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Documenti fondamentali

T9823

Sigma-Aldrich

Tetracycline hydrochloride

Biotechnology Performance Certified, suitable for cell culture, ≥95%

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About This Item

Formula empirica (notazione di Hill):
C22H24N2O8 · HCl
Numero CAS:
Peso molecolare:
480.90
Beilstein:
3844873
Numero CE:
Numero MDL:
Codice UNSPSC:
51101500
ID PubChem:

Grado

Biotechnology Performance Certified

Saggio

≥95%

tecniche

cell culture | mammalian: suitable

Impurezze

endotoxin, tested

Punto di fusione

220-223 °C (lit.)

Solubilità

H2O: soluble 50 mg/mL

Spettro attività antibiotica

Gram-negative bacteria
Gram-positive bacteria

Modalità d’azione

protein synthesis | interferes

Temperatura di conservazione

−20°C

Stringa SMILE

Cl.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O

InChI

1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
XMEVHPAGJVLHIG-FMZCEJRJSA-N

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Descrizione generale

Chemical structure: tetracycline

Applicazioni

Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne. It is used to study multidrug resistance as well as potential side effects such as acute pancreatitis. It has been used in target and resistance based mechanistic studies of novel antibiotics.

Azioni biochim/fisiol

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.
Tetracycline inhibits bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Tetracycline passively diffuses through porin channels in the bacterial cell membrane. It also binds to the bacterial 50S ribosomal subunit which may alter the cytoplasmic membrane, causing intracellular components to leak from bacterial cells. Mode of resistance is loss of cell wall permeability.

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


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Certificati d'analisi (COA)

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Trudy H Grossman et al.
Antimicrobial agents and chemotherapy, 56(5), 2559-2564 (2012-02-23)
TP-434 is a novel, broad-spectrum fluorocycline antibiotic with activity against bacteria expressing major antibiotic resistance mechanisms, including tetracycline-specific efflux and ribosomal protection. The mechanism of action of TP-434 was assessed using both cell-based and in vitro assays. In Escherichia coli
Increased risk of acute pancreatitis among tetracycline users in a Swedish population-based case-control study
Rickard Ljung, Jesper Lagergren, et al.
Gut, 10.1136, 300949-300949 (2011)
Ricardo E de Cristóbal et al.
The Journal of antimicrobial chemotherapy, 58(1), 31-36 (2006-05-12)
Starting from the observation that Escherichia coli tolC mutations severely reduced the high-level resistance to tetracycline afforded by Tn10- and plasmid-encoded Tet(A) pumps, we studied the mechanism of this susceptibility. The MIC of tetracycline for MC4100 tolC::Tn10 and several tolC
Yasuhiro Igarashi et al.
Journal of natural products, 74(4), 670-674 (2011-03-11)
A new spirotetronate-class polyketide, maklamicin (1), was isolated from the culture extract of an endophytic actinomycete of the genus Micromonospora. The structure and relative configuration of 1 were elucidated by interpretation of NMR and other spectroscopic data, and the absolute
Ruiling Qi et al.
Colloids and surfaces. B, Biointerfaces, 110, 148-155 (2013-05-29)
Fabrication of nanofiber-based drug delivery system with controlled release property is of general interest in biomedical sciences. In this study, we prepared an antibiotic drug tetracycline hydrochloride (TCH)-loaded halloysite nanotubes/poly(lactic-co-glycolic acid) composite nanofibers (TCH/HNTs/PLGA), and evaluated the drug release and

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