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Application of Small-Molecule Fluorescent Probes in the Development of Green Pesticides

Xiaohan Hou , Shengnan Liu , Qingzhi Gao

Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (6) : 1035 -1043.

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Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (6) : 1035-1043 DOI: 10.7536/PC200659
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Application of Small-Molecule Fluorescent Probes in the Development of Green Pesticides
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Abstract

Small-molecule fluorescent probes are widely applied in the fields of life science, medicinal chemistry and environmental science, due to their characteristics of high sensitivity and specificity, good stability and economic applicability. In pesticide chemistry, small-molecule fluorescent probes are frequently utilized in the detection of pesticide residues and heavy metal pollutions. With global strategic needs and rapid technological progress in green pesticide development, fluorescent probes are urgently desired as important molecular tools for design, screening and development of environmentally benign agrichemicals. This article aims to review the key updates of small-molecule fluorescent bioprobes in green pesticide R&D by covering their chemical design, molecular targeting, and screening mechanisms against different green pesticide biotargets, and to provide the current status on their research and application as well as future perspectives.

Contents

1 Introduction

2 Ryanodine receptor-targeted small-molecule fluorescent probes

2.1 Anthranilic diamide-based fluorescent probes

2.2 Phthalic diamide-based fluorescent probes

3 Chitin-targeted small molecule fluorescent probes

3.1 Chitin synthase-targeted fluorescent probes

3.2 Chitin related enzyme-targeted fluorescent probes

4 TypeⅢsecretion system-targeted small-molecule fluorescent probes

5γ-Aminobutyric acid receptor-targeted small-molecule fluorescent pesticides

6 Acetohydroxyacid synthase-targeted small-molecule fluorescent probes

7 Conclusion and outlook

Graphical abstract

Keywords

small-molecule fluorescent probe / green pesticides / ryanodine receptor / chitin synthase / high-throughput screening

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Xiaohan Hou, Shengnan Liu, Qingzhi Gao. Application of Small-Molecule Fluorescent Probes in the Development of Green Pesticides. Progress in Chemistry, 2021, 33(6): 1035-1043 DOI:10.7536/PC200659

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1 Introduction

Comprehensively promoting and developing the construction of ecological civilization is an important part of the overall layout of "five in one" in China, which emphasizes the development of ecological agriculture and the promotion of green prevention and control to achieve the development direction of modern agriculture with zero growth of pesticides. The safety of pesticides and the residues of pesticides in edible agricultural products are one of the important factors endangering human health. As early as the end of the 20th century, China put forward the concept of attaching importance to the development of ecological economy and "green pesticides" in view of the problems of farmland pollution and food safety caused by traditional chemical pesticides[1⇓~3]. Green pesticide, as its name implies, is a targeted pesticide product that can selectively inhibit or kill crop pests and pathogens, but is harmless to the health of human, livestock and natural enemies of pests, and does not destroy the ecological environment. It is mainly composed of insecticides, fungicides and herbicides[4]. The key scientific problems to be solved in the research and development of green pesticides are the exploration and discovery of specific biological targets for pathogens and agricultural pests, as well as the rational drug design and efficient drug screening based on these green targets[5]. In this process, the traditional method is mainly to obtain active lead compounds by screening target proteins or small molecule drugs labeled with isotopes. Due to the problems of high synthesis cost, radioactive pollution and difficult popularization of isotope labeling, the scientific research and innovation activities of production enterprises are restricted. With the rapid development of drug design technology and optical imaging technology, as well as the upgrading of pesticide screening technology, small molecule fluorescent probes oriented to the biological targets of green pesticides have become an important tool for studying the mechanism of action of pesticides, designing and screening new pesticide molecules, and accelerating the research and development of targeted green pesticides. In this paper, the frontier achievements and the latest developments of small molecule fluorescent probes in the field of green pesticide research and development were summarized, and the future trends of small molecule fluorescent probes in promoting the development of green agriculture were prospected.

2 Small Molecule Fluorescent Probes Targeting Rutin Receptor

Ryanodine receptor (RyR) is an important ion channel that controls the release of calcium (Ca2+) from endoplasmic reticulum storage and regulates the concentration of intracellular Ca2+. RyR is named for its high affinity binding to the plant alkaloid Ryanodine[6]. Since the amino acid sequence of mammalian RyR shares only 40% -50% homology with that of insect RyR, insect RyR has become an ideal target for the development of green insecticides, which have good control effects on Lepidoptera pests such as Spodoptera exigua, Plutella xylostella, Mythimna separata, Chilo suppressalis and Cnaphalocrocis medinalis. Anthranilic diamide and Phthalic diamide, two kinds of RyR-targeted green insecticides, have been developed by major pesticide companies and research institutes at home and abroad in recent years.They are flubendiamide, chlorantraniliprole, cyantraniliprole, chlorfenapyr, cyhalothrin, cyhalothrin, flubendiamide and Broflanilide[7][8][9][10][11][12][13][14,15]. Because of its high activity, novel mechanism of action and safety to mammals, this type of insecticide has rapidly replaced many traditional insecticides and occupied an absolute share in the pesticide market[16]. This also makes RyR one of the most important research targets in the development of green pesticides.

2.1 O-aminobenzamide RyR fluorescent probe

Orthranilamide Insect RyR Targeting Green Insecticides mainly include Chlorantraniliprole (Chlo) of Japanese Pesticide and DuPont Company, Cyantraniliprole (Cyan) of Syngenta Company, Tetrachlorantraniprole of Shenyang Research Institute of Chemical Industry, Cyclaniliprole developed by Japan and Tetraniliprol of Bayer Company[17][18][19][20][21]. As a natural substrate of RyR, ryanodine itself is not selective for insects and mammals, so ryanodine itself can not be used as a green pesticide. The anthranilamide green insecticides are proved to have different binding sites from the natural product ryanodine, so the design and development of the anthranilamide analog small molecule fluorescent probe can not only be used for researching the molecular mechanism of the insecticides,It is also helpful to establish a high-throughput screening system based on fluorescent probes for the design and efficient screening of new green pesticides.
Based on the molecular mother nucleus of two green insecticides, Chlo and Cyan, Liu et al. designed and synthesized RyR-specific fluorescent probes ChloF and CyanF with good stability and strong specificity by connecting hydroxycoumarin fluorophore with anthranilamide insecticide through "click chemistry" (Figure 1)[22]. The probe compound is used for carrying out a competitive binding test with a ryanodine radioligand and a corresponding radioactive pesticide molecule, and the probe is found to be capable of inhibiting the binding of a radioactive chlorantraniliprole ([3H]Chlo)) pesticide molecule with a receptor (IC50=34~39 nmol/L), and the probe is also found to be capable of stimulating the binding of a natural ryanodine radioligand ([3H]Ry)) with RyR (EC50=5~7 nmol/L). The above results confirmed that the probe did not share the same binding mode with the natural ligand of ryanodine in insect RyR, but shared the same binding site with Chlo. This phenomenon also verifies that Chlo and ChloF probes, as "Allosteric Regulator" ligands of RyR, can indirectly affect and regulate RyR calcium channels, which is of great significance for understanding the structural complexity of RyR channels. Although the insecticidal activity of the probe molecule against Plutella xylostella larvae was reduced compared with that of Chlo and Cyan (LC50=2.6~7.6 ppm). However, due to its good specificity and fluorescence stability, it is expected to play an important role in the design and screening of new pesticide molecules targeting RyR instead of radioactive probes.
In 2019, Chen and Liu et al studied the effect of the green pesticide Chlo on the mammalian ryanodine receptor RyR1 by using the fluorescence resonance energy transfer (FRET) technique between the tryptophan residues of RyR protein and the above fluorescent probe molecules, and further investigated the binding sites between Chlo and RyR[23]. The results showed that the affinity of Chlo for mammalian RyR1 was about 100-200 times lower than that for insect RyR1. This study not only confirms the safety of this class of insecticides, but also further clarifies that the binding mode between Chlo and insect RyR is different from all other RyR agonists or inhibitors, such as caffeine, ryanodine and ruthenium red, which explains the high selectivity of this class of green insecticides against insect RyR[24].

2.2 Phthalamide RyR fluorescent probe

Flubendiamide (Flu) is another kind of insect RyR-targeted green insecticide developed and marketed by Bayer in 2007, which belongs to phthalamide compounds. Similar to Chlo, Flu is also a potent calcium channel agonist, which activates the insect RyR to promote the sustained release of Ca2+ in the endoplasmic reticulum, eventually leading to muscle paralysis, vomiting, reflux, affecting feeding and death[25]. However, studies have shown that phthalamides and phthalodiamides have slightly different binding sites in the RyR target and do not overlap with ryanodine[26,27]. In order to confirm the absorption and distribution of Flu in insect tissues and clarify the binding sites of Flu and target RyR, our research group designed and synthesized a series of RyR-targeted fluorescent probes with insecticidal activity and fluorescence characteristics by using computer-aided design technology based on pharmacophore model to fuse the fluorophore 7-amino-4-methylcoumarin with Flu (Figure 2)[28]. Through calcium flux imaging studies, it was found that these probes could induce the release of calcium ions in Sf9 cells transfected by RyR of Plutella xylostella, resulting in cytoplasmic Ca2+ transients, and the effect of probe FluF was the most obvious (Figure 2). Subsequently, the competitive binding of the probe with Flu was observed by confocal fluorescence microscopy, which verified that FluF was enriched on the endoplasmic reticulum surface of Sf9 cells, and the competitive binding test with Flu confirmed that the probe compound had the same RyR binding mode as Flu, which laid the foundation for the establishment of high-throughput new drug screening. Finally, the absorption and distribution of FluF in the insect body were explored by the in vivo experiment of Plutella xylostella larva model, and it was found that the probe compound accumulated in the ganglion and midgut rich in RyR. Because the midgut is an important organ for many physiological activities of the diamondback moth, the results of this study indirectly verify the biological mechanism that Flu-like green pesticides can well inhibit the survival of the diamondback moth. FluF, a probe compound with fluorescence characteristics and insecticidal activity, is expected to replace radioactive isotopes as a molecular tool for the study of insect resistance mechanism to insecticides, the exploration of the binding differences of insecticides to ryanodine receptors in different species, and the fluorescent high-throughput screening of new green pesticides targeting insect RyR.
In view of the fact that insect RyR is one of the most concerned green pesticide biological targets at present and in the future, Liu et al. Introduced the near-infrared rhodamine fluorophore into Flu, designed and synthesized a Flu-R-L probe containing rhodamine substitution, and developed a fluorescence polarization detection method based on the Flu-R-L fluorescent probe (Figure 3)[29]. Flu-R-L has strong binding force (KD<25 nmol/L) with the Flu binding site on RyR, and has high fluorescence quantum yield and good solubility in RyR working buffer. At the concentration of 12.5 nmol/L, not all the specific binding sites on RyR were occupied by Flu-RL molecules, and the probe bound to RyR was sensitive to the competition of other target compounds. Based on the fluorescence polarization drug screening system established by the probe molecule, the compounds with potential binding activity to the Flu active site on RyR were screened and tested, and nine derivatives with strong Flu-like activity were found. Fluorescence polarization offers a number of key advantages over other assays, such as: it is performed in liquid phase, is non-radioactive, does not require separation of bound and free ligands, and reads quickly[30,31]. These reasonably designed small molecule fluorescent probes are of great significance for the establishment of in vitro screening methods for new pesticide candidates, especially for high-throughput screening.

3 Small Molecular Fluorescent Probes Targeting Chitin Receptor

Chitin receptor, also known as chitinase. It plays an important role in peritrophic membrane degradation, molting, body immune defense, cell proliferation, and growth and development in crustaceans, fungi, and insects[32]. Chitin synthase (CHS) is the key enzyme in Chitin biosynthesis. Inhibition of chitin synthesis by CHS can effectively prevent the growth of fungi or the shedding of insect larvae and pupae to achieve insecticidal effect. Because there is no CHS gene and chitin metabolism system in plants and mammals, the design and screening of chitin synthase inhibitors are expected to develop antifungal drugs and green pesticides with low toxicity and harmlessness to humans, and chitin synthase is recognized as one of the key targets for the development of green pesticides with strong specificity and good safety[33][34⇓~36].

3.1 Chitin synthetase small molecule fluorescent probe

Because the three-dimensional structure of chitin synthase and the biological mechanism of its catalytic synthesis of chitin are still not fully understood, the design of inhibitors and the development of fluorescent probes for chitin synthase are very challenging. Tritiated uridine-5 '-diphosphate-N-acetyl-glucosamine (3H-UDP-GlcNAc) and 13C uridine-5' -diphosphate-N-acetyl-glucosamine (13C-UDP-GlcNAc) were the first radiolabeled substrates developed for CHS activity assay, in which UDP-GlcNAc is an essential sugar donor for CHS biosynthesis of chitin[37]. Although radiolabeled substrates can be used to quantitatively detect the activity of CHS, the development of a non-radioactive CHS-targeted fluorescent probe can avoid radioactive hazards and is easy to operate, which can achieve rapid and efficient throughput activity screening, so it has important scientific value and broad application prospects. Bahmed et al designed and synthesized a CHS substrate small molecule fluorescent probe 6-O-dansyl-N-acetylglucosamine (DNAG) containing dansyl fluorophore on the basis of the radioactive substrate partial structure N-acetylglucosamine (GlcNAc),The activity of CHS can be evaluated more accurately by quantifying the decrease in fluorescence intensity after DNAG binds to CHS, and the results are consistent with those obtained by the radioactive method (fig. 4)[38].
For the design and synthesis of chitin synthase inhibitors, Yang et al of Dalian University of Technology have been committed to the frontier work in this field for many years, and have created a variety of lead compounds with CHS inhibitory activity, which plays an important role in leading the development of chitin targeted green pesticides in China[39].

3.2 Other small molecular fluorescent probes for chitinase

Chitin synthesis involves not only the key enzymes of chitin synthesis, but also a series of key enzymes of chitin metabolism, such as hexosaminidase and chitin hydrolase. Therefore, inhibiting the function of any one of the metabolic enzymes is expected to find green pesticide compounds that can effectively control pathogenic fungi, parasites and agricultural pests in animals and plants. 4-Methylumbelliferyl-β-D-glucosaminidase (4-MU-GlcNAc) and 4-nitrophenyl-N-acetyl-β-D-glucosaminidase (PNP-GlcNAc) are the most commonly used fluorogenic substrates for the detection of chitinase and hexosaminase[40]. Because of their universality, the use of these fluorescent substrate probes for drug screening is not an ideal choice. Zhang et al. Designed and developed a naphthalimide fluorescent Probe Probe-1C (Fig. 5) for the evaluation of small molecule inhibitors and hexosaminidase selective fluorescent probe with in vivo cell imaging function in 2019[41]. Compared with the traditional 4-MU-GlcNAc and PNP-GlcNAc, Probe-1C has the characteristics of high water solubility, good sensitivity and high fluorescence intensity. The probe not only can be used for a high-throughput microplate reader test system, but also can be used for rapidly screening hexosaminidase inhibitors of batch samples through visual identification.

4 Small Molecule Fluorescent Probes Targeting Bacterial Type Ⅲ Secretion System

Bacterial Type III secretion system (T3SS) is a transmembrane molecular device composed of protein complexes shared by many harmful pathogens, such as Colletotrichum capsici, Alternaria alternata, Botrytis cinerea and Xanthomonas oryzae, which can inject pathogenicity-related effectors secreted by pathogens into host cells to cause infection[42]. Traditional antibacterial drugs mostly affect the growth processes of bacteria, such as DNA replication, RNA transcription, protein synthesis and cell wall synthesis, to achieve the purpose of antibacterial. However, the abuse of antibacterial drugs has led to the emergence of large-scale drug resistance[43]. Inhibitors developed by targeting T3SS can interfere with the host infection pathway of pathogenic bacteria without affecting the survival of bacteria, so they will not lead to the emergence of drug resistance of pathogenic bacteria[44]. Therefore, targeting T3SS is regarded as a novel strategy for the development of novel anti-pathogenic microbial agents. In the past decade, a variety of natural products have shown T3SS inhibitory activity, and a large number of active small molecules have been screened out[45⇓~47]. Some of them regulate T3SS at the gene level, and some of them target the assembly components of T3SS[48]. At present, the precise biological targets and mechanisms of most T3SS inhibitors are not fully understood, so the development of small molecular fluorescent probes targeting T3SS system is of great significance in the development of new pathogen inhibitors, drug activity screening and mechanism of action. Previously, most high-throughput screening systems for T3SS inhibitors were achieved by using luciferase reporter systems and beta-lactamase reporter systems[49][50]. In 2010, Hang et al discovered a novel carboxypeptidase G2 (CPG2): Glu-CyFur reporter system that can be used to fluorescently detect the secretion of type III protein in Gram-negative pathogenic bacteria by using the characteristic that carboxypeptidase G2 (CPG2) can selectively cleave glutamic acid (Glu) from small molecular metabolites, while CPG2 glutamyl carboxypeptidases in most bacteria or higher eukaryotes are inactive (Fig. 6a)[51]. The Glu-CyFur compound is designed and synthesized based on glutamic acid (Glu) and a fluorescent molecule 2-dicyanomethylene-3-cyano-2,5-dihydrofuran (CyFur), and is a substrate-type fluorescent molecular probe of CPG2. The successful development of the probe provides a simpler, faster and more efficient method for evaluating cytokines and effectors affecting the secretion of protein toxins and discovering novel fungicides. For example, Hang et al., in order to evaluate the activity of traditional medicinal plants on the secretion of Salmonella typhimurium type III protein, used the reporter system to screen 120 kinds of traditional Chinese medicines with potential anti-infective activity, and revealed the mechanism of anti-bacterial infection effect of flavonoid polyphenol catechins[52,53][54]. As shown in fig. 6B, this assay uses CPG2 as an enzymatic reporter, and when CPG2 is secreted, it quickly and specifically reports the secretion of type III protein by cleaving the fluorescent substrate Glu-CyFur, which provides a sensitive method for monitoring the inhibitory activity of small molecules targeting T3SS. Using this method, Tsou et al. Successfully found that polyphenol catechins such as catechin gallate (CG) and epicatechin gallate (ECG) could completely inhibit the reporter gene activity of T3SS, while the inhibitory activity of catechin and gallic acid was less than 20% at 25 μmol/L. Therefore, the application of this screening system may provide a new platform for exploring new green plant metabolites resistant to pathogens.

5 Small Molecular Fluorescent Pesticide + Probe Targeting GABA Receptor

Gamma-aminobutyric acid (GABA) receptor (GABAR) is an important inhibitory neurotransmitter in mammals and insects, which is involved in mediating the rapid transmission of synapses in muscles and nerve cells, and is closely related to the physiological activity of nerve inhibition, so it is one of the important targets of insecticides[55]. Benzopyrazole insecticides targeting GABA receptors, such as fipronil, interfere with the normal function of the central nervous system by inhibiting insect GABA-gated chloride channels (GABACs), thus showing high insecticidal activity against a variety of crop pests, such as rice insects, termites, houseflies and so on[56,57]. However, the disadvantage of these pesticides is that they do not have phloem permeability and are difficult to inhibit sucking insects[58]. On the other hand, due to the gradual degradation and metabolism of pesticides in the environment, long-term exposure of some degradation or metabolic products to the environment poses a high risk to non-target organisms[59]. Therefore, it is urgent to improve the non-phloem uptake of phenylpyrazole pesticides and reveal their degradation pathways in the environment. Among them, fipronil and its toxic metabolites have caused pesticide residues and soil pollution due to poor photodegradation. In order to enhance the phloem mobility and photodegradability of fipronil, Chen et al. Synthesized a series of novel "fluorescent insecticides" -benzopyrazolamide derivatives (PAs) by introducing conjugated structures and organic chromophores into the parent structure of fipronil using a one-pot heating method (addition-elimination reaction of the fipronil with the corresponding acyl chloride derivatives) (Fig. 7A)[60]. Under the action of simulated solar radiation (Fig. 7B), these PAs not only enhanced their phloem mobility, but also enhanced their light absorption capacity under natural radiation through the extended conjugated system, thus showing good photodegradation. After photodegradation, PAs can be reconverted to fipronil parent fragments, thereby enhancing insecticidal activity. In addition, the fluorescence quantum yield of PAs was almost 4 times higher than that of fipronil, which can be used as a highly effective fluorescence probe to monitor the transport of pesticides in phloem and to track the uptake, internal transport pathway and distribution of pesticides after insects eat plants (Fig. 7B). With the rapid development of fluorescent labeling technology, the development of innovative small molecule probes with both fluorescent and insecticidal properties has laid a foundation for the fluorescent detection of pesticide residues, and also provided a new strategy for the efficient screening and development of green pesticides.

6 Small Molecule Fluorescent Probes Targeting Acetohydroxy Acid Synthase

Acetohydroxyacid Synthase (AHAS), also known as acetolactate Synthase (ALS), is a key enzyme that catalyzes the biosynthesis of valine, leucine and isoleucine, which are three branched-chain amino acids. It is widely distributed in plants, bacteria, fungi and algae, and does not exist in mammals. It is the target of herbicides widely used in many crops[61][62,63][64⇓~66]. At present, there are five main classes of acetohydroxy acid synthase inhibitor herbicides: sulfonylureas (SU), imidazolinones (IMI), triazolopyrimidines (TP), pyrimidinylbenzoic acids (PYB) and sulfonamides (SCT). They are widely used in the world because of their high herbicidal activity and mammalian safety[67][68][69][70][71,72][73,74].
With the long-term and extensive use of AHAS-inhibiting herbicides, many weeds show high levels of resistance and cross-resistance[75⇓~77]. Therefore, the development of new AHAS inhibitors with resistance is one of the important directions for the development of green herbicides. The traditional screening method for AHAS inhibitors is implemented by measuring the absorbance change of the natural catalytic substrate pyruvic acid at 333 nm by a discontinuous colorimetric method, which has low sensitivity, no continuity and can not achieve high throughput, so the screening efficiency is low[78][79]. In order to achieve high-throughput green herbicide screening for AHAS targets, Xie et al., based on the enzymatic reaction mechanism of AHAS, successfully designed intramolecular charge transfer (ICT) fluorescent small molecule fluorescent probes by using the characteristics of benzaldehyde derivatives that can not only act as AHAS recognition substrates, but also participate in AHAS catalytic reaction process[80]. As shown in Fig. 8, as the recognition substrate of AHAS, the fluorescent probe Probe-1 of benzaldehyde derivative substituted by the electron donating group at the para-position, after participating in the AHAS-mediated pyruvic acid catalysis process, generates a blue shift of fluorescence due to the breaking of the electron withdrawing effect of aldehyde carbonyl on the molecular conjugated system (Fig. 8 B, C), thus constructing a high-throughput screening system suitable for rapid discovery of AHAS-targeted herbicides.

7 Conclusions and outlook

Focusing on the research and development of new green pesticides, this paper systematically summarizes the development and application status of the most cutting-edge small molecule fluorescent probes in the field of green pesticides from the perspective of molecular design principles and target specificity. In the selection of fluorescent dyes, the fluorescent dyes used in the design of targeting probes cover fluorophores with different optical properties, ranging from short-wavelength blue coumarin to near-infrared rhodamine. On the one hand, from the perspective of high-throughput screening, besides the factors such as fluorescence intensity, fluorescence efficiency and photochemical stability of fluorescent dyes, the compatibility of fluorescent probes with aqueous screening systems (cells, enzymes) is very important. On the other hand, as far as the targeting selectivity of the fluorescent probe is concerned, because different targets exist in different positions and environments in the target test system, for example,The ryanodine receptor exists in the endoplasmic reticulum membrane of insect cells, and the chitin synthase and the secretion system of pathogenic bacteria belong to transmembrane molecular devices, so in the process of designing fluorescent probes, besides evaluating the water-soluble characteristics of fluorescent dyes (compatibility with screening systems),What is more important is how to meet the needs of targeted fluorescent probe design from both micro and macro aspects, that is, the probe molecules designed on the micro level need to have specific recognition for the target.In order to improve the target selectivity of the screening results, the whole probe molecule needs to be compatible with the screening system and reach the spatial position of the target distribution in the test system macroscopically. In a word, small molecule fluorescent probes with high selectivity, high specificity, high sensitivity, safety and low cost play an increasingly important role in the design, screening and development of new green pesticides, promoting the development of green agriculture, ensuring human health and ecological balance. At present, a large number of small molecular probes have been applied to the detection of pesticides, heavy metals and solvent residues, however, the research on fluorescent probes for green pesticide biological targets has just begun, and the research results with ideal application value are still few. As mentioned above, in addition to focusing on target orientation, there are many functional factors that need to be considered and challenged in the selection of fluorescent dyes and probe design concepts. For example, how to make small molecule fluorescent probes highly specific to mark specific biological targets at different growth and development stages of pests to help find new green pesticide targets? How can small molecule fluorescent probes be used to study the reproductive and metabolic processes of various insects? How to use small molecule fluorescent probes to study and reveal the resistance mechanism of pathogens and pests to pesticides? Faced with these challenges, the design and construction of molecular probes with stronger specificity and higher sensitivity for different purposes is the direction that scientists all over the world need to work together to tackle.

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Funding

National Key Research and Development Project(2017YFD0201403)

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