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S9007

Sigma-Aldrich

Spectinomycin dihydrochloride pentahydrate

potency: ≥603 μg per mg

Synonym(s):

Actinospectacin, Actinospectacin dihydrochloride pentahydrate, Spectinomycin, Spectinomycin HCL, Spectinomycin Hydrochloride, Spectinomycin hydrochloride

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About This Item

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:
51101500
PubChem Substance ID:
24899822
NACRES:
NA.85

biological source

synthetic (inorganic)

Quality Level

200

form

powder

potency

≥603 μg per mg

storage condition

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

color

white to pale buff

solubility

H2O: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

application(s)

agriculture

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

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.

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.

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

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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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
Stefan Schwarz et al.
The Journal of antimicrobial chemotherapy, 53(2), 379-382 (2004-01-20)
Prior to the renewal of spectinomycin licensing for veterinary uses in Germany, 154 Pasteurella multocida and 148 Mannheimia haemolytica strains from respiratory tract infections in cattle were investigated for their MICs of spectinomycin and other antimicrobial agents. The data obtained
Marty K Soehnlen et al.
Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc, 23(3), 547-551 (2011-09-13)
Mycoplasma bovis is an important pathogen of cattle, causing mastitis, pneumonia, conjunctivitis, otitis, and arthritis. Currently there are only a few reports of sensitivity levels for M. bovis isolates from the United States. Mycoplasma bovis isolates submitted to the Pennsylvania
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Cytostatic drugs have been widely used for chemotherapy for decades. However, many of them have been categorized as carcinogenic, mutagenic and teratogenic compounds, triggering widespread concerns about their occupational exposure and ecotoxicological risks to the environment. This review focuses on
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We report here the isolation of spectinomycin-resistant mutants in cultured cells of Medicago sativa line RegenSY-T2. Spectinomycin induces bleaching of cultured alfalfa cells due to inhibition of protein synthesis on the prokaryotic type 70S plastid ribosomes. Spontaneous mutants resistant to
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