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MedKoo Cat#: 592294 | Name: Lucanthone hydrochloride

Description:

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

Lucanthone hydrochloride is a novel acridine derivative which inhibits autophagic degradation and triggers apoptosis in colon cancer cells.

Chemical Structure

Lucanthone hydrochloride
Lucanthone hydrochloride
CAS#548-57-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 592294

Name: Lucanthone hydrochloride

CAS#: 548-57-2 (HCl)

Chemical Formula: C20H25ClN2OS

Exact Mass: 376.1376

Molecular Weight: 376.94

Elemental Analysis: C, 63.73; H, 6.69; Cl, 9.40; N, 7.43; O, 4.24; S, 8.51

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 #
479-50-5 (free base) 548-57-2 (HCl)
Synonym
BW 57-233; Lucanthone hydrochloride; Lucanthone monohydrochloride; Miracil D; Miracol; Ms. 752; Nilodin; NSC 14574; RP 3735; Scapuren; Tixantone
IUPAC/Chemical Name
9H-Thioxanthen-9-one, 1-((2-(diethylamino)ethyl)amino)-4-methyl-, monohydrochloride
InChi Key
LAOOXBLMIJHMFO-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H24N2OS.ClH/c1-4-22(5-2)13-12-21-16-11-10-14(3)20-18(16)19(23)15-8-6-7-9-17(15)24-20;/h6-11,21H,4-5,12-13H2,1-3H3;1H
SMILES Code
O=C1C2=C(SC3=C1C=CC=C3)C(C)=CC=C2NCCN(CC)CC.[H]Cl
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lucanthone hydrochloride is a novel acridine derivative which inhibits autophagic degradation.
In vitro activity:
Lucanthone downregulated protein expression of deubiquitinase DUB3, and a decreased expression level of DUB3 markedly led to enhance TRAIL-induced apoptosis. Moreover, lucanthone increased expression level of DR5 mRNA via downregulation of miR-216a-5p. Reference: Int J Mol Sci. 2021 Dec 21;23(1):17. https://pubmed.ncbi.nlm.nih.gov/35008442/
In vivo activity:
In vivo lucanthone slowed mouse tumor growth: reduced numbers of Olig2+ glioma cells, normalized tumor vasculature, and reduced tumor hypoxia. Reference: Front Oncol. 2022 Apr 14;12:852940. https://pubmed.ncbi.nlm.nih.gov/35494072/

Preparing Stock Solutions

The following data is based on the product molecular weight 376.94 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. Yoon JY, Woo SM, Seo SU, Song SR, Lee SG, Kwon TK. Lucanthone, Autophagy Inhibitor, Enhances the Apoptotic Effects of TRAIL through miR-216a-5p-Mediated DR5 Upregulation and DUB3-Mediated Mcl-1 Downregulation. Int J Mol Sci. 2021 Dec 21;23(1):17. doi: 10.3390/ijms23010017. PMID: 35008442; PMCID: PMC8744864. 2. Radin DP, Smith G, Moushiaveshi V, Wolf A, Bases R, Tsirka SE. Lucanthone Targets Lysosomes to Perturb Glioma Proliferation, Chemoresistance and Stemness, and Slows Tumor Growth In Vivo. Front Oncol. 2022 Apr 14;12:852940. doi: 10.3389/fonc.2022.852940. PMID: 35494072; PMCID: PMC9048484. 3. Radin DP, Smith G, Moushiaveshi V, Wolf A, Bases R, Tsirka SE. Lucanthone Targets Lysosomes to Perturb Glioma Proliferation, Chemoresistance and Stemness, and Slows Tumor Growth In Vivo. Front Oncol. 2022 Apr 14;12:852940. doi: 10.3389/fonc.2022.852940. PMID: 35494072; PMCID: PMC9048484. 4. Carew JS, Espitia CM, Esquivel JA 2nd, Mahalingam D, Kelly KR, Reddy G, Giles FJ, Nawrocki ST. Lucanthone is a novel inhibitor of autophagy that induces cathepsin D-mediated apoptosis. J Biol Chem. 2011 Feb 25;286(8):6602-13. doi: 10.1074/jbc.M110.151324. Epub 2010 Dec 10. PMID: 21148553; PMCID: PMC3057822.
In vitro protocol:
1. Yoon JY, Woo SM, Seo SU, Song SR, Lee SG, Kwon TK. Lucanthone, Autophagy Inhibitor, Enhances the Apoptotic Effects of TRAIL through miR-216a-5p-Mediated DR5 Upregulation and DUB3-Mediated Mcl-1 Downregulation. Int J Mol Sci. 2021 Dec 21;23(1):17. doi: 10.3390/ijms23010017. PMID: 35008442; PMCID: PMC8744864. 2. Radin DP, Smith G, Moushiaveshi V, Wolf A, Bases R, Tsirka SE. Lucanthone Targets Lysosomes to Perturb Glioma Proliferation, Chemoresistance and Stemness, and Slows Tumor Growth In Vivo. Front Oncol. 2022 Apr 14;12:852940. doi: 10.3389/fonc.2022.852940. PMID: 35494072; PMCID: PMC9048484.
In vivo protocol:
1. Radin DP, Smith G, Moushiaveshi V, Wolf A, Bases R, Tsirka SE. Lucanthone Targets Lysosomes to Perturb Glioma Proliferation, Chemoresistance and Stemness, and Slows Tumor Growth In Vivo. Front Oncol. 2022 Apr 14;12:852940. doi: 10.3389/fonc.2022.852940. PMID: 35494072; PMCID: PMC9048484. 2. Carew JS, Espitia CM, Esquivel JA 2nd, Mahalingam D, Kelly KR, Reddy G, Giles FJ, Nawrocki ST. Lucanthone is a novel inhibitor of autophagy that induces cathepsin D-mediated apoptosis. J Biol Chem. 2011 Feb 25;286(8):6602-13. doi: 10.1074/jbc.M110.151324. Epub 2010 Dec 10. PMID: 21148553; PMCID: PMC3057822.
1: Fu W, Li X, Lu X, Zhang L, Li R, Zhang N, Liu S, Yang X, Wang Y, Zhao Y, Meng X, Zhu WG. A novel acridine derivative, LS-1-10 inhibits autophagic degradation and triggers apoptosis in colon cancer cells. Cell Death Dis. 2017 Oct 5;8(10):e3086. doi: 10.1038/cddis.2017.498. PubMed PMID: 28981103; PubMed Central PMCID: PMC5682664. 2: Laev SS, Salakhutdinov NF, Lavrik OI. Inhibitors of nuclease and redox activity of apurinic/apyrimidinic endonuclease 1/redox effector factor 1 (APE1/Ref-1). Bioorg Med Chem. 2017 May 1;25(9):2531-2544. doi: 10.1016/j.bmc.2017.01.028. Epub 2017 Jan 21. Review. PubMed PMID: 28161249. 3: Carew JS, Nawrocki ST. Drain the lysosome: Development of the novel orally available autophagy inhibitor ROC-325. Autophagy. 2017 Apr 3;13(4):765-766. doi: 10.1080/15548627.2017.1280222. Epub 2017 Jan 24. PubMed PMID: 28118053; PubMed Central PMCID: PMC5388230. 4: Lima RT, Sousa D, Paiva AM, Palmeira A, Barbosa J, Pedro M, Pinto MM, Sousa E, Vasconcelos MH. Modulation of Autophagy by a Thioxanthone Decreases the Viability of Melanoma Cells. Molecules. 2016 Oct 10;21(10). pii: E1343. PubMed PMID: 27735867. 5: Mulholland K, Wu C. Computational Study of Anticancer Drug Resistance Caused by 10 Topisomerase I Mutations, Including 7 Camptothecin Analogs and Lucanthone. J Chem Inf Model. 2016 Sep 26;56(9):1872-83. doi: 10.1021/acs.jcim.6b00317. Epub 2016 Sep 1. PubMed PMID: 27564845. 6: Chowdhury SM, Surhland C, Sanchez Z, Chaudhary P, Suresh Kumar MA, Lee S, Peña LA, Waring M, Sitharaman B, Naidu M. Graphene nanoribbons as a drug delivery agent for lucanthone mediated therapy of glioblastoma multiforme. Nanomedicine. 2015 Jan;11(1):109-18. doi: 10.1016/j.nano.2014.08.001. Epub 2014 Aug 13. PubMed PMID: 25131339; PubMed Central PMCID: PMC4280300. 7: Thétiot-Laurent SA, Boissier J, Robert A, Meunier B. Schistosomiasis chemotherapy. Angew Chem Int Ed Engl. 2013 Jul 29;52(31):7936-56. doi: 10.1002/anie.201208390. Epub 2013 Jun 27. Review. PubMed PMID: 23813602. 8: Mitchell S, Steventon G, Waring R. Drug peptide conjugates in human urine? Xenobiotica. 2014 Jan;44(1):89-93. doi: 10.3109/00498254.2013.806838. Epub 2013 Jun 18. PubMed PMID: 23777287. 9: da Rocha Pitta MG, da Rocha Pitta MG, de Melo Rêgo MJ, Galdino SL. The evolution of drugs on schistosoma treatment: looking to the past to improve the future. Mini Rev Med Chem. 2013 Apr;13(4):493-508. Review. PubMed PMID: 23373654. 10: Carew JS, Kelly KR, Nawrocki ST. Autophagy as a target for cancer therapy: new developments. Cancer Manag Res. 2012;4:357-65. doi: 10.2147/CMAR.S26133. Epub 2012 Oct 11. PubMed PMID: 23091399; PubMed Central PMCID: PMC3474143. 11: Naidu MD, Agarwal R, Pena LA, Cunha L, Mezei M, Shen M, Wilson DM 3rd, Liu Y, Sanchez Z, Chaudhary P, Wilson SH, Waring MJ. Lucanthone and its derivative hycanthone inhibit apurinic endonuclease-1 (APE1) by direct protein binding. PLoS One. 2011;6(9):e23679. doi: 10.1371/journal.pone.0023679. Epub 2011 Sep 15. PubMed PMID: 21935361; PubMed Central PMCID: PMC3174134. 12: Carew JS, Espitia CM, Esquivel JA 2nd, Mahalingam D, Kelly KR, Reddy G, Giles FJ, Nawrocki ST. Lucanthone is a novel inhibitor of autophagy that induces cathepsin D-mediated apoptosis. J Biol Chem. 2011 Feb 25;286(8):6602-13. doi: 10.1074/jbc.M110.151324. Epub 2010 Dec 10. PubMed PMID: 21148553; PubMed Central PMCID: PMC3057822. 13: Naidu MD, Mason JM, Pica RV, Fung H, Peña LA. Radiation resistance in glioma cells determined by DNA damage repair activity of Ape1/Ref-1. J Radiat Res. 2010;51(4):393-404. PubMed PMID: 20679741. 14: Fishel ML, Kelley MR. The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target. Mol Aspects Med. 2007 Jun-Aug;28(3-4):375-95. Epub 2007 May 3. Review. PubMed PMID: 17560642. 15: Bases R. Clonogenicity of human leukemic cells protected from cell-lethal agents by heat shock protein 70. Cell Stress Chaperones. 2005 Spring;10(1):37-45. PubMed PMID: 15832946; PubMed Central PMCID: PMC1074569. 16: Luo M, Kelley MR. Inhibition of the human apurinic/apyrimidinic endonuclease (APE1) repair activity and sensitization of breast cancer cells to DNA alkylating agents with lucanthone. Anticancer Res. 2004 Jul-Aug;24(4):2127-34. PubMed PMID: 15330152. 17: Li Y, Logan TM, Edison AS, Webb A. Design of small volume HX and triple-resonance probes for improved limits of detection in protein NMR experiments. J Magn Reson. 2003 Sep;164(1):128-35. PubMed PMID: 12932464. 18: Mendez F, Goldman JD, Bases RE. Abasic sites in DNA of HeLa cells induced by lucanthone. Cancer Invest. 2002;20(7-8):983-91. PubMed PMID: 12449731. 19: Dassonneville L, Bailly C. Stimulation of topoisomerase II-mediated DNA cleavage by an indazole analogue of lucanthone. Biochem Pharmacol. 1999 Oct 15;58(8):1307-12. PubMed PMID: 10487533. 20: Del Rowe JD, Bello J, Mitnick R, Sood B, Filippi C, Moran J, Freeman K, Mendez F, Bases R. Accelerated regression of brain metastases in patients receiving whole brain radiation and the topoisomerase II inhibitor, lucanthone. Int J Radiat Oncol Biol Phys. 1999 Jan 1;43(1):89-93. PubMed PMID: 9989518.

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