Carubicin
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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.


Chemical Structure

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Carubicin
CAS# 50935-04-1 (free base)

Theoretical Analysis

MedKoo Cat#: 406273
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

Price and Availability

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5mg USD 250 Ready to ship
10mg USD 450 Ready to ship
25mg USD 950 Ready to ship
50mg USD 1650 Ready to ship
100mg USD 2950 Ready to ship
200mg USD 5250 Ready to ship
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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

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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

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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.


2: Dezhenkova LG, Teviashova AN, Olsuf'eva EN, Treshchalin ID, Shtil' AA, Preobrazhenskaia MN. [Anthracycline antibiotics and their derivatives-- inhibitors of topoisomerase I]. Bioorg Khim. 2008 May-Jun;34(3):430-2. Russian. doi: 10.1134/s1068162008030230. PMID: 18672696.


3: Asano T, Nakamura K, Fujii H, Horichi N, Ohmori T, Hasegawa K, Isoe T, Adachi M, Otake N, Fukunaga Y. Altered expression of topoisomerase IIalpha contributes to cross-resistant to etoposide K562/MX2 cell line by aberrant methylation. Br J Cancer. 2005 Apr 25;92(8):1486-92. doi: 10.1038/sj.bjc.6602498. PMID: 15798770; PMCID: PMC2362017.


4: 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. doi: 10.7164/antibiotics.57.143. PMID: 15112963.


5: Prokof'eva NG, Anisimov MM, Kiseleva MI, Rebachuk NM, Pokhilo ND. Tsitotoksicheskoe deĭstvie dammaranovykh triterpenoidov, vydelennykh iz list'ev berez [Cytotoxic activity of dammarane triterpenoids from birch leaves]. Izv Akad Nauk Ser Biol. 2002 Nov-Dec;(6):645-9. Russian. PMID: 12561324.


6: Toshchevikova AIu, Pisarev OA. Optimizatsiia usloviĭ preparativnoĭ khromatografii karminomitsina na karboksil'nom kationite [Optimization of conditions of preparative chromatography of carminomycin on a carboxylic cation exchanger]. Prikl Biokhim Mikrobiol. 2002 Mar-Apr;38(2):128-31. Russian. PMID: 11962206.


7: Monneret C. Recent developments in the field of antitumour anthracyclines. Eur J Med Chem. 2001 Jun;36(6):483-93. doi: 10.1016/s0223-5234(01)01244-2. PMID: 11525839.


8: Capobianco ML, De Champdoré M, Francini L, Lena S, Garbesi A, Arcamone F. New TFO conjugates containing a carminomycinone-derived chromophore. Bioconjug Chem. 2001 Jul-Aug;12(4):523-8. doi: 10.1021/bc000139z. PMID: 11459456.


9: Cutts SM, Parker BS, Swift LP, Kimura KI, Phillips DR. Structural requirements for the formation of anthracycline-DNA adducts. Anticancer Drug Des. 2000 Oct;15(5):373-86. PMID: 11354313.


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.


11: Mizumatsu S, Matsumoto K, Ono Y, Tamiya T, Furuta T, Ohmoto T. Intrathecal chemotherapy with MX2 for treating glioma dissemination in vivo. J Neurooncol. 2000 Aug;49(1):41-7. doi: 10.1023/a:1006436911670. PMID: 11131985.


12: Kuratsu JI, Arita N, Kayama T, Kubo N, Mori T, Sawamura Y, Ushio Y. Phase II trial of pre-irradiation KRN8602 (MX2) in malignant glioma patients. J Neurooncol. 2000 Jun;48(2):145-9. doi: 10.1023/a:1006482006138. PMID: 11083079.


13: Lutsenko SV, Feldman NB, Finakova GV, Gukasova NV, Petukhov SP, Posypanova GA, Skryabin KG, Severin SE. Antitumor activity of alpha fetoprotein and epidermal growth factor conjugates in vitro and in vivo. Tumour Biol. 2000 Nov- Dec;21(6):367-74. doi: 10.1159/000030142. PMID: 11006577.


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.