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Aniline Blue

Catalog Number: BT-264612

CAS Number: 28631-66-5

Molecular Formula: C32H25N3Na2O9S3

Molecular Weight: 737.7 g/mol

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Product Introduction

Description

Aniline Blue is a synthetic dye that belongs to the triphenylmethane family. It is commonly used in medical, environmental, and industrial research due to its unique properties. Aniline Blue is a cationic dye that binds to negatively charged molecules, such as nucleic acids and proteins. This paper will discuss the methods of synthesis or extraction, chemical structure, biological activity, applications, and future perspectives of Aniline Blue.

Properties

CAS Number

28631-66-5

Product Name

Aniline Blue

IUPAC Name

disodium;2-amino-3-methyl-5-[[4-(4-sulfonatoanilino)phenyl]-[4-(4-sulfophenyl)iminocyclohexa-2,5-dien-1-ylidene]methyl]benzenesulfonate

Molecular Formula

C32H25N3Na2O9S3

Molecular Weight

737.7 g/mol

InChI

InChI=1S/C32H27N3O9S3.2Na/c1-20-18-23(19-30(32(20)33)47(42,43)44)31(21-2-6-24(7-3-21)34-26-10-14-28(15-11-26)45(36,37)38)22-4-8-25(9-5-22)35-27-12-16-29(17-13-27)46(39,40)41;;/h2-19,34H,33H2,1H3,(H,36,37,38)(H,39,40,41)(H,42,43,44);;/q;2*+1/p-2

InChI Key

JOMYTEXBPBTBOK-VOAIEOAJSA-L

SMILES

CC1=CC(=CC(=C1N)S(=O)(=O)[O-])C(=C2C=CC(=NC3=CC=C(C=C3)S(=O)(=O)O)C=C2)C4=CC=C(C=C4)NC5=CC=C(C=C5)S(=O)(=O)[O-].[Na+].[Na+]

Solubility

Soluble in DMSO

Synonyms

C.I. Acid Blue 22

Canonical SMILES

CC1=CC(=CC(=C1N)S(=O)(=O)[O-])C(=C2C=CC(=[NH+]C3=CC=C(C=C3)S(=O)(=O)[O-])C=C2)C4=CC=C(C=C4)NC5=CC=C(C=C5)S(=O)(=O)[O-].[Na+].[Na+]

Method of Synthesis or Extraction

Aniline Blue can be synthesized by the reaction of aniline and paraformaldehyde in the presence of hydrochloric acid. The yield of this method is around 60%, and the reaction is exothermic, requiring careful temperature control. Another method involves the reaction of aniline and benzaldehyde in the presence of sulfuric acid, which yields a higher purity of Aniline Blue. However, this method is less efficient, with a yield of around 30%. Environmental and safety considerations must be taken into account during the synthesis of Aniline Blue, as the starting materials and by-products can be hazardous.

Chemical Structure and Biological Activity

The chemical structure of Aniline Blue consists of a triphenylmethane core with three aniline groups and a sulfonic acid group. Aniline Blue has a high affinity for nucleic acids and proteins, making it useful in staining and visualizing these molecules. Aniline Blue has been shown to inhibit the activity of DNA polymerase, an enzyme involved in DNA replication, and to induce apoptosis in cancer cells. Aniline Blue has also been found to have antimicrobial activity against Gram-positive bacteria.

Biological Effects

Aniline Blue has been shown to affect cell function and signal transduction pathways. It has been found to inhibit the growth of cancer cells and to induce apoptosis. Aniline Blue has also been shown to have neuroprotective effects in animal models of neurodegenerative diseases. However, Aniline Blue can also have toxic effects, particularly at high concentrations. It has been shown to induce oxidative stress and DNA damage in cells.

Applications

In medical research, Aniline Blue has been used in drug development, particularly in the development of anticancer drugs. It has also been used in clinical trials to visualize nucleic acids and proteins in tissues. Aniline Blue has potential benefits in the treatment of neurodegenerative diseases and as an antimicrobial agent. However, its potential toxic effects must be carefully considered. In environmental research, Aniline Blue has been used to study the effects of pollutants on ecosystems and to monitor water quality. Aniline Blue has also been used in industrial research to improve product quality and efficiency, particularly in the textile industry.

Future Perspectives and Challenges

One of the current limitations in the use and study of Aniline Blue is its potential toxicity. Further research is needed to determine safe concentrations and to understand the mechanisms of its toxic effects. Another challenge is the development of more efficient and environmentally friendly methods of synthesis. Future trends and prospects in the application of Aniline Blue in scientific research include its use in the development of new drugs and in the study of neurodegenerative diseases. Aniline Blue also has potential applications in the field of nanotechnology, particularly in the development of biosensors.
Conclusion:
Aniline Blue is a versatile dye with unique properties that make it useful in a variety of scientific research fields. Its chemical structure and biological activity have been well studied, and it has potential applications in drug development, environmental research, and industrial processes. However, its potential toxicity must be carefully considered, and further research is needed to fully understand its mechanisms of action and potential therapeutic effects.

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