Bisantrene Dihydrochloride - CAS 78186-34-2
Catalog number: B0084-379906
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C22H24Cl2N8
Molecular Weight:
471.39
COA:
Inquire
Targets:
Topoisomerase
Description:
Bisantrene Dihydrochloride is the hydrochloride salt of Bisantrene. Bisantrene, also referred to CL-216942, Cyabin or NSC-337766, an anthracene bishydrazone derivative, is topoisomerase II poisons and can intercalate into the DNA of tumor cells. Bisantrene leads to DNA single-strand breaks, DNA-protein crosslinking, and inhibition of DNA replication by intercalating with and disrupting the configuration of DNA. Bisantrene is an anthracycline chemotherapy agent notably for AML (Acute Myeloid Leukaemia), but one of the drawbacks of anthracycline chemotherapy agents like doxorubicin is their risk of cardiac toxicity and consequent heart failure. Bisantrene has been shown to have greatly reduced cardiac toxicity with similar antineoplastic activity.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-379906 50mg $269 In stock
B0084-379906 100mg $499 In stock
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Brife Description:
Topoisomerase II poisons and DNA intercalators
Appearance:
Solid powder
Synonyms:
N-[(E)-[10-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1H-imidazol-2-amine;dihydrochloride; 9,10-anthracenedicarboxaldehyde bis(4,5-dihydro-1H-imidazol-2-yl)hydrazone; bisantrene; bisantrene dihydrochloride; CL 216942; CL216,942; NSC 337766
Solubility:
Soluble to 8 mg/mL in deionized water
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -42℃ for long term (months to years).
MSDS:
Inquire
Shelf Life:
2 years
InChIKey:
KINULKKPVJYRON-PVNXHVEDSA-N
InChI:
1S/C22H22N8.2ClH/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22;;/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30);2*1H/b27-13+,28-14+;;
Canonical SMILES:
C1CN=C(N1)NN=CC2=C3C=CC=CC3=C(C4=CC=CC=C42)C=NNC5=NCCN5.Cl.Cl
Current Developer:
Update Pharma; Wyeth Pharmaceuticals
1.Remarkable interference with telomeric function by a G-quadruplex selective bisantrene regioisomer.
Folini M1, Pivetta C, Zagotto G, De Marco C, Palumbo M, Zaffaroni N, Sissi C. Biochem Pharmacol. 2010 Jun 15;79(12):1781-90. doi: 10.1016/j.bcp.2010.02.018. Epub 2010 Mar 3.
The use of small molecules able to induce and stabilize selected G-quadruplex arrangements can cause telomerase inhibition and telomere dysfunction in cancer cells, thus providing very selective therapeutic approaches. Effective stabilizers usually comprise a planar aromatic portion to grant effective stacking onto the G-quartet and positively charged side chains to exploit the highly negative charge density on the quadruplex grooves. Since the relative position of these two pharmacophoric moieties is expected to play an important role in DNA folding stabilization, we evaluated a series of anthracene derivatives substituted with one or two 4,5-dihydro-1H-imidazol-2-yl-hydrazonic groups (the bisantrene side chain) at different positions of the aromatic system. Indeed, the various regioisomers showed distinct binding affinities for telomeric G-quadruplex, and the most effective was the 1,5 and 1,7 bis-substituted analogues. On turn, the 1,8 regioisomer was poorly effective.
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CAS 78186-34-2 Bisantrene Dihydrochloride

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