Geneticin G418
featured

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

MedKoo CAT#: 563714

CAS#: 108321-42-2 (sulfate)

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

Chemical Structure

img
Geneticin G418
CAS# 108321-42-2 (sulfate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 563714
Name: Geneticin G418
CAS#: 108321-42-2 (sulfate)
Chemical Formula: C20H44N4O18S2
Exact Mass: 0.00
Molecular Weight: 692.700
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 2 Weeks
5g USD 750 2 Weeks
Bulk inquiry

Related CAS #: 49863-47-0 (free base)   108321-42-2 (sulfate),  

Synonym: Geneticin G418; Geneticin G-418; Geneticin G 418; Antibiotic G418;

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=S(O)(O)=O.O=S(O)(O)=O.N[C@H]1[C@@H]([C@H]([C@@H]([C@H](C1)N)O[C@@]2([C@@H]([C@H]([C@@H]([C@]([H])(O2)[C@@H](C)O)O)O)N)[H])O)O[C@@]3([C@@H]([C@H]([C@@](O)(CO3)C)NC)O)[H]

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/

Solubility Data

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

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.

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. 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: 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.
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Chen L, Gao Y, Zhu L, Song H, Zhao L, Liu A, Zhang G, Shi G. Establishment and characterization of a GES-1 human gastric epithelial cell line stably expressing miR-23a. Oncol Lett. 2018 Jul;16(1):977-983. doi: 10.3892/ol.2018.8765. Epub 2018 May 22. PubMed PMID: 29963172; PubMed Central PMCID: PMC6019959.

2: Vazquez N, Sanchez L, Marks R, Martinez E, Fanniel V, Lopez A, Salinas A, Flores I, Hirschmann J, Gilkerson R, Schuenzel E, Dearth R, Halaby R, Innis-Whitehouse W, Keniry M. A protocol for custom CRISPR Cas9 donor vector construction to truncate genes in mammalian cells using pcDNA3 backbone. BMC Mol Biol. 2018 Mar 14;19(1):3. doi: 10.1186/s12867-018-0105-8. PubMed PMID: 29540148; PubMed Central PMCID: PMC5853148.

3: Zhang M, Heldin A, Palomar-Siles M, Öhlin S, Bykov VJN, Wiman KG. Synergistic Rescue of Nonsense Mutant Tumor Suppressor p53 by Combination Treatment with Aminoglycosides and Mdm2 Inhibitors. Front Oncol. 2018 Jan 4;7:323. doi: 10.3389/fonc.2017.00323. eCollection 2017. PubMed PMID: 29354595; PubMed Central PMCID: PMC5758538.

4: Prokhorova I, Altman RB, Djumagulov M, Shrestha JP, Urzhumtsev A, Ferguson A, Chang CT, Yusupov M, Blanchard SC, Yusupova G. Aminoglycoside interactions and impacts on the eukaryotic ribosome. Proc Natl Acad Sci U S A. 2017 Dec 19;114(51):E10899-E10908. doi: 10.1073/pnas.1715501114. Epub 2017 Dec 5. PubMed PMID: 29208708; PubMed Central PMCID: PMC5754804.

5: Kanazawa H, Baba F, Koganei M, Kondo J. A structural basis for the antibiotic resistance conferred by an N1-methylation of A1408 in 16S rRNA. Nucleic Acids Res. 2017 Dec 1;45(21):12529-12535. doi: 10.1093/nar/gkx882. PubMed PMID: 29036479; PubMed Central PMCID: PMC5716097.

6: Bai R, Zhang Y, Wang C, Zhang F, Zhang Z, Sun F, Zhang Z. [Gene optimization and efficient expression of Trichoderma reesei Cel5A in Pichia pastoris]. Sheng Wu Gong Cheng Xue Bao. 2016 Oct 25;32(10):1381-1394. doi: 10.13345/j.cjb.160017. Chinese. PubMed PMID: 29027448.

7: Stepanenko AA, Heng HH. Transient and stable vector transfection: Pitfalls, off-target effects, artifacts. Mutat Res. 2017 Jul;773:91-103. doi: 10.1016/j.mrrev.2017.05.002. Epub 2017 May 16. Review. PubMed PMID: 28927539.

8: Fu T, Hu W, Chen Y, Wei H, Yang G. [High-level expression and characterization of Selenomonas ruminantium β-xylosidase in Pichia pastoris]. Sheng Wu Gong Cheng Xue Bao. 2017 May 25;33(5):785-795. doi: 10.13345/j.cjb.160433. Chinese. PubMed PMID: 28876033.

9: Crespo M, Vilar E, Tsai SY, Chang K, Amin S, Srinivasan T, Zhang T, Pipalia NH, Chen HJ, Witherspoon M, Gordillo M, Xiang JZ, Maxfield FR, Lipkin S, Evans T, Chen S. Colonic organoids derived from human induced pluripotent stem cells for modeling colorectal cancer and drug testing. Nat Med. 2017 Jul;23(7):878-884. doi: 10.1038/nm.4355. Epub 2017 Jun 19. Erratum in: Nat Med. 2018 Apr 10;24(4):526. PubMed PMID: 28628110; PubMed Central PMCID: PMC6055224.

10: Tavanafar F, Safaralizadeh R, Hosseinpour-Feizi MA, Mansoori B, Shanehbandi D, Mohammadi A, Baradaran B. Restoration of miR-143 expression could inhibit migration and growth of MDA-MB-468 cells through down-regulating the expression of invasion-related factors. Biomed Pharmacother. 2017 Jul;91:920-924. doi: 10.1016/j.biopha.2017.04.119. Epub 2017 May 12. PubMed PMID: 28511343.

11: Brown SD, Lorenz A. Single-step Marker Switching in Schizosaccharomyces pombe Using a Lithium Acetate Transformation Protocol. Bio Protoc. 2016 Dec 20;6(24). pii: e2075. doi: 10.21769/BioProtoc.2075. PubMed PMID: 28352647; PubMed Central PMCID: PMC5366253.

12: Branchini A, Ferrarese M, Campioni M, Castaman G, Mari R, Bernardi F, Pinotti M. Specific factor IX mRNA and protein features favor drug-induced readthrough over recurrent nonsense mutations. Blood. 2017 Apr 20;129(16):2303-2307. doi: 10.1182/blood-2016-09-738641. Epub 2017 Feb 14. PubMed PMID: 28196793; PubMed Central PMCID: PMC5408560.

13: Arnak R, Altun B, Tosato V, Bruschi CV. Multiple Antibiotic Resistance Plasmids Allow Scalable,PCR-Mediated DNA Manipulation and Near-Zero Background Cloning. Food Technol Biotechnol. 2016 Sep;54(3):257-265. PubMed PMID: 27956856; PubMed Central PMCID: PMC5151216.

14: Morales J, Kokkori S, Weidauer D, Chapman J, Goltsman E, Rokhsar D, Grossman AR, Nowack EC. Development of a toolbox to dissect host-endosymbiont interactions and protein trafficking in the trypanosomatid Angomonas deanei. BMC Evol Biol. 2016 Nov 11;16(1):247. PubMed PMID: 27835948; PubMed Central PMCID: PMC5106770.

15: Bencsik R, Boto P, Szabó RN, Toth BM, Simo E, Bálint BL, Szatmari I. Improved transgene expression in doxycycline-inducible embryonic stem cells by repeated chemical selection or cell sorting. Stem Cell Res. 2016 Sep;17(2):228-234. doi: 10.1016/j.scr.2016.08.014. Epub 2016 Aug 24. PubMed PMID: 27591479.

16: Dehler CE, Boudinot P, Martin SA, Collet B. Development of an Efficient Genome Editing Method by CRISPR/Cas9 in a Fish Cell Line. Mar Biotechnol (NY). 2016 Aug;18(4):449-52. doi: 10.1007/s10126-016-9708-6. Epub 2016 May 28. PubMed PMID: 27236514; PubMed Central PMCID: PMC5007268.

17: Chakraborty M, Sairam Reddy P, Laxmi Narasu M, Krishna G, Rana D. Agrobacterium-mediated genetic transformation of commercially elite rice restorer line using nptII gene as a plant selection marker. Physiol Mol Biol Plants. 2016 Jan;22(1):51-60. doi: 10.1007/s12298-015-0334-y. Epub 2016 Feb 4. PubMed PMID: 27186018; PubMed Central PMCID: PMC4840146.

18: Li T, Li P, Jia T, Jia X, Zhao X, Cheng Y. [Expression of mannose-binding lectin associated protein 19 (MAp19) in HeLa cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2016 Jan;32(1):49-53. Chinese. PubMed PMID: 26728378.

19: Zuccolo E, Bottino C, Diofano F, Poletto V, Codazzi AC, Mannarino S, Campanelli R, Fois G, Marseglia GL, Guerra G, Montagna D, Laforenza U, Rosti V, Massa M, Moccia F. Constitutive Store-Operated Ca(2+) Entry Leads to Enhanced Nitric Oxide Production and Proliferation in Infantile Hemangioma-Derived Endothelial Colony-Forming Cells. Stem Cells Dev. 2016 Feb 15;25(4):301-19. doi: 10.1089/scd.2015.0240. Epub 2016 Jan 26. PubMed PMID: 26654173.

20: Saaby L, Helms HC, Brodin B. IPEC-J2 MDR1, a Novel High-Resistance Cell Line with Functional Expression of Human P-glycoprotein (ABCB1) for Drug Screening Studies. Mol Pharm. 2016 Feb 1;13(2):640-52. doi: 10.1021/acs.molpharmaceut.5b00874. Epub 2016 Jan 5. PubMed PMID: 26651362.