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T8902

Sigma-Aldrich

Thiostrepton from Streptomyces azureus

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

Sinónimos:

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

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1 G
$162.45

$162.45

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1 G
$162.45

About This Item

Fórmula empírica (notación de Hill):
C72H85N19O18S5
Número de CAS:
1393-48-2
Peso molecular:
1664.89
EC Number:
215-734-9
MDL number:
MFCD00135828
UNSPSC Code:
12352200
PubChem Substance ID:
24900569
NACRES:
NA.77

$162.45

Precio de catálogo$171.00Ahorre 5 %

En stockDetalles

Solicitar un pedido a granel

Nombre del producto

Thiostrepton from Streptomyces azureus, ≥90% (HPLC)

Quality Level

200

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[1],[2],[3].

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCX0672
MKCW5955
MKCS9195
MKCV1517
MKCS6150

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Feifei Zhang et al.
Methods in enzymology, 516, 3-24 (2012-10-05)
Thiopeptides are a family of highly modified peptide metabolites, characterized by a macrocycle bearing a central piperidine/dehydropiperidine/pyridine ring, multiple thiazole rings, and several dehydrated amino acid residues. Thiopeptides have useful antibacterial, antimalarial, and anticancer properties but have not been adapted
M V Rodnina et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(17), 9586-9590 (1999-08-18)
The region around position 1067 in domain II of 23S rRNA frequently is referred to as the GTPase center of the ribosome. The notion is based on the observation that the binding of the antibiotic thiostrepton to this region inhibited
Antje Wolf et al.
Journal of molecular modeling, 19(2), 539-549 (2012-09-11)
With improvements in computer speed and algorithm efficiency, MD simulations are sampling larger amounts of molecular and biomolecular conformations. Being able to qualitatively and quantitatively sift these conformations into meaningful groups is a difficult and important task, especially when considering
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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