26430

Sigma-Aldrich

Chlortetracycline hydrochloride

suitable for fluorescence, BioReagent, from Streptomyces aureofaciens, ≥85.0% (HPLC)

Synonym(s):
7-Chlorotetracycline hydrochloride
Empirical Formula (Hill Notation):
C22H23ClN2O8 · HCl
CAS Number:
Molecular Weight:
515.34
Beilstein/REAXYS Number:
3858364
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

biological source

Streptomyces aureofaciens

product line

BioReagent

assay

≥85.0% (HPLC)

form

powder or crystals

color

faintly yellow to yellow

mp

210-215 °C (dec.) (lit.)

solubility

H2O: 50 mg/mL

fluorescence

λex 392 nm; λem 536 nm in 0.1 M Tris pH 8.0, 10 mM Ca2+

suitability

suitable for fluorescence

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

storage temp.

−20°C

SMILES string

Cl.CN(C)[C@H]1[C@@H]2CC3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)ccc(Cl)c4[C@@]3(C)O

InChI

1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7?,8-,15-,21-,22-;/m0./s1

InChI key

CBHYYLPALVVVEY-LYNLVHCPSA-N

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Related Categories

General description

Chemical structure: tetracycline

Application

Cell-permeable fluorescent probe for Ca2+ for measuring calcium flux in endoplasmic reticulum and other intracellular stores in situ.

Biochem/physiol Actions

Chlortetracycline is an antibiotic produced by some strains of Streptomyces aureofaciens.
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit.
Antimicrobial spectrum: Gram-positive. Less active against Gram-negative bacteria than tetracycline.
Mode of Resistance: Loss of cell wall permeability.

Packaging

5 g, 25 g, 100g

Quality

Recommended for fluorescent studies of calcium signaling in cells or tissues.

Other Notes

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Lindsay Gillan et al.
Theriogenology, 63(2), 445-457 (2005-01-01)
Most laboratory methods used to evaluate semen quality have not correlated highly with fertilizing capacity. The discovery of a variety of fluorochromes and compounds conjugated to fluorescent probes has enabled a more widespread analysis of sperm attributes, and in conjunction...
Claudia Cerella et al.
Annals of the New York Academy of Sciences, 1099, 490-493 (2007-04-21)
Many studies suggest that endoplasmic reticulum (ER) Ca2+ pool rather than cytosolic Ca2+ may play a crucial role in triggering apoptosis. In this study, we performed an image analysis of cells loaded with the fluorescent dye chlortetracycline (CTC) to in...
A E Oliver et al.
Biophysical journal, 78(4), 2116-2126 (2000-03-29)
The effect of temperature on the binding equilibria of calcium-sensing dyes has been extensively studied, but there are also important temperature-related changes in the photophysics of the dyes that have been largely ignored. We conducted a systematic study of thermal...
Dominik Hager et al.
Angewandte Chemie (International ed. in English), 51(26), 6525-6528 (2012-05-31)
Better late than never! Two herbicidins, members of an important family of nucleoside antibiotics, have been synthesized for the first time. The route integrates a stereoselective C-glycosylation with several reagent-controlled stereoselective transformations and a surprisingly facile and highly diastereoselective late-stage...
Zhizhong Li et al.
Journal of biochemical and molecular toxicology, 26(9), 331-336 (2012-06-26)
In this work, the interaction of chlortetracycline with bovine serum albumin (BSA) was investigated by fluorescence spectroscopy, circular dichroism (CD) spectroscopy, and molecular docking. Results indicated that chlortetracycline quenches BSA fluorescence mainly by a static quenching mechanism. The quenching constants...

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