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T8902

Sigma-Aldrich

Thiostrepton from Streptomyces azureus

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C72H85N19O18S5
Numéro CAS:
1393-48-2
Poids moléculaire :
1664.89
Numéro CE :
215-734-9
Numéro MDL:
MFCD00135828
Code UNSPSC :
12352200
ID de substance PubChem :
24900569
Nomenclature NACRES :
NA.77

product name

Thiostrepton from Streptomyces azureus, ≥90% (HPLC)

Pureté

≥90% (HPLC)

Solubilité

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

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria
parasites

Mode d’action

protein synthesis | interferes

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

NSFFHOGKXHRQEW-BXVAPQLOSA-N

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Description générale

Chemical structure: peptide

Application

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

Actions biochimiques/physiologiques

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

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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
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
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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