WARNING: This product is for research use only, not for human or veterinary use.
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.
MedKoo Cat#: 207091
Name: Gboxin chloride
CAS#: 2101315-36-8
Chemical Formula: C22H33ClN2O2
Exact Mass:
Molecular Weight: 392.968
Elemental Analysis: C, 67.24; H, 8.46; Cl, 9.02; N, 7.13; O, 8.14
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
| 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 |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMF | 10.0 | 25.45 | |
| DMSO | 27.83 | 70.83 | |
| Ethanol | 49.5 | 125.96 | |
| PBS (pH 7.2) | 10.0 | 25.45 | |
| Water | 6.0 | 15.27 |
The following data is based on the product molecular weight 392.968 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. 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 |
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.
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.
