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Key Documents

G1264

Sigma-Aldrich

Gentamicin sulfate salt

powder, non-animal origin, suitable for cell culture, BioReagent

Synonym(s):

Gentiomycin C

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About This Item

CAS Number:
EC Number:
MDL number:
UNSPSC Code:
12352207
eCl@ss:
42020823
PubChem Substance ID:
NACRES:
NA.76

product name

Gentamicin sulfate salt, powder, BioReagent, suitable for cell culture

biological source

Micromonospora purpurea

product line

BioReagent

form

powder

potency

~600 μg Gentamicin per mg

technique(s)

cell culture | mammalian: suitable

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

O=S(O)(O)=O.O[C@]1(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@@](CC[C@H]3N)([C@@H](C)NC)[H])[C@@H](N)C[C@H]2N)OC1)NC.O[C@]4(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]5[C@@H](O)[C@H](O[C@H]6O[C@@](CC[C@H]6N)([C@@H](C)N)[H])[C@@H](N)C[C@H]5N)OC4)NC.O[

InChI

1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

InChI key

RDEIXVOBVLKYNT-HDZPSJEVSA-N

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General description

Chemical structure: aminoglycoside
Gentamicin, also known as gentiomycin C, is an aminoglycoside, which is naturally produced by Gram-negative bacteria. This antibiotic functions by preventing protein synthesis. Gentamicin sulfate prevents the growth of both Gram positive and Gram negative bacteria, in vivo and in vitro. In tissue culture, gentamicin sulfate is used to inhibit the growth of various strains of mycoplasma.

Application

Gentamicin sulfate, a broad-spectrum antibiotic, has been used as a selection agent (gentamicin-resistance gene) in cell culture and molecular biology applications. This product is recommended for use at 50 mg/L.

Biochem/physiol Actions

Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site. The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.

Antimicrobial spectrum: Includes Gram-negative and Gram-positive bacteria, including strains resistant to tetracycline, chloramphenicol, kanamycin and colistin, particularly strains of Pseudomonas, Proteus, Staphylococcus and Streptococcus.

Components

Gentamicin is an aminoglycoside complex produced by fermentation of Micromonospora purpurea or M. echinospora. It is used as the sulfate salt. There are three components, each consisting of five basic nitrogens and requiring five equivalents of sulfuric acid per mole of gentamicin base.

Caution

Sterile solutions should be stored at 2-8°C. Solutions have also been shown to be stable at room temperature and in boiling aqueous buffers of pH 2-142.

Analysis Note

Solubility- freely soluble in water, practically insoluble in ethanol

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hongzhe Li et al.
PloS one, 6(4), e19130-e19130 (2011-05-10)
Exposure to intense sound or high doses of aminoglycoside antibiotics can increase hearing thresholds, induce cochlear dysfunction, disrupt hair cell morphology and promote hair cell death, leading to permanent hearing loss. When the two insults are combined, synergistic ototoxicity occurs
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Acta biomaterialia, 22, 155-163 (2015-04-30)
Over the last decades, wound dressings have evolved from a crude traditional gauze dressing to tissue-engineered scaffolds. Many types of wound dressing formats are commercially available or have been investigated. We developed and studied hybrid bilayer wound dressings which combine
A Rudin et al.
Applied microbiology, 20(6), 989-990 (1970-12-01)
Gentamicin is a more effective in vitro bacterial inhibitor than combined penicillinstreptomycin, is nontoxic to tissue culture monolayers, and does not inhibit virus replication.

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