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M6545

Sigma-Aldrich

Mitoxantrone dihydrochloride

≥97% (HPLC)

Synonym(s):

1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione dihydrochloride

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10 MG
R 1 348,48
50 MG
R 4 671,66

R 1 348,48

List PriceR 1 376,00
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10 MG
R 1 348,48
50 MG
R 4 671,66

About This Item

Empirical Formula (Hill Notation):
C22H28N4O6 · 2HCl
CAS Number:
70476-82-3
Molecular Weight:
517.40
EC Number:
274-619-1
MDL number:
MFCD00242943
UNSPSC Code:
12352005
PubChem Substance ID:
24278562
NACRES:
NA.25

R 1 348,48

List PriceR 1 376,00
Please contact Customer Service for Availability
Request a Bulk Order

Quality Level

100

Assay

≥97% (HPLC)

SMILES string

Cl[H].Cl[H].OCCNCCNc1ccc(NCCNCCO)c2C(=O)c3c(O)ccc(O)c3C(=O)c12

InChI

1S/C22H28N4O6.2ClH/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32;;/h1-4,23-30H,5-12H2;2*1H

InChI key

ZAHQPTJLOCWVPG-UHFFFAOYSA-N

Gene Information

human ... TOP2A(7153)

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Application

Mitoxantrone dihydrochloride has been used:
  • to induce calreticulin surface expression in cells[1][2]
  • as a genotoxin agent[3]
  • as a topoisomerase inhibitor[4]

Biochem/physiol Actions

Mitoxantrone is a cytostatic anthracenedione that intercalates in DNA and increases the incidence of double-strand breaks by stabilizing the cleavable complex of topoisomerase II and DNA. Mitoxantrone also displays broad immunosuppressive activity inhibiting proliferation of all classes of lymphocytes and inducing apoptosis of antigen-presenting T cells. It used clinically as a chemotherapeutic agent against leukemias and solid tumors and as an immune system modulator in multiple sclerosis.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H360

Hazard Classifications

Muta. 1B - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3297
MKCQ3047
MKCM8540
MKCL5878
MKCG7209

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Calreticulin as cancer treatment adjuvant: combination with photodynamic therapy and photodynamic therapy-generated vaccines.
Korbelik M
Frontiers in Oncology, 5, 15-15 (2015)
A RasGAP-derived cell permeable peptide potently enhances genotoxin-induced cytotoxicity in tumor cells.
Michod D
Oncogene, 23, 8971-8971 (2004)
Ceramide and sphingosine-1-phosphate act as photodynamic therapy-elicited damage-associated molecular patterns: cell surface exposure.
Korbelik M
International Immunopharmacology, 20, 359-359 (2014)
A high through-put screen for small molecules modulating MCM2 phosphorylation identifies Ryuvidine as an inducer of the DNA damage response.
FitzGerald J
PLoS ONE, 9, e98891-e98891 (2014)
James M Stankiewicz et al.
Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics, 10(1), 77-88 (2012-12-29)
Immunosuppressives have been used in multiple sclerosis (MS) since 1966. Today, we have many treatments for the relapsing forms of the disease, including 8 US Food and Drug Administration-approved therapies, with more soon to be introduced. Given the current treatment
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Articles

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

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