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S4692

Sigma-Aldrich

Sobuzoxane

≥99% (HPLC), solid

Synonym(s):

4,4′-(1,2-Ethanediyl)bis(1-iso­butoxycarbonylox­methyl-2,6-piperazinedione), MST-16

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About This Item

Empirical Formula (Hill Notation):
C22H34N4O10
CAS Number:
98631-95-9
Molecular Weight:
514.53
MDL number:
MFCD00866498
UNSPSC Code:
12352200
PubChem Substance ID:
24277932

assay

≥99% (HPLC)

form

solid

solubility

DMSO: 19 mg/mL

storage temp.

room temp

SMILES string

CC(C)COC(=O)OCN1C(=O)CN(CCN2CC(=O)N(COC(=O)OCC(C)C)C(=O)C2)CC1=O

InChI

1S/C22H34N4O10/c1-15(2)11-33-21(31)35-13-25-17(27)7-23(8-18(25)28)5-6-24-9-19(29)26(20(30)10-24)14-36-22(32)34-12-16(3)4/h15-16H,5-14H2,1-4H3

InChI key

OCOKWVBYZHBHLU-UHFFFAOYSA-N

Gene Information

human ... TOP2A(7153) , TOP2B(7155)

Application

Sobuzoxane was used to study the effect of topoisomerase II inhibition on expression of melanocytic antigens by tumor cells.[1]

Biochem/physiol Actions

Sobuzoxane is a DNA topoisomerase II inhibitor that induces apoptosis.
Sobuzoxane, a dioxopiperazine, chelates metal cations and reduces the generation of free radicals due to metal-anthracycline complexes. It interacts with topoisomerase II and blocks the formation of topoisomerase II-DNA complex.[2] Sobuzoxane effectively blocks cell proliferation and blocks cells in G2/M phase in selected human tumor cell lines.[3] It protects cardiomyocytes from the cardiotoxicity induced by prolonged doxorubicin treatment.[2]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
053K4600

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Timothy J Haggerty et al.
Cancer immunology, immunotherapy : CII, 60(1), 133-144 (2010-11-06)
While there are many obstacles to immune destruction of autologous tumors, there is mounting evidence that tumor antigen recognition does occur. Unfortunately, immune recognition rarely controls clinically significant tumors. Even the most effective immune response will fail if tumors fail
Da-Yong Lu et al.
Anti-cancer agents in medicinal chemistry, 10(1), 78-91 (2009-10-23)
Bisdioxopiperazine compounds, including ICRF-154 and razoxane (ICRF-159, Raz), are anticancer agents developed in the UK specifically targeting tumor metastases. Further two bisdioxopiperazine derivatives, probimane (Pro) and MST-16, have been synthesized at the Shanghai Institute of Materia Medica, Chinese Academy of
Lonnie P Swift et al.
Cancer chemotherapy and pharmacology, 61(5), 739-749 (2007-06-28)
The importance of understanding the mechanism of action of anticancer agents is sometimes overlooked in the pursuit of new and therapeutically advantageous compounds. Doxorubicin has long been identified as an inhibitor of the DNA-decatenating enzyme topoisomerase II, this being believed
Yoriko Inoue et al.
International journal of hematology, 79(3), 271-275 (2004-06-01)
Primary effusion lymphoma (PEL) is recognized as a unique clinicopathological entity associated with human herpesvirus 8 (HHV-8), and it occurs almost exclusively in human immunodeficiency virus (HIV)-infected individuals. In the majority of PEL cases, Epstein-Barr virus (EBV) has been found
T Okamoto et al.
Acta haematologica, 104(2-3), 128-130 (2001-01-13)
It is known that the topoisomerase II inhibitors, MST-16 (sobuzoxane) and VP-16 (etoposide), are effective for the treatment of lymphoma. Five patients with refractory or relapsed non-Hodgkin's lymphoma (NHL) were treated with a combination of oral MST-16 and VP-16 over
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