CN109400812A - A kind of synthetic method of anti-tumor activity crosslinking bagasse xylan caffeic acid ester-g-AM/BA - Google Patents
A kind of synthetic method of anti-tumor activity crosslinking bagasse xylan caffeic acid ester-g-AM/BA Download PDFInfo
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- CN109400812A CN109400812A CN201811226000.8A CN201811226000A CN109400812A CN 109400812 A CN109400812 A CN 109400812A CN 201811226000 A CN201811226000 A CN 201811226000A CN 109400812 A CN109400812 A CN 109400812A
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- bagasse xylan
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
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Abstract
The invention discloses a kind of synthetic methods for being crosslinked bagasse xylan caffeic acid ester-g-AM/BA.Using natural macromolecule biological activity bagasse xylan as primary raw material, acrylamide, butyl acrylate are grafted monomers, using potassium peroxydisulfate and sodium hydrogensulfite as initiation system, N, N '-methylene-bisacrylamide is that crosslinking bagasse xylan-g-AM/BA is made in crosslinking agent.Again using ammonium persulfate and zirconium sulfate as composite catalyst, caffeic acid is esterifying agent, carries out esterification with graft copolymer crosslinking bagasse xylan-g-AM/BA in dichloromethane solvent and synthesizes final product crosslinking bagasse xylan caffeic acid ester-g-AM/BA.The present invention by grafting to bagasse xylan, be crosslinked, be esterified three kinds of activity against organisms groups of composite modified introducing, so that final product further enhances the water solubility, anticancer, antibacterial isoreactivity of former bagasse xylan, there is certain application value in fields such as medicine, food.
Description
Technical field
The present invention relates to technical field of polymer materials, especially a kind of anti-tumor activity is crosslinked bagasse xylan caffeic acid
The synthetic method of ester-g-AM/BA.
Background technique
In recent years, xylan is as naturally occurring polymer, due to good biocompatibility, biological degradability
It is studied with nontoxicity in drug release, absorption and many other fields.Xylan is the second master after cellulose
Polysaccharide is led, is connect by β-Isosorbide-5-Nitrae xylose glycosidic bond with a variety of side groups.Due to having a large amount of free hydroxyl groups on the surface of xylan molecule, because
This can be esterified by etherificate, and oxidation, the methods of graft copolymerization carries out chemical modification, improves its own disadvantage, while improving life
Object activity.
Bagasse xylan derivative especially bagasse xylan esterification, graft copolymer have the work for directly inhibiting cancer cell
With the former anticancer effect can be enhanced by further modifying or introducing the group with antitumaous effect.With acrylamide (AM),
Butyl acrylate (BA) is grafted monomers and xylan graft copolymerization, can not only improve thermal stability, and can also increase
The anti-tumor activity of strong bagasse xylan.Studies have shown that caffeic acid can be by inhibiting tumour growth, reducing turning for liver neoplasm
In-migration achievees the effect that antitumor.If carrying out further esterification modification to bagasse xylan using caffeic acid as esterifying agent, not only
Bagasse xylan or the original biological function of its Grafted Derivatives are remained, and is further mentioned by introducing coffee acid groups
The high anti-tumor activity of bagasse xylan.
The present invention is using natural macromolecule biological activity bagasse xylan as primary raw material, acrylamide (AM), acrylic acid
Butyl ester (BA) is grafted monomers, and using potassium peroxydisulfate and sodium hydrogensulfite as initiation system, N, N '-methylene-bisacrylamide is to hand over
Join agent and crosslinking bagasse xylan-g-AM/BA is made.Again using ammonium persulfate and zirconium sulfate as composite catalyst, caffeic acid is esterification
Agent carries out esterification with graft copolymer bagasse xylan-g-AM/BA in dichloromethane solvent and synthesizes final product crosslinking
Bagasse xylan caffeic acid ester-g-AM/BA functional derivatives.
Summary of the invention
The purpose of the invention is to improve the bioactivity of bagasse xylan, expand application range, provides a kind of anti-swollen
The synthetic method of tumor activity crosslinking bagasse xylan caffeic acid ester-g-AM/BA.
Specific steps of the invention are as follows:
(1) 5~10g bagasse xylan is obtained into butt sugarcane to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Slag xylan.
(2) 0.5~0.6g potassium peroxydisulfate, 0.03~0.05g sodium hydrogensulfite are successively weighed in 50mL beaker, then plus
Enter 10~15mL distilled water and is made into initiator solution, it is spare.
(3) 3.0~5.0gAM, 3~5mL are weighed and analyzes pure BA in 100mL flask, then it is added 15 into flask~
20mL distilled water, 0.1~0.2g N, N '-methylene-bisacrylamide and 1~1.1g technical grade OP-10, using high-shear emulsifying
Machine is dispersed with stirring 1~1.5 hour, is prepared mixed monomer solution, is poured into 100mL constant pressure funnel, spare.
(4) butt bagasse xylan obtained by 3~4g step (1) is weighed to be added in 250mL four-hole boiling flask, add 15~
20mL deionized water is warming up to 30~40 DEG C, stirs 15~20 minutes.Mixed monomer solution obtained by a dropping step (3), 6 hours
It is added dropwise；Meanwhile initiator solution obtained by step (2) is added portionwise, every 8~10 minutes 0.3~0.5mL of dropwise addition, it is added dropwise
After the reaction was continued 2~4 hours.To after reaction, be cooled to room temperature.
(5) 20~30mL is added into step (4) resulting material to analyze pure acetone precipitating 20~30 minutes, filters and with 10
~20mL analyzes pure dehydrated alcohol washing, filters 2~3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes
Dry 24 hours to constant weight to get crosslinking bagasse xylan-g-AM/BA.
(6) it weighs 1~3g step (5) obtained intermediate product crosslinking bagasse xylan-g-AM/BA and is added to tetra- mouthfuls of 250mL
In flask, sequentially add 0.5~1g caffeic acid, 1~2g N, N- dicyclohexylcarbodiimide, 0.06~0.1g ammonium persulfate,
0.05~0.1g zirconium sulfate and 15~20mL analyze absolute dichloromethane, control reaction temperature at 60~75 DEG C, are stirred to react 7~9
Hour, system is cooled to room temperature.
(7) step (6) gained reactant material is filtered, filter cake uses 20~25mL dehydrated alcohol, 15~25mL analysis respectively
Pure acetone is respectively washed, is filtered 2~3 times, and filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chamber dry 24 hours to perseverance
Weight is crosslinked bagasse xylan caffeic acid ester-g-AM/BA to get final goal product.
(8) step (7) products therefrom crosslinking bagasse xylan caffeic acid ester-g-AM/BA is carried out using acid-base titration
Be esterified the measurement of degree of substitution, specific method and experimental procedure are as follows: the Product samples of precise about 0.5g are put into 250mL cone
In shape bottle, 5mL deionized water is added, then instills 3 drop phenolphthalein indicators.The sodium hydroxide of 2.5mL concentration 0.5mol/L is added
Solution shakes up.Concussion saponification 1 hour at room temperature.The inner wall of plug and conical flask is rinsed with 10mL deionized water, then is used
0.5mol/L hydrochloric acid standard solution is titrated to colourless, as terminal.The volume V of record consumption hydrochloric acid standard solution1.In identical item
Under part, blank titration, record consumption hydrochloric acid standard solution volume V are carried out with the bagasse xylan before esterification0.Carboxylic esterification replaces
The calculation formula for spending (DS) is as follows:
In formula:
wc--- the mass fraction of coffee acyl, % in target product；
V0--- titration bagasse xylan uses the amount of HCI standard solution, Unit/mL；
V1--- the standard solution amount of hydrochloric acid used in titration final product, Unit/mL；
CHCl--- the concentration of hydrochloric acid standard solution, unit mol/L；
M --- the quality of target product sample, unit g；
The relative molecular mass of M --- coffee acyl；
132 --- the relative molecular mass of bagasse xylan dewatering unit；
DS --- the degree of substitution of bagasse xylan caffeic acid ester.
(9) monomer grafting rate and grafting efficiency in determination step (7) products therefrom, specific method and steps are as follows: will be thick
After graft copolymer acetone precipitation, pure dehydrated alcohol is analyzed with 10~20mL respectively and is washed 2~3 times, is dried in vacuo at 55 DEG C
It dries in case to constant weight, obtains graft copolymer crude product.Then, use analysis pure acetone will as solvent in Soxhlet extractor
Crude product extracts 24 hours, and the taking-up of sample after extracting is put into 60 DEG C of vacuum ovens dry 24 hours and obtains pure connect to constant weight
Graft copolymer.The calculation method of grafting rate and grafting efficiency is as follows:
In formula:
Wg--- the quality of graft esterification copolymer, unit g；
W0--- the quality of former bagasse xylan, unit g；
W1--- the quality of grafted branches, unit g；
W2--- the quality of monomer, unit g；
G --- grafting rate, %；
GE --- grafting efficiency, %.
The shortcomings that gained target product of the invention not only improves bagasse xylan itself, and introduce anticancer activity group
Caffeic acid, AM, BA have synthesized the crosslinking bagasse xylan caffeic acid ester-g-AM/BA with anticancer activity.The Product formation work
Skill is easily controllable, raw material availability height, stable product quality, applies valence with important in the fields such as biological medicine and material
Value.
Detailed description of the invention
Fig. 1 is the SEM photograph of bagasse xylan.
Fig. 2 is the SEM photograph for being crosslinked bagasse xylan caffeic acid ester-g-AM/BA.
Fig. 3 is the IR figure of former bagasse xylan.
Fig. 4 is the IR figure for being crosslinked bagasse xylan caffeic acid ester-g-AM/BA.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram for being crosslinked bagasse xylan caffeic acid ester-g-AM/BA.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve for being crosslinked bagasse xylan caffeic acid ester-g-AM/BA.
Specific embodiment
Embodiment:
(1) 10g bagasse xylan is obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Glycan.
(2) 0.6g potassium peroxydisulfate, 0.05g sodium hydrogensulfite are successively weighed in 50mL beaker, 15mL distillation is then added
Water is made into initiator solution, spare.
(3) 5.0gAM, 5mL are weighed and analyzes pure BA in 100mL flask, be then added into flask 20mL distilled water,
0.2g N, N '-methylene-bisacrylamide and 1.1g technical grade OP-10, are dispersed with stirring 1.5 hours using high-shear emulsion machine,
Mixed monomer solution is prepared, is poured into 100mL constant pressure funnel, it is spare.
(4) it weighs butt bagasse xylan obtained by 4g step (1) to be added in 250mL four-hole boiling flask, adds 20mL and go
Ionized water is warming up to 40 DEG C, stirs 20 minutes.Mixed monomer solution obtained by a dropping step (3), is added dropwise for 6 hours；Meanwhile
Initiator solution obtained by step (2) is added portionwise, every 10 minutes dropwise addition 0.5mL, the reaction was continued 4 hours after being added dropwise.To
After reaction, it is cooled to room temperature.
(5) 30mL is added into step (4) resulting material to analyze pure acetone precipitating 30 minutes, filter and is analyzed with 20mL pure
Dehydrated alcohol washing filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to perseverance
Weight is to get crosslinking bagasse xylan-g-AM/BA.
(6) it weighs 1~3g step (5) obtained intermediate product crosslinking bagasse xylan-g-AM/BA and is added to tetra- mouthfuls of 250mL
In flask, 1g caffeic acid, 2g N, N- dicyclohexylcarbodiimide, 0.1g ammonium persulfate, 0.1g zirconium sulfate and 20mL are sequentially added
Absolute dichloromethane is analyzed, reaction temperature is controlled at 75 DEG C, is stirred to react 9 hours, system is cooled to room temperature.
(7) step (6) gained reactant material is filtered, filter cake uses 25mL dehydrated alcohol, 25mL analysis pure acetone each respectively
Washing filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chamber dry 24 hours to constant weight to get final
Target product is crosslinked bagasse xylan caffeic acid ester-g-AM/BA.
(8) acid-base titration is used to measure product caffeic acid esterification degree of substitution as 0.5345；Monomer grafting rate is 31%, is connect
Branch efficiency is 76%.
Product bagasse xylan caffeic acid ester-g-AM/BA is analyzed through IR, and the modified product of graft esterification exists
1739.55cm-1There are the carbonyl eigen vibration absorption peak of AM, 1658.55cm-1Place is amide stretching vibration absworption peak,
1515.84cm-1Place is phenyl ring skeleton stretching vibration absworption peak.Sem analysis the result shows that, surface is uneven, have piece
Shape packed structures, there is obviously gap and damaged rill, it was demonstrated that have sent out large change by modified original structure surface.Point
TG the and DTG curve of graft esterification product is analysed, 200 DEG C to 250 DEG C stages, mass loss reaches up to 35%, mainly
Caused by bagasse xylan caffeic acid ester-g-AM/BA itself decomposition, final product is in 800 DEG C of Shi Yuyuan bagasse xylan phases
It is significantly improved than thermal stability.Through the analysis of XRD it is found that product after esterification modification powder angle be 20.09 °, 21.46 °,
Peak crystallization increases at 24.92 °, 26.69 °, and for peak type compared with illustrating that crystalline content is more by force, crystal region is complete.
Claims (1)
1. a kind of synthetic method of anti-tumor activity crosslinking bagasse xylan caffeic acid ester-g-AM/BA, it is characterised in that specific step
Suddenly are as follows:
(1) 5 ~ 10g bagasse xylan it is poly- to be obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Sugar；
(2) 0.5 ~ 0.6g potassium peroxydisulfate, 0.03 ~ 0.05g sodium hydrogensulfite are successively weighed in 50mL beaker, then be added 10 ~
15mL distilled water is made into initiator solution, spare；
(3) 3.0 ~ 5.0gAM, 3 ~ 5mL are weighed and analyzes pure BA in 100mL flask, 15 ~ 20mL distillation is then added into flask
Water, 0.1 ~ 0.2g N, N '-methylene-bisacrylamide and 1 ~ 1.1g technical grade OP-10, are dispersed with stirring using high-shear emulsion machine
1 ~ 1.5 hour, mixed monomer solution is prepared, is poured into 100mL constant pressure funnel, it is spare；
(4) it weighs butt bagasse xylan obtained by 3 ~ 4g step (1) to be added in 250mL four-hole boiling flask, adds 15 ~ 20mL and go
Ionized water is warming up to 30 ~ 40 DEG C, stirs 15 ~ 20 minutes；Mixed monomer solution obtained by a dropping step (3), is added dropwise for 6 hours；
Meanwhile initiator solution obtained by step (2) is added portionwise, continue every 8 ~ 10 minutes 0.3 ~ 0.5mL of dropwise addition, after being added dropwise anti-
It answers 2 ~ 4 hours；To after reaction, be cooled to room temperature；
(5) 20 ~ 30mL is added into step (4) resulting material to analyze pure acetone precipitating 20 ~ 30 minutes, filters and with 10 ~ 20mL
It analyzes pure dehydrated alcohol washing, filter 2 ~ 3 times, filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24
Hour is to constant weight to get crosslinking bagasse xylan-g-AM/BA；
(6) it weighs 1 ~ 3g step (5) obtained intermediate product crosslinking bagasse xylan-g-AM/BA and is added to 250mL four-hole boiling flask
In, sequentially add 0.5 ~ 1g caffeic acid, 1 ~ 2g N, N- dicyclohexylcarbodiimide, 0.06 ~ 0.1g ammonium persulfate, 0.05 ~ 0.1g
Zirconium sulfate and 15 ~ 20mL analyze absolute dichloromethane, control reaction temperature at 60 ~ 75 DEG C, are stirred to react 7 ~ 9 hours, system cooling
To room temperature；
(7) step (6) gained reactant material is filtered, filter cake uses 20 ~ 25 mL dehydrated alcohols, 15 ~ 25 mL analysis pure C respectively
Ketone is respectively washed, is filtered 2 ~ 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of thermostatic drying chamber dry 24 hours to constant weight,
Up to crosslinking bagasse xylan caffeic acid ester-g-AM/BA.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
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| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
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| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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