US20220110905A1 - Efficient anti-bacterial hydroxy acid ester oligomer - Google Patents

Efficient anti-bacterial hydroxy acid ester oligomer Download PDF

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US20220110905A1
US20220110905A1 US17/510,375 US202117510375A US2022110905A1 US 20220110905 A1 US20220110905 A1 US 20220110905A1 US 202117510375 A US202117510375 A US 202117510375A US 2022110905 A1 US2022110905 A1 US 2022110905A1
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bacterial
hydroxy acid
present
hydroxybutyrate
ester
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Xuejun Chen
Guomin Zhou
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Zhejiang Enmat Biological Technology Co Ltd
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Zhejiang Enmat Biological Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • C07C69/68—Lactic acid esters
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to a technical field of biomedicine, and more particularly to an efficient anti-bacterial hydroxy acid ester oligomer.
  • Anti-bacterial agents refer to substances which keep the growth or reproduction of certain microorganisms (bacteria, fungi, yeasts, algae, viruses, etc.) below a certain level within a certain period of time. Anti-bacterial agents are widely used in textiles, plastics, detergents, medical supplies and other fields.
  • Cibi patent CN110452115A disclosed a poly-3-hydroxybutyrate oligomer, which is used to prepare anti-bacterial materials.
  • the minimum inhibitory concentration (MIC, unit mg/mL) is as follows:
  • the anti-bacterial activity of the above-mentioned oligomers is not high enough to meet the growing performance requirements for anti-bacterial products; and water solubility of the above-mentioned oligomers is not adjustable, resulting in a narrow application range.
  • the raw materials used in the synthesis process are expensive and are not biological-based material butyrolactone. Toxic catalysts and solvents are also used, resulting in complicated post-treatment processes.
  • bacteria Because bacteria have a highly organized cell membrane structure, they can effectively resist the combination and penetration of foreign invading molecules. Therefore, rational design of the anti-bacterial agents that effectively penetrate and destroy bacterial cell membranes is of great significance.
  • the present invention is based on long-term research, which shows that the use of the synergistic effect of the end groups and chain lengths of hydroxy acid ester oligomers can effectively improve the efficiency of the anti-bacterial agent during penetrating and destroying bacterial cell membranes, thereby achieving high anti-bacterial efficiency, and further achieving controllable water solubility of the anti-bacterial agent.
  • an object of the present invention is to provide an efficient anti-bacterial substance R-( ⁇ )-hydroxy acid ester oligomer.
  • the anti-bacterial substance R-( ⁇ )-hydroxy acid ester oligomer of the present invention has a pH value of nearly neutral, and has a general structural formula (I):
  • n is a natural number of 1-8;
  • R 1 is a C 1 -C 5 alkyl group;
  • R 2 is a C 2 -C 8 alkyl group;
  • m is a natural number of 0-3.
  • n is a natural number of 1-8, which means a degree of polymerization DP is 1-8;
  • R 1 is a C 1 -C 5 alkyl group, preferably a C 1 -C 2 alkyl group;
  • R 2 is a C 2 -C 8 alkyl group, preferably C 5 -C 6 alkyl group;
  • m is a natural number of 0-3, preferably m is 0 or 1.
  • a clogP value of the efficient anti-bacterial hydroxy acid ester oligomer is 1.5-3.0; more preferably 2.0-2.5.
  • the efficient anti-bacterial hydroxy acid ester oligomer has a general structural formula (II) or (III):
  • R 1 is the C 1 -C 5 alkyl group
  • R 2 is a C 2 -C 3 alkyl group
  • m 0-3
  • the R-( ⁇ )-hydroxy acid ester oligomer is a water-soluble substance.
  • R-( ⁇ )-hydroxy acid ester oligomer is a water-insoluble substance which is soluble in a variety of organic solvents (such as ethanol, n-butanol, dimethyl sulfoxide, acetone, ether).
  • the R-( ⁇ )-hydroxy acid ester oligomer is a water-insoluble substance which is soluble in a variety of organic solvents (such as ethanol, n-butanol, dimethyl sulfoxide, acetone, ether).
  • the water-soluble substance R-( ⁇ )-hydroxy acid ester oligomer has a general structural formula (IV):
  • n 2-3.
  • the water-insoluble substance R-( ⁇ )-hydroxy acid ester oligomer having a general structural formula (V):
  • the present invention rationally designs the end group and chain length structure of the substance of formula (I), and controls its clogP value, so that the substance of formula (I) of the present invention reaches an appropriate size, which maximizes the ability of the substance of formula (I) to penetrate into the bacteria and destroy the bacterial cell membrane, thereby achieving high anti-bacterial efficiency.
  • the present invention regulates the hydrophilicity and hydrophobicity of the R-( ⁇ )-hydroxy acid ester oligomer to obtain a bio-based anti-bacterial agent with controllable water solubility, which broadens application range such as food, medicine, and cosmetics.
  • a bio-based anti-bacterial agent with controllable water solubility, which broadens application range such as food, medicine, and cosmetics.
  • anti-bacterial agents with good water solubility convenient use and uniform dispersion of substances in water are required
  • the water-soluble hydroxy acid ester oligomer can better satisfy the utilization needs.
  • coatings, fibers, plastics, building materials and other fields require water-resistant anti-bacterial agents to ensure a long-lasting anti-bacterial effect, only water-insoluble hydroxy acid ester oligomer can meet the demands.
  • the raw materials used in the present invention are all bio-based raw ones, which are convenient and easy to obtain; toxic catalysts and solvents are avoided in the synthesis process, which means no complicated post-processing is needed, and the catalyst can be recycled.
  • the present invention is conducive to scaling up and producing, and is also conducive to meeting environmental protection requirements and reducing production costs.
  • FIG. 1 is a mass spectrometry result of a water-soluble R-( ⁇ )-3-hydroxybutyrate ethyl ester oligomer according to embodiment 1-1;
  • FIG. 2 is a mass spectrometry result of a water-insoluble R-( ⁇ )-3-hydroxybutyrate ethyl ester oligomer embodiment 1-2;
  • FIG. 3 is a nuclear magnetic spectrum of R-( ⁇ )-3-hydroxybutyrate hexyl ester.
  • FIG. 4 is a nuclear magnetic spectrum of R-( ⁇ )-2-hydroxypropionic hexyl ester.
  • catalyst types and reaction temperatures are changed on the basis of the embodiment 1-1, while other conditions are the same as those of the embodiment 1-1 to obtain the R-( ⁇ )-3-hydroxybutyrate ethyl ester oligomers with different polymerization degrees.
  • FIG. 1 is a mass spectrometry result of a water-soluble R-( ⁇ )-3-hydroxybutyrate ethyl ester oligomer according to embodiment 1-1.
  • FIG. 2 is a mass spectrometry result of a water-insoluble R-( ⁇ )-3-hydroxybutyrate ethyl ester oligomer embodiment 1-2.
  • the embodiments 2-2 to 2-8 change methanol into ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol and 1-octanol respectively, while other conditions are the same as those of the embodiment 2-1, so as to obtain R-( ⁇ )-3-hydroxybutyrate ethyl ester (yield 95%), R-( ⁇ )-3-hydroxybutyrate propyl ester (yield 93%), R-( ⁇ )-3-hydroxybutyrate butyl ester (yield 92%), R-( ⁇ )-3-hydroxybutyrate pentyl ester (yield 94%), R-( ⁇ )-3-hydroxybutyrate hexyl ester (yield 96%), R-( ⁇ )-3-hydroxybutyrate heptyl ester (yield 95%), and R-( ⁇ )-3-hydroxybutyrate octyl ester
  • FIG. 3 is a nuclear magnetic spectrum of R-( ⁇ )-3-hydroxybutyrate hexyl ester.
  • FIG. 4 is a nuclear magnetic spectrum of R-( ⁇ )-2-hydroxypropionic hexyl ester.
  • R-( ⁇ )-3-hydroxybutyric acid in the embodiment 2-1 is changed to R-( ⁇ )-lactic acid, and methanol is changed to 1-hexanol.
  • Other conditions are the same as those of the embodiment 2-1 to obtain R-( ⁇ )-lactate hexyl ester, wherein a yield is 94%, and a gas phase detection purity is about 100%.
  • the embodiments 3-2 and 3-3 change 1-hexanol to ethanol and 1-heptanol respectively, and other conditions are the same as those in the embodiment 3-1 to obtain R-( ⁇ )-lactate ethyl ester and R-( ⁇ )-lactate heptyl ester, wherein gas phase detection purity is about 100%.
  • R-( ⁇ )-lactic acid is changed to R-( ⁇ )-2-hydroxypropionic acid to obtain R-( ⁇ )-2-hydroxypropionic hexyl ester, wherein a gas phase detection purity is about 100%.
  • the data is theoretically estimated by using the ChemDraw Ultra 13.0 program; the basis and method of the anti-bacterial test method: Chinese Ministry of Health 2002 “Disinfection Technical Specifications”-2.1.8.4 Minimum Inhibitory Concentration Test (Nutrition Broth Method), the strain is Escherichia coli ATCC25922.

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  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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CN202111137059.1A CN113913474A (zh) 2020-10-26 2021-09-27 一种高效抗菌的羟基酸酯低聚物
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CN112359071A (zh) * 2020-10-26 2021-02-12 浙江英玛特生物科技有限公司 一种水溶性可控抗菌物质及合成工艺
CN113200849A (zh) * 2021-04-27 2021-08-03 香港理工大学 合成的3-羟基丁酸酯低聚物或寡聚物的分离纯化方法及其在抗菌抗病毒制品中的应用
CN115182161A (zh) * 2022-07-08 2022-10-14 浙江英玛特生物科技有限公司 采用scf技术将羟基酸酯低聚物固着在纤维表面的方法及抗菌抗病毒产品
CN115323774A (zh) * 2022-08-01 2022-11-11 浙江英玛特生物科技有限公司 基于饱和羟基酸酯低聚物scf体系的抗菌抗病毒纤维的制备方法及其产品
CN115627629A (zh) * 2022-09-08 2023-01-20 浙江英玛特生物科技有限公司 利用羟基酸酯低聚物复配防污剂对渔网绳缆的防污加工方法及其产品
CN115652626A (zh) * 2022-09-08 2023-01-31 浙江英玛特生物科技有限公司 基于scf技术的水溶性纤维抗菌化加工方法及其产品
DE102022124904A1 (de) 2022-09-28 2024-03-28 Tesa Se Aushärtbare Haftklebemasse mit verbesserten Klebeeigenschaften

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JP2022070249A (ja) 2022-05-12
CN113913474A (zh) 2022-01-11
CN112359071A (zh) 2021-02-12
EP3988536B1 (en) 2024-10-16
JP7432089B2 (ja) 2024-02-16
WO2022088286A1 (zh) 2022-05-05
US20240082201A1 (en) 2024-03-14
EP4292590A3 (en) 2024-03-13
EP4292590A2 (en) 2023-12-20
CN116178159A (zh) 2023-05-30

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