S-Gboxin
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MedKoo CAT#: 408009

CAS#: 2101317-21-7 (iodide)

Description: 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.


Price and Availability

Size
Price

50mg
USD 350
500mg
USD 1950
Size
Price

100mg
USD 550
1g
USD 3650
Size
Price

200mg
USD 950
2g
USD 5950

S-Gboxin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 408009
Name: S-Gboxin
CAS#: 2101317-21-7 (iodide)
Chemical Formula: C27H32F3IN2O2
Exact Mass:
Molecular Weight: 600.4647
Elemental Analysis: C, 54.01; H, 5.37; F, 9.49; I, 21.13; N, 4.67; O, 5.33


Related CAS #: 2101317-20-6 (cation)   2101317-21-7 (iodide)    

Synonym: S-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-]


Technical Data

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).

Harmonized System Code:
2934990300


Additional Information

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.


References

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.