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Sigma-Aldrich® Streptomycin sulfate salt

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MT-CM-S6501-25G

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Linear Formula:  C21H39N7O12 · 1.5 H2SO4

CAS Number:  3810-74-0

Molecular Weight:  728.69

Beilstein:  3894995

EC Number:  223-286-0

MDL number:  MFCD00037023

UNSPSC Code:  51281675

PubChem Substance ID:  24899705

NACRES:  NA.76

biological source:  Streptomyces griseus

Quality Level:  200

Form:  powder

Potency:  ≥720 I.U. per mg

mol wt:  calculated mol wt 1457.38

storage condition:

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

Color:  white to off-white

antibiotic activity spectrum:

Gram-negative bacteria

Gram-positive bacteria

mycobacteria

Mode of action:  protein synthesis | interferes

storage temp.:  2-8°C

SMILES string:

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]2[C@@H](O[C@@H](C)[C@]2(O)C=O)O[C@@H]3[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]3NC(N)=N.CN[C@H]4[C@H](O)[C@@H](O)[C@H](CO)O[C@H]4O[C@H]5[C@@H](O[C@@H](C)[C@]5(O)C=O)O[C@@H]6[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]6NC(N)=N

InChI:

1S/2C21H39N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;;/m00.../s1

InChI key:  QTENRWWVYAAPBI-YZTFXSNBSA-N

General description

(C21H39N7O12)2 ⋅3H2O4S

Chemical structure: aminoglycoside

Application

Streptomycin is used to study mechanisms of streptomycin resistance and is often used together with penicillin and other agents to inhibit bacterial contamination in cell culture applications. It is recommended for use in molecular biology applications at 25-50μg/mL, in cell culture applications at 100 mg/L and in embryo culture at 50 mg/L.

Biochem/physiol Actions

Mode of Action: Streptomycin acts by inhibiting prokaryote protein synthesis by binding to the S12 protein of the 30S ribosomal subunit, thus preventing the transition from imitation complex to chain-elongating ribosome. This causes miscoding or inhibits initiation.

Mode of Resistance: A mutation in rpsL, a gene for S12 ribosomal protein, prevents binding of streptomycin to the ribosome. An aminoglycoside phosphotransferase also inactivates streptomycin.

Antimicrobial spectrum: Streptomycin acts against gram-negative and gram-positive bacteria.

Preparation Note

Stock solutions should be prepared directly in the vial with sterile water at concentrations between 20-25 mg/mL.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place

Disclaimer

Solutions can be stored at 2-8°C for up to a month or at -20°C for more extended periods. At 37°C, solutions are stable for three days.