7-nitroindole is an organic compound with the chemical formula C8H6N2O2 and CAS number 6960-42-5. It is a yellow to orange crystalline powder with an aromatic odor. It is widely used in research in the fields of chemistry, pharmacology, and biology, including as a fungicide, antioxidant, and for its activity in DNA replication and repair. In the medical field, it also exhibits anti-cancer and neuroprotective effects. It is an important organic compound that plays a crucial role in scientific research and applications. It is a key raw material for synthesizing certain drugs. Through a series of chemical reactions, it can be converted into compounds with pharmacological activity, which can be used to treat various diseases.
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Chemical Formula |
C8H6N2O2 |
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Exact Mass |
162 |
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Molecular Weight |
162 |
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m/z |
162 (100.0%), 163 (8.7%) |
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Elemental Analysis |
C, 59.26; H, 3.73; N, 17.28; O, 19.73 |
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The following are related uses of 7-Nitroindole:
1. To study neurodegenerative diseases:
It can be used as one of the tool compounds for studying neurodegenerative diseases. According to research, it has a protective effect on neurons in the body, and can reduce the degree of DNA oxidation, lipid peroxidation and apoptosis, thereby preventing the death of nerve cells. In addition, it can be used as a tool compound to activate α-7 nicotinic acid acetylcholine receptor (nAChR) in nerve cells, and prevent neuron death through the response of nAChR and extracellular regulatory signals.
2. To study neuronal behavior:
Because it has protective effects on neurons, it is also used as a tool to study neuronal activity. Researchers can use it to detect the fluorescence of neurons, and then study the activity of neurons, the movement of the terminal and the response state. At the same time, this function can also help neuroscientists better understand the situation of neurons under normal and pathological conditions, and explore the possibility of treating neurodegenerative diseases in the future.
3. Study biological gene expression:
It has a chromosome staining effect and can combine with DNA to form a complex. In studying gene expression, researchers can use product as a fluorescent stain to visualize the distribution of DNA molecules that exhibit interest, such as switching genetic elements, in the nucleus. The above-mentioned properties of it endow it with a wide range of applications in biology, such as applying it to genetic diagnostic tests for certain diseases, and monitoring the expression of genes under different conditions through the monitoring of dyes.
4. Used as insecticide and fungicide:
Like other nitro compounds, the nitro group of it is easily reduced to nitroso, and then reacts with various enzymes of bacteria, thereby destroying its cell wall. Therefore, it acts as a fungicide. In addition, it is also used in the field of agriculture as an insecticide to help agricultural crops from insect damage.
In conclusion, it has a wide range of applications in many fields. From models that can simulate neurodegenerative diseases to helping neuroscientists better understand neuronal activity, gene expression, and pesticides and fungicides, it is one of the related applications of product.
7-nitroindole, as an organic compound, has unique nitro functional groups and indole rings in its chemical structure, which makes it have certain potential applications in the field of pesticides, especially as insecticides. The mechanism of action of these derivatives may involve multiple aspects, including interfering with the nervous system of insects, disrupting their physiological and metabolic processes, and inhibiting their growth and development.
The nervous system of insects is an important regulatory center for their life activities. Many insecticides achieve their insecticidal goals by interfering with the normal functioning of the insect nervous system. Some derivatives of 7-nitroindle may have similar mechanisms of action. They can simulate or interfere with the transmission process of insect neurotransmitters, such as acetylcholine and gamma aminobutyric acid (GABA), leading to dysfunction of the insect nervous system, resulting in symptoms such as paralysis, paralysis, and even death.
For example, some compounds containing nitro functional groups can inhibit the activity of acetylcholinesterase in insects, leading to the accumulation of acetylcholine in synaptic cleft, continuous stimulation of neural receptors, and keeping insects in a state of sustained excitation, ultimately resulting in death due to nerve fatigue. This mechanism of action is similar to certain organophosphate insecticides and carbamate insecticides.
The physiological metabolic processes of insects are the foundation of their life activities. Derivatives of 7-nitroindle may exert insecticidal effects by interfering with insect energy metabolism, substance metabolism, or detoxification metabolism. For example, some derivatives can inhibit the activity of respiratory chain enzymes in insects, block ATP synthesis, and lead to insufficient energy supply and death of insects. Or they can interfere with the lipid metabolism, protein metabolism, and other processes of insects, leading to stunted growth and development or even death.
In addition, some derivatives may also have the effect of inhibiting the activity of insect detoxifying enzymes. There are various detoxifying enzymes in insects, such as cytochrome P450 enzymes and glutathione S-transferase, which can catalyze the metabolism and excretion of foreign toxic substances. If derivatives of 7-nitroindle can inhibit the activity of these detoxifying enzymes, insects' ability to detoxify toxic substances will decrease, making them more susceptible to insecticide attacks.
The growth and development of insects is a complex process that involves the regulation of multiple genes and signaling pathways. Some derivatives of 7-nitroindle may inhibit insect growth and development by interfering with the normal functions of these genes and signaling pathways. For example, they can inhibit the synthesis or signaling pathways of molting hormones in insects, causing them to be unable to molt and grow normally. Or they can interfere with the juvenile hormone signaling pathway of insects, causing them to be in a larval state and unable to enter the adult stage.
In addition, some derivatives may also have the ability to inhibit insect reproduction. They can interfere with the development of insect reproductive cells, mating behavior, or egg laying processes, thereby reducing the reproductive rate of insects. This is of great significance for controlling pest populations and reducing pesticide use.
The chemical analysis of 7-Nitroindole requires the comprehensive application of multiple methods, including purity testing, structural characterization, and stability assessment, etc. The following provides an analysis from different perspectives:
Purity Detection Methods
Gas Chromatography (GC)
Using a gas chromatograph to separate the components in the mixture and employing a detector (such as a FID flame ionization detector) to quantitatively analyze the purity of 7-Nitroindole. This method is suitable for volatile samples and can detect trace impurities. For example, the purity of the product provided by a certain supplier is labeled as >98.0% (GC), indicating that its purity has been verified by gas chromatography.
High Performance Liquid Chromatography (HPLC)
For compounds that are unstable at high temperatures or have strong polarity, HPLC is a better choice. Separation is achieved using an reversed-phase column (such as a C18 column), combined with an ultraviolet detector (UV) or a diode array detector (DAD), enabling high-sensitivity detection. For example, the purity of 7-Nitroindole-2-carboxylic acid (a derivative) was verified by HPLC to be ≥98%.
Nuclear Magnetic Resonance Hydrogen Spectroscopy (1H NMR)
By analyzing the chemical shift, peak area, and coupling constant of hydrogen atoms, the molecular structure can be confirmed and purity evaluated. For example, in the 1H NMR spectrum of 7-Nitroindole, the signals of aromatic hydrogens (such as δ 8.16, 7.46 ppm) and the shift changes caused by the electron effect of the nitro group are key evidence for structure confirmation.
Structural Characterization Methods
Mass Spectrometry (MS)
Electrospray Ionization Mass Spectrometry (ESI-MS) or Electron Impact Mass Spectrometry (EI-MS) can determine the molecular ion peak and fragment peaks, verifying the molecular weight and structural fragments. For example, the molecular ion peak of 7-Nitroindole (m/z 162.15) is consistent with its molecular weight, supporting its chemical formula C8H6N2O2.
Infrared Spectroscopy (IR)
By detecting characteristic absorption peaks, the presence of functional groups can be confirmed. For example, the strong absorption peaks of the nitro group (1500-1600 cm⁻¹ and 1300-1400 cm⁻¹) and the C=C stretching vibration of the indole ring (1600-1650 cm⁻¹) are important evidence for the confirmation of the structure of 7-Nitroindole.
X-ray Single Crystal Diffraction (XRD)
For single crystal samples, XRD can precisely determine the molecular spatial configuration and bond lengths, angles, etc. For example, in a study, XRD was used to analyze the structure of the receptor containing the 7-Nitroindole group and the bis-dihydropyrophosphate ion complex, revealing its supramolecular interaction mode.
Stability Evaluation Methods
Thermogravimetric Analysis (TGA)
Under a programmed temperature increase condition, TGA can monitor the change in sample mass with temperature, evaluating thermal stability. For example, the melting point of 7-Nitroindole is 94-98°C. TGA can further determine its decomposition temperature, guiding the setting of storage conditions.
High Performance Liquid Chromatography Stability Test
The samples are placed in different temperatures (such as 4°C, 25°C, 40°C) or exposed to light, and samples are taken regularly for HPLC purity testing. For example, a study showed that 7-Nitroindole can be stably stored for 2 years at -20°C, but only for 1 year at 25°C.
Solubility Test
The solubility of the sample in different solvents (such as DMSO, water, alcohols) is determined to provide a reference for subsequent experiments. For example, the solubility of 7-Nitroindole in DMSO is 100 mg/mL (616.71 mM), and a newly opened DMSO should be used to avoid moisture absorption influence.
Application-oriented Analytical Methods
Photochemical Precursor Research
The 7-Nitroindole nucleoside can be used as a photochemical precursor to generate 2'-deoxyribose internal cleavage damage sites in DNA chains. The changes in the absorption spectrum after illumination can be monitored through ultraviolet-visible spectroscopy (UV-Vis) to verify the photolytic reaction activity.
Bioactivity screening
In drug development, the biological activity of 7-Nitroindole and its derivatives needs to be evaluated. For example, potential therapeutic compounds with value can be screened through enzyme inhibition tests (such as APE1 nucleases inhibition test) or cytotoxicity tests (such as MTT method).
FAQ
1. What is 7-nitroindole?
It is an organic compound of the indole class, with the structure where the 7th position of the indole ring is replaced by a nitro group (-NO₂). It is commonly used as a precursor for fluorescent probes or as a fluorescent marker in biochemical research.
2. What are the main applications?
It is mainly used as a raw material for the synthesis of fluorescent probes, especially for marking nucleotides in DNA/RNA sequencing; it is also used in the study of protein-nucleic acid interactions, as well as in optical physics/optical chemistry research.
3. What should be noted when using it?
It should be stored in a dark and cool place as it is sensitive to light; the operation should be carried out in a fume hood to avoid inhalation or skin contact; the waste should be treated as hazardous chemicals.
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