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T8902

Sigma-Aldrich

Thiostrepton from Streptomyces azureus

from Streptomyces azureus, ≥90% (HPLC), powder, FoxM1 inhibitor

Synonym(s):

Bryamycin, NSC 170365, NSC 81722, Thiactin, Thiostreptin A

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About This Item

Empirical Formula (Hill Notation):
C72H85N19O18S5
CAS Number:
1393-48-2
Molecular Weight:
1664.89
EC Number:
215-734-9
MDL number:
MFCD00135828
UNSPSC Code:
12352200
PubChem Substance ID:
24900569
NACRES:
NA.77

product name

Thiostrepton from Streptomyces azureus, ≥90% (HPLC)

Assay

≥90% (HPLC)

solubility

acetic acid: soluble 25 mg/mL, clear to hazy, yellow to brownish-yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
parasites

Mode of action

protein synthesis | interferes

storage temp.

−20°C

SMILES string

CCC(C)C1NC2C=Cc3c(cc(nc3C2O)C(=O)OC(C)C4NC(=O)c5csc(n5)C(NC(=O)C6CSC(=N6)C(\NC(=O)C(NC(=O)c7csc(n7)C8(CCC(=NC8c9csc4n9)c%10nc(cs%10)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)NC(=O)C(C)NC(=O)C(=C)NC(=O)C(C)NC1=O)C(C)O)=C\C)C(C)(O)C(C)O)C(C)O

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-

InChI key

NSFFHOGKXHRQEW-BXVAPQLOSA-N

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General description

Chemical structure: peptide

Application

Thiostrepton has been used as a selectable marker for recombinant Streptomyces cultures,,.

Biochem/physiol Actions

Peptide antibiotic that prevents the binding of elongation factor G (EF-G) and GTP to the 50S ribosomal subunit.

Preparation Note

Thiostrepton dissolves in acetic acid at 25 mg/ml to yield a clear to hazy, yellow-yellow brown solution.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P Arias et al.
Journal of bacteriology, 181(22), 6958-6968 (1999-11-13)
The ActII-ORF4 protein has been characterized as a DNA-binding protein that positively regulates the transcription of the actinorhodin biosynthetic genes. The target regions for the ActII-ORF4 protein were located within the act cluster. These regions, at high copy number, generate
Antje Wolf et al.
Bioorganic & medicinal chemistry, 20(24), 7194-7205 (2012-10-31)
The thiostrepton antibiotic inhibits bacterial protein synthesis by binding to a cleft formed by the ribosomal protein L11 and 23S's rRNA helices 43-44 on the 70S ribosome. It was proposed from crystal structures that the ligand restricts L11's N-terminal movement
Thiostrepton, proteasome inhibitors and FOXM1.
Andrei L Gartel
Cell cycle (Georgetown, Tex.), 10(24), 4341-4342 (2011-12-03)
O H Martínez-Costa et al.
The Journal of biological chemistry, 271(18), 10627-10634 (1996-05-03)
A 0.972-kilobase pair DNA fragment from Streptomyces lividans that induces the production of the blue-pigmented antibiotic actinorhodine in S. lividans when cloned on a multicopy plasmid has led to the isolation of a 4-kilobase pair DNA fragment from Streptomyces coelicolor
Ming Wang et al.
Cancer biology & therapy, 13(3), 184-189 (2012-02-23)
Bortezomib is well-known for inducing cell death in cancer cells, specifically through the mechanism of proteasome inhibition. Thiostrepton, a thiazole antibiotic, has also been described for its proteasome inhibitory action, although differing slightly to bortezomib in the proteasomal site to
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