CN-122010904-A - Fluorescent compound based on aza IR780 skeleton, preparation method and application thereof, and glutathione fluorescent probe reagent

Abstract

The invention relates to the technical field of fluorescent probes, in particular to a fluorescent compound based on an aza IR780 skeleton, a preparation method and application thereof and a glutathione fluorescent probe reagent. The compound has a structure shown in a formula (I) or a formula (II). The fluorescent compound based on the aza IR780 skeleton provided by the invention can be used as a probe to show a fluorescent response signal with specificity to glutathione and with double-channel opening, and can be successfully applied to the visual imaging of the concentration of glutathione in plants. Formula (I) Formula (II).

Inventors

• YIN JUN
• Ma Xiaoxie
• LIN ZIBO
• GUAN MINGYI
• BAO YUE
• LIU SHENGHUA

Assignees

• 华中师范大学

Dates

Publication Date

20260512

Application Date

20251217

Claims (10)

1. 1. A fluorescent compound based on an aza IR780 skeleton, characterized in that the compound has a structure represented by formula (I) or formula (II); Formula (I); Formula (II).
2. 2. A method for preparing a fluorescent compound based on an aza IR780 skeleton, characterized in that the fluorescent compound has a structure represented by formula (I), the method comprising: In the presence of a solvent and an alkaline substance, carrying out a first contact reaction on a compound Aza-IR780 and a compound NP-SO 2 Cl to obtain the fluorescent compound; Aza-IR780: ;NP-SO 2 Cl: ; Formula (I): 。
3. 3. a method for producing a fluorescent compound based on an aza IR780 skeleton, characterized in that the fluorescent compound has a structure represented by formula (II), the method comprising: In the presence of a solvent and an alkaline substance, carrying out a second contact reaction on a compound Cy-NMe-PZ and a compound NP-SO 2 Cl to obtain the fluorescent compound; Cy-NMe-Pz: ;NP-SO 2 Cl: ; formula (II): 。
4. 4. a method according to claim 2 or 3, wherein the basic substance is pyridine.
5. 5. A method according to claim 2 or 3, wherein the solvent is selected from at least one of tetrahydrofuran, N-dimethylformamide.
6. 6. A process according to claim 2 or 3, wherein the temperature of the first contact reaction and/or the second contact reaction is from 30 to 100 ℃.
7. 7. Use of the aza IR780 skeleton-based fluorescent compound according to claim 1 as a two-channel glutathione fluorescent probe.
8. 8. The use according to claim 7, wherein the fluorescent probe is used for dynamic detection of glutathione content in plant root tips and in vivo.
9. 9. The use according to claim 7, wherein the fluorescent probe is used for monitoring dynamic fluctuation of glutathione content caused by abiotic stress of plants and biotic stress models.
10. 10. A fluorescent probe reagent for glutathione, comprising a glutathione content monitoring effective amount of the fluorescent compound based on aza IR780 skeleton according to claim 1.

Description

Fluorescent compound based on aza IR780 skeleton, preparation method and application thereof, and glutathione fluorescent probe reagent Technical Field The invention relates to the technical field of fluorescent probes, in particular to a fluorescent compound based on an aza IR780 skeleton, a preparation method and application thereof and a glutathione fluorescent probe reagent. Background Plant redox homeostasis is critical for its survival and growth. Redox homeostasis refers to the state of equilibrium between intracellular oxidants and antioxidants. In this state of equilibrium, plants can cope with various biological and abiotic stresses while maintaining normal physiological functions such as cytoprotection, enzyme activity regulation, signal transduction, detoxification, disease resistance, and the like. However, if redox homeostasis is imbalanced, oxidative stress may result, causing damage to the plant. For example, abiotic stresses such as high temperature, low temperature, drought, waterlogging, ultraviolet light, pollution and the like may lead to unbalanced oxidative balance of plants, biotic stresses such as pathogen infection, insect feeding and competition for plants may also lead to activation of oxidative defense systems in plants, thereby generating more active oxygen and causing oxidative stress. Therefore, the assessment of the redox homeostasis in plants is helpful for timely grasping the growth state of the plants and guiding agricultural production and management, and has important significance for improving the stress resistance and yield of the plants. Glutathione is an excellent marker for evaluating redox homeostasis in plant stress as a non-enzymatic antioxidant substance, and glutathione-based fluorescent probes have been studied intensively in animals, however glutathione fluorescent probes for plants have been rarely reported. In summary, a high-sensitivity glutathione fluorescent probe is developed as a new strategy for assessing redox homeostasis in plant stress, and is of great importance in exploring its application in monitoring redox equilibrium states in various biotic/abiotic stress processes of plants. Disclosure of Invention The invention aims to provide a double-channel glutathione fluorescent probe based on an aza IR780 framework. In order to achieve the above object, a first aspect of the present invention provides a fluorescent compound based on an aza IR780 skeleton, the compound having a structure represented by formula (I) or formula (II); Formula (I); Formula (II). In a second aspect, the present invention provides a method for preparing a fluorescent compound based on an aza IR780 skeleton, the fluorescent compound having a structure represented by formula (I), the method comprising: In the presence of a solvent and an alkaline substance, carrying out a first contact reaction on a compound Aza-IR780 and a compound NP-SO 2 Cl to obtain the fluorescent compound; Aza-IR780:;NP-SO2Cl:; Formula (I): 。 a third aspect of the present invention provides another method for preparing a fluorescent compound based on an aza IR780 skeleton, the fluorescent compound having a structure represented by formula (II), the method comprising: In the presence of a solvent and an alkaline substance, carrying out a second contact reaction on a compound Cy-NMe-PZ and a compound NP-SO 2 Cl to obtain the fluorescent compound; Cy-NMe-Pz:;NP-SO2Cl:; formula (II): 。 a fourth aspect of the invention provides the use of a fluorescent compound based on an aza IR780 backbone as described in the first aspect as a dual channel glutathione fluorescent probe. In a fifth aspect, the present invention provides a fluorescent probe reagent comprising a glutathione content monitoring effective amount of the fluorescent compound based on aza IR780 skeleton described in the first aspect. The invention provides a double-channel glutathione fluorescent probe through reasonable molecular design, and the fluorescent probe shows the characteristics of an aza IR780 fluorophore and a naphthalimide sulfonamide recognition group. The fluorescent compound based on the aza IR780 skeleton can be applied to dynamic monitoring of plant glutathione. Through the technical scheme, the invention has at least the following beneficial effects: The dual-channel glutathione fluorescent probe based on the aza IR780 framework has good spectral response performance. The fluorescent probe provided by the invention has excellent selectivity and sensitivity when detecting glutathione. As will be seen from the following description of the present invention, the two probe molecules of the structures represented by formula (I) and formula (II) provided by the present invention have specific responses to GSH. The probe of formula (I) exhibited two absorption peaks of 694 nm and 835 nm in the buffer solution on the uv absorption spectrum, whereas the absorption peak was significantly reduced and converted to a broad peak after additi