS#: 50935-04-1 (free base)
Chemical Formula: C26H27NO10
Exact Mass: 513.16
Molecular Weight: 513.490
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
More Info:
Biological target: | |
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. PMID: 21199801; PMCID: PMC3074515.
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10: Mima T, Mostafa MG, Mori K. Antitumor effect and peritumoral brain edema formation in relation to MX2, ACNU, and doxorubicin therapy: a comparative analysis using rodent models of gliomas. Neurol Res. 2000 Dec;22(8):819-24. doi: 10.1080/01616412.2000.11740759. PMID: 11149245.
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14: Brandes AA, Pasetto LM, Monfardini S. New drugs in recurrent high grade gliomas. Anticancer Res. 2000 May-Jun;20(3B):1913-20. PMID: 10928126.
15: Park SJ, Kaye AH, Hill JS. An investigation of the cytotoxicity of the morpholino anthracycline MX2 against glioma cells in vitro. J Clin Neurosci. 2000 Jan;7(1):42-7. doi: 10.1054/jocn.1998.0131. PMID: 10847650.
16: Clarke K, Basser RL, Underhill C, Mitchell P, Bartlett J, Cher L, Findlay M, Dalley D, Pell M, Byrne M, Geldard H, Hill JS, Maher D, Fox RM, Green MD, Kaye AH. KRN8602 (MX2-hydrochloride): an active new agent for the treatment of recurrent high-grade glioma. J Clin Oncol. 1999 Aug;17(8):2579-84. doi: 10.1200/JCO.1999.17.8.2579. PMID: 10561325.
17: 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. doi: 10.1016/s0300-483x(99)00041-4. PMID: 10454220.
18: Takemoto Y, Sampi K, Kuraishi Y, Okabe K, Tamura K, Mizoguchi H, Saito H, Masaoka T, Ogawa M. A prospective randomized trial of KRN8602 and cytosine arabinoside vs. daunorubicin and cytosine arabinoside in adult patients with newly diagnosed acute myelogenous leukemia. The KRN8602 Leukemia Study Group. Int J Hematol. 1999 Jul;70(1):20-5. PMID: 10446490.
19: Andreeva SV. Ispol'zovanie nekotorykh pokazateleĭ iadryshkovogo apparata leĭkoznykh kletok bol'nykh ostrym mieloblastnym leĭkozom dlia rannego vyiavleniia rezistentnykh klonov [The use of the nucleolar apparatus indices of the leukemic cells in patients with acute myeloblastic leukemia for the early detection of resistant clones]. Lik Sprava. 1999 Mar;(2):77-80. Russian. PMID: 10424049.
20: Kuratsu J, Arita N, Kurisu K, Uozumi T, Hayakawa T, Ushio Y. A phase II study of KRN8602(MX2), a novel morpholino anthracycline derivative, in patients with recurrent malignant glioma. J Neurooncol. 1999 Apr;42(2):177-81. doi: 10.1023/a:1006118800753. PMID: 10421076.