Imide compounds for the photoactivated fluorescent detection of opioids

Abstract

The application discloses a kind of imide compounds for the photoactivation fluorescent detection method of opioid, comprising the following steps: S1, 1-100 equivalent imide compound, 10-10000 equivalent opioid and 0-100000 equivalent solvent are mixed, and mixture is prepared;S2, using 200nm-500nm light source or natural light is irradiated 5s-5000s to the mixture in S1 at room temperature, fluorescence phenomenon can be detected.This application will amide derivative (solid or liquid), opioid (solid or liquid) and solvent are mixed, under the irradiation of specific wavelength and power light source, imide molecule and the specific structure between drug molecule form similar to exciplex photo-irradiation product, the product will produce structure-dependent fluorescence, to carry out the specific recognition of drug molecule.The method is simple in operation, and sensitivity is high, specificity is strong, so opioid can be efficiently and rapidly qualitatively detected.

Description

Technical Field

[0001] This invention relates to the field of chemical detection technology, specifically to a photoactivated fluorescence detection method for opioid drugs using imide compounds. Background Technology

[0002] Drug testing plays a crucial role in protecting public health, maintaining social security, supporting law enforcement, promoting economic stability, protecting youth and vulnerable groups, supporting international cooperation and security, responding to public health emergencies, and driving scientific and technological progress; it is an indispensable part of modern society. Currently, gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography-mass spectrometry (HPLC-MS) are important methods for determining the structure and components of drugs. However, their application in practical scenarios is often inconvenient, leading to the rapid development and research of rapid testing tools such as test strips and colorimetric reagents. Commonly used chemical substances include Marquis Reagent (primarily used to detect methamphetamine, exhibiting different color reactions with different drugs), Scott Reagent (primarily used to detect cocaine, typically showing a blue or purple color), and Simon's Reagent (used to distinguish between dextrorotatory and levorotatory amphetamines), among others.

[0003] However, the limitations and singular mechanisms of drug testing reagents lead to a high number of false positives and false negatives. Furthermore, the complex sample pretreatment and high cost and resource requirements necessitate the research and widespread development of more advanced detection methods. Therefore, this invention provides a novel detection method for opioids and other drugs with a simple pretreatment process and a completely new mechanism of action. Summary of the Invention

[0004] The purpose of this invention is to solve the above-mentioned technical problems and provide a photoactivated fluorescence detection method for opioid drugs using imide compounds. The method of this invention involves mixing the drug with naphthaleneimide molecules, which generate fluorescence through interaction and binding under ultraviolet light excitation, thereby achieving qualitative detection of the drug.

[0005] The technical solution adopted in this invention is as follows: A photoactivated fluorescence detection method for opioid drugs using imide compounds, comprising the following steps:

[0006] S1. A mixture is prepared by mixing 1 to 100 equivalents of an imide compound, 10 to 10,000 equivalents of an opioid drug, and 0 to 100,000 equivalents of a solvent.

[0007] S2. Irradiate the mixture in S1 with a 200nm-500nm light source or natural light at room temperature for 5s-5000s to detect fluorescence.

[0008] Preferably, the imide compound has a structural formula of one of formulas (I), (II), (III), and (IV);

[0009]

[0010] R1, R8, R13, R16, R19, and R24 are each independently selected from hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, methoxy, nitro-substituted phenyl or benzyl, and hydrogen- or halogen-substituted alkyl groups of 1-20 carbon atoms, either linear or branched; R2-R7, R9-R12, R14-R18, R20-R23, and R25-R28 are each independently selected from hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, methoxy, and nitro.

[0011] Among them, the structural formula (I) of imide compounds includes:

[0012]

[0013] The structural formula (II) of imide compounds includes:

[0014]

[0015] The structural formula (III) of imide compounds includes:

[0016]

[0017] The structural formula (Ⅳ) of imide compounds includes:

[0018]

[0019] Further optimization reveals that the structural formula of opioid drugs is one of formulas (V), (VI), (VII), and (VIII);

[0020]

[0021] R29 is selected from hydrogen, methyl, halogen, cyano, mercapto, and phenyl; R30-R60 are each independently selected from hydrogen, mercapto, amide, 1-20 carbon atoms of straight or branched alkyl or alkyl alcohols, and phenyl with any substitution of hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, vinyl, methoxy, or nitro.

[0022] Among them, the structural formula (V) of opioid drugs includes:

[0023]

[0024] The structural formula (VI) of opioid drugs includes:

[0025]

[0026] The structural formula (VII) of opioid drugs includes:

[0027]

[0028] The structural formula (VIII) for opioid drugs includes:

[0029]

[0030] More preferably, the solvent is one of water, formamide, acetonitrile, methanol, ethanol, propanol, acetone, dioxane, tetrahydrofuran, methyl ethyl ketone, n-butanol, ethyl acetate, diethyl ether, isopropyl ether, dichloromethane, chloroform, bromoethane, benzene, chloropropane, toluene, carbon tetrachloride, carbon disulfide, cyclohexane, hexane, heptane, and kerosene.

[0031] More preferably, the light source is 350-420nm (5-20W) and the illumination time is 5s-180s.

[0032] The beneficial effects of this invention are as follows: This invention mixes amide derivatives (solid or liquid), opioid drugs (solid or liquid), and a solvent. Under irradiation with a light source of specific wavelength and power, a photoproduct similar to an excimer complex is formed between the imide molecule and the specific structure of the drug molecule. This product produces structure-dependent fluorescence, thereby enabling specific recognition of the drug molecule. This method is simple to operate, highly sensitive, and highly specific, thus allowing for the qualitative detection of opioid drugs. Attached Figure Description

[0033] Figure 1 The fluorescence spectrum (λ) in Example 1 ex =400nm) as the illumination time changes.

[0034] Figure 2 The fluorescence spectrum (λ) in Example 2 ex =400nm) as the illumination time changes.

[0035] Figure 3 The fluorescence spectrum (λ) in Example 3 ex =400nm) as the illumination time changes.

[0036] Figure 4 The fluorescence spectrum (λ) in Example 4 ex =400nm) as the illumination time changes.

[0037] Figure 5-8 This is a chromatogram of a drug mixture detected by chromatography-mass spectrometry.

[0038] Figure 9 Images showing the changes in I1 before and after exposure to light when it was added to drugs, flour, and sugar (observed from the naked eye). Detailed Implementation

[0039] The present invention will be further described below with reference to the accompanying drawings and specific embodiments.

[0040] Example 1

[0041] One equivalent of an imide molecule (I1) and 100 equivalents of a drug (V3) were mixed in an acetonitrile solution (1000 equivalents) and irradiated with 365nm (10W) light for 10 to 180 seconds. Figure 1 For fluorescence spectrum (λ) ex =400nm) as the illumination time changes.

[0042] Example 2

[0043] One equivalent of an imide molecule (I1) and 100 equivalents of a drug (VI2) were mixed in an acetonitrile solution (1000 equivalents) and irradiated with 365nm (10W) light for 10 to 180 seconds. Figure 2 For fluorescence spectrum (λ) ex =400nm) as the illumination time changes.

[0044] Example 3

[0045] One equivalent of an imide molecule (I1) and 100 equivalents of a drug (VII1) were mixed in an acetonitrile solution (1000 equivalents) and irradiated with 365nm (10W) light for 10 to 180 seconds. Figure 3 For fluorescence spectrum (λ) ex =400nm) as the illumination time changes.

[0046] Example 4

[0047] One equivalent of an imide molecule (I1) and 100 equivalents of a drug (VIII4) were mixed in an acetonitrile solution (1000 equivalents) and irradiated with 365nm (10W) light for 10 to 180 seconds. Figure 4 For fluorescence spectrum (λ) ex =400nm) as the illumination time changes.

[0048] Example 5

[0049] One equivalent of an imide molecule (I1) was dissolved in acetonitrile solution (1000 equivalents) and dropped onto a mixture of drugs (V1, V2, V3). Using granulated sugar and flour as controls, a significant fluorescence change was observed with the naked eye after 5 seconds of exposure to 365 nm (10W) light. Figure 5-8 For the detection of drug mixtures by chromatography-mass spectrometry (wherein) Figure 5High-performance liquid chromatography (HPLC) was used to confirm the presence of three components in the powder. Figure 6-8 (For mass spectrometry to detect the molecular structure of the three components) Figure 9 Images showing the changes in I1 before and after exposure to light when it was added to drugs, flour, and sugar (observed from the naked eye).

[0050] The specification and drawings of this invention are intended to be illustrative rather than restrictive. Based on this invention, those skilled in the art can make substitutions and modifications to some of the technical features without creative effort, and all such modifications are within the scope of protection of this invention.

Claims

1. A photoactivated fluorescence detection method for opioid drugs using imide compounds, characterized in that, Includes the following steps: S1. A mixture is prepared by mixing 1 to 100 equivalents of an imide compound, 10 to 10,000 equivalents of an opioid drug, and 0 to 100,000 equivalents of a solvent. S2. Irradiate the mixture in S1 with a 200 nm to 500 nm light source or natural light at room temperature for 5 s to 5000 s to detect fluorescence. The imide compound has a structural formula of one of formulas (I), (II), (III), and (IV); ； ； ； ； R1, R8, R13, R16, R19, and R24 are each independently selected from hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, methoxy, nitro-substituted phenyl or benzyl, and hydrogen- or halogen-substituted alkyl groups of 1-20 carbon atoms, either directly linked or branched; R2-R7, R9-R12, R14-R18, R20-R23, and R25-R28 are each independently selected from hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, methoxy, and nitro.

2. The detection method according to claim 1, characterized in that, The structural formula of opioid drugs is one of formulas (V), (VI), (VII), and (VIII); ； ； ； ； R29 is selected from hydrogen, methyl, halogen, cyano, mercapto, and phenyl; R30-R60 are each independently selected from hydrogen, mercapto, amide, 1-20 carbon atoms of straight or branched alkyl or alkyl alcohols, and phenyl with any substitution of hydrogen, halogen, amino, hydroxyl, carboxyl, cyano, mercapto, amide, vinyl, methoxy, or nitro.

3. The detection method according to claim 1, characterized in that, The solvent is one of the following: water, formamide, acetonitrile, methanol, ethanol, propanol, acetone, dioxane, tetrahydrofuran, methyl ethyl ketone, n-butanol, ethyl acetate, diethyl ether, isopropyl ether, dichloromethane, chloroform, bromoethane, benzene, chloropropane, toluene, carbon tetrachloride, carbon disulfide, cyclohexane, hexane, heptane, and kerosene.

4. The detection method according to claim 1, characterized in that, The light source is 350–420 nm, 5–20 W, and the illumination time is 5–180 s.

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