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T9823

Sigma-Aldrich

Tetracycline hydrochloride

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

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About This Item

Fórmula empírica (Notação de Hill):
C22H24N2O8 · HCl
Número CAS:
Peso molecular:
480.90
Beilstein:
3844873
Número CE:
Número MDL:
Código UNSPSC:
51101500
ID de substância PubChem:

grau

Biotechnology Performance Certified

Ensaio

≥95%

técnica(s)

cell culture | mammalian: suitable

Impurezas

endotoxin, tested

pf

220-223 °C (lit.)

solubilidade

H2O: soluble 50 mg/mL

espectro de atividade do antibiótico

Gram-negative bacteria
Gram-positive bacteria

Modo de ação

protein synthesis | interferes

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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Descrição geral

Chemical structure: tetracycline

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Palavra indicadora

Warning

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


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Visite a Biblioteca de Documentos

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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