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MedKoo Cat#: 571571 | Name: Aclacinomycin

Description:

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

Aclacinomycin A[1] is an anthracycline drug[2] that is used in the treatment of cancer. It sensitizes K562 chronic myeloid leukemia cells to imatinib through p38MAPK-mediated erythroid differentiation.

Chemical Structure

Aclacinomycin
CAS#66676-88-8

Theoretical Analysis

MedKoo Cat#: 571571

Name: Aclacinomycin

CAS#: 66676-88-8

Chemical Formula: C30H35NO10

Exact Mass: 569.2261

Molecular Weight: 569.61

Elemental Analysis: C, 63.26; H, 6.19; N, 2.46; O, 28.09

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Aclacinomycins; Siwenmycin
IUPAC/Chemical Name
methyl (1R,2R,4S)-4-(((2R,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-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
InChi Key
LJZPVWKMAYDYAS-QKKPTTNWSA-N
InChi Code
InChI=1S/C30H35NO10/c1-6-30(38)12-19(41-20-11-17(31(3)4)25(33)13(2)40-20)22-15(24(30)29(37)39-5)10-16-23(28(22)36)27(35)21-14(26(16)34)8-7-9-18(21)32/h7-10,13,17,19-20,24-25,32-33,36,38H,6,11-12H2,1-5H3/t13-,17-,19-,20-,24-,25+,30+/m0/s1
SMILES Code
OC1=CC=CC2=C1C(C3=C(O)C([C@@H](O[C@H]4C[C@H](N(C)C)[C@H](O)[C@H](C)O4)C[C@](O)(CC)[C@@H]5C(OC)=O)=C5C=C3C2=O)=O
Appearance
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 569.61 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
1: Bundale S, Begde D, Pillai D, Gangwani K, Nashikkar N, Kadam T, Upadhyay A. Novel aromatic polyketides from soil Streptomyces spp.: purification, characterization and bioactivity studies. World J Microbiol Biotechnol. 2018 Apr 24;34(5):67. doi: 10.1007/s11274-018-2448-1. PubMed PMID: 29691661. 2: Lee YL, Chen CW, Liu FH, Huang YW, Huang HM. Correction: Aclacinomycin A Sensitizes K562 Chronic Myeloid Leukemia Cells to Imatinib through p38MAPK-Mediated Erythroid Differentiation. PLoS One. 2017 Oct 11;12(10):e0186528. doi: 10.1371/journal.pone.0186528. eCollection 2017. PubMed PMID: 29020096; PubMed Central PMCID: PMC5636156. 3: Ye YB, Xu XJ, Chen YH, Zhang MW, Qiu DF, Guo ZW, He HQ. [Synergistic lethal effect of combined treatment of arsenic trioxide and aclacinomycin on human acute myeloid leukemia cell line KG-1a]. Zhonghua Zhong Liu Za Zhi. 2017 Apr 23;39(4):256-262. doi: 10.3760/cma.j.issn.0253-3766.2017.04.004. Chinese. PubMed PMID: 28550664. 4: Sakai T, Miyazaki T, Shin DM, Kim YS, Qi CF, Fariss R, Munasinghe J, Wang H, Kovalchuk AL, Kothari PH, Fermaintt CS, Atkinson JP, Perrino FW, Yan N, Morse HC 3rd. DNase-active TREX1 frame-shift mutants induce serologic autoimmunity in mice. J Autoimmun. 2017 Jul;81:13-23. doi: 10.1016/j.jaut.2017.03.001. Epub 2017 Mar 18. PubMed PMID: 28325644; PubMed Central PMCID: PMC5558601. 5: Ye L, Ren Y, Zhou X, Mei C, Ma L, Ye X, Wei J, Xu W, Meng H, Qian W, Mai W, Lou Y, Xu G, Qian J, Lou Y, Luo Y, Xie L, Lin P, Hu C, Jin J, Tong H. Decitabine priming prior to low-dose chemotherapy improves patient outcomes in myelodysplastic syndromes-RAEB: a retrospective analysis vs. chemotherapy alone. J Cancer Res Clin Oncol. 2017 May;143(5):873-882. doi: 10.1007/s00432-016-2331-0. Epub 2017 Jan 20. PubMed PMID: 28108816; PubMed Central PMCID: PMC5384967. 6: Gong G, Liu W, Wang S. Self-assembled albumin nanoparticles as a nanocarrier for aclacinomycin A. Nanotechnology. 2016 Nov 18;27(46):465602. Epub 2016 Oct 17. PubMed PMID: 27749275. 7: Beattie RJ, Hornsby TW, Craig G, Galan MC, Willis CL. Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations. Chem Sci. 2016 Apr 21;7(4):2743-2747. doi: 10.1039/c5sc04144a. Epub 2016 Jan 11. PubMed PMID: 28660050; PubMed Central PMCID: PMC5477037. 8: Fan C, Yu W, Mai W, Meng H, Qian W, Tong H, Huang J, Mao L, Suo S, Jin J. [Efficacy of HAA regimen in the treatment of 64 patients with refractory/relapsed acute myeloid leukemia]. Zhonghua Xue Ye Xue Za Zhi. 2016 Feb;37(2):100-4. doi: 10.3760/cma.j.issn.0253-2727.2016.02.003. Chinese. PubMed PMID: 27014977. 9: Ding B, Wang Z, Jiang X, Li X, Wang C, Zhong Q, Jiang L, Dai M, Zhang YU, Wei QI, Meng F. Palliative chemotherapy followed by methylation inhibitor in high-risk acute myeloid leukemia: An in vitro and clinical study. Mol Clin Oncol. 2015 Sep;3(5):1139-1144. Epub 2015 Jul 21. PubMed PMID: 26623066; PubMed Central PMCID: PMC4534877. 10: Furusawa H, Nakayama H, Funasaki M, Okahata Y. Kinetic characterization of small DNA-binding molecules interacting with a DNA strand on a quartz crystal microbalance. Anal Biochem. 2016 Jan 1;492:34-42. doi: 10.1016/j.ab.2015.09.015. Epub 2015 Sep 25. PubMed PMID: 26408811. 11: Hasan M, Fermaintt CS, Gao N, Sakai T, Miyazaki T, Jiang S, Li QZ, Atkinson JP, Morse HC 3rd, Lehrman MA, Yan N. Cytosolic Nuclease TREX1 Regulates Oligosaccharyltransferase Activity Independent of Nuclease Activity to Suppress Immune Activation. Immunity. 2015 Sep 15;43(3):463-74. doi: 10.1016/j.immuni.2015.07.022. Epub 2015 Aug 25. PubMed PMID: 26320659; PubMed Central PMCID: PMC4575271. 12: Feng C, Li X, Dong C, Zhang X, Zhang X, Gao Y. RGD-modified liposomes enhance efficiency of aclacinomycin A delivery: evaluation of their effect in lung cancer. Drug Des Devel Ther. 2015 Aug 11;9:4613-20. doi: 10.2147/DDDT.S85993. eCollection 2015. PubMed PMID: 26316700; PubMed Central PMCID: PMC4541546. 13: Yang XL, Wu YM, Cao YB, Li XH, Xu LX, Liu ZY, Liu B, Yan B, Li SW, DA WM, Wu XX. [Clinical Efficacy of Decitabine Combined with CAG Regimen for Myelodysplastic Syndrome-RAEB and Refractory Acute Myeloid Leukemia]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2015 Aug;23(4):1056-61. doi: 10.7534/j.issn.1009-2137.2015.04.030. Chinese. PubMed PMID: 26314446. 14: Grocholski T, Dinis P, Niiranen L, Niemi J, Metsä-Ketelä M. Divergent evolution of an atypical S-adenosyl-l-methionine-dependent monooxygenase involved in anthracycline biosynthesis. Proc Natl Acad Sci U S A. 2015 Aug 11;112(32):9866-71. doi: 10.1073/pnas.1501765112. Epub 2015 Jul 27. PubMed PMID: 26216966; PubMed Central PMCID: PMC4538628. 15: Ma XR, Wang J, Zhang WG, Chen YX, Cao XM, He AL, Liu J, Wang JL, Gu LF, Lei B, Zhang PY, Zhao WH, Yang Y, Wang FX, Xu Y. [Cohort Study on GHA and New Combined Priming Chemotherapeutic Regimens in Treatment of Refractory Acute Myeloid Leukemia and Myelodysplastic Syndrome]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2015 Apr;23(2):369-74. doi: 10.7534/j.issn.1009-2137.2015.02.014. Chinese. PubMed PMID: 25948187. 16: Goussetis DJ, Platanias LC. Synergism between arsenic trioxide and aclacinomycin in acute myeloid leukemia. Leuk Lymphoma. 2015;56(11):3010-1. doi: 10.3109/10428194.2015.1044450. Epub 2015 Jun 18. PubMed PMID: 25942383. 17: Ye Y, Xu X, Zhang M, Qiu D, Bai X, Wang J, Weng G, Zhou R, Guo Z, He H, Yi W, He X, Guo K. Low-dose arsenic trioxide combined with aclacinomycin A synergistically enhances the cytotoxic effect on human acute myelogenous leukemia cell lines by induction of apoptosis. Leuk Lymphoma. 2015;56(11):3159-67. doi: 10.3109/10428194.2015.1011155. Epub 2015 Jun 19. PubMed PMID: 25739941. 18: Zheng C, Cai X, Wu S, Liu Z, Shi Y, Zhou W. Enhancing effect of β-elemene emulsion on chemotherapy with harringtonine, aclacinomycin, and Ara-c in treatment of refractory/relapsed acute myeloid leukemia. Pak J Med Sci. 2014 Nov-Dec;30(6):1270-2. doi: 10.12669/pjms.306.5207. PubMed PMID: 25674121; PubMed Central PMCID: PMC4320713. 19: Cullen S, Ponnappan S, Ponnappan U. Redox-regulated pathway of tyrosine phosphorylation underlies NF-κB induction by an atypical pathway independent of the 26S proteasome. Biomolecules. 2015 Feb 9;5(1):95-112. doi: 10.3390/biom5010095. PubMed PMID: 25671697; PubMed Central PMCID: PMC4384113. 20: Shen M, Sun WJ, Huang ZX, Zhang JJ, An N, Li X. Partial remission of acute myeloid leukemia complicating multiple myeloma following COAP chemotherapy: A case report. Oncol Lett. 2015 Mar;9(3):1303-1306. Epub 2015 Jan 12. PubMed PMID: 25663902; PubMed Central PMCID: PMC4315064.

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