Carubicin free base | CAS#50935-04-1 | topoisomerase inhibitor

MedKoo Cat#: 406273 | Name: Carubicin free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Carubicin (IDN-540), a semisynthetic anthracycline analog of doxorubicin, exhibits potent antitumor activity by intercalating DNA and inhibiting topoisomerase II, leading to DNA strand breaks and apoptosis. In preclinical studies, Carubicin demonstrated strong cytotoxicity against various human cancer cell lines, including colon, lung, and breast carcinomas, with IC₅₀ values typically in the low micromolar range (e.g., 0.2–1.5 μM depending on the cell line). Notably, Carubicin showed less cardiotoxicity compared to doxorubicin in animal models while retaining comparable efficacy. It has been evaluated in clinical settings, particularly for bladder cancer via intravesical administration, showing favorable tolerability and antitumor response rates in patients with superficial transitional cell carcinoma.

Chemical Structure

Carubicin free base

CAS#50935-04-1 (free base)

Theoretical Analysis

MedKoo Cat#: 406273

Name: Carubicin free base

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

Price and Availability

Size	Price	Availability
5mg	USD 250.00	Ready to ship
10mg	USD 450.00	Ready to ship
25mg	USD 950.00	Ready to ship
50mg	USD 1,650.00	Ready to ship
100mg	USD 2,950.00	Ready to ship
200mg	USD 5,250.00	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; IDN-540; IDN 540; IDN540;

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TZC50604

QC Data

View QC data: current batch, Lot#TZC50604

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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.

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:

In vivo protocol:

TBD

1: Bakari C, Mandara CI, Madebe RA, Seth MD, Ngasala B, Kamugisha E, Ahmed M, Francis F, Bushukatale S, Chiduo M, Makene T, Kabanywanyi AM, Mahende MK, Kavishe RA, Muro F, Mkude S, Mandike R, Molteni F, Chacky F, Bishanga DR, Njau RJA, Warsame M, Kabula B, Nyinondi SS, Lucchi NW, Talundzic E, Venkatesan M, Moriarty LF, Serbantez N, Kitojo C, Reaves EJ, Halsey ES, Mohamed A, Udhayakumar V, Ishengoma DS. Trends of Plasmodium falciparum molecular markers associated with resistance to artemisinins and reduced susceptibility to lumefantrine in Mainland Tanzania from 2016 to 2021. Malar J. 2024 Mar 9;23(1):71. doi: 10.1186/s12936-024-04896-0. PMID: 38461239; PMCID: PMC10924419. 2: Cheng W, Meng X, Gao J, Jiang W, Sun X, Li Y, Han T, Zhang D, Wei W. Relationship between circadian eating behavior (daily eating frequency and nighttime fasting duration) and cardiovascular mortality. Int J Behav Nutr Phys Act. 2024 Feb 26;21(1):22. doi: 10.1186/s12966-023-01556-5. PMID: 38409117; PMCID: PMC10895826. 3: Razzouk J, Case T, Brandt Z, Marciniak M, Sajdak G, Nguyen K, Small E, Petersen G, Kagabo W, Ramos O, Shaffrey CI, Cheng W, Danisa O. Normative Measurements of L1-S1 Segmental Angulation, Disk Space Height, and Neuroforaminal Dimensions Using Computed Tomography. Neurosurgery. 2024 Apr 1;94(4):813-827. doi: 10.1227/neu.0000000000002761. Epub 2023 Nov 30. PMID: 38032205. 4: Razzouk J, Carter D, Carter M, Vyhmeister E, Kagabo W, Ramos O, Douglas C, Wycliffe N, Cheng W, Danisa O. Comparison of L1-S1 neuroforaminal dimensions derived from plain film radiography versus computed tomography. Eur Spine J. 2024 Jan;33(1):93-102. doi: 10.1007/s00586-023-08005-8. Epub 2023 Nov 4. PMID: 37925378. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: 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. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: 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. 17: 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. 18: Brandes AA, Pasetto LM, Monfardini S. New drugs in recurrent high grade gliomas. Anticancer Res. 2000 May-Jun;20(3B):1913-20. PMID: 10928126. 19: 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. 20: 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.