Napabucasin | BBI-608 | CAS#83280-65-3 | cancer cell stemness inhibitor

MedKoo Cat#: 206601 | Name: Napabucasin

Description:

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

Napabucasin, also known as BBI-608, is an orally available cancer cell stemness inhibitor with potential antineoplastic activity. Even though the exact target has yet to be fully elucidated, BBI608 appears to target and inhibit multiple pathways involved in cancer cell stemness. This may ultimately inhibit cancer stemness cell (CSC) growth as well as heterogeneous cancer cell growth. CSCs, self-replicating cells that are able to differentiate into heterogeneous cancer cells, appear to be responsible for the malignant growth, recurrence and resistance to conventional chemotherapies.

Chemical Structure

Napabucasin

CAS#83280-65-3

Theoretical Analysis

MedKoo Cat#: 206601

Name: Napabucasin

CAS#: 83280-65-3

Chemical Formula: C14H8O4

Exact Mass: 240.0423

Molecular Weight: 240.21

Elemental Analysis: C, 70.00; H, 3.36; O, 26.64

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 2,650.00	Ready to ship
1g	USD 3,750.00	Ready to ship
2g	USD 6,250.00	Ready to ship

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Related CAS #

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Synonym

BBI608; BBI 608; BB-I608; Napabucasin

IUPAC/Chemical Name

2-Acetylnaphtho[2,3-b]furan-4,9-dione

InChi Key

DPHUWDIXHNQOSY-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(C1=C2OC(C(C)=O)=C1)C3=C(C2=O)C=CC=C3

Appearance

Yellow 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, not in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C8R04B03

QC Data

View QC data: current batch, Lot#C8R04B03

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Napabucasin is a STAT3 inhibitor which blocks stem cell activity.

In vitro activity:

As shown in Figure 2A, napabucasin significantly decreased the viability of Huh7 and Hepa1-6 cells in a time- and concentration-dependent manner. Consistent with this, the proportion of napabucasin-treated cells in the G1-phase was significantly lower compared to that of the untreated controls, which corresponded to an increase in the G2/M-phase cells (P < 0.05; Figure 2B). Furthermore, the apoptosis rates in Huh7 cells increased to 11.11%, 14.38% and 62.99% respectively within 12 h of exposure to 1, 2 and 5 µM napabucasin (Figure 2C), and similar results were obtained with Hepa1-6 cells as well. Taken together, napabucasin inhibited HCC cell growth in a concentration-dependent manner by inducing apoptosis and G2/M-phase arrest. Reference: Front Pharmacol. 2020; 11: 597520. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7744694/

In vivo activity:

After injecting Napabucasin (10 mg/kg) for 1 month, the terminal mouse body weights were greatly reduced in the Napabucasin group compared with mice in the control group (Figure 4A). As shown in Figures 4B,C, the phosphorylation of STAT3 was obviously blocked after one-month of Napabucasin injections in this study’s immunofluorescence investigation. H&E staining shown that Napabucasin injection-induced bone loss in the femora (Figure 4D). Then this study assessed the bone mass of femora from mice injected with vehicle or Napabucasin by micro-CT. Parameters such as BMD (Figure 4G), BV/TV (Figure 4H), Tb.Th. (Figure 4I), and Tb.N. (Figure 4J) were apparently reduced after 1-month injections of Napabucasin, while Tb.Sp. (Figure 4K) increased. However, Ct.Th. (Figure 4L) did not differ in this experiment. These results implied that the STAT3 inhibitor Napabucasin decreased the bone mass of WT mice. Reference: Front Cell Dev Biol. 2021; 9: 648866. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8014090/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	41.63

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 240.21 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.

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. Li Y, Han Q, Zhao H, Guo Q, Zhang J. Napabucasin Reduces Cancer Stem Cell Characteristics in Hepatocellular Carcinoma. Front Pharmacol. 2020 Dec 3;11:597520. doi: 10.3389/fphar.2020.597520. PMID: 33343368; PMCID: PMC7744694. 2. Schmidtova S, Dorssers LCJ, Kalavska K, Gillis AJM, Oosterhuis JW, Stoop H, Miklikova S, Kozovska Z, Burikova M, Gercakova K, Durinikova E, Chovanec M, Mego M, Kucerova L, Looijenga LHJ. Napabucasin overcomes cisplatin resistance in ovarian germ cell tumor-derived cell line by inhibiting cancer stemness. Cancer Cell Int. 2020 Aug 3;20:364. doi: 10.1186/s12935-020-01458-7. PMID: 32774158; PMCID: PMC7397611. 3. Huang X, Jin A, Wang X, Gao X, Xu H, Chung M, Dai Q, Yang Y, Jiang L. Napabucasin Induces Mouse Bone Loss by Impairing Bone Formation via STAT3. Front Cell Dev Biol. 2021 Mar 18;9:648866. doi: 10.3389/fcell.2021.648866. PMID: 33816498; PMCID: PMC8014090. 4. Leijten NM, Bakker P, Spaink HP, den Hertog J, Lemeer S. Thermal Proteome Profiling in Zebrafish Reveals Effects of Napabucasin on Retinoic Acid Metabolism. Mol Cell Proteomics. 2021 Feb 13;20:100033. doi: 10.1074/mcp.RA120.002273. Epub ahead of print. PMID: 33594990; PMCID: PMC7950114.

In vitro protocol:

In vivo protocol:

1. Huang X, Jin A, Wang X, Gao X, Xu H, Chung M, Dai Q, Yang Y, Jiang L. Napabucasin Induces Mouse Bone Loss by Impairing Bone Formation via STAT3. Front Cell Dev Biol. 2021 Mar 18;9:648866. doi: 10.3389/fcell.2021.648866. PMID: 33816498; PMCID: PMC8014090. 2. Leijten NM, Bakker P, Spaink HP, den Hertog J, Lemeer S. Thermal Proteome Profiling in Zebrafish Reveals Effects of Napabucasin on Retinoic Acid Metabolism. Mol Cell Proteomics. 2021 Feb 13;20:100033. doi: 10.1074/mcp.RA120.002273. Epub ahead of print. PMID: 33594990; PMCID: PMC7950114.

1: Zhang Y, Jin Z, Zhou H, Ou X, Xu Y, Li H, Liu C, Li B. Suppression of prostate cancer progression by cancer cell stemness inhibitor napabucasin. Cancer Med. 2016 Feb 21. doi: 10.1002/cam4.675. [Epub ahead of print] PubMed PMID: 26899963. 2: Li Y, Rogoff HA, Keates S, Gao Y, Murikipudi S, Mikule K, Leggett D, Li W, Pardee AB, Li CJ. Suppression of cancer relapse and metastasis by inhibiting cancer stemness. Proc Natl Acad Sci U S A. 2015 Feb 10;112(6):1839-44. doi: 10.1073/pnas.1424171112. Epub 2015 Jan 20. PubMed PMID: 25605917; PubMed Central PMCID: PMC4330785.