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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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Takamichi Ito et al.
Scientific reports, 14(1), 4048-4048 (2024-02-20)
Extramammary Paget disease (EMPD) is a rare skin cancer that primarily affects older individuals predominantly in areas with apocrine sweat glands. Although most early EMPD lesions are indolent, patients with metastatic EMPD have a poor prognosis due to the lack
M L Chiu et al.
The Journal of biological chemistry, 274(29), 20578-20586 (1999-07-10)
Microbial metabolites isolated in screening programs for their ability to activate transcription of the tipA promoter (ptipA) in Streptomyces lividans define a class of cyclic thiopeptide antibiotics having dehydroalanine side chains ("tails"). Here we show that such compounds of heterogeneous
Kheng Newick et al.
PloS one, 7(6), e39404-e39404 (2012-07-05)
Thiostrepton (TS) is a thiazole antibiotic that inhibits expression of FOXM1, an oncogenic transcription factor required for cell cycle progression and resistance to oncogene-induced oxidative stress. The mechanism of action of TS is unclear and strategies that enhance TS activity
Mahmoud Aboulaila et al.
Antimicrobial agents and chemotherapy, 56(6), 3196-3206 (2012-03-07)
The apicoplast housekeeping machinery, specifically apicoplast DNA replication, transcription, and translation, was targeted by ciprofloxacin, thiostrepton, and rifampin, respectively, in the in vitro cultures of four Babesia species. Furthermore, the in vivo effect of thiostrepton on the growth cycle of
O H Martínez-Costa et al.
Journal of bacteriology, 181(14), 4353-4364 (1999-07-10)
The sequence of a 4.8-kbp DNA fragment adjacent to the right-hand end of the actinorhodin biosynthetic (act) cluster downstream of actVB-orf6 from Streptomyces coelicolor A3(2) reveals six complete open reading frames, named orf7 to orf12. The deduced amino acid sequences
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