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SML1183

Sigma-Aldrich

BMH-21

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H20N4O2
CAS Number:
896705-16-1
Molecular Weight:
360.41
MDL number:
MFCD27225377
UNSPSC Code:
12352200
PubChem Substance ID:
329825705
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

faint yellow to dark orange

solubility

DMSO: 1 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

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)

InChI key

BXYDVWIAGDJBEC-UHFFFAOYSA-N

General description

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

Application

BMH-21 has been used in cell culture.

Biochem/physiol Actions

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
A targeting modality for destruction of RNA polymerase I that possesses anticancer activity.
Peltonen K, et al.
Cancer Cell, 25(1), 77-90 (2014)
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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