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41785

Sigma-Aldrich

Dimidium bromide

BioReagent, suitable for fluorescence, ~95% (AT)

Synonym(s):

3,8-Diamino-5-methyl-6-phenylphenanthridinium bromide, Trypadine, phenanthridinium 1553

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About This Item

Empirical Formula (Hill Notation):
C20H18BrN3
CAS Number:
518-67-2
Molecular Weight:
380.28
Beilstein/REAXYS Number:
3809779
EC Number:
208-256-7
MDL number:
MFCD00011757
UNSPSC Code:
12171500
PubChem Substance ID:
57650090
NACRES:
NA.32

product line

BioReagent

assay

~95% (AT)

form

solid

mp

243-248 °C (lit.)

fluorescence

λex 306 nm; λem 612 nm in 50 mM Tris pH 8.0 (DNA)
λex 480 (pH 7.6, low ionic strength)

suitability

suitable for fluorescence

SMILES string

[Br-].C[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14

InChI

1S/C20H17N3.BrH/c1-23-19-12-15(22)8-10-17(19)16-9-7-14(21)11-18(16)20(23)13-5-3-2-4-6-13;/h2-12,22H,21H2,1H3;1H

InChI key

MQOKYEROIFEEBH-UHFFFAOYSA-N

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General description

Dimidium Bromide is a trypanocidal drug that is known to affect nucleic acid synthesis in many organisms e.g. tissue culture cells.

Application

Dimidium Bromide is used as a binding agent to natural DNA based on base-pair specificity. It is used as a fluorescence agent for nucleic acid experiments.
Intercalating probe for nucleic acids.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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G Dougherty
The International journal of biochemistry, 14(6), 493-504 (1982-01-01)
1. The absorption spectrum of three phenanthridine drugs (ethidium, dimidium and prothidium bromide) bound to natural DNAs of differing G-C content were obtained using a novel mixing scheme and analysed according to the excluded site binding model. 2. Ethidium bromide
Nuclear transplantation studies of the action of dimidium bromide on amoebae.
S E Hawkins et al.
Nature, 222(5188), 86-87 (1969-04-05)
T N Beliaeva et al.
Tsitologiia, 31(11), 1363-1368 (1989-11-01)
A natural DNA-intercalator plant benzo-c-phenanthridine alkaloid sanguinarine is more toxic for mouse transformed fibroblast L-cells in culture than synthetic DNA-intercalator ethidium bromide (EtB) and alkaloid berberine. Dimidium bromide is also an inhibitor of the L-cell growth. In assay conditions, growth
[Chemoprophylaxis of bovine trypanosomiasis T. congolense and T. vivax by phenathridinium S. 1553].
J DEOM
Annales de la Societe belge de medecine tropicale (1920), 30(1), 25-29 (1950-03-01)
T P Mozhenok et al.
Tsitologiia, 40(6), 585-590 (1998-10-21)
Effect of DNA-intercalators ethidium bromide (EB, 0.005 and 0.015 mM) and dimidium bromide (DB, 0.005 and 0.010 mM) and antioxidative compounds acetylsalicylic acid (ASA, 0.05 and 0.50 mM) and beta-carotene (0.01, 0.02, 0.05 mM) on the phagosome-lysosome (P-L) fusion and
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