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S2647

Sigma-Aldrich

Spectinomycin dihydrochloride pentahydrate

powder, γ-irradiated

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Empirical Formula (Hill Notation):
C14H24N2O7 · 2HCl · 5H2O
CAS Number:
22189-32-8
Molecular Weight:
495.35
EC Number:
244-554-3
MDL number:
MFCD00150886
UNSPSC Code:
12352200
PubChem Substance ID:
24899532
NACRES:
NA.85

biological source

synthetic (inorganic)

Quality Level

200

grade

for molecular biology

sterility

γ-irradiated

form

powder

potency

≥500 μg per mg

storage condition

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

color

white to off-white

solubility

H2O: soluble at 

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

suitability

nonselective for Escherichia coli
nonselective for coliforms

SMILES string

O.O.O.O.O.Cl.Cl.CN[C@@H]1[C@H](O)[C@H](NC)[C@H]2O[C@]3(O)[C@@H](O[C@H](C)CC3=O)O[C@@H]2[C@H]1O

InChI

1S/C14H24N2O7.2ClH.5H2O/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14;;;;;;;/h5,7-13,15-16,18-20H,4H2,1-3H3;2*1H;5*1H2/t5-,7-,8+,9+,10+,11-,12-,13+,14+;;;;;;;/m1......./s1

InChI key

DCHJOVNPPSBWHK-UXXUFHFZSA-N

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General description

Chemical structure: aminoglycoside

Application

Spectinomycin is an aminocyclitol antibiotic derived from Streptomyces spectabilis. It has been shown to have a wide variety of uses, including treating acute gonorrheal urethritis and cervictis, to mark cell layers to monitor cell fate during leaf development, as a selection marker in plant related transformation systems for plant cells containing the marker gene Spcr, to study respiratory tract infections of cattle caused by Pasteurella multocida and Mannheimia haemolytica, and to generate plants deficient for the plastid-encoded RNA polymerase on MS-agar media. Spectinomycin also has use in amplification of low copy number plasmid carrying replicons. It is recommended for use in cell culture applications at 7.5-20 mg/L.

Biochem/physiol Actions

Mode of Action: Spectinomycin acts by inhibiting protein synthesis and elongation by binding to the bacterial 30S ribosomal subunit and interfering with peptidyl tRNA translocation.

Mode of Resistance: A mutation in rpsE, the gene for ribosomal protein S5, prevents the binding of spectinomycin. Resistance is also conferred by the aminoglycoside-3′-adenyltransferase gene (aadA).

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

Packaging

100MG

Caution

Solutions can be stored at 2-8°C for several weeks or at -20°C for more extended periods.

Preparation Note

Stock solutions should be prepared at 10 mg/mL in water and filter sterilized.

Other Notes

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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Susanna Ricci et al.
Infection and immunity, 70(9), 4968-4976 (2002-08-17)
Ferric uptake regulator (Fur) and Fur-like proteins form an important family of transcriptional regulators in many bacterial species. In this work we have characterized a Fur-like protein, the peroxide regulator PerR, in an M1 serotype of Streptococcus pyogenes. To determine
K Matsumoto et al.
Journal of bacteriology, 180(1), 100-106 (1998-01-09)
The psd gene of Bacillus subtilis Marburg, encoding phosphatidylserine decarboxylase, has been cloned and sequenced. It encodes a polypeptide of 263 amino acid residues (deduced molecular weight of 29,689) and is located just downstream of pss, the structural gene for
Praveen Kumar et al.
Journal of separation science, 35(4), 498-504 (2012-01-28)
The effect of mobile-phase constituents (pH and ionic strength) and chromatographic behaviour of ten aminoglycosides (streptomycin, dihydrostreptomycin, spectinomycin, apramycin, paramomycin, kanamycin A, gentamycin C1, gentamycin C2/C2a, gentamycin C1a and neomycin) in the bare silica, amino, amide and zwitterionic phases of
Amber M Hotto et al.
G3 (Bethesda, Md.), 1(7), 559-570 (2012-03-03)
Noncoding RNAs (ncRNA) are widely expressed in both prokaryotes and eukaryotes. Eukaryotic ncRNAs are commonly micro- and small-interfering RNAs (18-25 nt) involved in posttranscriptional gene silencing, whereas prokaryotic ncRNAs vary in size and are involved in various aspects of gene
Magnus Unemo et al.
Antimicrobial agents and chemotherapy, 57(2), 1057-1061 (2012-11-28)
Gonorrhea may become untreatable, and new treatment options are essential. Verified resistance to spectinomycin is exceedingly rare. However, we describe a high-level spectinomycin-resistant (MIC, >1,024 μg/ml) Neisseria gonorrhoeae strain from Norway with a novel resistance mechanism. The resistance determinant was
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