BIO-acetoxime | CAS# 667463-85-6 | GSK-3a/b inhibitor

MedKoo Cat#: 407198 | Name: BIO-acetoxime

Description:

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

BIO-Acetoxime is a potent and selective GSK-3a/b inhibitor that reduces invasiveness of gliomas and extends animal survival in intracranial glioma models. Also, BIO-Acetoxime induces Wnt signaling and inhibits CD8+ T cell effector differentiation. BIO-acetoxime is a synthetic derivative of a compound from the Mediterranean mollusk Hexaplex trunculus. BIO-Acetoxime protects cells from varicella infection. BIO-acetoxime may suppress viral gene expression and protect oral epithelial cells from HSV-1 infection.

Chemical Structure

BIO-acetoxime

CAS# 667463-85-6

Theoretical Analysis

MedKoo Cat#: 407198

Name: BIO-acetoxime

CAS#: 667463-85-6

Chemical Formula: C18H12BrN3O3

Exact Mass: 397.0062

Molecular Weight: 398.22

Elemental Analysis: C, 54.29; H, 3.04; Br, 20.07; N, 10.55; O, 12.05

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 1,950.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,450.00	2 Weeks

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Synonym

BIO-acetoxime; (2′Z,3′E)-6-Bromoindirubin-3′-acetoxime, 6-Bromoindirubin acetoxime, 6-Bromoindirubin-3′-acetoxime, BIA

IUPAC/Chemical Name

(2Z,3E)-3-(acetoxyimino)-6'-bromo-[2,3'-biindolinylidene]-2'-one

InChi Key

MENDIXKFTXYTHJ-HPBPSMLHSA-N

InChi Code

InChI=1S/C18H12BrN3O3/c1-9(23)25-22-16-12-4-2-3-5-13(12)20-17(16)15-11-7-6-10(19)8-14(11)21-18(15)24/h2-8,20H,1H3,(H,21,24)/b17-15-,22-16+

SMILES Code

O=C1NC2=C(C=CC(Br)=C2)/C1=C3NC4=C(C=CC=C4)C/3=N\OC(C)=O

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, 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

Instruction

View handling instruction

Biological target:

BIO-acetoxime (BIA) is a potent and selective GSK-3 inhibitor, with IC50s of both 10 nM for GSK-3α/β.

In vitro activity:

Furthermore, addition of BIO-acetoxime before, simultaneously with or after HSV-1 infection significantly reduced viral yields. Collectively, BIO-acetoxime may suppress viral gene expression and protect oral epithelial cells from HSV-1 infection. Reference: Arch Virol. 2013 Jun;158(6):1287-96. https://pubmed.ncbi.nlm.nih.gov/23392633/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	22.6	56.75

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 398.22 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. Hsu MJ, Hung SL. Antiherpetic potential of 6-bromoindirubin-3'-acetoxime (BIO-acetoxime) in human oral epithelial cells. Arch Virol. 2013 Jun;158(6):1287-96. doi: 10.1007/s00705-013-1629-3. Epub 2013 Feb 8. PMID: 23392633.

In vitro protocol:

In vivo protocol:

TBD

1: Khan KA, Dô F, Marineau A, Doyon P, Clément JF, Woodgett JR, Doble BW, Servant MJ. Fine-Tuning of the RIG-I-Like Receptor/Interferon Regulatory Factor 3-Dependent Antiviral Innate Immune Response by the Glycogen Synthase Kinase 3/β-Catenin Pathway. Mol Cell Biol. 2015 Sep 1;35(17):3029-43. doi: 10.1128/MCB.00344-15. Epub 2015 Jun 22. PubMed PMID: 26100021; PubMed Central PMCID: PMC4525315. 2: Duffy DJ, Krstic A, Schwarzl T, Higgins DG, Kolch W. GSK3 inhibitors regulate MYCN mRNA levels and reduce neuroblastoma cell viability through multiple mechanisms, including p53 and Wnt signaling. Mol Cancer Ther. 2014 Feb;13(2):454-67. doi: 10.1158/1535-7163.MCT-13-0560-T. Epub 2013 Nov 26. PubMed PMID: 24282277. 3: Hsu MJ, Hung SL. Antiherpetic potential of 6-bromoindirubin-3'-acetoxime (BIO-acetoxime) in human oral epithelial cells. Arch Virol. 2013 Jun;158(6):1287-96. doi: 10.1007/s00705-013-1629-3. Epub 2013 Feb 8. PubMed PMID: 23392633. 4: Wang B, Liu J, Ma LN, Xiao HL, Wang YZ, Li Y, Wang Z, Fan L, Lan C, Yang M, Hu L, Wei Y, Bian XW, Chen D, Wang J. Chimeric 5/35 adenovirus-mediated Dickkopf-1 overexpression suppressed tumorigenicity of CD44⁺ gastric cancer cells via attenuating Wnt signaling. J Gastroenterol. 2013 Jul;48(7):798-808. doi: 10.1007/s00535-012-0711-z. Epub 2012 Nov 28. PubMed PMID: 23188090. 5: Spokoini R, Kfir-Erenfeld S, Yefenof E, Sionov RV. Glycogen synthase kinase-3 plays a central role in mediating glucocorticoid-induced apoptosis. Mol Endocrinol. 2010 Jun;24(6):1136-50. doi: 10.1210/me.2009-0466. Epub 2010 Apr 6. PubMed PMID: 20371704.