CN109275662A - A kind of medicament of Antiphytoviral - Google Patents
A kind of medicament of Antiphytoviral Download PDFInfo
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- CN109275662A CN109275662A CN201710597721.9A CN201710597721A CN109275662A CN 109275662 A CN109275662 A CN 109275662A CN 201710597721 A CN201710597721 A CN 201710597721A CN 109275662 A CN109275662 A CN 109275662A
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- small molecule
- medicament
- molecule agent
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to pesticide fields, specifically disclose a kind of medicament of Antiphytoviral, which includes small molecule agent shown in formula (I), or include the pharmaceutically acceptable salt containing chemical structure shown in formula (I), wherein R1、R2And R3It is respectively selected from one of hydrogen, nitro, nitroso, sulfonic group, carboxyl, amino or azo, halogen atom, C1-10 alkyl, C2-10 alkenyl or C2-10 alkynyl group.Small molecule agent of the present invention shows good inhibitory effect to viral silencing suppressor, and the present invention is proved by effect experiment, which has efficient antiviral effect.
Description
Technical field
The present invention relates to pesticide fields, specifically, being related to a kind of pesticide of Antiphytoviral.
Background technique
The viroses of plant are one of important diseases of crops, there is the title of " plant cancer ", are produced every year to Global Agriculture
Bring loss is up to multi-million dollar.In recent years, especially for industrial crops, the harm of the viroses of plant is got worse.Such as
Tobacco virus loses when serious or even completely economic value once the quality of morbidity tobacco leaf at least decline 2-3 grade, and by
In extremely difficult prevention and treatment, caused by economic loss considerably beyond tobacco nosomycosis, become and threaten maximum one on tobacco leaf production
Class disease.
It is that comprehensive metabolism for relying on host is proliferated after infecting plant due to plant virus, is difficult do not influencing host just
It carries out going out for specificity to virus in the case where normal metabolic function to remove, so the prevention and treatment for virosis is extremely difficult.Both at home and abroad
The viral medicine of existing prevention and treatment such as Ningnanmycin, S- methyl benzo [1,2,3] thiadiazoles -7- carbothioic acid ester (BTH,
Syn.acibenzolar-S-methyl) etc., it is main that resistance (System acquired is obtained by induction plant generation system
Resistance it) works, effect is poor and only prevention effect.In fact, having therapeutic effect for plant virus at present
Medicine can be described as very few.
The RNA Silencing Mechanisms (RNA silencing) found in recent years have been considered as plant to antiviral most main
It is also most important defense mechanism.In simple terms, i.e., after virus infection, the nucleic acid of its own can cause plant generation to be directed to should
The degradation of nucleic acid specificity, to achieve the purpose that elimination virus.But it is similar to armament to compete, virus also evolves one accordingly
Silencing suppressor (Viral RNA silencing suppressor) is planted to keep out this mean of defense of plant RNA silencing.Such as
The Hc-Pro of marmor upsilon, plumpox virus coding, the 2b and Tombusvirus coding of Cucumovirus coding
P19 etc..Its mechanism of action in conjunction with the tiny RNA to play an important role in RNA silencing mainly by interfering entire silencing
Mechanism.So plant can be helped to win the victory of armament competition if finding the medicament that can effectively inhibit viral silencing suppressor
Benefit achievees the purpose that effectively to treat virosis.
As concept of the people to environmental protection is more and more clear, the problem of traditional chemical pesticide high poison high residue also further
Paid attention to.And many ingredients in natural products, there is high-efficiency low-toxicity, Environmental compatibility is good, poisons to human body and environment small
The features such as.Therefore, a kind of antiviral pesticide of new high-efficiency with accurate molecular target is filtered out from natural products library, is had
Significant and value.
Summary of the invention
In order to solve the problems in the existing technology, the purpose of the present invention is according to most current virus interaction molecular mechanism,
A kind of new high-efficiency antiviral agent with accurate molecular target is provided.
In order to achieve the object of the present invention, technical scheme is as follows:
The present invention has screened a kind of to target proteins tool using viral silencing suppressor as target from natural products library
There is the small molecule agent (ZINC compound database, ID:ZINC72332803) of good inhibitory effect and is demonstrate,proved by effect experiment
Bright, which has efficient antiviral effect.
On this basis, the present invention provides a kind of medicament of Antiphytoviral, which includes small point shown in formula (I)
Sub- medicament, or include the pharmaceutically acceptable salt containing chemical structure shown in formula (I).
The small molecule agent has structure shown in formula (I):
Wherein, R1、R2And R3It is respectively selected from hydrogen, nitro, nitroso, sulfonic group, carboxyl, amino or azo, halogen atom, C1-
One of 10 alkyl, C2-10 alkenyl or C2-10 alkynyl group.
In a specific embodiment of the invention, which includes small molecule agent shown in formula (II):
On the basis of it is the small molecule agent shown in formula (I), R1For hydrogen, R2For methyl, R3The case where for methyl, life
Entitled 2- (((seven methyl-15s of (6aR, 6bR, 12aR) -2,2,6a, 6b, 9,9,12a--oxo icosahedron -1H-1,4a- (ring
Oxygen methyl) methyl-1 0- yl) oxygroup) carbonyl) benzoic acid.The present invention is through experimental study, small molecule agent shown in formula (II)
Apparent inhibiting effect is shown to viral silencing suppressor.
Further, the present invention also provides the small molecule agent as shown in formula (I)/formula (II) or its is pharmaceutically acceptable
Salt inhibit viral silencing suppressor (Viral RNA silencing suppressor) in application.The virus silencing
Repressor includes but is not limited to P19,2b, Hc-Pro etc..
Because most viruses have silencing suppressor, the present invention target targeted to the medicament of the Antiphytoviral
Virus is not particularly limited.
Optionally and preferably, such as marmor upsilon, the plumpox virus of the repressor containing Hc-Pro;Kind of the repressor containing 2b
Eggplant aspermy virus, Cucumovirus etc.;The Carnation Italian ringspot virus of the repressor containing P19, Tombusvirus
Deng.
The medicament also is understood as a kind of pharmaceutical composition, includes a effective amount of formula (I)/formula (II) compound or its medicine
Acceptable salt on.Same application prevention and treatment disease as caused by plant virus.
The beneficial effects of the present invention are:
The present invention provides such as formula (I)/formula (II) compound represented new applications, it was found that it is inhibiting viral silencing
New opplication in terms of repressor, and a kind of medicament of Antiphytoviral is provided based on this.
Detailed description of the invention
Fig. 1 is that 1 small molecular medicament of the embodiment of the present invention is applied to inhibit the Activity determination EMSA examination of silencing suppressor P19
It tests.
Fig. 2 is that 2 small molecular medicament of the embodiment of the present invention is applied to inhibit the Activity determination EMSA examination of silencing suppressor 2b
It tests.
Specific embodiment
The preferred embodiment of the present invention is described in detail below in conjunction with embodiment.It will be appreciated that following real
Providing merely to play the purpose of explanation for example is applied, is not used to limit the scope of the present invention.The skill of this field
Art personnel without departing from the spirit and purpose of the present invention, can carry out various modifications and replace to the present invention.
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
Embodiment 1
The small molecule agent is that structural formula is as follows:
The small molecule agent is applied to inhibit the Activity determination electrophoretic gel mobility test of silencing suppressor P19
(Electrophoretic mobility shift assay, EMSA), result is as shown in Figure 1.By P19 and the small molecule medicine
Agent mixes in combination buffer, and sufficiently reaction 25 minutes at room temperature.Wherein P19 concentration is 2 μM, which is
0.5-10ppm.The siRNA of final concentration of 50nM is then added, continues room temperature reaction 25 minutes after mixing well.Then electrophoresis turns
Colour developing observation result after film.In the result that develops the color, only siRNA can show band, and be in figure lower position (Unbound
Shown in siRNA arrow).Silencing suppressor albumen in conjunction with siRNA after meeting so that siRNA electrophoresis rate is slack-off, electrophoresis distance becomes
It is short, so being in figure upper position (shown in P19-siRNA complex arrow).And when addition compound and the albumen can be inhibited
When in conjunction with siRNA, siRNA restores original electrophoresis rate again, so showing that Band signal enhances below figure.
In Fig. 1,1 swimming lane is negative control, contains only siRNA.2 swimming lanes are positive control, contain siRNA and P19.3-9 swimming
Road is experimental group, contains siRNA and P19, and contain the small molecule agent, concentration gradient 0.5,1,2,4,6,8,10ppm.
As can be seen that negative control group band comes across the figure lower part position unbound siRNA.Repressor albumen is added in positive control
Later, part siRNA and protein binding are shown in the band of figure top P19-siRNA complex.And when addition increasing concen-trations
Small molecule agent when, the band on figure top gradually weakens, and illustrates that the small molecule agent can effectively prevent silencing suppressor albumen
With the association reaction of siRNA.As shown, the small molecule agent of 10ppm concentration can well inhibit the P19 of 2 μM of concentration with
The association reaction of siRNA.
Embodiment 2
The small molecule agent is that structural formula is as follows:
The small molecule agent is applied to inhibit the Activity determination EMSA test of silencing suppressor 2b, result such as Fig. 2 institute
Show.2b and the small molecule agent are mixed in combination buffer, sufficiently reaction 25 minutes at room temperature.Wherein 2b concentration is 2 μM,
The small molecule agent concentration is 0.5-20ppm.The siRNA of final concentration of 50nM is then added, it is anti-to continue room temperature after mixing well
It answers 25 minutes.Then colour developing observation result after electrophoresis transferring film.In the result that develops the color, only siRNA can show band, and under figure
Portion position (shown in Unbound siRNA arrow).Silencing suppressor albumen in conjunction with siRNA after meeting so that siRNA electrophoresis rate
Slack-off, electrophoresis distance shortens, so being in figure upper position (shown in P19-siRNA complex arrow).And when addition chemical combination
Object and can inhibit the albumen in conjunction with siRNA when, siRNA restores original electrophoresis rate again, so showing that item is taken a message below figure
Number enhancing.
In Fig. 2,1 swimming lane is negative control, contains only siRNA.2 swimming lanes are positive control, contain siRNA and 2b.3-9 swimming lane
For experimental group, contain siRNA and 2b, and contains the small molecule agent, concentration gradient 0.5,2,3,4,5,10,20ppm.It can
To find out, negative control group band comes across the figure lower part position unbound siRNA.Positive control be added repressor albumen it
Afterwards, part siRNA and protein binding are shown in the band of figure top 2b-siRNA complex.And when addition increasing concen-trations
When small molecule agent, the band on figure top gradually weakens, illustrate the small molecule agent can effectively prevent silencing suppressor albumen with
The association reaction of siRNA.As shown, the small molecule agent of 4ppm concentration can well inhibit the 2b and siRNA of 2 μM of concentration
Association reaction.
Embodiment 3
Control efficiency of the formula (II) compound of the present invention to tomato bushy stunt virus.
Experimental method:
The 4-5 leaf phase is selected, Ben Shi cigarette similar in growing way is fully ground the fresh disease of frank 0.3g with 30mL distilled water
Leaf, 1% virus inoculation liquid pass through diatomite frictional inoculation, 2 leaves of every plant of inoculation.2 hours after inoculation, 1,3 day with 150ppm medicine
The aqueous solution of agent sprays.Every processing group sets 20 plants.
The the 8th, 11,14 day calculating disease index, the results are shown in Table 1 after inoculation.
A. severity Scaling standard:
0 grade-asymptomatic.
There are light symptoms in 1 grade-inoculation leaf.
2 grades-mono- to the bright arteries and veins of two panels system blade, deformation.
The deformation of 3 grades-majority upper blade or the necrosis of main side arteries and veins, diseased plant are downgraded.
4 grades-whole plants are severely deformed or downright bad.
B. disease index
Disease index=[∑ (the disease numbers of sheets at different levels × opposite value of series)/(investigation total leaf number × 9)] × 100%
C. control efficiency
Control efficiency (%)=[(control disease index-processing disease index)/control disease index] × 100%
Table 1
Embodiment 4
Control efficiency of the formula (II) compound of the present invention to cucumber mosaic virus.
The 4-5 leaf phase is selected, Ben Shi cigarette similar in growing way is fully ground the fresh disease of frank 0.3g with 30mL distilled water
Leaf, 1% virus inoculation liquid pass through diatomite frictional inoculation, 2 leaves of every plant of inoculation.2 hours after inoculation, 1,3 day with 150ppm medicine
The aqueous solution of agent sprays.Every processing group sets 20 plants.The 9th, 15,20 calculate disease index after inoculation, the results are shown in Table 2.
A. severity Scaling standard:
0 grade-asymptomatic.
There are light symptoms in 1 grade-inoculation leaf.
2 grades-mono- to the bright arteries and veins of two panels system blade, deformation.
3 grades-majority upper blade floral leaf, sallow or deformation.
4 grades-complete stool blade floral leaf, severely deformed or downright bad, diseased plant is downgraded serious.
B. disease index
Disease index=[∑ (the disease numbers of sheets at different levels × opposite value of series)/(investigation total leaf number × 9)] × 100%
C. control efficiency
Control efficiency (%)=[(control disease index-processing disease index)/control disease index] × 100%
Table 2
Embodiment 5
Control efficiency of the formula (II) compound of the present invention to Brassica 2 et 4.
Virus inoculation is the Brassica 2 et 4 for carrying GFP fluorescin, can be by observing fluorescence directly come quantitative disease
Poison.Select the 4-5 leaf phase, Ben Shi cigarette similar in growing way is fully ground the fresh sick leaf of frank 0.4g with 20mL distilled water, and 2%
Virus inoculation liquid is rinsed after waiting blades dry with clear water by diatomite frictional inoculation.It 2 hours after inoculation, is administered within 1,3 day, uses
The aqueous solution of 150ppm medicament sprays.3 after inoculation, the disease of control group and drug-treated group with fluorescence signal is recorded respectively within 4,5 days
Malicious quantity.
14 plants of every processing group, every plant of 2-3 piece leaf.Each record time point takes different leaves, 3 repetitions.And it counts as the following formula
Calculate the inhibiting rate to virus.
Y=(C-A)/C*100%
Wherein Y is the inhibiting rate of the compounds on viral, and C is the viral load of control group, and A is the disease of compound processing group
Malicious quantity.It the results are shown in Table 3.
Table 3
Embodiment 6
Control efficiency of the formula (II) compound of the present invention to plumpox virus.
The 4-5 leaf phase is selected, Ben Shi cigarette similar in growing way is fully ground the fresh disease of frank 0.3g with 30mL distilled water
Leaf, 1% virus inoculation liquid pass through diatomite frictional inoculation, 2 leaves of every plant of inoculation.2 hours after inoculation, 1,3 day with 150ppm medicine
The aqueous solution of agent sprays.Every processing group sets 15 plants, the 8th, 10,12 day calculating disease index after inoculation.
It the results are shown in Table 4.
A. severity Scaling standard:
0 grade-asymptomatic.
There are light symptoms in 1 grade-inoculation leaf.
2 grades-mono- to two panels system blade it is mottled, deformation.
3 grades-majority upper blade chlorisis, deformation, diseased plant are downgraded.
4 grades-complete stool blade chlorisis, severely deformed or downright bad, diseased plant is downgraded serious.
B. disease index
Disease index=[∑ (the disease numbers of sheets at different levels × opposite value of series)/(investigation total leaf number × 9)] × 100%
C. control efficiency
Control efficiency (%)=[(control disease index-processing disease index)/control disease index] × 100%
Table 4
Small molecule agent compound of the invention has been retouched by specific example as the application of antivirotic
It states, those skilled in the art can use for reference the content of present invention, and the links such as appropriate feed change, process conditions are corresponding other to realize
Purpose, correlation change all without departing from the contents of the present invention, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, fall within the scope of the claimed invention without departing from theon the basis of the spirit of the present invention.
Claims (6)
1. a kind of medicament of Antiphytoviral, which is characterized in that the medicament includes small molecule agent shown in formula (I), or including
Pharmaceutically acceptable salt containing chemical structure shown in formula (I):
Wherein, R1、R2And R3It is respectively selected from hydrogen, nitro, nitroso, sulfonic group, carboxyl, amino or azo, halogen atom, C1-10 alkane
One of base, C2-10 alkenyl or C2-10 alkynyl group.
2. Antiphytoviral medicament according to claim 1, which is characterized in that the medicament includes small point shown in formula (II)
Sub- medicament:
3. small molecule agent shown in formula (I) or its pharmaceutically acceptable salt are inhibiting the application in viral silencing suppressor.
4. application according to claim 3, which is characterized in that the viral silencing suppressor includes but is not limited to P19,2b
Or Hc-Pro.
5. small molecule agent shown in formula (II) or its pharmaceutically acceptable salt are inhibiting the application in viral silencing suppressor.
6. application according to claim 5, which is characterized in that the viral silencing suppressor includes but is not limited to P19,2b
Or Hc-Pro.
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CN201710597721.9A CN109275662A (en) | 2017-07-20 | 2017-07-20 | A kind of medicament of Antiphytoviral |
PCT/CN2017/114842 WO2019015223A1 (en) | 2017-07-20 | 2017-12-06 | Agent against plant virus |
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CN201710597721.9A CN109275662A (en) | 2017-07-20 | 2017-07-20 | A kind of medicament of Antiphytoviral |
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CN201710597721.9A Pending CN109275662A (en) | 2017-07-20 | 2017-07-20 | A kind of medicament of Antiphytoviral |
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WO (1) | WO2019015223A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111825738A (en) * | 2019-04-18 | 2020-10-27 | 中检科医药科技(北京)集团有限公司 | Betulin derivative and hydrophilic modification product thereof, nano solution and preparation method thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092634A (en) * | 2007-05-25 | 2007-12-26 | 中国科学院微生物研究所 | Method for breeding plant of anti cucumber mosaic virus |
CN102443602A (en) * | 2011-10-27 | 2012-05-09 | 江苏省农业科学院 | Construction method of RNA interference carriers for interfering in a plurality of genes of silencing rice black-streaked dwaf disease |
CN104822833A (en) * | 2012-10-16 | 2015-08-05 | 孟山都技术公司 | Methods and compositions for controlling plant viral infection |
-
2017
- 2017-07-20 CN CN201710597721.9A patent/CN109275662A/en active Pending
- 2017-12-06 WO PCT/CN2017/114842 patent/WO2019015223A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101092634A (en) * | 2007-05-25 | 2007-12-26 | 中国科学院微生物研究所 | Method for breeding plant of anti cucumber mosaic virus |
CN102443602A (en) * | 2011-10-27 | 2012-05-09 | 江苏省农业科学院 | Construction method of RNA interference carriers for interfering in a plurality of genes of silencing rice black-streaked dwaf disease |
CN104822833A (en) * | 2012-10-16 | 2015-08-05 | 孟山都技术公司 | Methods and compositions for controlling plant viral infection |
Non-Patent Citations (1)
Title |
---|
梁艳辉: "《STN检索报告》", 8 February 2011 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111825738A (en) * | 2019-04-18 | 2020-10-27 | 中检科医药科技(北京)集团有限公司 | Betulin derivative and hydrophilic modification product thereof, nano solution and preparation method thereof |
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