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Rhodamine 110 is an excellent oxazine-based green fluorescent dye. Endowed with core properties including high photostability, high quantum yield, pH insensitivity (stable fluorescence within the pH range of 4–10), and favorable biocompatibility, it has become a commonly used fluorescent tool across multiple fields.Its excitation wavelength ranges from 498 to 502 nm and emission wavelength from 520 to 527 nm, which makes it fully compatible with 488 nm lasers and standard FITC filters, thus boasting broad applicability. Active functional groups such as carboxyl groups and NHS esters can be introduced into the dye through structural modification to flexibly regulate its performance, achieving both high specificity and practicality.
|
Chemical Formula |
C20H15ClN2O3 |
|
Exact Mass |
366 |
|
Molecular Weight |
367 |
|
m/z |
366 (100.0%), 368 (32.0%), 367 (21.6%), 369 (6.9%), 368 (2.2%) |
|
Elemental Analysis |
C, 65.49; H, 4.12; Cl, 9.66; N, 7.64; O, 13.09 |
Application
Cellular and In Vivo Imaging
Owing to its high photostability and pH insensitivity, it and its derivatives are widely used in cellular imaging and in vivo tracking. In cellular imaging, they can be applied to fluorescence microscopy observation and confocal microscopy imaging of both live and fixed cells, clearly revealing the subcellular localization, distribution, and dynamic changes of target molecules. Examples include mitochondria-targeted imaging (its cationic form can accumulate in mitochondria) and visualization of cellular signal transduction pathways.
In in vivo imaging, after tail vein injection or local administration, Rhodamine 110 can be used to real-time track the distribution and metabolic processes of labeled molecules in model organisms such as mice and zebrafish embryos. DBCO-modified derivatives can complete in vivo labeling within minutes, providing a real-time visualization tool for biomedical research. Meanwhile, its stable fluorescent signal is resistant to photobleaching, which can meet the requirements of long-term imaging.
Biological Evidence Detection
In forensic science, it can be used for the detection and identification of biological fluid traces, addressing the limitations of traditional detection methods such as poor specificity and DNA damage. By synthesizing Rhodamine 110-based fluorescent peptide substrates, trace localization can be achieved through the enzymatic hydrolysis of body fluid-specific proteases. After spraying the substrate on suspicious areas, if body fluids such as blood, semen, or saliva are present, the specific proteases in them will cleave the substrate to release fluorescence.
The fluorescent signal enables precise localization of biological fluid traces without interfering with subsequent DNA extraction and typing.
This detection method is suitable for concealed, trace, or background-dark biological fluid traces. Compared with traditional techniques such as ultraviolet lamp irradiation and colorimetry, it has the advantages of strong specificity, high sensitivity, and minimal damage to forensic samples. It can significantly improve the efficiency and accuracy of forensic biological evidence analysis, providing key clues for criminal investigation.
Application Expansion in Materials and Optics Fields
Beyond the biomedical field, Rhodamine 110 can also be applied in scenarios such as material modification and optical device fabrication. In materials science, it can be introduced as a fluorescent probe into materials like metal-organic frameworks (MOFs) and mesoporous silica to prepare fluorescent functional materials, which are used in environmental monitoring and visualization of drug delivery carriers. Its modifiability allows conjugation with PEG derivatives and block copolymers, optimizing the biocompatibility and targeting ability of materials.
In the optics field, it can serve as a laser dye for the manufacture of dye lasers. Additionally, its fluorescent properties can be applied to the research and development of optical devices such as color filters, liquid crystal displays (LCDs), and light-emitting diodes (LEDs). It can also be used to optimize the performance of materials like solar cells and optical waveguides, improving the luminous efficiency and stability of devices by virtue of its stable optical properties.
Copper is an important trace element in the human body. The loss of copper in the body will lead to metabolic disorders and many diseases, such as increased cholesterol, decreased arterial elasticity, and increased blood pressure. The research of copper ion bioluminescence probe has been a hot topic. Zhao et al. designed and synthesized a new rhodamine lactam derivative 5 in 2009, and applied it to the detection of Cu2+in aqueous solutions and living cells.
The reaction of this colorimetric probe to copper ion is instantaneous and reversible, and it will not interfere with the colorimetric and fluorescence signals of copper ion when the concentration of other metal ions is very high. This feature makes it well meet the special requirements of biomedicine and environmental monitoring. At present, these probes have been widely used to detect the concentration of copper ions in environmental systems and imaging the distribution of copper ions in living cells. Their excellent comprehensive performance indicates an excellent application prospect.
Iron ion probe:
Iron is an essential trace element in the human body. It mainly exists in the form o
f complex ions in the human body, forms hemoglobin and myoglobin with heme, protein, etc., and plays a role in transporting and storing oxygen in the body. Because of the paramagnetism of Fe3+, the general Fe3+fluorescence probes are fluorescence quenching type, which is not conducive to the fluorescence imaging and in situ detection of Fe3+in bovine objects.
Therefore, the design of fluorescence enhanced Fe3+fluorescence probe based on the closed loop to open loop conversion mechanism of it molecules has gradually attracted attention.
Mercury is a highly toxic metal. Mercury elements and mercury ions can enter the environment through various ways. After long-term exposure and ingestion, the human body will have serious nausea, vomiting, abdominal pain, kidney function damage and other diseases, which are extremely harmful. As people attach great importance to the toxicity of mercury, the research on Hg2+fluorescent probes is increasing in recent years. Xu et al. designed and synthesized a rhodamine thiohydrazide for ultraviolet and fluorescence detection of Hg2+in the aqueous phase.
The stoichiometric ratio of the probe to Hg2+is 2 ∶ 1. Qian et al. designed and synthesized a highly selective rhodamine Hg2+fluorescence probe, which can not only realize the fluorescence detection of Hg2+, but also preliminarily judge the existence of Hg2+using color reaction. The probe is reversible. When EDTA is added to the equilibrium system of color development, the purple red of the system becomes colorless. In addition, fast fluorescence response is another feature of this probe. After adding Hg2+, stable and strong fluorescence is generated immediately. Compared with similar probes that require a certain balance time, this probe is more suitable for real-time analysis of environmental or biological samples.
Staining procedure
(1) Dissolve 0.4mgRh123 in 1mL DMSO to prepare 1mMRh123-DMSO solution.
(2) Prepare cells with slides. The number of cells should be 5 × 104~5 × 105 pieces/mL.
(3) Incubate the slide and wash the cells with PBS or Hank's solution.
(4) Dilute 1mM Rh123 solution with culture medium to prepare 1~20µ M Rh123 buffer.
(5) Add Rh123 buffer solution to the slide and incubate it at 37 ℃ for 30 minutes to 1 hour.
(6) Remove Rh123 buffer and wash cells with culture medium (after washing cells, add 10% formalin buffer and incubate for 15-20 minutes, then wash with PBS for fixation).
(7) The cells were observed with a fluorescent microscope with a fluorescein filter.
Storage conditions: Store at room temperature and away from light, dissolve in DMSO to prepare mother liquor, and then store at - 20 ℃.
What are the side effects of this compound?
Cytotoxicity
Concentration dependence: At low concentrations (below 10 μ M), no cytotoxicity was observed against human lymphoblasts. When the concentration exceeds 100 μ M, the substance will cause the death of Friend leukemia cells.
Cell Accumulation: It accumulates in human lymphoblasts and Friend leukemia cells, and may alter the pH value inside the cells, especially in the form of cations accumulated in mitochondria
Animal experiment results
Acute toxicity: In vivo studies have shown that based on the intravenous LD50 acute toxicity value, its toxicity is lower than that of its parent molecule Rhodamine B. The LD50 value of RHODAMINE 110 is 140.0mg/kg, while the LD50 value of this substance is 89.5mg/kg.
Organ effects: After ingestion of this substance and Rhodamine B, both molecules induce liver and kidney enlargement. Male rats showed more significant liver and kidney enlargement after exposure than female rats. The testicular weight of male rats given this compound increased.
Pharmacokinetics: Its pharmacokinetics were evaluated by two doses: oral administration (3 and 10mg/kg) and intravenous administration (3mg/kg). After oral administration, its absorption is not very fast and it takes more than 2 hours to be absorbed from the intestine into the bloodstream. The maximum plasma concentrations (Cmax) of the two oral doses were 283.4 and 657.0 ng/mL, respectively, reaching at 140 and 210 minutes. The area under the drug time curve (AUC) for the two doses was 138.1 ± 20.3 and 444.0 ± 170.8 hng/mL, respectively, indicating that AUC is proportional to the oral dose. The clearance rates (Cl) of the two oral doses were 7.94 and 8.61 mL/min/kg, respectively.
Side effect
Liver and kidney damage
Due to the fact that ingestion of this substance can cause enlargement of the liver and kidneys, long-term use or high-dose exposure may lead to damage to these organs. The liver and kidneys are important metabolic and excretory organs in the human body, and damage may lead to functional impairment, which in turn affects overall health.
Effects on the reproductive system
In animal experiments, an increase in testicular weight was observed in male rats given it, which may indicate that the substance has a certain impact on the reproductive system. Long term exposure or high-dose use may lead to reproductive dysfunction, such as decreased sperm quantity or quality, impaired fertility, etc.
Cytotoxic effects
Although it has no cytotoxicity to human lymphoblasts at low concentrations, it can cause death of Friend leukemia cells at high concentrations. This indicates that the substance has potential cytotoxic effects and may cause damage to normal cells, especially in high doses or long-term use.
Allergic reactions
As a foreign chemical substance, this substance may cause allergic reactions in the human body. The symptoms of allergic reactions may include rash, itching, difficulty breathing, laryngeal edema, etc., which can be life-threatening in severe cases.
Other potential side effects
Due to its chemical structure and properties, it may also cause other potential side effects, such as neurological damage, digestive system discomfort, etc. The specific manifestations and degrees of these side effects may vary from individual to individual, and may also be related to dosage and usage.
Precautions for use
For scientific research purposes only
It is currently only for scientific research purposes and not used as a medicine, family backup medicine, or for other purposes. In scientific research experiments, it is necessary to strictly follow the experimental guidelines and operating procedures to avoid unnecessary exposure and contamination.
Avoid long-term exposure
Due to its potential cytotoxicity and organ damage effects, long-term exposure or high-dose use should be avoided. During the experimental process, the dosage and duration of use should be strictly controlled to reduce potential harm to experimental animals and humans.
Pay attention to personal protection
When using, appropriate personal protective equipment such as gloves, masks, and goggles should be worn. Avoid direct contact with skin and eyes to prevent inhalation or ingestion.
Storage and disposal
This substance should be stored in a dry, cool, well ventilated place, away from sources of fire and heat. Abandoned items should be disposed of in accordance with the regulations of the local environmental protection department to avoid causing pollution to the environment.
FAQ
Is it soluble in water?
Solubility in water: slightly soluble. 77000 l/(mol.cm) (at lambda max.)
What is the wavelength of it?
It is a sensitive and selective substrate for assaying proteinases in solution or inside living cells. The excitation wavelength is 498 nm and the emission wavelength is 521 nm.
What is rhodamine dye used for?
Rhodamine dye, a xanthene dye, is often used as a tracer (Rhodamine WT) in water quality assessments. It's had wide use as a 'time of travel' dye for both surface water and groundwater systems with the ability to stain organic materials.
What is rhodamine 123 used for?
Rhodamine 123, a cell-permeating fluorescent dye, has been widely used to evaluate the mitochondrial membrane potential status of living cells based on membrane potential-dependent accumulation.
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