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C0378

Sigma-Aldrich

Chloramphenicol

≥98% (HPLC)

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Synonym(s):
D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin
Linear Formula:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
CAS Number:
Molecular Weight:
323.13
Beilstein:
2225532
EC Number:
MDL number:
UNSPSC Code:
51101500
PubChem Substance ID:
NACRES:
NA.76

Quality Level

Assay

≥98% (HPLC)

form

powder or crystals

pKa 

5.5

mp

149-153 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
mycoplasma

Mode of action

protein synthesis | interferes

storage temp.

room temp

SMILES string

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

InChI key

WIIZWVCIJKGZOK-RKDXNWHRSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Chemical structure: phenicole

Application

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It is often used for bacterial selection in molecular biology applications at 10-20μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.
Chloramphenicol has been used as a bacteriostatic non potent antibiotic. It has been used for the selection/growth of positive bacterial cells.

Biochem/physiol Actions

Mode of Action: Chloramphenicol inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

Caution

Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

Preparation Note

Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

Other Notes

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

Pictograms

Health hazardCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Repr. 2

WGK

WGK 3

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)

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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Targeting antibacterial agents by using drug-carrying filamentous bacteriophages.
Yacoby I et al.
Antimicrobial Agents and Chemotherapy, 50, 2087-2087 (2006)
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Tomanov K and Bachmair A
Bio-protocol null
Kyle J Wayne et al.
Journal of bacteriology, 192(17), 4388-4394 (2010-07-14)
The WalRK two-component regulatory system coordinates gene expression that maintains cell wall homeostasis and responds to antibiotic stress in low-GC Gram-positive bacteria. Phosphorylated WalR (VicR) of the major human respiratory pathogen Streptococcus pneumoniae (WalR(Spn)) positively regulates transcription of several surface
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Cell reports, 27(2), 334-342 (2019-04-02)
We have previously described the existence of membranous nanotubes, bridging adjacent bacteria, facilitating intercellular trafficking of nutrients, cytoplasmic proteins, and even plasmids, yet components enabling their biogenesis remain elusive. Here we reveal the identity of a molecular apparatus providing a

Protocols

To measure chloramphenicol acetyltransferase activity, this procedure uses DTNB and coenzyme A. The reaction of DTNB with the –SH group on CoA results in a colorimetric increase at 412 nm.

Preparation of Plasmid DNA by Alkaline Lysis with SDS: Maxipreparation between Cold Spring Harbor Laboratory Press and our research team.

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