S-Gboxin | CAS#2101317-21-7

MedKoo Cat#: 408009 | Name: S-Gboxin

Description:

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

S-Gboxin is an active analogue of Gboxin with potent antitumour activity. S-Gboxin inhibits growth of mouse and human glioblastoma (GBM) with an IC50 of 470 nM. Gboxin is an oxidative phosphorylation inhibitor that targets glioblastoma. Gboxin inhibits the growth of primary mouse and human glioblastoma cells but not that of mouse embryonic fibroblasts or neonatal astrocytes. Gboxin rapidly and irreversibly compromises oxygen consumption in glioblastoma cells.

Chemical Structure

S-Gboxin

CAS#2101317-21-7 (iodide)

Theoretical Analysis

MedKoo Cat#: 408009

Name: S-Gboxin

CAS#: 2101317-21-7 (iodide)

Chemical Formula: C27H32F3IN2O2

Exact Mass: 0.0000

Molecular Weight: 600.46

Elemental Analysis: C, 54.01; H, 5.37; F, 9.49; I, 21.13; N, 4.67; O, 5.33

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 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,250.00	2 Weeks

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Related CAS #

2101315-36-8 (chloride) 2101317-20-6 (cation) 2101317-21-7 (iodide)

Synonym

S-Gboxin; Gboxin

IUPAC/Chemical Name

3-(2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoethyl)-1-methyl-2-(3-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-3-ium iodide

InChi Key

DCAJNAWCJSUZDG-DZJKTSMVSA-M

InChi Code

InChI=1S/C27H32F3N2O2.HI/c1-17(2)21-13-12-18(3)14-24(21)34-25(33)16-32-23-11-6-5-10-22(23)31(4)26(32)19-8-7-9-20(15-19)27(28,29)30;/h5-11,15,17-18,21,24H,12-14,16H2,1-4H3;1H/q+1;/p-1/t18-,21+,24-;/m1./s1

SMILES Code

FC(C1=CC(C2=[N+](CC(O[C@H]3[C@H](C(C)C)CC[C@@H](C)C3)=O)C4=CC=CC=C4N2C)=CC=C1)(F)F.[I-]

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 and water

Shelf Life

>3 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

Gboxin relies on its positive charge to associate with mitochondrial oxidative phosphorylation complexes in a manner that is dependent on the proton gradient of the inner mitochondrial membrane, and it inhibits the activity of F0F1 ATP synthase. Gboxin-resistant cells require a functional mitochondrial permeability transition pore that regulates pH and thus impedes the accumulation of Gboxin in the mitochondrial matrix. Administration of a metabolically stable Gboxin analogue inhibits glioblastoma allografts and patient-derived xenografts. Gboxin toxicity extends to established human cancer cell lines of diverse organ origin, and shows that the increased proton gradient and pH in cancer cell mitochondria is a mode of action that can be targeted in the development of antitumour reagents.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SGA360 competitively binds to AhR (IC50 = 3 µM) and represses serum amyloid A 1 (SAA1) gene expression induced by IL-1β in Huh7 cells.

In vitro activity:

S-Gboxin selectively reduced β-catenin-associated cell viability and tumor formation. Reference: J Transl Med. 2023 Jan 26;21(1):50. https://pubmed.ncbi.nlm.nih.gov/36703130/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	DMSO	93.3	155.43
	Water	1.0	1.67

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 600.46 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. Wu Y, Yang S, Han L, Shang K, Zhang B, Gai X, Deng W, Liu F, Zhang H. β-catenin-IRP2-primed iron availability to mitochondrial metabolism is druggable for active β-catenin-mediated cancer. J Transl Med. 2023 Jan 26;21(1):50. doi: 10.1186/s12967-023-03914-0. PMID: 36703130; PMCID: PMC9879242. 2. Jiao X, Yu X, Gong C, Zhu H, Zhang B, Wang R, Yuan Y. Erythrocyte-cancer Hybrid Membrane-camouflaged Mesoporous Silica Nanoparticles Loaded with Gboxin for Glioma-targeting Therapy. Curr Pharm Biotechnol. 2022;23(6):835-846. doi: 10.2174/1389201022666210719164538. PMID: 34825635.

In vitro protocol:

In vivo protocol:

To be determined

1: Shi Y, Lim SK, Liang Q, Iyer SV, Wang HY, Wang Z, Xie X, Sun D, Chen YJ, Tabar V, Gutin P, Williams N, De Brabander JK, Parada LF. Gboxin is an oxidative phosphorylation inhibitor that targets glioblastoma. Nature. 2019 Mar;567(7748):341-346. doi: 10.1038/s41586-019-0993-x. Epub 2019 Mar 6. PubMed PMID: 30842654.