602-52-8

Basic information

• Product Name: 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride
• Synonyms: 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride;Homidium chloride;2,7-Diamino-10-ethyl-9-phenanthridinium chloride;(8-amino-5-ethyl-6-phenyl-phenanthridin-5-ium-3-yl)amine chloride;5-ethyl-6-phenyl-phenanthridin-5-ium-3,8-diamine chloride;5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine chloride;2,7-Diamino-9-phenyl-10-ethylphenanthridinium chloride
• CAS NO: 602-52-8
• Molecular Formula: C₂₁H₂₀N₃*Cl
• Molecular Weight: 349.8566
• EINECS: 210-018-2
• Mol File: 602-52-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride(602-52-8)
• EPA Substance Registry System: 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride(602-52-8)

Safety Data

• Hazardous Substances Data: 602-52-8(Hazardous Substances Data)

Usage

General Description

3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride is a chemical compound primarily used as a fluorescent staining agent for nucleic acids in biological research and clinical diagnostics. It is a cationic dye that binds to DNA and RNA, emitting a bright orange fluorescence upon excitation with ultraviolet light. This property makes it an essential tool for visualizing and quantifying nucleic acids in gel electrophoresis, fluorescence microscopy, and flow cytometry. Additionally, it has been studied as a potential anti-cancer agent due to its ability to bind to DNA and interfere with cell division. However, its use as a therapeutic agent is limited due to its potential cytotoxicity and lack of selectivity towards cancer cells. Overall, 3,8-diamino-5-ethyl-6-phenylphenanthridinium chloride is an important chemical in both biomedical research and clinical diagnostics.

InChI:InChI=1/C21H19N3.ClH/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

Synthetic route

C30H27N4O3(1+)*H2O4P(1-) → [3H]-Ethidium (602-52-8) + 3-urea-ethidium chloride

Conditions	Yield
With hydrogenchloride; water In methanol at 96℃; for 1h;

C30H27N4O3(1+)*H2O4P(1-) → [3H]-Ethidium (602-52-8) + 8-urea-ethidium chloride

Conditions	Yield
With hydrogenchloride; water In methanol at 96℃; for 1h;

[3H]-Ethidium (602-52-8) + 3-amino-benzamidine hydrochloride → 5-ethyl-3,8-diamino-7-(3-carbamimidoyl-phenylazo)-6-phenyl-phenanthridinium; chloride-hydrochloride + 5-ethyl-3-amino-8--6-phenyl-phenanthridinium chloride-hydrochloride

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite

[3H]-Ethidium (602-52-8) + 4-amino-benzamidine hydrochloride → 5-ethyl-3,8-diamino-7-(4-carbamimidoyl-phenylazo)-6-phenyl-phenanthridinium; chloride-hydrochloride + 5-ethyl-3-amino-8--6-phenyl-phenanthridinium chloride-hydrochloride

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite

[3H]-Ethidium (602-52-8) + 3-amino-benzamidine hydrochloride → 5-ethyl-3-amino-8-[N'-(3-carbamimidoyl-phenyl)-triazenyl]-6-phenyl-phenanthridinium; chloride-hydrochloride (6798-24-9) + 5-ethyl-3,8-diamino-7(or 9)-<3-carbamimidoyl-phenylazo>-6-phenyl-phenanthridinium chloride-hydrochloride

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite

[3H]-Ethidium (602-52-8) + 4-amino-benzamidine hydrochloride → 5-ethyl-3-amino-8-[N'-(4-carbamimidoyl-phenyl)-triazenyl]-6-phenyl-phenanthridinium; chloride-hydrochloride (4174-67-8) + 5-ethyl-3,8-diamino-7(or 9)-<4-carbamimidoyl-phenylazo>-6-phenyl-phenanthridinium chloride-hydrochloride

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite

Downstream Products

• 4174-67-8 5-ethyl-3-amino-8-[N'-(4-carbamimidoyl-phenyl)-triazenyl]-6-phenyl-phenanthridinium; chloride-hydrochloride 
• 6798-24-9 5-ethyl-3-amino-8-[N'-(3-carbamimidoyl-phenyl)-triazenyl]-6-phenyl-phenanthridinium; chloride-hydrochloride 

Relevant articles and documents

NOVEL ANTI-VIRAL AGENTS BASED UPON DERIVATIVES OF THE AROMATIC HETEROCYCLE PHENANTHRIDINE

A series of substituted phenanthridine derivatives has been synthesized by converting the amines at the 3- and 8- positions of ethidium bromide into guanidine, pyrrole, urea, and various substituted ureas. The resulting derivatives exhibit unique spectral properties that change upon binding nucleic acids. The compounds have an enhanced affinity and specificity for HIV-1 Rev Response Element as compared to ethidium bromide.