Thiostrepton
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Hodoodo CAT#: H592438

CAS#: 1393-48-2

Description: Thiostrepton is an antibiotic that inhibits bacterial protein synthesis. Thiostrepton Inhibits mRNA-tRNA translocation by GTPase elongation factor G (EF-G), EF-TU(GTP)-catalyzed aa-tRNA delivery and the activity of initiation factor 2 (IF-2).


Chemical Structure

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Thiostrepton
CAS# 1393-48-2

Theoretical Analysis

Hodoodo Cat#: H592438
Name: Thiostrepton
CAS#: 1393-48-2
Chemical Formula: C72H85N19O18S5
Exact Mass: 1,663.49
Molecular Weight: 1,664.887
Elemental Analysis: C, 51.94; H, 5.15; N, 15.99; O, 17.30; S, 9.63

Price and Availability

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1g USD 340
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Synonym: Thiostrepton; NSC 170365; NSC-170365; NSC170365

IUPAC/Chemical Name: N/A

InChi Key: NSFFHOGKXHRQEW-DVRIZHICSA-N

InChi Code: 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+

SMILES Code: C=C(C(NC(C(N)=O)=C)=O)NC(C1=CSC(C2=NC(C3=CSC(C(C(C)OC(C4=CC(C(C)O)=C(C=CC(NC(C(NC(C)C(NC(C(NC(C)C5=O)=O)=C)=O)=O)C(C)CC)C6O)C6=N4)=O)N7)=N3)C(CC2)(N5)C8=NC(C(NC(C(N/C(C9=NC(C(NC(C(O)(C)C(C)O)C%10=NC(C7=O)=CS%10)=O)CS9)=C/C)=O)C(O)C)=O)=CS8)=N1)=O

Appearance: Solid powder

Purity: >90% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,664.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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4: Kalathil D, Prasad M, Chelladurai M, John S, Nair AS. Thiostrepton degrades mutant p53 by eliciting an autophagic response in SW480 cells. J Cell Physiol. 2018 Oct;233(10):6938-6950. doi: 10.1002/jcp.26601. Epub 2018 Apr 17. PubMed PMID: 29665004.

5: Dai Z, Zhu MM, Peng Y, Jin H, Machireddy N, Qian Z, Zhang X, Zhao YY. Endothelial and Smooth Muscle Cell Interaction via FoxM1 Signaling Mediates Vascular Remodeling and Pulmonary Hypertension. Am J Respir Crit Care Med. 2018 Apr 17. doi: 10.1164/rccm.201709-1835OC. [Epub ahead of print] PubMed PMID: 29664678.

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7: Fang P, Madden JA, Neums L, Moulder RK, Forrest ML, Chien J. Olaparib-induced Adaptive Response Is Disrupted by FOXM1 Targeting that Enhances Sensitivity to PARP Inhibition. Mol Cancer Res. 2018 Jun;16(6):961-973. doi: 10.1158/1541-7786.MCR-17-0607. Epub 2018 Mar 15. PubMed PMID: 29545475.

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11: Jin P, Chen FX, Li YZ, Zhang QQ, Zhang J. The clinical and experimental research on the treatment of endometriosis with thiostrepton. Anticancer Agents Med Chem. 2018 Jan 7. doi: 10.2174/1871520618666180108100211. [Epub ahead of print] PubMed PMID: 29308746.

12: Bourgeois A, Lambert C, Habbout K, Ranchoux B, Paquet-Marceau S, Trinh I, Breuils-Bonnet S, Paradis R, Nadeau V, Paulin R, Provencher S, Bonnet S, Boucherat O. FOXM1 promotes pulmonary artery smooth muscle cell expansion in pulmonary arterial hypertension. J Mol Med (Berl). 2018 Feb;96(2):223-235. doi: 10.1007/s00109-017-1619-0. Epub 2017 Dec 30. PubMed PMID: 29290032.

13: Toda H, Itoh N. Development of a Novel Escherichia coli-Kocuria Shuttle Vector Using the Cryptic pKPAL3 Plasmid from K. palustris IPUFS-1 and Its Utilization in Producing Enantiopure (S)-Styrene Oxide. Front Microbiol. 2017 Nov 27;8:2313. doi: 10.3389/fmicb.2017.02313. eCollection 2017. PubMed PMID: 29230202; PubMed Central PMCID: PMC5711781.

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16: Key HM, Miller SJ. Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids. J Am Chem Soc. 2017 Nov 1;139(43):15460-15466. doi: 10.1021/jacs.7b08775. Epub 2017 Oct 20. PubMed PMID: 28975793; PubMed Central PMCID: PMC5736372.

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20: Lin Z, Ji J, Zhou S, Zhang F, Wu J, Guo Y, Liu W. Processing 2-Methyl-l-Tryptophan through Tandem Transamination and Selective Oxygenation Initiates Indole Ring Expansion in the Biosynthesis of Thiostrepton. J Am Chem Soc. 2017 Sep 6;139(35):12105-12108. doi: 10.1021/jacs.7b05337. Epub 2017 Aug 23. PubMed PMID: 28820583.