4-[2-[4-(Bishexadecylamino)phenyl]ethenyl]-1-methylpyridinium iodide
[CAS# 114041-00-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Methylpyridine
• Name: 4-[2-[4-(Bishexadecylamino)phenyl]ethenyl]-1-methylpyridinium iodide
• Molecular Formula: C₄₆H₇₉N₂.I
• Molecular Weight: 787.05
• CAS Registry Number: 114041-00-8
• EC Number: 634-549-8
• SMILES: CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)C1=CC=C(C=C1)/C=C/C2=CC=[N+](C=C2)C.[I-]

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

4-[2-[4-(dihexadecylamino)phenyl]vinyl]-1-methylpyridinium iodide, commonly known as fluorescent dye, is an important compound in the field of bioimaging and molecular electronics. Its discovery marks a major advance in the development of dyes with high specificity and sensitivity. The discovery of this compound stems from the need for efficient and stable fluorescent dyes. It is synthesized by integrating the pyridine core with a vinyl linker and a dihexadecylamino-substituted phenyl group. The iodide ion serves as a counterion to balance the positive charge on the pyridine. The synthesis involves a multistep reaction, first forming the vinyl bond, then quaternization with methyl iodide, and finally the addition of the dihexadecylamino group. This structural arrangement is designed to enhance the fluorescence properties and solubility in various solvents, making it an ideal candidate for bioimaging applications.

The structure of this compound has several key elements: the pyridine ring provides a stable positive charge, promoting strong interactions with cellular components and enhancing fluorescence; the vinyl group connects the pyridine to the benzene ring, helping to form a conjugated system that is essential for fluorescence; the dihexadecylamino chain improves the hydrophobicity and membrane affinity of the dye, allowing it to embed into lipid bilayers and cell membranes; and the iodide ion maintains charge balance, affecting the solubility and crystallization properties of the dye.

4-[2-[4-(dihexadecylamino)phenyl]vinyl]-1-methylpyridinium iodide is widely used in cell imaging due to its strong fluorescence and ability to penetrate cell membranes. It selectively binds to lipid-rich regions, such as membranes and vesicles, providing high-contrast images of cellular structures. The compound is suitable for live cell imaging because it can stain cells without significant cytotoxicity. It allows real-time observation of cellular processes such as endocytosis, exocytosis, and intracellular trafficking. It can adjust the fluorescence of the dye by modifying its structure or combining it with other fluorescent dyes. This feature supports multicolor imaging, using different dyes to label various cellular components simultaneously. This technology is essential for visualizing complex biological interactions and pathways within cells.

In molecular electronics, 4-[2-[4-(bis-hexadecylamino)phenyl]vinyl]-1-methylpyridinium iodide is used as a fluorescent probe to study the electronic properties of materials. Its fluorescence is affected by changes in the electronic environment, making it a useful tool for studying electron transfer processes, molecular interactions, and material conductivity. The dye has been developed for use in OLEDs due to its strong fluorescence and stability. It acts as an emissive layer, contributing to the color and efficiency of light-emitting devices. The compound is used to develop fluorescence-based sensors for detecting specific ions, molecules, or environmental conditions. Its sensitivity to changes in the surrounding environment enables it to act as a sensor that converts chemical or physical changes into a measurable fluorescent signal.

In biomedical research, the dye is used to label and track specific proteins, lipids, or other biomolecules within cells. This capability supports studies of disease mechanisms, drug delivery, and cellular responses to therapeutic interventions. The fluorescent properties of the dye can be used in diagnostic assays to help detect the presence of specific biomolecules or pathogens.

In materials science, the compound is used to study the properties of polymers, nanomaterials, and other advanced materials. Its fluorescent properties provide insights into material structure, dynamics, and interactions, supporting the development of new materials with tailored properties.

References

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DOI: 10.1007/978-3-540-68764-1_61

2006. Sub-lethal concentrations of waterborne copper are toxic to lateral line neuromasts in zebrafish (Danio rerio). Hearing Research.
DOI: 10.1016/j.heares.2005.10.015

2013. Labeling Hair Cells and Afferent Neurons in the Posterior Lateral-Line System of Zebrafish. Cold Spring Harbor Protocols.
DOI: 10.1101/pdb.prot079467