N-[(7R,8S)-2-Carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide,(1→528)-lactone 硫链丝菌肽

CAS 1393-48-2 MFCD00135828

化学结构图

1393-48-2
SMILES: C=C(NC(=O)C(=C)NC(=O)c1csc(C2=N[C@H]3c4csc(n4)[C@H]4NC(=O)c5csc(n5)[C@H]([C@@](C)(O)[C@@H](C)O)NC(=O)[C@H]5CSC(=N5)/C(=C\C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c5csc(n5)[C@]3(CC2)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@H](C(C)CC)N[C@@H]2C=Cc3c([C@H](C)O)cc(nc3[C@H]2O)C(=O)O[C@@H]4C)n1)C(N)=O

化学属性

Mol. FormulaC72H85N19O18S5
Mol. Weight1665.06
TSCANo
Melting Point248-250
Density1.64
SolubilitySoluble in DMSO (10 mg/ml), chloroform (10 mg/ml), dioxane, pyridine, glacial acetic acid, and DMF. Insoluble in water

别名和识别编码

Chemical NameN-[(7R,8S)-2-Carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-alaninamide,(1→528)-lactone
CAS Number1393-48-2
MDL NumberMFCD00135828
PubChem Substance ID24900569
EC Number215-734-9
Synonym Antibiotic A 8506 Thiactin 硫链丝菌素 Bryamycin X 146 Antibiotic X 146 Antibiotic 6761-31 A-8506 Thiostrepton from Streptomyces azureus
Merck Number14,9364
Chemical Name Translation硫链丝菌肽
LabNetwork Molecule IDLN02125555
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分类

  • {SNA} Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Application, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Chemical Structure Class, Gene Regulation and Expression, Genetic Marker Selection, Interferes with Protein Synthesis, L - Z, Mechanism of Action, Peptides, RNA-Protein Translation Inhibitors, Spectrum of Activity, T
  • {SNA} Antibacterial, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Application, Bioactive Small Molecule Alphabetical Index, Chemical Structure Class,

产品应用

  • A protein synthesis-inhibiting antibiotic

相关文献及参考

  • Starosta, A., et al.; Chem. Biol., 16, 1087 (2009),
  • Merck: 14,9364

安全信息

WGK Germany3
GHS Symbol
Hazard statements
  • H302 Harmful if swallowed 吞食有害
RTECSXN6300100
Signal word
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Hazard Codes Xn
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
Precautionary statements
Storage condition 储存温度:-20℃ 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 41 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),396,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ANTCAO Antibiotics and Chemotherapy (Washington, DC).  (Washington, DC)
   V.1-12, 1951-62.  For publisher information, see CLMEA3.
   Volume(issue)/page/year: 6,63,1956

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),396,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),397,1980

其他信息

  • 硫链丝菌素可溶于氯仿，二氯甲烷，二恶烷，吡啶，冰醋酸，DMF。几乎不溶于水、低级醇、非极性有机溶剂、稀酸和碱。1％的DMSO溶液浓度是不稳定的，应新鲜配制和避光。
  • Thiostrepton is a cyclic peptide antibiotic, densely packed with thiazoles and other structurally intriguing moieties. Thiostrepton exhibits antibiotic activity through blockade of ribosome turnover after an elongation step in protein synthesis by inhibiting both the dissociation of elongation factor G (EF-G) from the ribosome and the release of inorganic phosphate from EF-G following GTP hydrolysis. Thiostrepton is also described to show efficacy against cancer cell growth through downregulation of the forkhead box M1 (FOXM1) transcription factor, commonly overexpressed in many malignancies. Thiostrepton is an inhibitor of FOXM1

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics T-Z - Antibiotics A to Z
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Chemical Structure Class - Antibiotics
  4. Peptides - Chemical Structure Class
  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Spectrum of Activity - Antibiotics
  4. Antibacterial - Spectrum of Activity
  5. L - Z - Antibacterial
  1. Functional Group 官能团索引
  2. imidothioester

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