Gboxin chloride
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MedKoo CAT#: 207091

CAS#: 2101315-36-8

Description: Gboxin chloride is an oxidative phosphorylation inhibitor that targets glioblastoma but not embryonic fibroblasts or neonatal astrocytes. Gboxin rapidly and irreversibly compromises oxygen consumption in glioblastoma cells. 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.

Chemical Structure

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Gboxin chloride
CAS# 2101315-36-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 207091
Name: Gboxin chloride
CAS#: 2101315-36-8
Chemical Formula: C22H33ClN2O2
Exact Mass: 0.00
Molecular Weight: 392.968
Elemental Analysis: C, 67.24; H, 8.46; Cl, 9.02; N, 7.13; O, 8.14

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2850 Ready to ship
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Synonym: Gboxin; Gboxin chloride

IUPAC/Chemical Name: 2-Ethyl-1-(2-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)-2-oxoethyl)-3-methyl-1H-benzo[d]imidazol-3-ium chloride

InChi Key: UBWVTCCKVGOTBG-VYZBTARASA-M

InChi Code: InChI=1S/C22H33N2O2.ClH/c1-6-21-23(5)18-9-7-8-10-19(18)24(21)14-22(25)26-20-13-16(4)11-12-17(20)15(2)3;/h7-10,15-17,20H,6,11-14H2,1-5H3;1H/q+1;/p-1/t16-,17+,20-;/m1./s1

SMILES Code: C[N+]1=C(CC)N(CC(O[C@H]2[C@H](C(C)C)CC[C@@H](C)C2)=O)C3=CC=CC=C31.[Cl-]

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

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-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.

Biological target: Gboxin is an oxidative phosphorylation (OXPHOS) inhibitor that targets glioblastoma. Gboxin inhibits the activity of F0F1 ATP synthase.
In vitro activity: 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. Reference: Nature. 2019 Mar;567(7748):341-346. https://pubmed.ncbi.nlm.nih.gov/30842654/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 25.45
DMSO 27.8 70.83
Ethanol 49.5 125.96
PBS (pH 7.2) 10.0 25.45
Water 6.0 15.27

Preparing Stock Solutions

The following data is based on the product molecular weight 392.97 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.

Recalculate based on batch purity %
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. 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. PMID: 30842654; PMCID: PMC6655586.
In vitro protocol: 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. PMID: 30842654; PMCID: PMC6655586.
In vivo protocol: TBD

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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.