Nile Red Powder CAS 7385-67-3

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Nile red powder, also known as Nile red in English, has the molecular formula C20H18N2O2, CAS 7385-67-3, and a molecular weight of 318.37. Melting point 203-205 ° C, boiling point 484.7 ± 45.0 ° C at 760 mmHg, density 2.2330. It is a light resistant and lipophilic staining agent that emits strong fluorescence in hydrophobic (lipid rich) environments, with minimal fluorescence in aqueous media. The compound appears as a dark red powder, soluble in water (partially miscible) and methanol (1 mg/mL).

Insoluble in water, soluble in various organic solvents and emitting fluorescence, with high affinity for triglycerides and cholesterol, making it the most ideal lipid fluorescent dye in hydrophobic environments; Nile red can also bind with phospholipids to color the cell membrane; Other hydrophobic molecules such as hydrophobic proteins can also be stained.

Application of Nile Red

Nile red powder has fluorescent properties and can be used as a fluorescent dye for staining microplastics, lipids, proteins, etc. It is commonly used in fluorescence microscopy and flow cytometry to detect intracellular lipid droplets. Through Nile red staining and fluorescence microscopy observation of bacterial cells containing PHB and non PHB lipid storage substances, it was confirmed that Nile red is a good fluorescent staining agent for lipid storage substances in bacterial cells with high sensitivity. It can be used for fluorescence microscopy observation of PHB and PHB lipid storage substances, and can distinguish the two to a certain extent.

The Nile red fluorescence staining method for lipid determination has been applied to some species of microalgae, but it cannot be used in some green algae with thick cell walls due to its difficulty in staining. Researchers selected four strains of microalgae and improved the method of measuring lipids using Nile red fluorescence staining. They used a 20% dimethyl sulfoxide solution as a penetrant and pretreated the algal cells at 35-40 ℃ to enhance the binding of Nile red to intracellular lipids; The OD540 of algal cell density is within the range of 0.8-1.1. Adding 15 μ L of Nile red acetone solution with a mass concentration of 0.1 mg/mL.

Based on the principle that Nile red combines with intracellular oil components and emits fluorescence under ultraviolet light, and the fluorescence intensity is related to the oil content, deep-sea yeast strains were screened for oil production by cultivating yeast in a medium supplemented with Nile red and observing colony fluorescence. The 26S rDNA D1/D2 region sequence analysis method was used to identify the selected oil producing yeast strains, and a rapid method for measuring oil content by Nile red staining was established.

 

Hypochloric acid (HOCl) plays a crucial role in the natural defense system, but abnormal levels of this species can lead to various diseases such as cell damage and human aging. Therefore, the development of new fluorescent probes for non-destructive cell tissue detection of HOCl in the field of biological sciences is of great significance. The current two-photon excitation fluorescence (TPEF) probes based on Nile red derivatives have the disadvantages of poor water solubility and low efficiency. On the basis of introducing a bicyclized alkyl amine group at the 9th position of Nile red, a fused phenyl substituent molecule (Nil-OH-6) is introduced at the 2nd and 3rd positions.

 

The two-photon absorption cross-section value can reach up to 243GM, and the quantum yield is 0.49.In addition, modifying the molecular end of Nile red derivatives with different hetero spiro rings or N, N-dialkyl fused amino groups can maintain the high fluorescence efficiency of Nile red derivatives as two-photon probes while improving the solubility of the probes. The design strategy proposed in this study to improve solubility while considering the fluorescence efficiency of probe molecules provides a reliable theoretical basis and new approach for the subsequent synthesis of practical Nile red derivative TPEF probes.

Nile red can be used to prepare Nile red dye lasers for acid detection, and this research has broad application prospects in fields such as biochemical detection, laser chemistry, and laser spectroscopy technology.

Use Nile red staining to quickly assist in the detection of microplastics in water environment samples. Firstly, Nile red dye solution was prepared from Nile red and acetone solution, and an organic film stained with ink was prepared; Secondly, before dyeing, add the Nile Red dye solution filtered through an organic membrane to the water sample to dye it light blue;

Filter the dyed water sample using an organic membrane stained with ink. Finally, place the filtered organic membrane in a culture dish and evenly coat the membrane with glue to fix the substances on the membrane for subsequent analysis and use. The dye prepared by this method is easy and fast to prepare, with good adsorption effect and simple staining method. Compared with direct visual inspection, it not only has shorter time consumption and lower cost, but also eliminates some interference from non plastic materials.

 

Nile red molecules have large aromatic rings and electron withdrawing groups that can form hydrogen bonds with water molecules in the ground state. They are particularly sensitive to the environment of solubilization in the surfactant micelle barrier layer, and exhibit dual fluorescence in the aqueous solution of dodecyltrimethylammonium bromide micelles, with emission wavelengths at 578 and 630 nm, respectively. The anti ion dissociation degree of sodium dodecyl sulfate micelles is greater than that of micelles, which not only increases the polarity of the surrounding environment of Nile red.

 

But also increases the solvation water, resulting in enhanced hydrogen bonding with Nile red and low fluorescence intensity of ammonium bromide micelles. However, it effectively promotes the formation of intramolecular twisted charge transfer excited states, and its population can even reach over 98%. Only a single fluorescence peak at 634nm appears on the surface. Nile red's sensitivity to the environment reflects well the incomplete structural information of the initial formation of micelles by surfactants, making it a good probe for detecting the aggregation behavior of such amphiphilic molecules with strong interactions.

adverse reaction

Skin irritation and allergic reactions

According to SDS reports from Apollo Scientific and Chemicalbook, Nile Red may cause skin irritation, particularly in sensitive individuals. After contact, redness, itching, or burning sensation may occur, and symptoms usually subside within 24-48 hours after detachment. However, long-term or repeated exposure may exacerbate skin damage.

Gastrointestinal reactions (ingestion)

Although there is no clear lethal dose reported, ingestion of Nile Red powder may cause nausea, vomiting, abdominal pain, and diarrhea. The dissolution of powder in the gastrointestinal tract may release irritating components and damage the mucosal barrier.First aid advice: If accidental ingestion occurs, immediately dilute with plenty of water and seek medical assistance. Do not induce vomiting to prevent powder from refluxing into the respiratory tract and causing secondary injury.

Eye irritation

Nile Red is highly irritating to the eyes and may cause conjunctival congestion, tearing, photophobia, and foreign body sensation. In severe cases, corneal epithelial damage may lead to blurred vision or temporary blindness.Mechanism analysis: After dust particles enter the conjunctival sac, they break down the mucosal barrier through mechanical friction and chemical stimulation, activate the trigeminal nerve endings, and trigger inflammatory reactions.

Respiratory irritation

Inhaling Nile Red dust may cause dryness in the nasopharynx, coughing, chest tightness, and shortness of breath. Under high concentration exposure, bronchial spasms or asthma like symptoms may occur, especially for asthma patients or those with allergies.Toxicological basis: Although there is a lack of long-term inhalation toxicity data, fluorescent dyes with similar structures (such as Rhodamine B) have been shown to induce respiratory inflammation.

Nile Red (CAS number: 7385-67-3) is a lipophilic fluorescent dye, chemically named 9- (diethylamino) -5H benzo [a] phenoxazin-5-one, with the molecular formula C ₂ ₀ H ₁ ₈ N ₂ O ₂ and a molecular weight of 318.37 g/mol. Its melting point is 203-205 ° C, and it is a crystalline solid at room temperature. This compound is widely used in the fields of cell biology, lipid metabolism research, and materials science due to its strong fluorescence properties in a lipid environment (emission wavelength varies with solvent polarity, from deep red to yellow gold).

FAQ

• What does Nile red dissolve in?

Nile red is soluble in organic solvents such as DMSO and dimethyl formamide. The solubility of nile red in these solvents is approximately 1 mg/ml. Nile red is also slightly soluble in ethanol. Nile red is sparingly soluble in aqueous buffers.

• What is Nile red chemical?

Nile red is an organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group. It has a role as a fluorochrome and a histological dye.

• What are the advantages of using Nile red?

Among the various fluorescent dyes, Nile Red is applied widely for microbial lipid measurement due to its advantages of high specificity for combining with microbial lipids, stability for detection, easy for staining, and low cost of operation.

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