CN110330547B - Pentapeptide mimic of insect pharyngeal-suppression side voxel and application thereof - Google Patents
Pentapeptide mimic of insect pharyngeal-suppression side voxel and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1021—Tetrapeptides with the first amino acid being acidic
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Abstract
The invention belongs to the technical field of pesticides, and particularly relates to a pentapeptide mimetic of insect pharyngeal-inhibitory side voxel and application thereof, wherein the pentapeptide mimetic is a compound shown as a formula A and has the following structure:
wherein: r1Is selected from benzyl or phenyl with substituent selected from hydrogen, monosubstituted halogen, nitro, methyl or trifluoromethyl; r2Is selected from-CH2COOH or-CH2CONH2；R3Is selected from 4-NO2、4‑F、4‑Cl、4‑Br、4‑CF3、4‑OH、4‑CH3、4‑OCH3、4‑OCH2CH33,4, 5-trimethoxy, 4-N, N-dimethyl or 4-phenyl. The compound is safe and efficient, is simple and convenient to synthesize, and has potential development and application prospects.
Description
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to a pentapeptide mimetic of insect pharyngeal-suppression side voxel and application thereof.
Background
The traditional pesticide makes remarkable contribution in the aspects of preventing and controlling pests, guaranteeing grain safety and the like. Meanwhile, due to the unreasonable use of the pesticides by people and the inherent defects of some pesticides, a series of problems are brought, such as pesticide resistance of pests, pesticide residue, poor selectivity and the like. Therefore, the search for new, efficient and safe insecticides is the focus of the current pesticide development. Insect Growth Regulators (IGRs) can affect the normal growth and development of insects, thus resulting in incomplete metamorphosis or death of larvae, and are known as agricultural chemicals in the 21 st century. The Allatostatin (ASTs) is a kind of insect neuropeptide, which is a small peptide composed of several to tens of amino acids and can act on the allatosome to inhibit the synthesis of juvenile hormone, thus influencing the growth and development of insects. The insect growth regulator has the advantages of high activity, good selectivity, environmental friendliness, simple structure, easiness in modification and the like, and is considered as a potential insect growth regulator. However, due to the inherent disadvantages of natural peptides, such as easy degradation, poor transport function, and large molecular flexibility, the application of natural ASTs in pest control is limited.
In order to overcome various defects of natural ASTs, people modify the structure of the ASTs and create a novel juvenile hormone synthesis inhibitor, for example, Stay and the like determine that a pentapeptide sequence Tyr-Ser-Phe-Gly-Leu-amide is the shortest sequence for regulating and controlling juvenile hormone synthesis. Hayes et al believe that the secondary structure of the C-terminal amino acid sequence is important for biological activity. Pratt et al further demonstrated the pentapeptide sequence YXFGL-NH2Is a functional region necessary for AST activity. In addition, the natural AST is modified by means of electron isosteres, unnatural amino acid substitution and the like, such as Piulachs, Nachman and the like, and the reasonable structural modification with the natural core pentapeptide as a lead is feasible. A new class of AST mimetics was reported by Nachman et al in 2007. In the above documents, the AST structural modification is mainly characterized by 2: 1) the amino acids in natural AST are mostly replaced by natural amino acids such as Ala, or non-natural amino acids such as Aic, Cpa and aromatic acid, etc., to obtain analogues with very similar structures. 2) Most compounds retain the original in vitro biological activity of AST, and improve the enzymolysis resistance of the compounds. But has the following disadvantages: the compound has complex structure (simulating active peptide above pentapeptide), partial structure even more complex than natural peptide, and synthesisHigh cost and is not suitable for being developed as a new pesticide.
The present inventors have also made efforts in recent years to modify the AST structure in order to find a highly active compound having a novel structure, and have applied for related patents concerning the invention, see patent documents 1 to 5.
Documents of the prior art
Patent document
Patent document 1: CN 101519430A;
patent document 2: CN 101519431A;
patent document 3: CN 101519432A;
patent document 4: CN 101519433A;
patent document 5: CN 102093251A;
patent document 6: CN 104693274B.
Disclosure of Invention
Technical problem to be solved by the invention
The object of the present invention is to provide an AST analogue which has excellent juvenile hormone activity inhibition and is easy to synthesize.
Means for solving the technical problem
In view of the above problems, the present invention provides a compound represented by formula a, which has the following structure:
wherein:
R1is selected from benzyl or phenyl with substituent selected from hydrogen, monosubstituted halogen, nitro, methyl or trifluoromethyl.
R2Is selected from-CH2COOH or-CH2CONH2。
R3Is selected from 4-NO2、4-F、4-Cl、4-Br、4-CF3、4-OH、4-CH3、4-OCH3、4-OCH2CH33,4, 5-trimethoxy, 4-N, N-dimethyl or 4-phenyl.
In one embodiment, R in the formula A1Is selected from4-fluorobenzyl, 4-chlorobenzyl, 2-chlorobenzyl, 4-iodobenzyl, 4-trifluoromethylbenzyl, 4-nitrobenzyl, 4-methylbenzyl or phenyl.
In one embodiment, R in the formula A1Is 4-fluorobenzyl, 4-chlorobenzyl, 2-chlorobenzyl, 4-iodobenzyl, 4-trifluoromethylbenzyl, phenyl, R2is-CH 2COOH, R3Is 4-NO2。
In one embodiment, R in the formula A1Is 4-fluorobenzyl, 4-trifluoromethylbenzyl, R2is-CH2COOH, R3Is 4-Br.
In one embodiment, R in the formula A1Is 4-chlorobenzyl, 4-iodobenzyl, R2is-CH2COOH， R3Is 4-CF3。
In one embodiment, R in the formula A1Is benzyl, R2is-CH2CONH2,R3Is 4-CF3、4-OH、 4-NO24-ethoxy, 4-Br or 4-phenyl.
According to a second aspect of the present invention, there is provided a process for the preparation of the above compound, wherein the preparation is by solid phase organic synthesis.
According to a third aspect of the present invention, there is provided a use of the above compound for cockroach control.
According to a fourth aspect of the present invention, there is provided a use of the above compound in the control of diamondback moth.
According to a fifth aspect of the present invention, there is provided a pharmaceutical composition of the above compound, further comprising a carrier, wherein the carrier is selected from one or more of diluents, excipients, fillers, binders, wetting agents, absorption enhancers, surfactants, lubricants and stabilizers.
The invention has the advantages of
The invention takes a lateral-pharyngeal-depressor pentapeptide analogue H17 with good activity in the previous stage as a lead, adopts an active substructure splicing method, modifies 1 st, 2 nd and 3 rd amino acids in the structure, and obtains an AST analogue with good juvenile hormone activity inhibition by introducing an electron-withdrawing group, a hydrophilic group, a substituted benzyl group or a phenyl group, wherein the in vitro activity of part of compounds is far superior to that of the lead H17, and the analogue has certain biological activity for killing diamondback moth larvae. The compound is safe and efficient, is simple and convenient to synthesize, and has potential development and application prospects.
Further features of the present invention will become apparent from the following description of exemplary embodiments.
Detailed Description
One embodiment of the present disclosure will be specifically described below, but the present disclosure is not limited thereto.
Compared with the earlier stage research, the invention is characterized in that: around the former stage of the hypopharynx inhibiting pentapeptide mimics with good activity (see CN101519433), the 2 nd amino acid, the 3 rd amino acid and the substituent on the benzene ring at the N terminal in the structure are modified, hydrophilic groups are introduced into the 2 nd amino acid for modification, substituted benzyl or phenyl is introduced into the 3 rd amino acid for modification, and a plurality of substituents are introduced into the benzene ring at the N terminal for optimization, so that the AST analogues with good juvenile hormone inhibiting activity are obtained, and the in vitro activity of part of compounds is far superior to that of core pentapeptide, and is also superior to that of high-activity analogues found at the former stage. In order to further develop the application value of the AST analogue, the Pacific Potentilla rapae AST receptor (GenBank: AIS40016.1) is subjected to BLAST (basic Local Alignment Search tool) comparison through NCBI, and the homology of the Pacific Potentilla rapae AST receptor and the predicted cabbage moth AST-A type receptor (NCBI Reference Sequence: XP _011557732.1) is found to be 59.09%, which indicates that the cabbage moth A type receptor has certain homology with the Pacific Potentilla rapae receptor. Based on the above, the invention expands the insecticidal spectrum of the AST analogue, and finds that the AST analogue has better inhibitory activity on the growth of diamondback moth larvae for the first time.
The compounds of formula A provided by the invention are all obtained by a solid phase organic synthesis method (reference: Chan WG, White PD. Fmoc solid phase peptide synthesis A Practical Approach, Oxford University Press, 2000; pp.9-74.).
The ex vivo bioassay experiments of the present invention employed GC-MS/MS (Kai, Z.P.; Yin, Y.; Zhang, Z.R.; Huang, J.; Tobe, S.S.; Chen, S.S., A rapid qualitative analysis for subsequent reactions and intermediates in the biological pathway using gases chromatography and mass spectrometry, J chromatography A2018, 1538,67-74.) of Kengpeng et al to test the in vitro activity of the compound of formula A in inhibiting the synthesis of juvenile hormone of Periplaneta pacifica (dipodia puncta).
The insecticidal activity screening method for diamondback moth larvae is based on pesticide biological activity test standard operation specification-pesticide paper (Gubao root, Liu science master edition, chemical industry press, 2016), and adopts a leaf dipping method (SOP-SC-2052) to evaluate the inhibitory activity of the diamondback moth larvae.
For the agent for controlling cockroaches and diamondback moths, which contains the compound of formula a as an active ingredient, one or more carriers acceptable in pesticide formulations may be added as needed, including diluents, excipients, fillers, binders, wetting agents, absorption promoters, surfactants, lubricants, stabilizers and the like, which are conventional in pesticide formulations. The prepared medicine has various dosage forms, such as powder, microemulsion, bait, microcapsule, missible oil and the like.
Examples
The present invention is described in more detail by way of examples, but the present invention is not limited to the following examples. Unless otherwise specified, "part" means "part by mass".
Example 1
The compound of formula A of the invention is prepared according to the method of polypeptide solid phase synthesis.
Taking compound A1 as an example, the preparation method is as follows:
(1) resin activation: 440mg Rink Amide-AM resin was weighed, activated with 5mL DCM for 3h, cleaved with 20% piperidine DMF solution for 20min, washed 3 times with DMF and DCM, and the reaction monitored with Kaiser's reagent.
(2) And Leu grafting: Fmoc-Leu-OH (3 fold equiv.), HBTU (3 fold equiv.), HOBt (3 fold equiv.), DIEA (6 fold equiv.) was added, dissolved in 5mL of DMF, stirred at room temperature for 2h, the reaction solution was removed, DMF and DCM were washed 3 times each, and Kaiser's reagent was used to monitor the reaction. Then 20% piperidine DMF solution was added for cutting for 20min and DMF was washed 3 times.
(3) And Gly is grafted: Fmoc-Gly-OH (3 fold equivalent), HBTU (3 fold equivalent), HOBt (3 fold equivalent), DIEA (6 fold equivalent) was added, dissolved in 5mL of DMF, stirred at room temperature for 2h, the reaction solution was removed, DMF and DCM were washed 3 times each, and Kaiser's reagent was used to monitor the reaction. Then 20% piperidine DMF solution was added for cutting for 20min and DMF was washed 3 times.
(4) Phe (4-F) grafting: Fmoc-Phe (4-F) -OH (3 fold equiv.), HBTU (3 fold equiv.), HOBt (3 fold equiv.), DIEA (6 fold equiv.), dissolved in 5mL of DMF, stirred at room temperature for 2h, the reaction solution was removed, each washed 3 times with DMF and DCM, and the reaction was monitored with Kaiser's reagent. Then 20% piperidine DMF solution was added for cutting for 20min and DMF was washed 3 times.
(5) Asp connection: Fmoc-Asp (OtBu) -OH (3 fold equivalent), HBTU (3 fold equivalent), HOBt (3 fold equivalent), DIEA (6 fold equivalent), dissolved in 5mL DMF, stirred at room temperature for 2h, the reaction solution was removed, washed 3 times each with DMF and DCM, and the reaction was monitored with Kaiser's reagent. Then 20% piperidine DMF solution is added for cutting for 20min, and the solution is washed 3 times by DMF.
(6) Grafting 4-nitro-cinnamic acid: 4-Nitrophenylacrylic acid (3-fold equivalent), HBTU (3-fold equivalent), HOBt (3-fold equivalent), DIEA (6-fold equivalent) was added, dissolved in 5mL of DMF, stirred at room temperature for 2 hours, the reaction solution was removed, DMF and DCM were washed 3 times each, and the reaction was monitored with Kaiser's reagent.
(7) Cleavage, removal of side chain protecting groups: adding 250mg phenol, 0.50mL water, 0.50mL thioanisole, 9.00mL TFA into the resin, stirring at room temperature for 2.5h, filtering, removing TFA, adding 30mL anhydrous ether, centrifuging at 3000r/min for 5min to obtain white precipitate, drying in vacuum, and detecting by mass spectrometry.
(8) The crude product was purified by HPLC. After acetonitrile in the collected solution is removed, the pure product is prepared by freeze-drying. The chromatographic column is a C18 semi-preparative column.
Compounds A2-A32 were prepared as described above.
The structure, high resolution mass spectrometry data, and physical, chemical and activity data of the compound of formula a are listed in table 1.
TABLE 1 Structure, high resolution Mass Spectrometry data (HRMS), physical Properties and Activity data for Compounds of formula A
Example 2 in vitro inhibitory Activity of Compounds of the invention on juvenile hormone biosynthesis in Periplaneta pacifica
The present invention adopts GC-MS/MS bioassay method of Kai, Z.P.; Yin, Y.; Zhang, Z.R.; Huang, J.; Tobe, S.S.; Chen, S.S.J. Chromatogr.A.2018,1538,67) of Kai, Z.P. The female adults, which had just emerged, were collected and, by day 7, the pharyngeal sideroplasms were dissected out. Preparing a target compound into a mother solution of 10mmol/L, and sequentially diluting to measuring solutions of 1mmol/L, 0.1mmol/L, 0.01mmol/L, 0.001mmol/L and 0.0001 mmol/L. Then, 10uL of the measurement solution with different concentrations was taken by a 1-10uL pipette and added to a 1.5mL centrifuge tube containing 990uL M199 medium, and after thorough mixing, the obtained concentrations were 0.01mmol/L, 0.001mmol/L, 0.0001mmol/L, 0.00001mmol/L and 0.000001mmol/L, respectively. 100uL of the prepared liquid medicine is measured and added into a small glass tube, a pharyngeal side body is placed in each small tube, and 8-16 times of repeated concentration setting are carried out. The glass vial was incubated for 3 hours at room temperature in the dark. After the culture, 200uL of n-hexane was used to extract juvenile hormone from the medium, and citronellol was used as an internal standard. GC-MS/MS is used for analyzing the capacity of juvenile hormone synthesized by the eustachian pacifica pharyngeal sidesome under different concentrations of different compounds. IC50 values were calculated for juvenile hormone biosynthesis inhibitory activity using GraphPad Prism 5. The results of ex vivo bioassay of the compound of formula a are shown in table 1.
Table 1 the results show that: the compound of the formula A can obviously inhibit the synthesis of juvenile hormone of Periplaneta pacifica (Diploptera punctata), and the in vitro activity of A1-A5, A7, A12, A14, A16, A21, A22, A25, A31 and A32 is superior to that of lead H17, wherein the in vitro activity of analogues A2, A5, A14, A21, A25 and A31 reaches nanomolar level. The in vitro activity of the analogue A14 is 34 times of that of the lead H17, the activity is greatly improved, and the analogue A14 is a potential insect growth regulator lead and has further application and development values.
EXAMPLE 3 biological Activity of partial Compounds of the invention on Plutella xylostella at 200mg/L
Use of pentapeptide mimetics of the class of insect orosoxin according to any one of claims 1 to 3 in the control of diamondback moth. The screening method for the insecticidal activity of the diamondback moth comprises the following steps: performing active primary screening on a sample at the concentration of 200mg/L by adopting a leaf soaking method; and selecting standard test insects which are continuously fed indoors and have consistent physiological state. The crude drug was dissolved in a small amount of DMF and then diluted with 0.05% aqueous TritonX-100. Repeating each concentration for 4 times, repeating each concentration for 30 test insects, and setting blank control; selecting cabbage leaves growing all the time, immersing the cabbage leaves into 200mg/L liquid medicine for 5s, airing the cabbage leaves indoors for 2 hours, putting the cabbage leaves into a culture dish with the diameter of 9cm, and inoculating 2-year-old larvae of the plutella xylostella with the same size. Examining the results for 96 hours and calculating the corrected mortality rate; the small brush pen or the tweezers are used for touching the insect body slightly, and the insect body cannot move normally, namely the insect body is considered to be dead; the plutella xylostella-killing biological activity of the selected compounds is shown in table 2.
TABLE 2 Plutella xylostella killing bioactivity of some ASTs analogues of the invention at a concentration of 200mg/L
Table 2 the results show that: the selected partial compounds all have certain diamondback moth killing biological activity, wherein the analog A7 has the best activity, and further application and development values are realized.
The present invention is not limited to the above embodiments, and any changes or substitutions that can be easily made by those skilled in the art within the technical scope of the present invention are also within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (3)
1. A compound of formula A, characterized by the following structure:
wherein:
in the formula A, R1Is 4-chlorobenzyl, R2is-CH2COOH,R3Is 4-NO2；
Or wherein:
in the formula A, R1Is 4-trifluoromethylbenzyl, R2is-CH2COOH,R3Is 4-NO2；
Or wherein:
in the formula A, R1Is 4-fluorobenzyl, R2is-CH2COOH，R3Is 4-Br;
or wherein:
in the formula A, R1Is 4-chlorobenzyl, R2is-CH2COOH,R3Is 4-CF3；
Or wherein:
in the formula A, R1Is phenyl, R2is-CH2COOH,R3Is 4-CF3。
2. Use of a compound according to claim 1 for the control of plutella xylostella.
3. The use of a pharmaceutical composition comprising the compound of claim 1 for the control of plutella xylostella, further comprising a carrier, wherein the carrier is selected from one or more of diluents, excipients, fillers, binders, humectants, absorption enhancers, surfactants, lubricants, and stabilizers.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0421935A2 (en) * | 1989-10-02 | 1991-04-10 | Sandoz Ltd. | Insect neuropeptides |
| CN101519433A (en) * | 2009-03-20 | 2009-09-02 | 中国农业大学 | Insect allatostatin analogue modified by (substituted) phenylacrylic acid and application thereof in black beetle prevention |
| CN104693274A (en) * | 2015-02-12 | 2015-06-10 | 中国农业大学 | Pentapeptide analogue of insect allatostatin and application thereof |
-
2019
- 2019-08-05 CN CN201910715376.3A patent/CN110330547B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0421935A2 (en) * | 1989-10-02 | 1991-04-10 | Sandoz Ltd. | Insect neuropeptides |
| CN101519433A (en) * | 2009-03-20 | 2009-09-02 | 中国农业大学 | Insect allatostatin analogue modified by (substituted) phenylacrylic acid and application thereof in black beetle prevention |
| CN104693274A (en) * | 2015-02-12 | 2015-06-10 | 中国农业大学 | Pentapeptide analogue of insect allatostatin and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| 《3D-QSAR based optimization of insect neuropeptide allatostatin analogs》;WANG M Z等;《Bioorg Med Chem Lett》;20190202;第29卷(第7期);第890-895页 * |
| 《N 端结构改造的抑咽侧体素拟肽类化合物的设计、合成及生物活性研究》;汪梅子等;《中国科学: 化学》;20161020;第46卷(第11期);第1235-1241页 * |
| 《昆虫神经肽抑咽侧体素及其类似物的研究进展》;汪梅子等;《农药学学报》;20190630;第21卷(第3期);第255-272页 * |
| WANG M Z等.《3D-QSAR based optimization of insect neuropeptide allatostatin analogs》.《Bioorg Med Chem Lett》.2019,第29卷(第7期),第890-895页. * |
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