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Chetomin (Synonyms: NSC 289491)

Catalog No.GC17405

An inhibitor of HIF signaling

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Chetomin Chemical Structure

Cas No.: 1403-36-7

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Sample solution is provided at 25 µL, 10mM.

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Background

Chetomin, an antibiotic metabolite of chaetomium cochliodes, is an inhibitor of HIF-1 by weaken transcription of HIF-1 and recently is raised interests as a cancer chemotherapeutic agent.[1]
HIF-1 (hypoxia-inducible factors 1) is transcription factor which respond to changes of cellular environment oxygen. [2] HIF-1 complex belongs to the PAS subfamily of the basic helix-loop-helix family of transcription factors and is composed of an alpha subunit and a beta subunit which formed a heterodimer. [3] HIF-1 can upregulate several genes such as glycolysis enzymes, vascular endothelial growth factor to promote survival rate of cells in hopoxia conditions through binding to HIF-responsive elements in the promoters. NF- Kappa B was shown a direct modulator of HIF-1alpha in normal condition but in low-oxygen conditions HIF-1alpha still stable with an unknown mechanism. [4]
Chetomin selectively inhibited HIF-1 activities through disruption of the interaction of HIF-1with its transcriptional coactivator p300. Early-passage human fibrosarcoma HT1080 cells stably transfected EGFP plasmid with a hypoxia-responsive 5HRE-hCMVmp promoter were pretreated with chetomin showed dose and incubation-time dependent EGFP fluorescence signal suppression. And pretreatment of 150nM chetomin for 4h showed maximum suppressive effects, indicated the inhibition of HIF-dependent transcription. Also, 150nM chetomin decreased expression of VEGF and CA9 under hapoxic conditions in HT1010 cells. Chetomin increased cell survival rate under hypoxia compared mormoxia conditions, indicated that chetomin can enhanced radiation treatment efficacy under severely hypoxic conditions.[5]

References:
[1] Timothy R. Welch and Robert M. Williams. Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative, Late-Stage Biosynthetic Intermediate. Tetrahedron (2013) 69(2): 770–773
[2] Smith TG, Robbins PA, Ratcliffe PJ. The human side of hypoxia-inducible factor. Br. J. Haematol. (2008)141(3): 325–34
[3] Jiang BH, Rue E, Wang GL, Roe R, Semenza GL. Dimerization, DNA binding, and transactivation properties of hypoxia-inducible factor 1. J. Biol. Chem. (1996) 271(30):17771-17778
[4] Van Uden P, Kenneth NS, Rocha S. Regulation of hypoxia-inducible factor-1 alpha by NF-kappa B. Biochem. J. (2008) 412(3): 477-484
[5] Adrian Staab, Jürgen Loeffler, Harun M Said, Désirée Diehlmann, Astrid Katzer, Melanie Beyer, Markus Fleischer, Franz Schwab, Kurt Baier, Hermann Einsele, Michael Flentje and Dirk Vordermark. Effects of HIF-1 inhibition by chetomin on hypoxia-related transcription and radiosensitivity in HT 1080 human fibrosarcoma  Cells. BMC Cancer (2007) 7 :213

Chemical Properties

Cas No. 1403-36-7 SDF
Synonyms NSC 289491
Chemical Name (3S,5aR,10bS,11aS)-2,3,5a,6,10b,11-hexahydro-3-(hydroxymethyl)-10b-(3-[(1S,4S)-3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]oct-1-yl)methyl]-1H-indol-1-yl]-2-methyl-3,11a-epidithio-11aH-pyrazino[1,2:1,5]pyrrolo[2,3-b]indo
Canonical SMILES O=C([C@@](N1C)(SS2)CC3=CN([C@@]([C@]4([H])N5)(C[C@@]6(SS7)N4C([C@@]7(CO)N(C)C6=O)=O)C8=C5C=CC=C8)C9=C3C=CC=C9)N(C)[C@]2(CO)C1=O
Formula C31H30N6O6S4 M.Wt 710.87
Solubility 5mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 1.4067 mL 7.0336 mL 14.0673 mL
5 mM 0.2813 mL 1.4067 mL 2.8135 mL
10 mM 0.1407 mL 0.7034 mL 1.4067 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 30 reference(s) in Google Scholar.)

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