Geneticin sulfate | CAS#108321-42-2 | aminoglycoside antibiotic

MedKoo Cat#: 563714 | Name: Geneticin sulfate

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Description:

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

Geneticin G418 is an aminoglycoside antibiotic, blocking polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells.

Chemical Structure

Geneticin sulfate

CAS#108321-42-2 (sulfate)

Theoretical Analysis

MedKoo Cat#: 563714

Name: Geneticin sulfate

CAS#: 108321-42-2 (sulfate)

Chemical Formula: C20H44N4O18S2

Exact Mass: 0.0000

Molecular Weight: 692.70

Elemental Analysis: C, 34.68; H, 6.40; N, 8.09; O, 41.57; S, 9.26

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 750.00	2 Weeks

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Related CAS #

49863-47-0 (free base) 108321-42-2 (sulfate)

Synonym

Geneticin sulfate; Geneticin disulfate; G418 sulfate; G 418 sulfate; G-418 sulfate; Antibiotic G418 sulfate;

IUPAC/Chemical Name

(2R,3S,4R,5R,6S)-5-amino-6-(((1R,2S,3S,4R,6S)-4,6-diamino-3-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-((R)-1-hydroxyethyl)tetrahydro-2H-pyran-3,4-diol bis(sulfate)

InChi Key

UHEPSJJJMTWUCP-DHDYTCSHSA-N

InChi Code

InChI=1S/C20H40N4O10.2H2O4S/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19;2*1-5(2,3)4/h6-19,24-30H,4-5,21-23H2,1-3H3;2*(H2,1,2,3,4)/t6-,7+,8-,9-,10-,11+,12+,13-,14-,15-,16+,17-,18-,19-,20+;;/m1../s1

SMILES Code

O[C@@H]1[C@@H]([C@H](O)C)O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@@H]3[C@H](O)[C@@H](NC)[C@@](C)(O)CO3)[C@H](N)C[C@@H]2N)[C@H](N)[C@H]1O.O=S(O)(O)=O.O=S(O)(O)=O

Appearance

Solid powder

Purity

>95% (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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

G-418 disulfate (Geneticin sulfate), is an aminoglycoside antibiotic, inhibits protein synthesis in eukaryotes and prokaryotes.

In vitro activity:

Higher G418 concentration led also to same but prompter and devastating results. Interestingly, identical treatment with G418 in NSB at room temperature failed to mediate cell death in Acanthamoeba, making temperature stress a precondition to cell death induction. In addition, G418 is able to cause cell death in trophozoites cells even after its removal after an hour which is an indication that it is an initiator of cell death rather than the executor (Fig. 2B). Reference: Parasitol Res. 2019 Feb;118(2):641-651. https://pubmed.ncbi.nlm.nih.gov/30617503/

In vivo activity:

Preparations of G418 obtained from three different manufacturers interfered with RML prion infection in CAD5(pIRESneo3) cells (Fig. 2H). Moreover, this effect was not specific to the RML strain since G418 also hindered infection of CAD5(pcDNA3) cells with the 22L strain of mouse prions (Fig. 2, I and J). Thus, G418 obstructs de novo prion infection in cells challenged with mouse prion strains. Reference: J Biol Chem. 2021 Sep;297(3):101073. https://pubmed.ncbi.nlm.nih.gov/34390689/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	100.0	168.17
	Water	92.3	155.25

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 692.70 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. Koutsogiannis Z, MacLeod ET, Maciver SK. G418 induces programmed cell death in Acanthamoeba through the elevation of intracellular calcium and cytochrome c translocation. Parasitol Res. 2019 Feb;118(2):641-651. doi: 10.1007/s00436-018-6192-0. Epub 2019 Jan 7. PMID: 30617503; PMCID: PMC6349814. 2. Yallop CA, Svendsen I. The effects of G418 on the growth and metabolism of recombinant mammalian cell lines. Cytotechnology. 2001 Mar;35(2):101-14. doi: 10.1023/A:1017550902771. PMID: 19003287; PMCID: PMC3449461. 3. Arshad H, Patel Z, Mehrabian M, Bourkas MEC, Al-Azzawi ZAM, Schmitt-Ulms G, Watts JC. The aminoglycoside G418 hinders de novo prion infection in cultured cells. J Biol Chem. 2021 Sep;297(3):101073. doi: 10.1016/j.jbc.2021.101073. Epub 2021 Aug 12. PMID: 34390689; PMCID: PMC8413896. 4. Heier CR, DiDonato CJ. Translational readthrough by the aminoglycoside geneticin (G418) modulates SMN stability in vitro and improves motor function in SMA mice in vivo. Hum Mol Genet. 2009 Apr 1;18(7):1310-22. doi: 10.1093/hmg/ddp030. Epub 2009 Jan 15. PMID: 19150990; PMCID: PMC2655772.

In vitro protocol:

In vivo protocol:

1. Arshad H, Patel Z, Mehrabian M, Bourkas MEC, Al-Azzawi ZAM, Schmitt-Ulms G, Watts JC. The aminoglycoside G418 hinders de novo prion infection in cultured cells. J Biol Chem. 2021 Sep;297(3):101073. doi: 10.1016/j.jbc.2021.101073. Epub 2021 Aug 12. PMID: 34390689; PMCID: PMC8413896. 2. Heier CR, DiDonato CJ. Translational readthrough by the aminoglycoside geneticin (G418) modulates SMN stability in vitro and improves motor function in SMA mice in vivo. Hum Mol Genet. 2009 Apr 1;18(7):1310-22. doi: 10.1093/hmg/ddp030. Epub 2009 Jan 15. PMID: 19150990; PMCID: PMC2655772.

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