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28097-03-2,MFCD00133163
Catalog No.:AA00BE7F

28097-03-2 | Chaetocin

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1mg
99+%
in stock  
$48.00   $34.00
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5mg
99+%
in stock  
$121.00   $85.00
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10mg
99+%
in stock  
$181.00   $127.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE7F
Chemical Name:
Chaetocin
CAS Number:
28097-03-2
Molecular Formula:
C30H28N6O6S4
Molecular Weight:
696.8399
MDL Number:
MFCD00133163
SMILES:
OCC12SSC3(N(C1=O)C1Nc4c(C1(C3)C13CC56N(C3Nc3c1cccc3)C(=O)C(SS5)(N(C6=O)C)CO)cccc4)C(=O)N2C
Properties
Computed Properties
 
Complexity:
1400  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
2  

Downstream Synthesis Route

[1]Iwasa,Eriko;Hamashima,Yoshitaka;Fujishiro,Shinya;Eisuke,Higuchi;Ito,Akihiro;Yoshida,Minoru;Sodeoka,Mikiko[JournaloftheAmericanChemicalSociety,2010,vol.132,#12,p.4078-4079]

[2]Fujishiro,Shinya;Dodo,Kosuke;Iwasa,Eriko;Teng,Yuou;Sohtome,Yoshihiro;Hamashima,Yoshitaka;Ito,Akihiro;Yoshida,Minoru;Sodeoka,Mikiko[BioorganicandMedicinalChemistryLetters,2013,vol.23,#3,p.733-736]

[1]Iwasa,Eriko;Hamashima,Yoshitaka;Fujishiro,Shinya;Eisuke,Higuchi;Ito,Akihiro;Yoshida,Minoru;Sodeoka,Mikiko[JournaloftheAmericanChemicalSociety,2010,vol.132,#12,p.4078-4079]

[1]Kim,Justin;Movassaghi,Mohammad[JournaloftheAmericanChemicalSociety,2010,vol.132,#41,p.14376-14378]

[1]Locationinpatent:experimentalpartCherblanc,Fanny;Lo,Ya-Pei;DeGussem,Ewoud;Alcazar-Fuoli,Laura;Bignell,Elaine;He,Yanan;Chapman-Rothe,Nadine;Bultinck,Patrick;Herrebout,WouterA.;Brown,Robert;Rzepa,HenryS.;Fuchter,MatthewJ.[Chemistry-AEuropeanJournal,2011,vol.17,#42,p.11868-11875]

[2]Cherblanc,FannyL.;Chapman,KathrynL.;Reid,Jim;Borg,AaronJ.;Sundriyal,Sandeep;Alcazar-Fuoli,Laura;Bignell,Elaine;Demetriades,Marina;Schofield,ChristopherJ.;Dimaggio,PeterA.;Brown,Robert;Fuchter,MatthewJ.[JournalofMedicinalChemistry,2013,vol.56,#21,p.8616-8625]

[3]Fujishiro,Shinya;Dodo,Kosuke;Iwasa,Eriko;Teng,Yuou;Sohtome,Yoshihiro;Hamashima,Yoshitaka;Ito,Akihiro;Yoshida,Minoru;Sodeoka,Mikiko[BioorganicandMedicinalChemistryLetters,2013,vol.23,#3,p.733-736]

C30H32N6O6S4 
  28097-03-2 

[1]Fujishiro,Shinya;Dodo,Kosuke;Iwasa,Eriko;Teng,Yuou;Sohtome,Yoshihiro;Hamashima,Yoshitaka;Ito,Akihiro;Yoshida,Minoru;Sodeoka,Mikiko[BioorganicandMedicinalChemistryLetters,2013,vol.23,#3,p.733-736]

Literature

Title: Arsenic silences hepatic PDK4 expression through activation of histone H3K9 methylatransferase G9a.

Journal: Toxicology and applied pharmacology 20160801

Title: Chaetocin inhibits IBMX-induced melanogenesis in B16F10 mouse melanoma cells through activation of ERK.

Journal: Chemico-biological interactions 20160205

Title: Oncoepigenomics: making histone lysine methylation count.

Journal: European journal of medicinal chemistry 20121001

Title: Histone methyltransferase inhibitors induce HIV-1 recovery in resting CD4(+) T cells from HIV-1-infected HAART-treated patients.

Journal: AIDS (London, England) 20120731

Title: Inhibition of histone H3K9 methyltransferases by gliotoxin and related epipolythiodioxopiperazines.

Journal: The Journal of antibiotics 20120501

Title: Anti-leukemia activity of chaetocin via death receptor-dependent apoptosis and dual modulation of the histone methyl-transferase SUV39H1.

Journal: Leukemia 20120401

Title: The anticancer effects of chaetocin are independent of programmed cell death and hypoxia, and are associated with inhibition of endothelial cell proliferation.

Journal: British journal of cancer 20120117

Title: The Suv39H1 methyltransferase inhibitor chaetocin causes induction of integrated HIV-1 without producing a T cell response.

Journal: FEBS letters 20111116

Title: Epigenetic regulation of HIV-1 transcription.

Journal: Epigenomics 20110801

Title: Hypoxia-inducible factor inhibitors: a survey of recent patented compounds (2004 - 2010).

Journal: Expert opinion on therapeutic patents 20110201

Title: Antihepatoma activity of chaetocin due to deregulated splicing of hypoxia-inducible factor 1α pre-mRNA in mice and in vitro.

Journal: Hepatology (Baltimore, Md.) 20110101

Title: General approach to epipolythiodiketopiperazine alkaloids: total synthesis of (+)-chaetocins A and C and (+)-12,12'-dideoxychetracin A.

Journal: Journal of the American Chemical Society 20101020

Title: Unnatural enantiomer of chaetocin shows strong apoptosis-inducing activity through caspase-8/caspase-3 activation.

Journal: Bioorganic & medicinal chemistry letters 20100901

Title: Remodeling of nuclear architecture by the thiodioxoxpiperazine metabolite chaetocin.

Journal: Experimental cell research 20100610

Title: Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi.

Journal: Bioorganic & medicinal chemistry 20100401

Title: Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.

Journal: Journal of the American Chemical Society 20100331

Title: The anticancer agent chaetocin is a competitive substrate and inhibitor of thioredoxin reductase.

Journal: Antioxidants & redox signaling 20090501

Title: Chemical probes for histone-modifying enzymes.

Journal: Nature chemical biology 20081001

Title: Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress.

Journal: Blood 20070315

Title: Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9.

Journal: Nature chemical biology 20050801

Title: Greiner D, et al. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat Chem Biol. 2005 Aug;1(3):143-5.

Title: Tibodeau JD, et al. The anticancer agent chaetocin is a competitive substrate and inhibitor of thioredoxin reductase. Antioxid Redox Signal. 2009 May;11(5):1097-106.

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