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Thiostrepton

SKU
T-1202
  • CAS:1393-48-2
  • Formula:C72H85N19O18S5
  • MW:1664.89 Da
  • Appearance:White to off-white powder
  • Purity:>90% (HPLC)

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SDS
CofA
Product Name Qty
Thiostrepton, Thiazole-containing peptide antibiotic
1 g
$164.60
Thiostrepton, Thiazole-containing peptide antibiotic
5 g
$705.32
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Description

Thiostrepton is a thiazole-containing peptide antibiotic from Streptomyces. It is generally used for Gram-negative and Gram-positive bacteria and is employed as a selective marker for recombinant DNA/plasmid technologies.

The thiazole antibiotic inhibits protein synthesis by preventing binding of elongation factor G (EF-G) and GTP to 50S ribosomal subunit and affects the function of initiation factor IF2.

Thiostrepton has shown anticancer properties such as induction of apoptosis and suppression of cell growth in human cancer cells. For example, it blocks expression of FoxM1-regualted genes and thus suppresses the transcription factor, FoxM1, which is related to cell proliferation and commonly overexpressed in tumor cell lines. This antibiotic arrests cell cycle at G1 and S phases and induces cell death in cancer cells.

 

Applications

• Selective marker for recombinant DNA/plasmid technology

• Protein synthesis inhibitor

• Inhibition of FoxM1 expression in cancer cells

 

Reference

• “Thiostrepton selectively targets breast cancer cells through inhibition of forkhead box M1 expression”

• “Thiostrepton: A ribosomal inhibitor of translocation”

• “The transcription factor FOXM1 is a cellular target of the natural product thiostrepton”

• “Initiation Factor IF2, Thiostrepton and Micrococcin Prevent the Binding of Elongation Factor G to the Escherichia coli Ribosome”

 

Not for human therapeutic use or for medicinal purposes. For research applications only.

More Information
Alternate Name/Synonyms
Bryamycin; Thiactin; Alaninamide; Gargon; Antibiotic X 146
SKU
T-1202
CAS #
1393-48-2
Chemical Name
N-[3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl]-2-[(11E)-37-butan-2-yl-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetra
Chemical Formula
C72H85N19O18S5
Molecular Weight
1664.89 Da
Appearance
White to off-white powder
Purity
>90% (HPLC)
Solubility
Soluble in DMSO (15 mg/mL) and chloroform (5 mg/mL)
Melting Point
245-250 °C
Storage Temp
-20°C, desiccated
THERAPEUTIC AREA
Infectious Diseases
USE
Thiostrepton has been used as a selectable marker for recombinant Streptomyces cultures. 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.
MDL NUMBER
MFCD00135828
CHEMACX
X1011724-3
INCHI
InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1
SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)NC(=C)C(=O)N[C@H](C(=O)N[C@]23CCC(=N[C@@H]2c4csc(n4)[C@H]([C@H](OC(=O)c5cc(c6c(n5)[C@H]([C@H](N1)C=C6)O)[C@H](C)O)C)NC(=O)c7csc(n7)[C@@H](NC(=O)[C@H]8CSC(=N8)/C(=C/C)/NC(=O)[C@@H](NC(=O)c9csc3n9)[C@@H](C)O)[C@@](C)([C@@H](
RTECS
XN6300100
Handling
Avoid contact with skin, eyes or clothing. Use personal protective equipment as required. Wash contaminated clothing before reuse. Do not breathe dust/fume/gas/mist/vapors/spray. Do not eat, drink or smoke when using this product. Corrosive hazard. Wear protective gloves/clothing and eye/face protection.
Certificate of Analysis 1
T-1202, J1239.pdf
Certificate of Analysis 2
T-1202, J1066.pdf
GHS PICTOGRAMS
Handling Avoid contact with skin, eyes or clothing. Use personal protective equipment as required. Wash contaminated clothing before reuse. Do not breathe dust/fume/gas/mist/vapors/spray. Do not eat, drink or smoke when using this product. Corrosive hazard. Wear protective gloves/clothing and eye/face protection.
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