WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100012
CAS#: 75443-99-1 (HCl)
Description: Aclarubicin is an oligosaccharide anthracycline antineoplastic antibiotic isolated from the bacterium Streptomyces galilaeus. Aclarubicin intercalates into DNA and interacts with topoisomerases I and II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. Aclarubicin is antagonistic to other agents that inhibit topoisomerase II, such as etoposide, teniposide and amsacrine. This agent is less cardiotoxic than doxorubicin and daunorubicin.
MedKoo Cat#: 100012
Name: Aclarubicin hydrochloride
CAS#: 75443-99-1 (HCl)
Chemical Formula: C42H54ClNO15
Exact Mass: 847.32
Molecular Weight: 848.34
Elemental Analysis: C, 59.46; H, 6.42; Cl, 4.18; N, 1.65; O, 28.29
Related CAS #: 75443-99-1 (HCl); 57576-44-0 (free base).
Synonym: Aclacinomycin; Aclacinomycin A hydrochloride; Aclarubicin Hydrochloride; Antibiotic MA144A1. Aclacin; Aclacinomycine; Aclacinon; Aclaplastin; Jaclacin. ACM; ACMA. MA144A1
IUPAC/Chemical Name: (1R,2R,4S)-methyl 4-(((2R,5S,6S)-4-(dimethylamino)-5-(((2S,4S,5S,6S)-4-hydroxy-6-methyl-5-(((2R,6S)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate hydrochloride
InChi Key: KUSMIBXCRZTVML-ZRMZNYNWSA-N
InChi Code: InChI=1S/C42H53NO15.ClH/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29;/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3;1H/t18-,19-,20-,24?,27-,28-,29-,30-,31-,35-,39+,40+,42+;/m0./s1
SMILES Code: O=C([C@H]1[C@@](O)(CC)C[C@H](O[C@H]2CC(N(C)C)[C@H](O[C@H]3C[C@H](O)[C@H](O[C@H]4CCC([C@H](C)O4)=O)[C@H](C)O3)[C@H](C)O2)C5=C(O)C6=C(C(C7=CC=CC(O)=C7C6=O)=O)C=C15)OC.[H]Cl
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 in water
Shelf Life: >2 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
| Biological target: | Aclacinomycin A hydrochloride (Aclarubicin hydrochloride) shows discrete specificity for the CTRL (chymotrypsin-like) activity of the 20S proteasome. Aclacinomycin A hydrochloride is also a dual inhibitor of topoisomerase I and II. |
| In vitro activity: | ACR-induced apoptosis was assessed by caspase-3/7 activity. The caspase-3/7 activity after 6-h ACR treatment was remarkably increased at 0.2 and 0.5 μM in HL-60 cells (0.2 μM, p<0.01; 0.5 μM, p<0.001), and at 0.5 μM in HP100 cells (p<0.001). Caspase-3/7 in HL-60 cells had significant higher activity than that in HP100 cells at 0.2 and 0.5 μM (Figure 2B) (0.2 μM, p<0.001; 0.5 μM, p<0.05). These events were in good agreement with DNA ladder formation induced by ACR. Reference: Anticancer Res. 2019 Jul;39(7):3443-3451. https://pubmed.ncbi.nlm.nih.gov/31262868/ |
| In vivo activity: | TBD |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 125.0 | 147.35 |
The following data is based on the product molecular weight 848.34 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. Mizutani H, Hayashi Y, Hashimoto M, Imai M, Ichimaru Y, Kitamura Y, Ikemura K, Miyazawa D, Ohta K, Ikeda Y, Maeda T, Yoshikawa M, Hiraku Y, Kawanishi S. Oxidative DNA Damage and Apoptosis Induced by Aclarubicin, an Anthracycline: Role of Hydrogen Peroxide and Copper. Anticancer Res. 2019 Jul;39(7):3443-3451. doi: 10.21873/anticanres.13490. PMID: 31262868. 2. Gajek A, Rogalska A, Koceva-Chyła A. Aclarubicin in subtoxic doses reduces doxorubicin cytotoxicity in human non-small cell lung adenocarcinoma (A549) and human hepatocellular carcinoma (HepG2) cells by decreasing DNA damage. Toxicol In Vitro. 2019 Mar;55:140-150. doi: 10.1016/j.tiv.2018.12.015. Epub 2018 Dec 20. PMID: 30579959. |
| In vitro protocol: | 1. Mizutani H, Hayashi Y, Hashimoto M, Imai M, Ichimaru Y, Kitamura Y, Ikemura K, Miyazawa D, Ohta K, Ikeda Y, Maeda T, Yoshikawa M, Hiraku Y, Kawanishi S. Oxidative DNA Damage and Apoptosis Induced by Aclarubicin, an Anthracycline: Role of Hydrogen Peroxide and Copper. Anticancer Res. 2019 Jul;39(7):3443-3451. doi: 10.21873/anticanres.13490. PMID: 31262868. 2. Gajek A, Rogalska A, Koceva-Chyła A. Aclarubicin in subtoxic doses reduces doxorubicin cytotoxicity in human non-small cell lung adenocarcinoma (A549) and human hepatocellular carcinoma (HepG2) cells by decreasing DNA damage. Toxicol In Vitro. 2019 Mar;55:140-150. doi: 10.1016/j.tiv.2018.12.015. Epub 2018 Dec 20. PMID: 30579959. |
| In vivo protocol: | TBD |
1: Shin DH, Choi KS, Park SA, Cho BS, Lee HS, Ryu JS, Kim TY, Lee CK, Song S, Chung YB. Extensive intracellular accumulation of ID-6105, a novel anthracycline, in SK-OV-3 ovarian cancer cells. Arch Pharm Res. 2008 Oct;31(10):1355-61. Epub 2008 Oct 29. PubMed PMID: 18958428.
2: Swift LP, Cutts SM, Nudelman A, Levovich I, Rephaeli A, Phillips DR. The cardio-protecting agent and topoisomerase II catalytic inhibitor sobuzoxane enhances doxorubicin-DNA adduct mediated cytotoxicity. Cancer Chemother Pharmacol. 2008 Apr;61(5):739-49. Epub 2007 Jun 27. PubMed PMID: 17594094.
3: Zhu H, Huang M, Yang F, Chen Y, Miao ZH, Qian XH, Xu YF, Qin YX, Luo HB, Shen X, Geng MY, Cai YJ, Ding J. R16, a novel amonafide analogue, induces apoptosis and G2-M arrest via poisoning topoisomerase II. Mol Cancer Ther. 2007 Feb;6(2):484-95. PubMed PMID: 17308047.
4: Koceva-Chyła A, Wiecławska B, Jóźwiak Z, Bryszewska M. Combined effect of low-power laser irradiation and anthraquinone anticancer drug aclarubicin on survival of immortalized cells: Comparison with mitoxantrone. Cell Biol Int. 2006 Aug;30(8):645-52. Epub 2006 Apr 25. PubMed PMID: 16857396.
5: Goodell JR, Madhok AA, Hiasa H, Ferguson DM. Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity. Bioorg Med Chem. 2006 Aug 15;14(16):5467-80. Epub 2006 May 19. PubMed PMID: 16713270.
6: Liao Z, Thibaut L, Jobson A, Pommier Y. Inhibition of human tyrosyl-DNA phosphodiesterase by aminoglycoside antibiotics and ribosome inhibitors. Mol Pharmacol. 2006 Jul;70(1):366-72. Epub 2006 Apr 17. PubMed PMID: 16618796.
7: Koceva-Chyła A, Jedrzejczak M, Skierski J, Kania K, Jóźwiak Z. Mechanisms of induction of apoptosis by anthraquinone anticancer drugs aclarubicin and mitoxantrone in comparison with doxorubicin: relation to drug cytotoxicity and caspase-3 activation. Apoptosis. 2005 Dec;10(6):1497-514. PubMed PMID: 16215684.
8: Wang T, Chen FY, Gu CH, Zhong H, Teng Y, Ouyang RR. [Transfection of HL-60 cells with CYP3A5 gene induces drug-resistant phenotype]. Zhonghua Zhong Liu Za Zhi. 2005 Aug;27(8):461-4. Chinese. PubMed PMID: 16188140.
9: Ryu JS, Lee HS, Hong YS, Lee JJ, Sohn UD, Kim TY. In vivo antitumor efficacy and cardiotoxicity of novel anthracycline ID6105 (11-hydroxy-aclacinomycin X, Hyrubicin). Cancer Chemother Pharmacol. 2006 Jun;57(6):811-8. Epub 2005 Sep 21. Erratum in: Cancer Chemother Pharmacol. 2007 Feb;59(2):283-4. PubMed PMID: 16175393.
10: Lehmann M, Vilar Kde S, Franco A, Reguly ML, Rodrigues de Andrade HH. Activity of topoisomerase inhibitors daunorubicin, idarubicin, and aclarubicin in the Drosophila Somatic Mutation and Recombination Test. Environ Mol Mutagen. 2004;43(4):250-7. PubMed PMID: 15141364.
