Hycanthone

• CAT Number: I007230
• CAS Number: 3105-97-3
• Molecular Formula: C20H24N2O2S
• Molecular Weight: 356.48176
• Purity: ≥95%
• Synonyms: 1-((2-(diethylamino)ethyl)amino)-4-(hydroxymethyl)-9H-thioxanthen-9-one
• Solubility: Soluble in DMSO, not in water
• Storage: Store at -20°C
• IUPAC Name: 1-[2-(diethylamino)ethylamino]-4-(hydroxymethyl)thioxanthen-9-one
• InChI: InChI=1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3
• InChIKey: MFZWMTSUNYWVBU-UHFFFAOYSA-N
• SMILES: O=C1C2=C(SC3=C1C=CC=C3)C(CO)=CC=C2NCCN(CC)CC

Hycanthone (CAT: I007230) is an antiparasitic agent that was originally developed as a schistosomicide for the treatment of schistosomiasis, a parasitic disease caused by Schistosoma worms. It works by interfering with the DNA of the parasite, inhibiting its replication and causing its death. However, hycanthone is no longer widely used for the treatment of schistosomiasis due to the availability of safer and more effective alternatives. It has also been investigated for its potential anticancer activity, as it has shown cytotoxic effects against various cancer cell lines.

Reference

1:Exposure to hycanthone alters chromatin structure around specific gene functions and specific repeats in Schistosoma mansoni. Roquis D, Lepesant JM, Villafan E, Boissier J, Vieira C, Cosseau C, Grunau C.Front Genet. 2014 Jul 16;5:207. doi: 10.3389/fgene.2014.00207. eCollection 2014. PMID: 25076965 Free PMC Article
2:Lucanthone and its derivative hycanthone inhibit apurinic endonuclease-1 (APE1) by direct protein binding. 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.PLoS One. 2011;6(9):e23679. doi: 10.1371/journal.pone.0023679. Epub 2011 Sep 15. PMID: 21935361 Free PMC Article
3:Molecular analysis of the TK locus in L5178Y large and small colony mouse lymphoma cell mutants induced by hycanthone methanesulfonate. el-Tarras A, Dubins JS, Warner J, Hoffman C, Cobb RR.Mutat Res. 1995 Nov;332(1-2):89-95. PMID: 7500995
4:Evaluation of external-beam radiation therapy plus 5-fluorouracil (5-FU) versus external-beam radiation therapy plus hycanthone (HYC) in confined, unresectable pancreatic cancer. Earle JD, Foley JF, Wieand HS, Kvols LK, McKenna PJ, Krook JE, Tschetter LK, Schutt AJ, Twito DI.Int J Radiat Oncol Biol Phys. 1994 Jan 1;28(1):207-11. PMID: 8270443
5:Schistosoma mansoni: genetic complementation analysis shows that two independent hycanthone/oxamniquine-resistant strains are mutated in the same gene. Pica-Mattoccia L, Dias LC, Moroni R, Cioli D.Exp Parasitol. 1993 Dec;77(4):445-9. PMID: 8253157
6:Preferential intercalation at AT sequences in DNA by lucanthone, hycanthone, and indazole analogs. A footprinting study. Bailly C, Waring MJ.Biochemistry. 1993 Jun 15;32(23):5985-93. PMID: 8389585
7:Schistosoma mansoni: hycanthone/oxamniquine resistance is controlled by a single autosomal recessive gene. Cioli D, Pica-Mattoccia L, Moroni R.Exp Parasitol. 1992 Dec;75(4):425-32. PMID: 1493874
8:Sex differences in micronucleus induction with hycanthone methanesulfonate in bone marrow cells of mice. Kliesch U, Adler ID.Mutat Res. 1992 Dec;283(4):249-53. PMID: 1383797
9:Hycanthone resistance in schistosomes correlates with the lack of an enzymatic activity which produces the covalent binding of hycanthone to parasite macromolecules. Pica-Mattoccia L, Archer S, Cioli D.Mol Biochem Parasitol. 1992 Oct;55(1-2):167-75. PMID: 1435868
10:Genetic complementation analysis of two independently isolated hycanthone-resistant strains of Schistosoma mansoni. Pica-Mattoccia L, Dias LC, Cioli D.Mem Inst Oswaldo Cruz. 1992;87 Suppl 4:211-4. PMID: 1343897 Free Article