BBI608 - CAS 83280-65-3
Catalog number: 83280-65-3
Category: Inhibitor
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Molecular Formula:
C14H8O4
Molecular Weight:
240.21
COA:
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Targets:
Others
Description:
Napabucasin is an orally-administered small molecule which can block cancer stem cell (CSC) self-renewal and induces cell death in CSCs as well as non-stem cancer cells. It appears to target and inhibit multiple pathways involved in cancer cell stemness.
Purity:
>98%
Synonyms:
BBI608; BBI 608; BB-I608; Napabucasin
MSDS:
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InChIKey:
DPHUWDIXHNQOSY-UHFFFAOYSA-N
InChI:
InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
Canonical SMILES:
CC(=O)C1=CC2=C(O1)C(=O)C3=CC=CC=C3C2=O
1.Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.
Eyong KO;Kumar PS;Kuete V;Folefoc GN;Nkengfack EA;Baskaran S Bioorg Med Chem Lett. 2008 Oct 15;18(20):5387-90. doi: 10.1016/j.bmcl.2008.09.053. Epub 2008 Sep 17.
Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 microg/ml. All the tested samples showed dose-dependent activity.
2.Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis.
Eyong KO;Krohn K;Hussain H;Folefoc GN;Nkengfack AE;Schulz B;Hu Q Chem Pharm Bull (Tokyo). 2005 Jun;53(6):616-9.
Newbouldiaquinone (1), a new naphthoquinone-anthraquinone coupled pigment and a new ceramide named newbouldiamide (2), have been isolated from Newbouldia laevis, besides the known compounds lapachol (3), canthic acid, oleanolic acid, 2-methyl-9,10-anthracenedione, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-(4-hydroxyphenyl)ethyl triacontanoate, beta-sitosterol and beta-sitosterol glucopyranoside. The structure elucidations of the isolated new compounds were performed on the basis of spectroscopic and chemical evidence. Preliminary studies showed that 1 is moderately antibacterial against Gram-positive Bacillus megaterium and that 3 has moderate herbicidal and antibacterial activities.
3.Napabucasin: An Update on the First-in-Class Cancer Stemness Inhibitor.
Hubbard JM;Grothey A Drugs. 2017 Jul;77(10):1091-1103. doi: 10.1007/s40265-017-0759-4.
Napabucasin (BBI608) is an orally administered small molecule that blocks stem cell activity in cancer cells by targeting the signal transducer and activator of transcription 3 pathway. The signal transducer and activator of transcription 3 pathway is over-activated in many types of cancer and has been shown to be an important pathway in cancer stem cell-mediated propagation of cancer. Cancer stem cells are a subpopulation of cancer cells considered to be the primary source of tumor growth, metastasis, and resistance to conventional therapies, and thus, responsible for cancer relapse. This review describes the clinical development program of this first-in-class cancer stemness inhibitor, including preclinical discovery, early clinical trials, current phase III clinical trial evaluation, and future therapeutic combinations. The therapeutic potential of napabucasin was first reported in a preclinical study that demonstrated the potent anti-tumor and anti-metastatic activity of napabucasin in several different cancer types, both in vitro and in vivo. In mouse models, napabucasin was effective both as a monotherapy and in combination with other agents; in particular, synergy was observed with paclitaxel in vivo.
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CAS 83280-65-3 BBI608

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