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T8902

Sigma-Aldrich

Thiostrepton aus Streptomyces azureus

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

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C72H85N19O18S5
CAS-Nummer:
1393-48-2
Molekulargewicht:
1664.89
EG-Nummer:
215-734-9
MDL-Nummer:
MFCD00135828
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24900569
NACRES:
NA.77

product name

Thiostrepton aus Streptomyces azureus, ≥90% (HPLC)

Assay

≥90% (HPLC)

Löslichkeit

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

Wirkungsspektrum von Antibiotika

Gram-negative bacteria
Gram-positive bacteria
parasites

Wirkungsweise

protein synthesis | interferes

Lagertemp.

−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-

InChIKey

NSFFHOGKXHRQEW-BXVAPQLOSA-N

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Allgemeine Beschreibung

Chemical structure: peptide

Anwendung

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

Biochem./physiol. Wirkung

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

Angaben zur Herstellung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Verteporfin ≥94% (HPLC)

Sigma-Aldrich

SML0534

Verteporfin

Anisomycin aus Streptomyces griseolus ≥98% (HPLC), solid

Sigma-Aldrich

A9789

Anisomycin aus Streptomyces griseolus

Nalidixinsäure ≥98%

Sigma-Aldrich

N8878

Nalidixinsäure

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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