MC3181

• CAT Number: I031643
• Molecular Formula: C12H15N3O6S
• Molecular Weight: 329.327
• Purity: 98%
• Synonyms: MC3181; MC 3181; MC-3181
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2-(2-(2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)ethoxy)ethoxy)ethan-1-ol
• InChI: InChI=1S/C12H15N3O6S/c16-3-4-19-5-6-20-7-8-22-10-2-1-9(15(17)18)11-12(10)14-21-13-11/h1-2,16H,3-8H2
• InChIKey: HBUVTZWKAJNMMO-UHFFFAOYSA-N
• SMILES: OCCOCCOCCSC1=CC=C([N+]([O-])=O)C2=NON=C21

MC3181 is an antiproliferative agent. MC3181 also reduces the invasiveness of melanoma tumors and lowers the incidence of metastasis in vitro.

Reference

1: Di Paolo V, Fulci C, Rotili D, De Luca A, Tomassi S, Serra M, Scimeca M, Geroni C, Quintieri L, Caccuri AM. Characterization of water-soluble esters of nitrobenzoxadiazole-based GSTP1-1 inhibitors for cancer treatment. Biochem Pharmacol. 2020 Aug;178:114060. doi: 10.1016/j.bcp.2020.114060. Epub 2020 May 29. PMID: 32473836.
2: Sciarretta F, Fulci C, Palumbo C, Rotili D, Tentori L, Graziani G, Caccuri AM. Effects of Glutathione Transferase-Targeting Nitrobenzoxadiazole Compounds in Relation to PD-L1 Status in Human Melanoma Cells. Chemotherapy. 2019;64(3):138-145. doi: 10.1159/000503339. Epub 2019 Oct 22. PMID: 31639786.
3: De Luca A, Carpanese D, Rapanotti MC, Viguria TM, Forgione MA, Rotili D, Fulci C, Iorio E, Quintieri L, Chimenti S, Bianchi L, Rosato A, Caccuri AM. The nitrobenzoxadiazole derivative MC3181 blocks melanoma invasion and metastasis. Oncotarget. 2017 Feb 28;8(9):15520-15538. doi: 10.18632/oncotarget.14690. PMID: 28107182; PMCID: PMC5362503.
4: Palumbo C, De Luca A, Rosato N, Forgione M, Rotili D, Caccuri AM. c-Jun N-terminal kinase activation by nitrobenzoxadiazoles leads to late-stage autophagy inhibition. J Transl Med. 2016 Feb 4;14:37. doi: 10.1186/s12967-016-0796-x. PMID: 26847645; PMCID: PMC4743117.
5: Graziani G, Artuso S, De Luca A, Muzi A, Rotili D, Scimeca M, Atzori MG, Ceci C, Mai A, Leonetti C, Levati L, Bonanno E, Tentori L, Caccuri AM. A new water soluble MAPK activator exerts antitumor activity in melanoma cells resistant to the BRAF inhibitor vemurafenib. Biochem Pharmacol. 2015 May 1;95(1):16-27. doi: 10.1016/j.bcp.2015.03.004. Epub 2015 Mar 17. PMID: 25795251.
6: De Luca A, Rotili D, Carpanese D, Lenoci A, Calderan L, Scimeca M, Mai A, Bonanno E, Rosato A, Geroni C, Quintieri L, Caccuri AM. A novel orally active water-soluble inhibitor of human glutathione transferase exerts a potent and selective antitumor activity against human melanoma xenografts. Oncotarget. 2015 Feb 28;6(6):4126-43. doi: 10.18632/oncotarget.2798. PMID: 25595904; PMCID: PMC4414177.