CN111150845A - Preparation process and application of synergistic chemical and photodynamic lignin functional material - Google Patents
Preparation process and application of synergistic chemical and photodynamic lignin functional material Download PDFInfo
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- CN111150845A CN111150845A CN202010063857.3A CN202010063857A CN111150845A CN 111150845 A CN111150845 A CN 111150845A CN 202010063857 A CN202010063857 A CN 202010063857A CN 111150845 A CN111150845 A CN 111150845A
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- lignin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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Abstract
The invention belongs to the technical field of functional material preparation, and particularly relates to a preparation process and application of a synergistic chemical and photodynamic lignin functional material. The lignin functional material takes magnesium lignosulfonate as a carrier, and an antibacterial and anti-inflammatory drug is coated by a chemical crosslinking photosensitizer Ce6, so that the effects of synergetic chemistry and photodynamic antibacterial and anti-inflammatory effects and rapid wound healing are achieved. The preparation process provided by the invention has the advantages of simple route, mild process conditions, good stability of the obtained material, good antibacterial effect and suitability for wound healing in biomedicine.
Description
Technical Field
The invention belongs to the technical field of functional materials, and particularly relates to a preparation process and application of a synergistic chemical and photodynamic lignin functional material.
Background
The lignin is the only non-fossil resource capable of providing renewable aryl compounds in the nature, contains various functional groups (such as aryl, methoxy, carbonyl, carboxyl and the like) and active sites, and is rich in resources. However, industrial lignin, a by-product of the paper industry, is mostly directly burned for power generation, and is utilized by less than 2%, mainly in the form of lignosulfonate, as an additive for building materials. Because of good biocompatibility and no toxicity of lignin, the lignin or lignin derivatives are subjected to functional modification, so that the lignin is one of important methods for realizing high-value utilization of lignin, and direct or indirect benefits can be obtained.
Furthermore, in recent years, the widespread and continuous use of antibiotics has led to the development of antibiotic-resistant bacteria, and the emergence of this phenomenon has prompted us to prepare a novel drug-resistant antibacterial material. For example, chinese patent No. 1 (application No. CN201810431508.5) discloses a bio-based material with antibacterial effect, which is derived from bio-based products prepared by microbial fermentation and has significant antibacterial effect on various bacteria and fungi.
The new-generation photosensitizer Ce6 has excellent performances of strong photodynamic reaction, small toxic and side effects and the like, and is widely applied to photodynamic research. For example, chinese patent 2 (application No. cn201110372002.x) discloses a nano photosensitizer drug delivery system for photodynamic therapy and a preparation method thereof, wherein the drug delivery system in the method is composed of chitosan, Ce6 and a single-walled carbon nanotube.
The magnesium lignosulphonate is a lignin derivative, has good water solubility and stable chemical property, is used as a carrier in the functional material, and magnesium ions can promote the proliferation and migration of normal cells and obviously accelerate the healing of wound surfaces.
Disclosure of Invention
The invention aims to provide a preparation process and application of a synergistic chemical and photodynamic lignin functional material which has the functions of resisting bacteria, promoting wound healing and having stable performance by taking industrial lignin with wide sources as a raw material. In order to solve the problems, the technical scheme adopted by the invention is summarized as the following process, and the process comprises the following characteristic steps in sequence:
step 1: weighing a certain amount of alkali lignin, adding water (with the lignin concentration of 1 wt%) and uniformly stirring, adjusting the pH value to 9-10, heating to 75-85 ℃, slowly adding 20-40% of formaldehyde solution, reacting at the temperature for 2-3 hours, heating to 100-150 ℃ after the time is over, slowly adding 20-30% of magnesium sulfite hexahydrate, reacting at the temperature for 2-4 hours, cooling and collecting after the reaction is over to obtain sulfomethylated magnesium lignosulfonate;
step 2: dissolving a certain amount of photosensitizer Ce6 in dimethyl sulfoxide, adding 1-ethyl- (3-dimethylaminopropyl) -carbonyldiimine hydrochloride and 4-dimethylaminopyridine, and stirring to react for 4-8 hours to prepare a solution containing the photosensitizer and a catalyst;
and step 3: dissolving the sulfomethylated magnesium lignosulfonate prepared in the step 1 in water, slowly adding the sulfomethylated magnesium lignosulfonate into the solution prepared in the step 2, continuously stirring for 12-24 hours, pouring the solution into a 1000D dialysis bag for dialysis, and then freeze-drying to obtain sulfomethylated magnesium lignosulfonate-Ce 6;
and 4, step 4: mixing epigallocatechin gallate and the sulfomethylated magnesium lignosulfonate-Ce 6 in the molar mass ratio of 1: 2-1: 50 under stirring to form micelles, and pouring the micelles into a 1000D dialysis bag for dialysis to obtain the lignin functional material with the synergetic chemical and photodynamic functions.
In the technical scheme, the mass ratio of the sulfomethylated magnesium lignosulfonate used in the step 3 to the photosensitizer Ce6 used in the step 2 is 2: 1-4: 1.
The lignin functional material prepared according to the technical scheme has good application in wound healing in biomedicine, and is characterized by being widely applied to unexpected wounds or postoperative wounds.
Detailed Description
The invention will be more fully and more readily understood by reference to the following examples, which are given to illustrate the invention more clearly, and are not intended to limit the invention in any way.
Example 1:
the preparation process of the synergistic chemical and photodynamic lignin functional material comprises the following specific steps:
step 1: weighing a certain amount of alkali lignin, adding water (with the lignin concentration of 1 wt%) and uniformly stirring, adjusting the pH value to 9, heating to 78 ℃, slowly adding 25% formaldehyde solution, reacting at the temperature for 2 hours, heating to 120 ℃ after the time is over, slowly adding 20% magnesium sulfite hexahydrate, reacting at the temperature for 2.5 hours, and cooling and collecting after the reaction is over to obtain sulfomethylated magnesium lignosulfonate;
step 2: dissolving a certain amount of photosensitizer Ce6 in dimethyl sulfoxide, adding 1-ethyl- (3-dimethylaminopropyl) -carbonyldiimine hydrochloride and 4-dimethylaminopyridine, and stirring to react for 5 hours to prepare a solution containing the photosensitizer and a catalyst;
and step 3: dissolving the sulfomethylated magnesium lignosulfonate prepared in the step 1 in water, slowly adding the dissolved solution prepared in the step 2, continuously stirring for 16 hours, pouring the solution into a 1000D dialysis bag for dialysis, and then freeze-drying to obtain sulfomethylated magnesium lignosulfonate-Ce 6;
and 4, step 4: mixing epigallocatechin gallate and the sulfomethylated magnesium lignosulfonate-Ce 6 in the molar mass ratio of 1: 5 under stirring to form micelles, and pouring the micelles into a 1000D dialysis bag for dialysis to obtain the lignin functional material with the synergetic chemical and photodynamic functions.
Wherein the mass ratio of the sulfomethylated magnesium lignosulfonate taken in the step 3 to the photosensitizer Ce6 taken in the step 2 is 2: 1.
Example 2:
the preparation process of the synergistic chemical and photodynamic lignin functional material comprises the following specific steps:
step 1: weighing a certain amount of alkali lignin, adding water (with the lignin concentration of 1 wt%) and uniformly stirring, adjusting the pH value to 10, heating to 80 ℃, slowly adding 30% formaldehyde solution, reacting at the temperature for 2.5 hours, heating to 130 ℃ after the time is over, slowly adding 25% magnesium sulfite hexahydrate, reacting at the temperature for 3 hours, and cooling and collecting after the reaction is over to obtain sulfomethylated magnesium lignosulfonate;
step 2: dissolving a certain amount of photosensitizer Ce6 in dimethyl sulfoxide, adding 1-ethyl- (3-dimethylaminopropyl) -carbonyldiimine hydrochloride and 4-dimethylaminopyridine, and stirring to react for 6 hours to prepare a solution containing the photosensitizer and a catalyst;
and step 3: dissolving the sulfomethylated magnesium lignosulfonate prepared in the step 1 in water, slowly adding the dissolved solution prepared in the step 2, continuously stirring for 18 hours, pouring the solution into a 1000D dialysis bag for dialysis, and then freeze-drying to obtain sulfomethylated magnesium lignosulfonate-Ce 6;
and 4, step 4: mixing epigallocatechin gallate and the sulfomethylated magnesium lignosulfonate-Ce 6 in the molar mass ratio of 1: 10 under stirring to form micelles, and pouring the micelles into a 1000D dialysis bag for dialysis to obtain the lignin functional material with the synergetic chemical and photodynamic functions.
Wherein the mass ratio of the sulfomethylated magnesium lignosulfonate taken in the step 3 to the photosensitizer Ce6 taken in the step 2 is 3: 1.
Example 3:
the preparation process and application of the synergistic chemical and photodynamic lignin functional material comprise the following specific steps:
step 1: weighing a certain amount of alkali lignin, adding water (with the lignin concentration of 1 wt%) and uniformly stirring, adjusting the pH value to 10, heating to 82 ℃, slowly adding 35% formaldehyde solution, reacting at the temperature for 3 hours, heating to 140 ℃ after the time is over, slowly adding 30% magnesium sulfite hexahydrate, reacting at the temperature for 3.5 hours, and cooling and collecting after the reaction is over to obtain sulfomethylated magnesium lignosulfonate;
step 2: dissolving a certain amount of photosensitizer Ce6 in dimethyl sulfoxide, adding 1-ethyl- (3-dimethylaminopropyl) -carbonyldiimine hydrochloride and 4-dimethylaminopyridine, and stirring to react for 7 hours to prepare a solution containing the photosensitizer and a catalyst;
and step 3: dissolving the sulfomethylated magnesium lignosulfonate prepared in the step 1 in water, slowly adding the dissolved solution prepared in the step 2, continuously stirring for 20 hours, pouring the solution into a 1000D dialysis bag for dialysis, and then freeze-drying to obtain sulfomethylated magnesium lignosulfonate-Ce 6;
and 4, step 4: mixing epigallocatechin gallate and the sulfomethylated magnesium lignosulfonate-Ce 6 in the molar mass ratio of 1: 25 under stirring to form micelles, and pouring the micelles into a 1000D dialysis bag for dialysis to obtain the lignin functional material with the synergetic chemical and photodynamic functions.
Wherein the mass ratio of the sulfomethylated magnesium lignosulfonate taken in the step 3 to the photosensitizer Ce6 taken in the step 2 is 4: 1.
Claims (3)
1. A preparation process and application of a synergistic chemical and photodynamic lignin functional material are characterized by sequentially comprising the following steps:
step 1: weighing a certain amount of alkali lignin, adding water (with the lignin concentration of 1 wt%) and uniformly stirring, adjusting the pH value to 9-10, heating to 75-85 ℃, slowly adding 20-40% of formaldehyde solution, reacting at the temperature for 2-3 hours, heating to 100-150 ℃ after the time is over, slowly adding 20-30% of magnesium sulfite hexahydrate, reacting at the temperature for 2-4 hours, cooling and collecting after the reaction is over to obtain sulfomethylated magnesium lignosulfonate;
step 2: dissolving a certain amount of photosensitizer Ce6 in dimethyl sulfoxide, adding 1-ethyl- (3-dimethylaminopropyl) -carbonyldiimine hydrochloride and 4-dimethylaminopyridine, and stirring to react for 4-8 hours to prepare a solution containing the photosensitizer and a catalyst;
and step 3: dissolving the sulfomethylated magnesium lignosulfonate prepared in the step 1 in water, slowly adding the sulfomethylated magnesium lignosulfonate into the solution prepared in the step 2, continuously stirring for 12-24 hours, pouring the solution into a 1000D dialysis bag for dialysis, and then freeze-drying to obtain sulfomethylated magnesium lignosulfonate-Ce 6;
and 4, step 4: mixing epigallocatechin gallate and the sulfomethylated magnesium lignosulfonate-Ce 6 in the molar mass ratio of 1: 2-1: 50 under stirring to form micelles, and pouring the micelles into a 1000D dialysis bag for dialysis to obtain the lignin functional material with the synergetic chemical and photodynamic functions.
2. The preparation process of the lignin functional material according to claim 1, wherein the mass ratio of sulfomethylated magnesium lignosulfonate taken in the step 3 to the photosensitizer Ce6 taken in the step 2 is 2: 1-4: 1.
3. Use of the lignin functional material prepared according to claim 1 for biomedical wound healing, characterized by accidental or post-operative wounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202010063857.3A CN111150845A (en) | 2020-01-20 | 2020-01-20 | Preparation process and application of synergistic chemical and photodynamic lignin functional material |
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| CN202010063857.3A CN111150845A (en) | 2020-01-20 | 2020-01-20 | Preparation process and application of synergistic chemical and photodynamic lignin functional material |
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| CN111150845A true CN111150845A (en) | 2020-05-15 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102585940A (en) * | 2012-02-29 | 2012-07-18 | 福州大学 | Sulfomethylated alkali lignin-formaldehyde-sulfonated acetone polymer coal water slurry additive |
| CN104194002A (en) * | 2014-08-20 | 2014-12-10 | 华南理工大学 | High-sulfonation-degree lignosulfonate containing alkyl sulfonic acid, and preparation method and application thereof |
| WO2017196961A1 (en) * | 2016-05-10 | 2017-11-16 | North Carolina State University | Photodynamic compositions, methods of making, and uses thereof |
| CN108892743A (en) * | 2018-05-28 | 2018-11-27 | 南京工业大学 | For the nanometric photosensitizer of light power antibacterial, preparation method and application |
-
2020
- 2020-01-20 CN CN202010063857.3A patent/CN111150845A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102585940A (en) * | 2012-02-29 | 2012-07-18 | 福州大学 | Sulfomethylated alkali lignin-formaldehyde-sulfonated acetone polymer coal water slurry additive |
| CN104194002A (en) * | 2014-08-20 | 2014-12-10 | 华南理工大学 | High-sulfonation-degree lignosulfonate containing alkyl sulfonic acid, and preparation method and application thereof |
| WO2017196961A1 (en) * | 2016-05-10 | 2017-11-16 | North Carolina State University | Photodynamic compositions, methods of making, and uses thereof |
| CN108892743A (en) * | 2018-05-28 | 2018-11-27 | 南京工业大学 | For the nanometric photosensitizer of light power antibacterial, preparation method and application |
Non-Patent Citations (3)
| Title |
|---|
| 刘学等: "自然启发的设计用于光动力治疗的单线态氧可降解的木质素基纳米平台的开发", 《中国化学会第一届全国纤维素学术研讨会论文集》 * |
| 张志鸣等: "高温磺甲基化碱木质素染料分散剂的制备及性能", 《精细化工》 * |
| 申羽佳等: "表没食子儿茶素-3•没食子酸酯抑制小鼠皮肤外伤愈合组织基质金属蛋白酶1的表达", 《解剖学报》 * |
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Application publication date: 20200515 |