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Merck
CN

T9823

四环素 盐酸盐

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

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关于此项目

经验公式(希尔记法):
C22H24N2O8 · HCl
化学文摘社编号:
分子量:
480.90
EC Number:
200-593-8
UNSPSC Code:
51101500
PubChem Substance ID:
Beilstein/REAXYS Number:
3844873
MDL number:
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InChI key

XMEVHPAGJVLHIG-FMZCEJRJSA-N

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

SMILES string

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

grade

Biotechnology Performance Certified

assay

≥95%

technique(s)

cell culture | mammalian: suitable

impurities

endotoxin, tested

mp

220-223 °C (lit.)

solubility

H2O: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

−20°C

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General description

Chemical structure: tetracycline

Application

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.

Biochem/physiol Actions

作用机制:四环素通过细胞膜中的 proin 通道被动扩散,与 30S 核糖体结合,并通过阻止氨酰基 tRNA 进入 mRNA-核糖体复合物上的受体位点来抑制蛋白质合成。它也与细菌的 50S 核糖体亚基结合,改变膜并导致细胞内成分从细菌细胞中泄漏。通过洗涤可以逆转抑制作用,这表明起到抗菌作用的是可逆结合的抗生素,而不是不可逆结合的药物。

耐药性机制:这种作用通过细胞壁通透性的丧失而失活。

抗菌谱:包括对革兰氏阳性和革兰氏阴性细菌的广泛抗菌活性。
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.

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

涉药品监管产品
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分析证书(COA)

Lot/Batch Number

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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
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
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)
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
Biyang Deng et al.
Food chemistry, 134(4), 2350-2354 (2013-02-28)
A novel and sensitive determination for tetracycline (TC) in crucian carp muscle was developed by using capillary electrophoresis coupled with electrochemiluminescence (ECL) detection. The conditions affected separation and detection were examined in detail. The linearity range of TC concentration was

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