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1239-45-8 molecular structure
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3,8-diamino-5-ethyl-6-phenylphenanthridin-5-ium bromide

ChemBase ID: 127319
Molecular Formular: C21H20BrN3
Molecular Mass: 394.3076
Monoisotopic Mass: 393.08405966
SMILES and InChIs

SMILES:
CC[n+]1c2cc(ccc2c2ccc(cc2c1c1ccccc1)N)N.[Br-]
Canonical SMILES:
CC[n+]1c(c2ccccc2)c2cc(N)ccc2c2c1cc(N)cc2.[Br-]
InChI:
InChI=1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H
InChIKey:
ZMMJGEGLRURXTF-UHFFFAOYSA-N

Cite this record

CBID:127319 http://www.chembase.cn/molecule-127319.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3,8-diamino-5-ethyl-6-phenylphenanthridin-5-ium bromide
IUPAC Traditional name
ethidium bromide
Synonyms
2,7-Diamino-10-ethyl-6-phenylphenanthridinium bromide
2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide
3,8-Diamino-1-ethyl-6-phenylphenantridinium bromide
5-Ethyl-6-phenyl-phenanthridine-3,8-diamine bromide
Ethidium bromide
Homidium bromide
EtBr
Ethidium bromide
Ethidium bromide solution
3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide
2,7-Diamino-9-phenyl-10-ethylphenanthridinium Bromide
2,7-Diamino-9-phenylphenanthridine Ethobromide
Dromilac
Ethidium bromide
溴化乙啶 溶液
溴化乙锭
3,8-二氨基-5-乙基-6-苯基菲啶溴化物
胡米溴铵
溴化乙啶
CAS Number
1239-45-8
EC Number
231-791-2
214-984-6
MDL Number
MFCD00011724
Beilstein Number
3642536
Merck Index
144731
PubChem SID
24869725
24869723
24894683
162221640
24894408
24894418
24894653
PubChem CID
14710
CHEBI ID
4883
ATC CODE
QP51AX06
CHEMBL
284328
Chemspider ID
14034
KEGG ID
C11161
Unique Ingredient Identifier
059NUO2Z1L
Wikipedia Title
Ethidium_bromide

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.91901684  LogD (pH = 7.4) -0.9133308 
Log P -0.9132578  Molar Refractivity 101.9975 cm3
Polarizability 41.86951 Å3 Polar Surface Area 55.92 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
~ 40 g/l in water expand Show data source
H2O: soluble10 mg/mL, opaque, very dark red expand Show data source
Apperance
Purple-red solid expand Show data source
Melting Point
260 - 262 °C expand Show data source
260-262 °C (dec.)(lit.) expand Show data source
ca 261°C dec. expand Show data source
Flash Point
> 100 °C expand Show data source
Absorption Wavelength
λmax 506 nm expand Show data source
Fluorescence
λex 480 nm; λem 620 nm in H2O expand Show data source
λex 518 nm; λem 605 nm (bound to DNA) expand Show data source
λex 530 nm; λem 600 nm in 50 mM phosphate buffer pH 7.0 (upon binding to DNA) expand Show data source
RTECS
SF7950000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Highly toxic Highly toxic (T+) expand Show data source
UN Number
2810 expand Show data source
2811 expand Show data source
UN2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
3 expand Show data source
I expand Show data source
Risk Statements
22-26-68 expand Show data source
23-68 expand Show data source
R25 R36/37/38 R46 expand Show data source
Safety Statements
28-36/37-45-63 expand Show data source
36/37-45 expand Show data source
S22 S24/25 S26 S36/37/39 S45 S53 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
NFPA704
NFPA 704 diagram
0
4
0
expand Show data source
GHS Hazard statements
H302-H330-H341 expand Show data source
H330-H302-H341 expand Show data source
H331-H341 expand Show data source
GHS Precautionary statements
P260-P281-P284-P310 expand Show data source
P260-P304+P340-P320-P330-P405-P501A expand Show data source
P261-P281-P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2810 6.1/PG 3 expand Show data source
UN 2811 6.1/PG 1 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
~95% (HPLC) expand Show data source
≥95.0% expand Show data source
≥95.0% (HPLC) expand Show data source
95% expand Show data source
98% (dry wt.) expand Show data source
Concentration
~1% in H2O expand Show data source
10 mg/mL expand Show data source
10 mg/mL in H2O expand Show data source
500 μg/mL in H2O expand Show data source
Grade
for fluorescence expand Show data source
for molecular biology expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
suitable for gel electrophoresis expand Show data source
Product Line
BioReagent expand Show data source
Empirical Formula (Hill Notation)
C21H20BrN3 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 46067 external link
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Sigma Aldrich - E1510 external link
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Packaging
10 mL in glass bottle
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Sigma Aldrich - 46065 external link
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Other Notes
Intercalating agent and fluorescent label for DNA. Review6; Destruction and decontamination of solutions7
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5Frameshift mutagen which intercalates double-stranded DNA and RNA.
Sigma Aldrich - E1385 external link
Application
溴化乙啶 (EtBr) 为聚丙烯酰胺凝胶电泳或琼脂糖凝胶电泳中最常用的核酸染料。EtBr 在结合到双链 RNA 上时其荧光可提高 21 倍,在结合到双链 DNA 上可提高 25 倍,从而使得在低染料浓度 (10μg/ml) 下无需背景脱色。溴化乙啶已用于核酸的许多荧光分析。1,2,3已表明它可结合到单链 DNA(虽然强度不高)和三链 DNA 上。4由于 EtBr 能够结合到 DNA 上,因此它是 DNA 聚合酶的抑制剂。5
Biochem/physiol Actions
溴化乙啶可插入双链 DNA 和 RNA 中,并作为移码诱变剂。它还可与吖啶橙结合用于区分存活的、凋亡的和坏死的细胞。
Reconstitution
对于在电泳后进行凝胶染色,应先用水将储存液样品稀释到 0.5μg/ml,再将凝胶孵育 15-30 分钟。通常无需脱色,但是如果必须降低背景色,则可在水中脱色 15 分钟。然后可在紫外灯箱(254nm 波长)中检测 DNA 条带。也可将溴化乙啶加到凝胶和电泳缓冲液(终浓度 0.5μg/ml)中,并在电泳后立即显影。
Sigma Aldrich - 160539 external link
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5Frameshift mutagen which intercalates double-stranded DNA and RNA.
Frameshift mutagen which intercalates double-stranded DNA and RNA.
Sigma Aldrich - E8751 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
溴化乙啶可插入双链 DNA 和 RNA 中,并作为移码诱变剂。它还可与吖啶橙结合用于区分存活的、凋亡的和坏死的细胞。
包装
1, 5, 10, 25 g in glass bottle
Reconstitution
对于在电泳后进行凝胶染色,应先用水将储存液样品稀释到 0.5μg/ml,再将凝胶孵育 15-30 分钟。通常无需脱色,但是如果必须降低背景色,则可在水中脱色 15 分钟。然后可在紫外灯箱(254nm 波长)中检测 DNA 条带。也可将溴化乙啶加到凝胶和电泳缓冲液(终浓度 0.5μg/ml)中,并在电泳后立即显影。
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5Frameshift mutagen which intercalates double-stranded DNA and RNA.
Sigma Aldrich - 09-0617 external link
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Suitability
for biological purposes
Sigma Aldrich - 09-0615 external link
Biochem/physiol Actions
Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.
Reconstitution
For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.
Application
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids.1,2,3 It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA.4 Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.5Frameshift mutagen which intercalates double-stranded DNA and RNA.
Suitability
for biological purposes
Toronto Research Chemicals - E890700 external link
Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Waring, M.J., et al.: J. Mol. Biol., 13, 269 (1965)
  • • Probst, G.S., et al.: Environ. Mutagen., 3, 11 (1965)
  • • Reviews: J.-B. Le Pecq, Methods of Biochemical Analysis, vol. 20,Wiley, N.Y. (1971), p41; M. Waring, Antibiotics, vol. 3, Springer-Verlag (1975), p141.
  • • Intercalation agent for DNA.
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