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G1264

Sigma-Aldrich

Gentamicin sulfate salt

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

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Synonym(s):
Gentiomycin C
CAS Number:
1405-41-0
EC Number:
215-778-9
MDL number:
MFCD00270181
UNSPSC Code:
12352207
eCl@ss:
42020823
PubChem Substance ID:
329799833
NACRES:
NA.76

biological source

Micromonospora purpurea

Quality Level

200

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
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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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
Arnaud Gutierrez et al.
Molecular cell, 68(6), 1147-1154 (2017-12-12)
Physiologic and environmental factors can modulate antibiotic activity and thus pose a significant challenge to antibiotic treatment. The quinolone class of antibiotics, which targets bacterial topoisomerases, fails to kill bacteria that have grown to high density; however, the mechanistic basis
Inge Van Der Linden et al.
International journal of environmental research and public health, 11(10), 10105-10124 (2014-10-01)
It is accepted that irrigation water is a potential carrier of enteric pathogens, such as Salmonella and E. coli O157:H7 and, therefore, a source for contamination of fresh produce. We tested this by comparing irrigation water samples taken from five
S A Sergeev et al.
Acta naturae, 3(4), 66-72 (2012-06-01)
The use of stem cell technologies in retinal defect reparation therapy has produced beneficial results. Nowadays, numerous protocols exist which provide a neural differentiation of the stem cells transplanted into the retina. However, questions concerning the functional replacement of the
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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