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Fluorexon is a compound widely used in the fields of chemistry and biology, typically appearing as a bright yellow powder or orange red crystal (its sodium salt). It has good solubility in ethanol and alkali, but is slightly soluble in water. And its sodium salt is soluble in water and exhibits yellow and green fluorescence characteristics. As a fluorescent indicator, it has unique fluorescence properties. After being dissolved in water, its sodium salt exhibits yellow and green fluorescence properties, which make it have important application value in fields such as biology and medicine. For example, in cell imaging experiments, calcein can be used as a cytoplasmic dye to observe the distribution and changes of intracellular calcium ions. As a multifunctional compound, it has broad application prospects in fields such as biology and medical research, chemical analysis and detection, and industrial applications. Its unique fluorescence properties, low cytotoxicity, and good chelating ability make calcein an indispensable tool in scientific research and industrial fields.
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Chemical Formula |
C30H26N2O13 |
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Exact Mass |
622 |
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Molecular Weight |
623 |
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m/z |
622 (100.0%), 623 (32.4%), 624 (2.7%), 624 (2.7%), 624 (2.4%) |
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Elemental Analysis |
C, 57.88; H, 4.21; N, 4.50; O, 33.41 |
Fluorexon , as a multifunctional compound, has a wide range of applications in scientific research and industrial fields.
1. Biology and Medical Research
(1) Cell imaging and experiments:
Calcein is an important fluorescent dye for cell imaging, which can be obtained through molecular cloning and chemical synthesis methods. It is widely used in cell analysis, protein localization, and research on intracellular signal transduction. Calcein can efficiently and sensitively detect changes in calcium ion concentration, providing a powerful tool for cellular calcium ion signaling, calcium kinetics research, and drug screening.
(2) Active cell detection:
Calcein is often used as a fluorescent probe to detect the vitality of live cells. Through its low cytotoxicity, calcein can freely diffuse through the cell membrane and penetrate into the cytoplasm of living cells, and then observe the fluorescence signal inside the cell under a fluorescence microscope to evaluate the activity and functional status of the cell.
(3) Drug screening and toxicity assessment:
Calcein is related to the determination of several drugs, including cytotoxicity, oxidative function, and neurotoxicity. In the process of drug screening and toxicity assessment, calcein can be used to detect the impact of drugs on cell activity, thereby evaluating the safety and efficacy of drugs.
2. Chemical analysis and detection
(1) Complex indicator:
Calcein, as a complex indicator, has a wide range of applications in the field of chemical analysis. It is mainly used for complexometric titration of calcium ions. Through its unique fluorescence properties, the color changes during the titration process can be observed intuitively, thereby achieving accurate measurement of calcium ion concentration.
(2) Fluorescent indicator:
Calcein green can also be used as a fluorescent indicator to detect the concentration of other metal ions such as strontium, barium, copper, manganese, etc. By complexing with these metal ions, the fluorescence properties of calcein will change, thereby achieving detection and quantitative analysis of these metal ions.
(3) Fluorescence detection:
In the fluorescence detection of constant temperature amplification reaction, calcein also plays an important role. When the amplification reaction forms pyrophosphate ions, manganese ions combine with pyrophosphate ions to form manganese pyrophosphate, causing the generation of fluorescence signals. By monitoring changes in fluorescence signals, the process and results of amplification reactions can be tracked in real-time.
3. Industrial applications
(1) Indicator and dye:
Calcein can be used as an indicator and dye in the industrial field. For example, in the analysis of phosphate ore, calcium yellow green can be used as a calcium yellow green indicator, indicating the calcium content in phosphate ore through its color change. In addition, calcium yellow green can also be used for dyeing and coloring in industries such as textiles and leather.
(2) Environmental monitoring:
Calcium yellow green pigment also has certain application value in the field of environmental monitoring. For example, in water quality monitoring, calcein can be used to detect the concentration of calcium ions in water, thereby evaluating the hardness and degree of pollution of water quality. In addition, calcein can also be used to detect heavy metal ions and other pollutants in wastewater.
Fluorexon, with the chemical formula C ∝₀ H ₂₆ N ₂ O ₁ ∝, is a bright yellow powdery organic fluorescent compound, and its sodium salt forms orange red crystals. As a "chameleon" in the field of fluorescent probes, calcein has shown wide application value in analytical chemistry, biomedical, materials science and other fields due to its unique fluorescence properties, high selectivity and low toxicity. The following elaborates on its purpose from multiple dimensions:
1. Complexometric titration indicator
Calcein is a classic indicator for complexometric titration of metal ions such as calcium, strontium, barium, copper, and manganese. Multiple carboxyl groups (- COOH) in its molecular structure can form stable complexes with metal ions, leading to significant changes in fluorescence color or intensity, indicating the endpoint of titration. For example, in calcium ion titration, when calcein chelates with EDTA (ethylenediaminetetraacetic acid), the fluorescence changes from yellow green to colorless, and the sensitivity of endpoint determination reaches 0.1 μ mol/L. In the 1970s, this technology was introduced into soil exchangeable calcium determination, overcoming the interference of traditional indicators (such as chrome black T) caused by magnesium ion precipitation and adsorption, significantly improving detection accuracy.
2. Fluorescence detection probe
Calcein emits yellow green fluorescence (λ em=515nm) when excited by ultraviolet light (λ ex=495nm), which can be used for quantitative measurement of calcium ion concentration in biological samples. It has better selectivity than fluorescein, lower binding affinity with magnesium and strontium ions, and good water solubility (up to 50mg in 1mol/L NaOH), making it suitable for calcium ion detection in complex systems such as plasma and cell fluid. For example, in the study of calcium signaling in myocardial cells, calcein can monitor intracellular calcium ion fluctuations in real time, revealing the molecular mechanisms of arrhythmia.
3. Multi metallic element analysis
In addition to calcium, calcein can also be used for the detection of strontium, barium, copper, manganese, cobalt, nickel, molybdenum, and chromium ions. Selective determination of specific ions can be achieved by adjusting the pH of the solution or adding masking agents such as EDTA. For example, in environmental monitoring, calcein combined with ion chromatography can simultaneously detect multiple heavy metal ions in water samples with a sensitivity of ppb level.
Biomedical Science: The 'Fluorescent Key' for Cell Research and Disease Diagnosis
1. Staining and Functional Analysis of Living Cells
Calcein AM: As a membrane permeable fluorescent esterase substrate, Calcein AM can freely diffuse into living cells and be hydrolyzed into Calcein by cytoplasmic esterase, emitting strong green fluorescence (λ ex=490nm, λ em=515nm). Due to the lack of esterase activity in dead cells, this probe only labels live cells and is widely used for cell viability detection, short-term labeling, and flow cytometry analysis. For example, in the study of tumor cell drug resistance, the combination of Calcein AM and propidium iodide (PI) can distinguish live cells, apoptotic cells, and necrotic cells with a sensitivity of over 95%.
Multicolor fluorescent derivatives: To address the limitation of single color, AAT Bioquest has developed blue (Calcein Blue AM, λ em=441nm) and orange (Calcein Orange) ™ Diacetate,λem=545nm), Calcein Red ™ AM, λ em=576nm) and Calcein Deep Red ™ AM, λ em=663nm) fluorescent derivative, supporting multi-color labeling and functional analysis of live cells. For example, in immune cell co culture experiments, the combination of Calcein Blue AM and GFP labeled T cells can track cell migration and interactions in real-time.
2. Bone metabolism research
Calcein is a "fluorescent ruler" for studying bone metabolism. Its calcium dependent fluorescence properties enable it to label active bone formation surfaces, and combined with micro computed tomography (μ CT) technology, it can quantitatively analyze bone formation rate and mineralization degree. For example, in the study of osteoporosis, the dual labeling method of calcein (interval injection labeling) can reveal the dynamic changes of bone turnover, providing a basis for drug efficacy evaluation.
3. Drug delivery system evaluation
Calcein can be used as a model drug to evaluate the cellular uptake and release efficiency of delivery systems such as nanoparticles and liposomes. For example, in the research of anti-cancer drug carriers, the fluorescence intensity of nanoparticles loaded with calcein is positively correlated with drug release after being taken up by cells, which can intuitively reflect the performance of the carrier.
Materials Science: Fluorescent Additives for Contact Lenses and Biomaterials
1. Assessment of Soft Contact Lenses
Calcein can be used for oxygen permeability and surface morphology detection of soft contact lenses. Its fluorescence characteristics can reveal the microporous structure and moisture distribution in the lens material, optimizing product design. For example, in the research and development of silicon hydrogel lenses, the calcein staining method can quantitatively analyze the oxygen permeability coefficient of the lenses to ensure wearing comfort.
2. Tracer of Biodegradable Materials
Calcein can be used as a tracer to label the degradation process of biodegradable materials such as polylactic acid and polycaprolactone. Through fluorescence microscopy observation, the degradation rate and product distribution of materials in vivo can be tracked in real time, providing a basis for the design of tissue engineering scaffolds.
1. Oil extraction
Calcium green pigment, as a drilling fluid additive, can improve crude oil recovery through thickening and stabilizing effects. Its dosage is usually 0.05% -0.2%, which can withstand high temperature and high pressure environments and reduce formation damage. For example, in deep-sea drilling, calcein can reduce the filtration loss of drilling fluid and prevent wellbore collapse.
2. Textile printing and dyeing
Calcein, as a fluorescent whitening agent, can be used for dyeing natural fibers such as cotton and hemp. Its yellow green fluorescence can enhance the whiteness and vividness of fabrics, and it has excellent washability. For example, in the production of high-end bed sheets, the calcein dyeing method can increase the whiteness of the product by 20% -30%, meeting export standards.
Emerging fields: Innovative elements of 3D printing and intelligent packaging
1. 3D printing of biomaterials
Calcium green pigment and nanocellulose composite can be used to prepare biodegradable 3D printed scaffolds. Its fluorescence characteristics support real-time monitoring of the printing process, ensuring structural accuracy. For example, in tissue engineering, calcium green pigment labeled scaffolds can guide cell directed growth and promote angiogenesis.
2. Intelligent packaging materials
Calcium green pigment based intelligent packaging can monitor the freshness of food. By using color changes to indicate the degree of meat spoilage, the sensitivity reaches ppm level. For example, in cold chain logistics, the fluorescence quenching of calcium yellow green film when encountering volatile amine substances (such as putrescine) can intuitively reflect the deterioration of food.
The laboratory synthesis method of Fluorexon mainly involves two main pathways: molecular cloning method and chemical synthesis method. The following will elaborate on these two methods and their corresponding chemical equations.
1. Molecular cloning method
Molecular cloning is a method of preparing calcein through genetic engineering technology. The basic idea of this method is to extract gene sequences from the fluorescent proteins naturally present in the jellyfish Aequorea Victoria (green jellyfish), and then clone and express them in expression systems such as E. coli, ultimately obtaining a large amount of calcein.
Step Introduction
1. Obtaining gene sequence:
Firstly, extract the gene sequence of fluorescent protein from the green jellyfish Aequorea Victoria.
2. Gene cloning:
Using genetic engineering techniques, the gene sequence of fluorescent proteins is cloned into an appropriate vector, such as a plasmid.
3. Expression system construction:
Plasmids containing fluorescent protein gene sequences are introduced into expression systems such as Escherichia coli for cultivation and expression.
4. Extraction and purification of calcein:
Through a series of biochemical methods, calcein is extracted and purified from the expression system.
2. Chemical synthesis method
The chemical synthesis method is to synthesize fluorescent substances of calcein through chemical synthesis methods. This method requires the use of specific chemical raw materials and a series of chemical reactions to synthesize calcein.
Step Introduction
1. Raw material preparation:
Prepare the required chemical raw materials, such as fluorescein, sodium hydroxide, iminodiacetic acid, formaldehyde, etc.
2. Reaction synthesis:
Dissolve fluorescein in ethanol, add raw materials such as sodium hydroxide, iminodiacetic acid, formaldehyde, etc., and carry out reaction synthesis under certain temperature and conditions.
3. Purification and crystallization:
Through steps such as water purification, impurities are removed to obtain pure calcium yellow green. If a sodium salt of calcein is needed, further salt formation reactions can be carried out.
Chemical synthesis methods may involve similar reaction steps as follows:
(1) C20H12O5+C2H6O → Fluorescein ethanol solution
(2) Fluorescein ethanol solution+NaOH+C4H7NO4+CH2O → Reaction intermediate
(3) Reaction intermediates → C30H26N2O13+by-products (such as H2O)
Please note that the above equation is only for illustration, and the actual reaction process may be more complex and may involve multiple intermediate steps and products.
The laboratory synthesis methods of calcein mainly include molecular cloning and chemical synthesis. Molecular cloning utilizes genetic engineering techniques to extract fluorescent protein gene sequences from living organisms, and clones and expresses them in an expression system; The chemical synthesis law synthesizes fluorexon through chemical raw materials and chemical reactions. These two methods each have their own characteristics and are suitable for different research needs and application scenarios. In practical applications, suitable synthesis methods can be selected based on specific research objectives and experimental conditions.
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