Thiostrepton
SKU
T-1202
- CAS:1393-48-2
- Formula:C72H85N19O18S5
- MW:1664.89 Da
- Appearance:White to Off-white powder
- Purity:>90% (HPLC)
SDS
CofA
Thiostreptin is a thiazole-containing peptide antibiotic used in molecular biology applications. The thiostrepton-resistant gene is commonly used as a selective marker for recombinant DNA/plasmid technologies. Thiostrepton inhibits protein synthesis by preventing binding of GTP to 50S ribosomal subunit. Activation of TLR7–9 has been linked to autoimmune diseases such as rheumatoid arthritis, lupus, and psoriasis. Thiostrepton has been shown to be a novel TLR7–9 inhibitor1. Thiostrepton inhbits FoxM1 which ultimately suppresses tumor formation in ovarian cancer cells2.
2.) http://carcin.oxfordjournals.org/content/36/4/498.full.pdf+html
More Information
Alternate Name/Synonyms
Thiostrepton; Bryamycin; Thiactin; Alaninamide; Gargon
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
Preparation
N/A
Storage Temp
-20°C, desiccated
THERAPEUTIC AREA
Infectious Diseases
USE
Thiostrepton has been used as a selectable marker for recombinant Streptomyces cultures as it is one of the cyclic peptides from Steretomyces that is active against gram-positive bacteria. It 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.
Merck Index
N/A
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
Certificate of Analysis 2
| 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. |