Geneticin
[CAS# 108321-42-2]

Identification

• Classification: Inorganic chemical industry >> Inorganic salt >> Metal sulfides and sulfates
• Name: Geneticin
• Synonyms: G418 sulfate
• Molecular Formula: C₂₀H₄₀N₄O₁₀.2(H₂SO₄)
• Molecular Weight: 692.70
• CAS Registry Number: 108321-42-2
• EC Number: 600-864-4
• SMILES: CC([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@H]3[C@H]([C@@H]([C@](CO3)(C)O)NC)O)N)N)N)O)O)O.OS(=O)(=O)O.OS(=O)(=O)O

Properties

• Solubility: DMSO 129 mg/mL, Water 129 mg/mL (Expl.)

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H317-H319-H334-H360
• Safety Statements: P203-P233-P260-P261-P264-P264+P265-P271-P272-P280-P284-P302+P352-P304+P340-P305+P351+P338-P318-P321-P332+P317-P333+P317-P337+P317-P342+P316-P362+P364-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	1A	H360
Acute toxicity	Acute Tox.	4	H332
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Geneticin, also known as G418, is an aminoglycoside antibiotic that is widely used in molecular biology for the selection of genetically modified cells. Its primary function is as a selective agent that inhibits protein synthesis in eukaryotic cells by binding to the ribosome, preventing the elongation of polypeptides. This mechanism of action is similar to other aminoglycosides, but Geneticin is particularly noted for its ability to selectively inhibit cells that do not possess resistance genes, making it valuable in gene therapy and research.

Geneticin was originally developed as an antibiotic to treat bacterial infections, but its application in genetic research has proven to be more significant. It is commonly used in experiments that involve transfection, where foreign DNA is introduced into cells. When cells are transfected with a plasmid containing a resistance gene to Geneticin, they acquire resistance to the drug. This allows researchers to selectively grow only those cells that have successfully incorporated the desired gene, as untransfected cells will be killed by the antibiotic. This process is fundamental in studies of gene expression, protein function, and cell biology.

In addition to its use in molecular biology, Geneticin has also been utilized in experiments studying resistance mechanisms. The antibiotic is often employed to explore cellular pathways that confer resistance to aminoglycosides, offering insights into mechanisms of antibiotic resistance. Furthermore, Geneticin's ability to inhibit protein synthesis has been leveraged in various assays to investigate the cellular processes that depend on translation.

Over the years, Geneticin has become indispensable in laboratories worldwide, particularly in the fields of cell biology and genetics, where its role in selecting and maintaining genetically modified cells is crucial. It has helped advance research in areas such as cancer biology, gene therapy, and functional genomics. While its primary use remains as a selection agent in cell culture, the broader understanding of its biochemical effects continues to contribute to advances in cellular research and therapeutic development.

References

2022. Phase 1 Study to Investigate the Safety, Tolerability, and Pharmacokinetics of EPI‐589 in Healthy Participants. Clinical Pharmacology in Drug Development, 11(10).
DOI: 10.1002/cpdd.1146

2023. An Exploratory Trial of EPI-589 in Amyotrophic Lateral Sclerosis (EPIC-ALS): Protocol for a Multicenter, Open-Labeled, 24-Week, Single-Group Study. JMIR Research Protocols, 12.
DOI: 10.2196/42032