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L2774

Sigma-Aldrich

Lincomycin hydrochloride

suitable for cell culture, BioReagent

Synonym(s):

Lincocin hydrochloride, Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-α-D-galactooctopyranoside hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H34N2O6S · HCl
CAS Number:
859-18-7
Molecular Weight:
443.00
Beilstein:
4171650
EC Number:
212-726-7
MDL number:
MFCD00083647
UNSPSC Code:
12352207
PubChem Substance ID:
329817401
NACRES:
NA.76

product name

Lincomycin hydrochloride, BioReagent, suitable for cell culture

product line

BioReagent

Quality Level

200

potency

800-900 units per mg

technique(s)

cell culture | mammalian: suitable

color

white to yellow-white

solubility

H2O: 4 mL, clear, colorless to faintly yellow (200 mg + 4 mL H2O)

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O

InChI

1S/C18H34N2O6S.ClH/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1

InChI key

POUMFISTNHIPTI-BOMBIWCESA-N

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General description

Chemical structure: macrolide

Application

Lincomycin hydrochloride is an antibiotic used to study the inhibition of protein synthesis, bacterial antibiotic resistance and protein and surfactant binding. It is produced by Streptomyces lincolnensis var. lincolnensis, and has been used in the treatment of Staphylococcal, Streptococcal, and Bacterioides fragilis infections.

Biochem/physiol Actions

Mode of action: Lincomycin inhibits bacterial protein synthesis by forming cross-links within the peptidyl transferase loop region of the 23S rRNA.†

Antimicrobial spectrum: Lincomycin hydrochloride is effective against gram-positive bacteria.

Preparation Note

This product is soluble in water at 50 mg/mL, yielding a clear, colorless solution.

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

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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Liu Duan et al.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 375(1801), 20190402-20190402 (2020-05-05)
Chloroplast-to-nucleus retrograde signalling (RS) is known to impact plant growth and development. In Arabidopsis, we and others have shown that RS affects seedling establishment by inhibiting deetiolation. In the presence of lincomycin, a chloroplast protein synthesis inhibitor that triggers RS
Yongjian Qiu et al.
Nature communications, 10(1), 140-140 (2019-01-13)
Ambient temperature sensing by phytochrome B (PHYB) in Arabidopsis is thought to operate mainly at night. Here we show that PHYB plays an equally critical role in temperature sensing during the daytime. In daytime thermosensing, PHYB signals primarily through the
Michael E Ruckle et al.
Plant physiology, 159(1), 366-390 (2012-03-03)
We previously provided evidence that plastid signaling regulates the downstream components of a light signaling network and that this signal integration coordinates chloroplast biogenesis with both the light environment and development by regulating gene expression. We tested these ideas by
Shogo Ogami et al.
Biochimica et biophysica acta, 1817(8), 1322-1330 (2012-02-14)
The sensitivity to high light conditions of Photosystem II with either PsbA1 (WT*1) or PsbA3 (WT*3) as the D1 protein was studied in whole cells of the thermophilic cyanobacterium Thermosynechococcus elongatus. When the cells are cultivated under high light conditions
Erica Belgio et al.
Biophysical journal, 102(12), 2761-2771 (2012-06-28)
The maximum chlorophyll fluorescence lifetime in isolated photosystem II (PSII) light-harvesting complex (LHCII) antenna is 4 ns; however, it is quenched to 2 ns in intact thylakoid membranes when PSII reaction centers (RCIIs) are closed (Fm). It has been proposed
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