CN105085930A - Novel dendritic macromolecule and its preparation method and use - Google Patents
Novel dendritic macromolecule and its preparation method and use Download PDFInfo
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- CN105085930A CN105085930A CN201410607868.8A CN201410607868A CN105085930A CN 105085930 A CN105085930 A CN 105085930A CN 201410607868 A CN201410607868 A CN 201410607868A CN 105085930 A CN105085930 A CN 105085930A
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- dendritic macromole
- polyamide
- amine
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Abstract
The invention discloses a preparation method and use of a novel tadpole-shaped compound containing a dendritic macromolecule. The novel tadpole-shaped compound has the dendritic macromolecule as a head and the chain-type hydrophilic compound as a tail. The invention discloses the preparation method and use of the novel tadpole-shaped compound. The novel tadpole-shaped compound can be fertilized in human or animal bodies in a normal fertility process and improves and an ovum fertility rate by at least three times.
Description
Technical field
The tadpole shape that the invention discloses a kind of novelty contains the Synthesis and applications of the compound of dendritic macromole, the compound of this tadpole shape take dendritic macromole as head, with the compound that hydrophilic chain compound is afterbody, the invention discloses Preparation Method And The Use.The compound of this tadpole shape can improve the rate of fertilization more than 3 times of ovum in the internal fertilization of human or animal and normal reproduction process.
Background technology
At present, because environmental pollution and life stress increase day by day, young man and wife's incidence of infertility significantly increases, and not only makes some families be perplexed, also brings very large unstable to society.Some wildlifes in imminent danger, due to can not effective fertility, cause the extinction of species.Success ratio in vitro fertilization only rests on about 50%, and operates lengthy and tedious, cannot efficiently and take time and effort consumptive material.The present inventor has invented a kind of brand-new tadpole shape compound, this tadpole shape compound can make sperm in vivo in fertilization process, be combined with ovum readily through uterine tube, combination rate exceedes common more than 3 times of becoming pregnant, and namely this tadpole shape compound can make human or animal have the ability breeding filial generation more strongly in non-i.e. normal reproduction process in vitro fertilization.
This tadpole shape compound prepared by the present invention can at utmost make sperm be combined with ovum after Mammals sexual intercourse, has the ability improving ovum fertilization rate in the natural growing process in Mammalian Reproduction field.The experimentation on animals that the compounds of this invention carries out shows, the new compound of this similar tadpole shape that has a beginning and an end makes the ovum fertilization rate of mouse at least improve 3 times in the internal fertilization and normal reproduction process of mouse.
Summary of the invention
A kind of new compound containing dendritic macromole of the similar tadpole shape that has a beginning and an end in the structure be shown below, the dendritic macromole of its feature to be head be approximate sphericity is formed, afterbody is made up of one section of linear hydrophilic chain compound, form a compound like tadpole shape, its structure is as follows:
In structure
Representative is that half m after the m of kernel decomposes for dendritic macromole is for dendritic macromole with S-S, wherein m is that the m of the height cladodification of approximate sphericity is for dendritic macromole for dendritic macromole, wherein m is the algebraically of dendritic macromole, m gets the multiple of integer between 0-50 and 0.5, its main body is polyamide-amide, the chemical group of most surface can be primary amine groups, also can chemically modified be hydroxyl, monoethanolamine, amino ethyl ethanolamine, three (methylol) aminomethane, 3-methoxycarbonyl pyrrolidone, amino acid, carboxylic acid sodium, succinamic acid, any one of Trimethoxy silane etc.
Representative take S-S as kernel, and the m of the height cladodification of approximate sphericity is for dendritic macromole, and wherein m is the algebraically of dendritic macromole, m gets the multiple of integer between 0-50 and 0.5, and its main body is polyamide-amide, and the chemical group of most surface can be primary amine groups, also can chemically modified be hydroxyl, monoethanolamine, amino ethyl ethanolamine, three (methylol) aminomethane, 3-methoxycarbonyl pyrrolidone, amino acid, carboxylic acid sodium, succinamic acid, any one of Trimethoxy silane etc.And the Linker in structure represents a kind of branch structure compound with three Ge Zhicha branches, a branch is connected with hydrophilic chain, another two branches are connected with the core chemistry of half dendritic macromole, formed one like tadpole shape containing dendritic macromole be head, hydrophilic chain compound is the compound of afterbody.This branched compound contains the active group that can react with sulfydryl-SH.This branched compound, preferably
，
。
1. the hydrophilic chain Hydrophilicchain in the structure of compound is the compound of one section of hydrophilic long-chain shape, is selected from polyvinyl alcohol, polyoxyethylene glycol, polypyrrole alkane ketone, polyethers, polyoxyethylene block copolymer, or their multipolymer.The preferred polyoxyethylene glycol of the present invention, its molecular weight is 100-100000.
The preparation method of the compound that the present invention invents, is characterized in that:
1) will be with S-S the dendritic macromole of core, wherein m is the algebraically of dendritic macromole, and m gets the multiple of integer between 0-50 and 0.5, G
mbe decomposed under the catalysis of vitamins C, dithiothreitol (DTT) or sodium bisulfite and be good for half active dendritic macromole G with SH
ma;
2) branched compound L inker and linear hydrophilic chain compound H ydrophilicChain side coupling generate the ol cpds B with apparatus derivatorius;
3) compd A stirred overnight in the solvent of 0-20 degree of the compd B of a times mole and twice mole is reacted, and the both sides of branch are reacted with the SH of the kernel of half dendrimer A respectively, are obtained by reacting the Compound C of tadpole shape containing dendritic macromole;
4) will Compound C freeze-drying 24-96 hour in vacuum drying oven of the tadpole shape of gained be prepared, obtain the finished product for subsequent use;
React described structure as follows
Dendrimer compound Gm:
；
Compd A:
；
Compd B:
Wherein this structure
Belong to the structure in Linker structure;
Compound C:
。Wherein chemical step 1-3 selects solvent to be selected from: methyl ether, ether, sherwood oil, benzene, toluene, pyridine, tetrahydrofuran (THF), trifluoroacetic acid, chloroform, tetracol phenixin, 3-(2-pyridine dimercapto) propionic acid N-hydroxy-succinamide ester, tricresyl phosphate (2-chloroethyl) ester, methylene dichloride, methyl alcohol, ethanol, methylene dichloride, dimethyl sulfoxide (DMSO), N, one or more in dinethylformamide, N, N'-dicyclohexylcarbodiimide.This new use of a compound having a beginning and an end similar tadpole shape is greatly promote that sperm is combined with ovum in the internal fertilization and normal reproduction process of human or animal, makes it be very easy to form zygote.Compound of the present invention can make the ovum fertilization rate of human or animal at least improve 3 times.
Preparation method of the present invention is specific as follows:
1) will be with S-S the dendritic macromole polyamide-amine G of core
mits main body is polyamide-amide, and the chemical group of most surface can be primary amine groups, can chemically modified be also hydroxyl, monoethanolamine, amino ethyl ethanolamine, three (methylol) aminomethane, 3-methoxycarbonyl pyrrolidone, amino acid, carboxylic acid sodium, succinamic acid, any one of Trimethoxy silane etc.(all dendritic macromoles are all commercially available), wherein m is the algebraically of dendritic macromole, and m gets the multiple of integer between 0-50 and 0.5, G
munder the catalysis of vitamins C (commercially available), dithiothreitol (DTT) (commercially available) or sodium bisulfite (commercially available), in organic solution, reduction decomposition is be good for half active dendritic macromole G with SH
ma;
2) branched compound L inker(is commercially available, also can prepare) (commercially available with one section of linear hydrophilic chain compound, also can prepare) be under the condition of 5-9 at PH, reaction coupling in normal-temperature reaction 1-48 hour generates the compd B with branched structure, and then freeze-drying is for subsequent use;
3) compd A of the compd B of a times mole and twice mole spends the night low speed 50rpm-500rpm stirring reaction in the solvent of 0-20 degree, is obtained by reacting the dendrimer C containing medicines structure;
4) the dendrimer C preparing gained is directly washed rear freeze-drying for subsequent use; Or add lyophilized vaccine (potassium sorbate, N.F,USP MANNITOL, Xylo-Mucine etc.), in vacuum drying oven, freeze-drying 24-96 hour, obtains the finished product for subsequent use;
For subsequent use after Compound C freeze-drying, for animal regulation and control sex after weigh.
The compound containing dendritic macromole of tadpole shape of the present invention farthest can promote the combination of X sperm and ovum after the normal sexual intercourse of human or animal, the combination of very big raising y sperm and ovum, has the ability improving ovum fertilization rate in the natural growing process in human or animal's field of reproduction.Compound of the present invention also can be used for the auxiliary material application of some medicines due to the speciality of itself or applies as genophore, also can be used for flocculation agent, tensio-active agent or mould material.
At present, because environmental pollution and life stress increase day by day, young man and wife's incidence of infertility significantly increases, and not only makes some families be perplexed, also brings very large unstable to society.Some wildlifes in imminent danger, due to can not effective fertility, cause the extinction of species.Success ratio in vitro fertilization only rests on about 50%, and operates lengthy and tedious, cannot efficiently and take time and effort consumptive material.The present inventor has invented a kind of brand-new tadpole shape compound, this tadpole shape compound can make sperm in vivo in fertilization process, be combined with ovum readily through uterine tube, combination rate exceedes common more than 3 times of becoming pregnant, and namely this tadpole shape compound can make human or animal have the ability breeding filial generation more strongly in non-i.e. normal reproduction process in vitro fertilization.
This tadpole shape compound prepared by the present invention can at utmost make sperm be combined with ovum after Mammals sexual intercourse, has the ability improving ovum fertilization rate in the natural growing process in Mammalian Reproduction field.The experimentation on animals that the compounds of this invention carries out shows, the new compound of this similar tadpole shape that has a beginning and an end makes the ovum fertilization rate of mouse at least improve 3 times in the internal fertilization and normal reproduction process of mouse.
In sum, tadpole shape compound of the present invention invention and application will bring great social effect and scientific meaning.
accompanying drawing illustrates:
fig. 1the nuclear magnetic resonance map of the end product of embodiment 1.
fig. 2the nuclear magnetic resonance map of the end product of embodiment 2.
Embodiment
Specific embodiment is described in further detail the present invention below, but the present invention not only limits to following examples.
Preparation embodiment is as follows:
embodiment 1
1) the dendritic macromole polyamide-amine G3(taking S-S as core is purchased), 20 degrees Celsius under the catalysis of sodium bisulfite (being purchased) 24 hours in methylene dichloride and methyl alcohol (1:1) solution reduction decomposition be good for half active dendritic macromole G with SH
3;
Be reduced to
2) the branched compound L inker(of 1 mole is commercially available, also can prepare) be under the condition of 7.5 at PH, under normal temperature condition, be that the polyoxyethylene glycol (being purchased) ended up reacts and within 20 hours, reacts coupling and generate compd B with branched structure with methoxyl group with the other end of the end band carboxyl of 1 mole, then freeze-drying is for subsequent use;
+
N approximates 100.
3) compd B of a mole and the compd A of two moles spend the night low speed 100rpm stirring reaction in the solvent of 10 degree in N, N'-dicyclohexylcarbodiimide and chloroformic solution, are obtained by reacting the dendrimer C containing medicines structure;
+
4), after being washed in aqueous by the C containing dendrimer and hydrophilic compounds preparing gained, in vacuum drying oven, freeze-drying 48 hours, obtains the finished product for subsequent use;
embodiment 2
1) the dendritic macromole polyamide-amine G2(taking S-S as core is purchased), 15 degrees Celsius under the catalysis of vitamins C (being purchased) 24 hours in dimethyl sulphoxide solution reduction decomposition be good for half active dendritic macromole G2 with SH;
reduction
2) the branched compound L inkerA(of 1 mole is commercially available, also can prepare) at N, adding diacetyl oxide under dinethylformamide and trifluoroacetic acid catalysis, to generate LinkerB(also commercially available), then LinkerB is under the condition of 6.5 at PH, react with the polyoxyethylene glycol (being purchased) that the other end of amino ends up with methoxyl group with one end of 1 mole under normal temperature and within 24 hours, react coupling and generate compd B with branched structure, then freeze-drying is for subsequent use;
（linkerA）
TFA；anhydr；DMF
（linkerB）
+
N approximates 200
3) compd B of a mole and the compd A of two moles spend the night low speed 200rpm stirring reaction in the aqueous solution of the sherwood oil of 20 degree, are obtained by reacting the dendrimer C containing medicines structure;
4), after being washed in aqueous by the C containing dendrimer and hydrophilic compounds preparing gained, in vacuum drying oven, freeze-drying 24 hours, obtains the finished product for subsequent use;
effect experimental is as follows:
(molecular weight is 5000 for the freeze-drying sample prepared by embodiment 1-2 and polyoxyethylene glycol, be available commercially from sigma) and dendritic macromole polyamide amine PAMAMG3(be available commercially from sigma) all weigh identical weight, the thing medication group of 10mg/100ml is configured to distilled water solution, compare group with distilled water, investigate the compounds of this invention to the effect of rate of fertilization.
Embodiment is tested:
Laboratory animal and grouping
Buy and be used for NIH mouse in zooperal 7 week age, male and female are normal after separating raises for experiment after 2 weeks, and adapt to the environment of experiment with this, mouse freely takes food, drink water, every day changes fresh water, changes bedding and padding 1 time weekly.Foodstuff amount through observation mouse is 5g/(every every day).By the method for random packet, laboratory animal is divided into 5 groups, is respectively control group and 4 medication groups, often organize each 40 NIH female mices, be divided into medication group 4 groups, be specially embodiment 1-2 group, polyoxyethylene glycol group, PAMAM(G3) group, and blank group.
The foundation of animal model
Fixing mouse, the vaginal tract of all for medication group 4 groups female mouse is all instilled the pharmaceutical aqueous solution of 3 corresponding medicines, concentration is 10mg/100ml, is respectively embodiment 1, embodiment 2, polyoxyethylene glycol group, PAMAM(G3) aqueous solution organized.Control group distilled water instills.Then immediately by male mouse and female mouse with cage 1 day, wherein male mouse and female mouse ratio are 1:1, namely often organize and all put into 40 male mouse, divide cage after 1 day.Female mouse raises 2 months, normally feeds, and notes collecting and often organizes and newly give birth to mouse, so as not to hinder by adult rats.Newborn mice number and sex is added up after February.
Experimental result
Experimental result is in table 1
The sex of the new fertility mouse that table 1 is respectively organized and number
| Group | New fertility male mice | New fertility female mice | Fertility total mice order |
| Normal group | 5 | 5 | 10 |
| Embodiment 1 group | 15 | 18 | 33 |
| Embodiment 2 groups | 15 | 17 | 32 |
| Polyoxyethylene glycol group | 4 | 5 | 9 |
| PAMAM group | 5 | 4 | 9 |
As can be seen from experimental result, after employing the medicine of embodiment, the mouse number of fertility exceeds Normal group more than 3 times, can find out that the rate of fertilization of the ovum of the animal employing compound of the present invention has been enhanced more than three times.
Claims (10)
1. a kind of new compound containing dendritic macromole polyamide-amine PAMAM of the similar tadpole shape that has a beginning and an end in the structure be shown below, the dendritic macromole polyamide-amine of its feature to be head be approximate sphericity is formed, afterbody is made up of one section of linear hydrophilic chain compound, form a compound like tadpole shape, its structure is as follows:
In the structure of the 2. compound of claim 1
Representative is that half m after the m of kernel decomposes for dendritic macromole polyamide-amine is for dendritic macromole polyamide-amine with S-S, wherein m is that the m of the height cladodification of approximate sphericity is for dendritic macromole polyamide-amine for dendritic macromole, wherein m is the algebraically of dendritic macromole, m gets the multiple of integer between 0-50 and 0.5, its main body is polyamide-amide, the chemical group of most surface can be primary amine groups, also can chemically modified be hydroxyl, monoethanolamine, amino ethyl ethanolamine, three (methylol) aminomethane, 3-methoxycarbonyl pyrrolidone, amino acid, carboxylic acid sodium, succinamic acid, any one of Trimethoxy silane etc.
3. the compound of claim 1, Linker wherein in structure represents a kind of branch structure compound with three Ge Zhicha branches, a branch is connected with hydrophilic chain, another two branches are connected with the core chemistry of half dendritic macromole, formed one like tadpole shape containing dendritic macromole be head, hydrophilic chain compound is the compound of afterbody.
4. the compound of claim 1, the hydrophilic chain in the structure of compound is the compound of one section of hydrophilic long-chain shape, is selected from polyvinyl alcohol, polyoxyethylene glycol, polypyrrole alkane ketone, polyethers, polyoxyethylene block copolymer, or their multipolymer.
5. the compound of claim 4, the hydrophilic chain in the structure of compound is the compound of one section of hydrophilic long-chain shape, and preferred polyoxyethylene glycol, molecular weight is 100-100000.
6. the branched compound L inker of claim 3, this branched compound L inker contains the active group that can react with sulfydryl-SH.
7. the branched compound of claim 6, preferably
8. as claim 1-7 the present invention the preparation method of compound that invents, it is characterized in that:
1) will be with S-S the dendritic macromole G of core
m, wherein m is the algebraically of dendritic macromole, and m gets the multiple of integer between 0-50 and 0.5, G
mbe decomposed under the catalysis of vitamins C, dithiothreitol (DTT) or sodium bisulfite and be good for half active dendritic macromole G with SH
ma;
2) branched compound L inker and linear hydrophilic chain compound H ydrophilicChain side coupling generate the ol cpds B with apparatus derivatorius;
3) compd A stirred overnight in the solvent of 0-20 degree of the compd B of a times mole and twice mole is reacted, and the both sides of branch are reacted with the SH of the kernel of half dendrimer A respectively, are obtained by reacting the Compound C of tadpole shape containing dendritic macromole;
4) will Compound C freeze-drying 24-96 hour in vacuum drying oven of the tadpole shape of gained be prepared, obtain the finished product for subsequent use;
React described structure as follows
Dendrimer compound Gm:
Compd A:
Compd B:
Wherein this structure
Belong to the structure in Linker structure;
Compound C:
9. the method for claim 8, wherein said chemical step 1-3 selects solvent to be selected from: methyl ether, ether, sherwood oil, benzene, toluene, pyridine, tetrahydrofuran (THF), trifluoroacetic acid, chloroform, tetracol phenixin, 3-(2-pyridine dimercapto) propionic acid N-hydroxy-succinamide ester, tricresyl phosphate (2-chloroethyl) ester, methylene dichloride, methyl alcohol, ethanol, methylene dichloride, dimethyl sulfoxide (DMSO), N, one or more in dinethylformamide, N, N'-dicyclohexylcarbodiimide.
10. the purposes of the compound of claim 1, this new use of a compound having a beginning and an end similar tadpole shape is greatly promote that sperm is combined with ovum in the internal fertilization and normal reproduction process of human or animal, make it be very easy to form zygote, the compound of this invention can make the ovum fertilization rate of human or animal at least improve 3 times.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106046387A (en) * | 2015-04-15 | 2016-10-26 | 韩冰 | Novel high-efficiency gene vector, and preparation and application thereof |
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| CN104558626A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
| CN104558624A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
| CN104558620A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
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Patent Citations (6)
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| CN103127526A (en) * | 2013-02-27 | 2013-06-05 | 万礼 | Tree-like polymer targeting nanometer drug delivery carrier and its preparation method |
| CN104558627A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Novel dendrimer as well as preparation and application thereof |
| CN104558625A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Novel dendrimer as well as preparation and application thereof |
| CN104558626A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
| CN104558624A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
| CN104558620A (en) * | 2013-10-15 | 2015-04-29 | 韩冰 | Preparation and usage of novel dendrimer |
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| CN106046387A (en) * | 2015-04-15 | 2016-10-26 | 韩冰 | Novel high-efficiency gene vector, and preparation and application thereof |
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