Nile red
Catalog Number: BT-255768
CAS Number: 7385-67-3
Molecular Formula: C₂₀H₁₈N₂O₂
Molecular Weight: 318.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Nile Red is a fluorescent dye that has gained significant attention in various fields of research due to its unique properties. It is a lipophilic dye that can selectively stain lipids, making it a useful tool for studying lipid metabolism and lipid-related diseases. Nile Red has also been found to have potential therapeutic and environmental applications. We will also explore the current limitations and future prospects of Nile Red in scientific research.
Properties
CAS Number
7385-67-3
Product Name
Nile red
IUPAC Name
9-(diethylamino)benzo[a]phenoxazin-5-one
Molecular Formula
C₂₀H₁₈N₂O₂
Molecular Weight
318.4 g/mol
InChI
InChI=1S/C20H18N2O2/c1-3-22(4-2)13-9-10-16-18(11-13)24-19-12-17(23)14-7-5-6-8-15(14)20(19)21-16/h5-12H,3-4H2,1-2H3
InChI Key
VOFUROIFQGPCGE-UHFFFAOYSA-N
SMILES
CCN(CC)C1=CC2=C(C=C1)N=C3C4=CC=CC=C4C(=O)C=C3O2
Synonyms
9-diethylamino-5H-benzo(a)phenoxazine-5-one
nile red
nile red
Canonical SMILES
CCN(CC)C1=CC2=C(C=C1)N=C3C4=CC=CC=C4C(=O)C=C3O2
Method of Synthesis or Extraction
Nile Red can be synthesized using various methods, including the reaction of 9-diethylamino-5H-benzo[a]phenoxazine-5-one with benzoyl chloride or benzoyl bromide. The yield of this method is relatively low, ranging from 10-20%. Another method involves the reaction of 9-diethylamino-5H-benzo[a]phenoxazine-5-one with 2-naphthoyl chloride, which yields a higher yield of 50-60%. However, this method requires the use of toxic solvents such as chloroform and benzene, which pose environmental and safety concerns.
Nile Red can also be extracted from natural sources such as the seeds of Bixa orellana, commonly known as annatto. The extraction process involves the use of organic solvents such as ethanol or methanol. This method has been found to be more environmentally friendly and yields a higher amount of Nile Red compared to chemical synthesis.
Nile Red can also be extracted from natural sources such as the seeds of Bixa orellana, commonly known as annatto. The extraction process involves the use of organic solvents such as ethanol or methanol. This method has been found to be more environmentally friendly and yields a higher amount of Nile Red compared to chemical synthesis.
Chemical Structure and Biological Activity
Nile Red has a molecular formula of C20H18N2O and a molecular weight of 306.37 g/mol. It has a planar structure with a central benzophenoxazine ring and two diethylamino groups that contribute to its lipophilic properties. Nile Red has been found to selectively stain neutral lipids such as triglycerides, cholesterol esters, and free fatty acids.
Nile Red has been shown to have various biological activities, including anti-inflammatory, antioxidant, and anticancer properties. It has been found to inhibit the growth of cancer cells by inducing apoptosis and inhibiting cell proliferation. Nile Red has also been found to have neuroprotective effects by reducing oxidative stress and inflammation in the brain.
Nile Red has been shown to have various biological activities, including anti-inflammatory, antioxidant, and anticancer properties. It has been found to inhibit the growth of cancer cells by inducing apoptosis and inhibiting cell proliferation. Nile Red has also been found to have neuroprotective effects by reducing oxidative stress and inflammation in the brain.
Biological Effects
Nile Red has been found to affect cell function and signal transduction by selectively staining lipids and altering lipid metabolism. It has been used to study the role of lipids in various cellular processes such as autophagy, lipid droplet formation, and membrane dynamics. Nile Red has also been found to have potential therapeutic and toxic effects. Its lipophilic properties make it a potential drug delivery agent for lipophilic drugs. However, its toxicity and potential side effects need to be further studied.
Applications
Nile Red has various applications in medical, environmental, and industrial research. In medical research, Nile Red has been used to study lipid-related diseases such as obesity, diabetes, and atherosclerosis. It has also been used in drug development to screen for lipophilic drugs and to study drug delivery mechanisms. Clinical trials have shown promising results in using Nile Red as a diagnostic tool for detecting lipid-related diseases.
In environmental research, Nile Red has been used to study the effects of pollutants on lipid metabolism in aquatic organisms. It has also been used in pollution management to detect and quantify lipids in wastewater and soil samples. Nile Red has also been found to have potential applications in sustainability and environmental impact by studying the role of lipids in carbon sequestration and biofuel production.
In industrial research, Nile Red has been used to improve product quality and efficiency in various manufacturing processes such as food processing and oil refining. It has also been used to study the health and safety considerations of lipophilic compounds in the workplace.
In environmental research, Nile Red has been used to study the effects of pollutants on lipid metabolism in aquatic organisms. It has also been used in pollution management to detect and quantify lipids in wastewater and soil samples. Nile Red has also been found to have potential applications in sustainability and environmental impact by studying the role of lipids in carbon sequestration and biofuel production.
In industrial research, Nile Red has been used to improve product quality and efficiency in various manufacturing processes such as food processing and oil refining. It has also been used to study the health and safety considerations of lipophilic compounds in the workplace.
Future Perspectives and Challenges
Despite the potential applications of Nile Red in various fields of research, there are still limitations and challenges that need to be addressed. The toxicity and potential side effects of Nile Red need to be further studied to ensure its safety in medical and environmental applications. The development of more efficient and environmentally friendly methods of synthesis or extraction of Nile Red is also needed. Future trends and prospects in the application of Nile Red in scientific research include the development of new fluorescent dyes with improved properties and the use of Nile Red in combination with other imaging techniques for more comprehensive studies of lipid metabolism.
Conclusion
Nile Red is a versatile fluorescent dye that has found various applications in medical, environmental, and industrial research. Its lipophilic properties make it a useful tool for studying lipid metabolism and lipid-related diseases. Nile Red has also been found to have potential therapeutic and environmental applications. However, further studies are needed to address the limitations and challenges of Nile Red in scientific research.
Conclusion
Nile Red is a versatile fluorescent dye that has found various applications in medical, environmental, and industrial research. Its lipophilic properties make it a useful tool for studying lipid metabolism and lipid-related diseases. Nile Red has also been found to have potential therapeutic and environmental applications. However, further studies are needed to address the limitations and challenges of Nile Red in scientific research.
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