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SML1183

Sigma-Aldrich

BMH-21

≥98% (HPLC)

Synonyme(s) :

N-[2-(Dimethylamino)ethyl]-12-oxo-2H-benzo[g]pyrido[2,1-b]quinazoline-4-carboxamide

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About This Item

Formule empirique (notation de Hill):
C21H20N4O2
Numéro CAS:
896705-16-1
Poids moléculaire :
360.41
Numéro MDL:
MFCD27225377
Code UNSPSC :
12352200
ID de substance PubChem :
329825705
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

faint yellow to dark orange

Solubilité

DMSO: 1 mg/mL, clear (warmed)

Température de stockage

2-8°C

Chaîne SMILES 

O=C(N(C=CC=C1C(NCCN(C)C)=O)C1=N2)C(C2=C3)=CC4=C3C=CC=C4

InChI

1S/C21H20N4O2/c1-24(2)11-9-22-20(26)16-8-5-10-25-19(16)23-18-13-15-7-4-3-6-14(15)12-17(18)21(25)27/h3-8,10,12-13H,9,11H2,1-2H3,(H,22,26)

Clé InChI

BXYDVWIAGDJBEC-UHFFFAOYSA-N

Description générale

BMH-21 is a planar heterocyclic small molecule DNA intercalator.

Application

BMH-21 has been used in cell culture.

Actions biochimiques/physiologiques

BMH-21 has the ability to bind ribosomal DNA and prevent RNA polymerase I (Pol I) transcription and results in the disintegration of the nucleolus. It does not impair DNA damage detection. BMH-21 is considered as an important activator of the p53 pathway.
BMH-21 is a potent inhibitor of RNA Pol I. BMH-21 binds strongly to GC-rich DNA sequences, ultimately inhibiting RNA Pol I, blocking transcription and disrupting the nucleolar structure. BMH-1 causes dissociation of the RPA194 catalytic subunit from Pol I, and disassembly of Pol I:DNA complexes. The compound BMH-21 inhibits proliferation of a broad range of tumor cell lines.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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A targeting modality for destruction of RNA polymerase I that possesses anticancer activity.
Peltonen K, et al.
Cancer Cell, 25(1), 77-90 (2014)
BMH-21 inhibits viability and induces apoptosis by p53-dependent nucleolar stress responses in SKOV3 ovarian cancer cells.
Fu X, et al.
Oncology Reports, 38(2), 859-865 (2017)
Leah Bury et al.
eLife, 9 (2020-11-12)
Although originally thought to be silent chromosomal regions, centromeres are instead actively transcribed. However, the behavior and contributions of centromere-derived RNAs have remained unclear. Here, we used single-molecule fluorescence in-situ hybridization (smFISH) to detect alpha-satellite RNA transcripts in intact human
Lisa M Ogawa et al.
Molecular biology of the cell, 32(9), 956-973 (2021-03-11)
Nucleoli are dynamic nuclear condensates in eukaryotic cells that originate through ribosome biogenesis at loci that harbor the ribosomal DNA. These loci are known as nucleolar organizer regions (NORs), and there are 10 in a human diploid genome. While there
Laureen Colis et al.
Oncotarget, 5(12), 4361-4369 (2014-06-24)
DNA intercalation is a major therapeutic modality for cancer therapeutic drugs. The therapeutic activity comes at a cost of normal tissue toxicity and genotoxicity. We have recently described a planar heterocyclic small molecule DNA intercalator, BMH-21, that binds ribosomal DNA

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