WO2017026044A1 - Détecteur de glucose et procédé de détection de glucose - Google Patents

Détecteur de glucose et procédé de détection de glucose Download PDF

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WO2017026044A1
WO2017026044A1 PCT/JP2015/072700 JP2015072700W WO2017026044A1 WO 2017026044 A1 WO2017026044 A1 WO 2017026044A1 JP 2015072700 W JP2015072700 W JP 2015072700W WO 2017026044 A1 WO2017026044 A1 WO 2017026044A1
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glucose
monomer
boronic acid
turbidity
hydrophilic
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PCT/JP2015/072700
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English (en)
Japanese (ja)
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桂史 塚本
モウアッド ラムラニ
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株式会社メニコン
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Priority to PCT/JP2015/072700 priority Critical patent/WO2017026044A1/fr
Priority to JP2016571444A priority patent/JP6194127B2/ja
Publication of WO2017026044A1 publication Critical patent/WO2017026044A1/fr

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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/483—Physical analysis of biological material
    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04—Contact lenses for the eyes

Definitions

  • the present invention relates to a glucose detector and a glucose detection method.
  • a glucose detector for example, a sensor for detecting a cis-type diol-containing specimen, which has a holographic element containing a boronic acid group and changes optical properties by reacting with glucose is proposed.
  • a glucose detector a contact lens having a holographic element containing a boronic acid group and reacting with glucose to change optical characteristics has been proposed (for example, see Patent Document 2).
  • an optical change is detected as a change in peak wavelength using a visible light source.
  • the present invention has been made in view of such problems, and a glucose detector and a glucose detection method capable of detecting glucose by effectively utilizing the action of a boronic acid group and glucose by changing the physical properties of the polymer.
  • the main purpose is to provide
  • the present inventors have used a polymer composed of a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer, and the action of a boronic acid group and glucose.
  • a polymer composed of a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer By combining the hydrophilic and hydrophobic balance of the whole polymer, it was found that glucose can be detected by effectively utilizing the action of boronic acid groups and glucose by changing the physical properties of the polymer, and the present invention has been completed.
  • the glucose detector of the present invention is It includes a polymer composed of at least a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer represented by the chemical formula (1), and the turbidity of the polymer changes depending on the amount of glucose present. .
  • the glucose detection method of the present invention includes Using the glucose detector comprising a polymer composed of at least a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer represented by the chemical formula (1), the turbidity of which varies depending on the amount of glucose present. Glucose is detected based on the change in turbidity.
  • FIG. 1 is a scheme showing an example of an equilibrium relationship between a phenylboronic acid group and glucose. Regarding the binding and dissociation of the boronic acid group and glucose, there is the equilibrium relationship of FIG. 1, and the boron atom of the boronic acid group is most likely to bind to glucose when taking a tetrahedral structure (FIG. 1 (2)). (See Non-Patent Document 1: Tetrahedron 2002, 58, 5291-5300, for example).
  • the hydrophilic monomer and the hydrophobic monomer in the polymer chain are combined. It is presumed that the side chain affects the boron atom of the boronic acid group and can be stabilized with a tetrahedral structure.
  • the hydrophilic-hydrophobic balance appropriately so that the hydrophilic-hydrophobic change of the polymer chain accompanying the binding and dissociation of boronic acid group and glucose affects the hydrophilic-hydrophobic property of the whole polymer, It is presumed that the detection sensitivity of the action of acid groups and glucose can be further increased.
  • the glucose detector of the present invention does not require special processing (formation of a hologram or the like) after polymer preparation, it can be prepared more easily, leading to efficiency during mass production.
  • the glucose detector of the present invention comprises a polymer composed of at least (A) a hydrophilic monomer, (B) a hydrophobic monomer, and (C) a boronic acid-containing monomer represented by chemical formula (1).
  • the hydrophilic monomer means a monomer having an octanol / water-partition coefficient (LogPow value) of 1.0 or less
  • the hydrophobic monomer means an octanol / water-partition coefficient (LogPow value) of 1.0.
  • LogPow value octanol / water-partition coefficient
  • logPow value octanol / water-partition coefficient
  • the hydrophilic monomer is a monomer having a LogPow value of 1.0 or less, but the LogPow value is preferably ⁇ 1.0 or more, more preferably ⁇ 0.8 or more. Further, the LogPow value of the hydrophilic monomer is preferably 0.8 or less, and more preferably 0.6 or less.
  • the hydrophilic monomer has, for example, one or more of nitrogen-containing groups (for example, amino groups) and hydroxy groups as hydrophilic groups, and one or more of acryloyl group, methacryloyl group, vinyl group and the like as bonding groups. It may be included.
  • hydrophilic monomer examples include acrylamide (AA), 2-hydroxyethyl acrylate (HEA), 2-hydroxyethyl methacrylate, N, N′-dimethylacrylamide (DMAA), N-vinyl-2-pyrrolidone, 1- 1 or more selected from methyl-3-methylene-2-pyrrolidinone and the like.
  • AA acrylamide
  • HAA 2-hydroxyethyl acrylate
  • DMAA N′-dimethylacrylamide
  • N-vinyl-2-pyrrolidone 1- 1 or more selected from methyl-3-methylene-2-pyrrolidinone and the like.
  • AA, HEA, DMAA and the like are preferable.
  • the hydrophobic monomer is a monomer having a LogPow value exceeding 1.0, but the LogPow value is preferably 1.1 or more, and more preferably 1.2 or more. Further, the LogPow value of the hydrophobic monomer is preferably 5.0 or less, and more preferably 3.0 or less.
  • the hydrophobic monomer may have, for example, one or more of hydrophobic alkyl group, alkylene group, phenyl group, and the like, and one or more of acryloyl group, methacryloyl group, vinyl group, and the like as a bonding group. Good. Examples of the hydrophobic monomer include one or more selected from ethyl acrylate (EA), N-phenylacrylamide (NPA), and the like.
  • Examples of the boronic acid-containing monomer include those represented by chemical formula (1). Moreover, as a boronic acid containing monomer, it is good also as a monomer of Chemical formula (2), for example. Alternatively, examples of the boronic acid-containing monomer include Z-acrylamide phenylboronic acid (Z-APB: where Z is 2 to 4) represented by chemical formula (3).
  • the content Mi of the hydrophilic monomer is preferably in the range of 30 (mol%) to 80 (mol%), for example.
  • the content Mo of the hydrophobic monomer is preferably in the range of, for example, 10 (mol%) to 60 (mol%).
  • the content Mb of the boronic acid-containing monomer is preferably in the range of 4 (mol%) to 30 (mol%).
  • each content rate shall say the content rate with respect to the total amount (mol) of a hydrophilic monomer, a hydrophobic monomer, and a boronic acid containing monomer.
  • the molar ratio Mi / Mb which is the content Mi (mol%) of the hydrophilic monomer with respect to the content Mb (mol%) of the boronic acid-containing monomer, is preferably 1 or more, and is preferably 3.2 or more. Is more preferable. Further, the molar ratio Mi / Mb is preferably 10 or less, and more preferably 7.6 or less. When the molar ratio Mi / Mb is in the range of 1 to 10, the change in turbidity with respect to the amount of glucose present is clear and preferable.
  • the molar ratio Mo / Mb which is the content Mo (mol%) of the hydrophobic monomer with respect to the content Mb (mol%) of the boronic acid-containing monomer, is preferably 1 or more, and is 1.5 or more. Is more preferable. Further, the molar ratio Mo / Mb is preferably 15 or less, and more preferably 11.4 or less. When the molar ratio Mo / Mb is in the range of 1 to 15, the change in turbidity with respect to the amount of glucose present is clear and preferable.
  • the hydrophilic monomer is acrylamide
  • the molar ratio Mi / Mb is in the range of 3.2 to 7.6 and the molar ratio Mo / Mb is in the range of 5 to 11.4.
  • the hydrophilic monomer is 2-hydroxyethyl acrylate
  • the molar ratio Mi / Mb is in the range of 5 to 7.5
  • the molar ratio Mo / Mb is in the range of 1.5 to 4 in particular.
  • the hydrophilic monomer is N, N-dimethylacrylamide
  • the molar ratio Mi / Mb is in the range of 4.5 to 5
  • the molar ratio Mo / Mb is in the range of 4 to 4.5. Particularly preferred.
  • the hydrophilic / hydrophobic balance value HHB is preferably 25 or more, and more preferably 33 or more. Further, the hydrophilic / hydrophobic balance value HHB is preferably 75 or less, more preferably 69 or less. When the hydrophilic / hydrophobic balance value HHB is in the range of 25 to 75, the change in turbidity with respect to the amount of glucose is clear and preferable.
  • the hydrophilic / hydrophobic balance value HHB is determined by the distribution coefficient Li and content ratio Mi (mol%) of the hydrophilic monomer, the distribution coefficient Lo and content ratio Mo (mol%) of the hydrophobic monomer, and the distribution coefficient Lb of the boronic acid-containing monomer.
  • the content Mb (mol%) is a value obtained using the mathematical formula (1).
  • the partition coefficient Li of the hydrophilic monomer is the octanol / water-partition coefficient (LogPow value) of the hydrophilic monomer
  • the partition coefficient Lo of the hydrophobic monomer is the octanol / water-partition coefficient (LogPow value) of the hydrophobic monomer.
  • the partition coefficient Lb of the boronic acid-containing monomer is the octanol / water-partition coefficient (LogPow value) of the boronic acid-containing monomer.
  • the LogPow value for example, a calculated value using software such as ALGOPS which is online software can be used. Moreover, the experimental value obtained from well-known literature can also be used.
  • this glucose detector contains acrylamide (AA) as a hydrophilic monomer, ethyl acrylate (EA) as a hydrophobic monomer, and Z-phenylacrylamide boronic acid (Z-APB) as a boronic acid-containing monomer
  • AA acrylamide
  • EA ethyl acrylate
  • Z-APB Z-phenylacrylamide boronic acid
  • the molar ratio is Mi / Mb is preferably in the range of 3.2 to 7.6, and the molar ratio Mo / Mb is preferably in the range of 5 to 11.4.
  • the hydrophilic / hydrophobic balance value HHB is preferably in the range of 41 to 56.
  • this glucose detector contains 2-hydroxyethyl acrylate (HEA) as a hydrophilic monomer, ethyl acrylate (EA) as a hydrophobic monomer, and Z-phenylacrylamide boronic acid (Z-APB) as a boronic acid-containing monomer
  • HAA 2-hydroxyethyl acrylate
  • EA ethyl acrylate
  • Z-APB Z-phenylacrylamide boronic acid
  • the molar ratio Mi / Mb is preferably in the range of 5 to 7.5
  • the molar ratio Mo / Mb is preferably in the range of 1.5 to 4.
  • the hydrophilic / hydrophobic balance value HHB is preferably in the range of 33 to 57.
  • This glucose detector contains N, N-dimethylacrylamide (DMAA) as a hydrophilic monomer, ethyl acrylate (EA) as a hydrophobic monomer, and Z-phenylacrylamide boronic acid (Z-APB) as a boronic acid-containing monomer.
  • DMAA N, N-dimethylacrylamide
  • EA ethyl acrylate
  • Z-APB Z-phenylacrylamide boronic acid
  • the molar ratio Mi / Mb is preferably in the range of 4.5 to 5
  • the molar ratio Mo / Mb is preferably in the range of 4 to 4.5.
  • the hydrophilic / hydrophobic balance value HHB is preferably in the range of 63 to 69.
  • the turbidity of the polymer changes depending on the amount of glucose due to the action of the boronic acid group of the boronic acid-containing monomer and glucose.
  • the turbidity change of the glucose detector can be visually determined, for example, colorless and transparent, partially turbid, or entirely turbid.
  • the turbidity T is a value obtained by imaging a glucose detector and performing image processing. The turbidity T is obtained as follows. First, the glucose detector after being immersed in a predetermined solution is imaged, and ImageJ which is image processing software in the public domain is used for the captured image, and the gray value G of the captured image is measured.
  • the turbidity T is obtained by Equation (2), where Gs is the gray value of the glucose detector and Gb is the gray value of the background on which the sample is placed.
  • Gs is the gray value of the glucose detector
  • Gb is the gray value of the background on which the sample is placed.
  • the glucose detector can use turbidity change (Turbidity Change Ratio: TCR) due to the amount of glucose as an index.
  • TCR turbidity Change Ratio
  • the turbidity change TCR is, for example, when the turbidity at the first concentration of glucose is T (+), and the turbidity at the second concentration lower than the first concentration is T ( ⁇ ).
  • the turbidity T (+) is a value in a 1M glucose phosphate buffer solution as a first concentration
  • the turbidity T ( ⁇ ) is a value in a phosphate buffer solution as a second concentration.
  • the turbidity change TCR may be obtained.
  • the turbidity change TCR is preferably 1.3 or more, more preferably 1.5 or more, and further preferably 2.0 or more.
  • the phosphate buffer solution was disodium hydrogen phosphate dodecahydrate 0.6 w / v%, sodium dihydrogen phosphate dihydrate 0.05 w / v%, sodium chloride 0.83 w / v% Consists of
  • the polymer contained in the glucose detector may be a hydrogel.
  • the glucose detector may be incorporated in an ophthalmic member, and the ophthalmic member may be a contact lens.
  • the glucose concentration contained in tear fluid has a correlation with blood glucose level (see Non-Patent Document 2: Current Eye Research, 2006, Vol. 31, No. 11, 895-901).
  • the glucose concentration contained in saliva has a correlation with the blood glucose level (see Non-Patent Document 3: Journal of Biomedicine and Biotecnology, Vol2009, Article ID430426). Therefore, with this glucose detector, it is possible to determine the blood glucose level from, for example, tears or saliva. For this reason, the glucose detection body of this invention can grasp
  • the glucose detector of the present invention may further contain a cross-linking agent.
  • the crosslinking agent include compounds having a plurality of polymerization groups among acryloyl group, methacryloyl group, vinyl group and allyl group.
  • the glucose detector of the present invention may further contain a polymerizable dye, may further contain an ultraviolet absorber, may further contain a photopolymerization initiator, and may be photosensitized. An agent may be further included.
  • the glucose detector may include non-polymerizable additives such as a water-soluble organic solvent, a surfactant, a refreshing agent, and a thickening agent.
  • the ophthalmic member incorporating the glucose detector is not particularly limited as long as the change in turbidity of the glucose detector can be confirmed, but a contact lens is preferable.
  • the contact lens incorporating the glucose detector is preferably a conventionally known contact lens such as an oxygen permeable hard contact lens, a hydrogel lens, or a silicone hydrogel lens, and more preferably a hydrogel lens. It is also possible to combine with a contact lens having a colored portion as typified by a fashionable contact lens so that the change in turbidity can be confirmed more effectively.
  • the oxygen permeable hard contact lens is a non-water-containing contact lens containing at least one or more of fluorine-containing methacrylate compound, silicon-containing methacrylate compound, silicon-containing styrene compound and the like as a main component.
  • the hydrogel lens is a hydrous contact lens containing at least one or more of (meth) acrylate compound, vinyl compound and the like as main components, and more specifically, 2-hydroxyethyl methacrylate, methacrylic acid, A contact lens comprising at least one or more of DMAA, N-vinyl-2-pyrrolidone, ethylene glycol dimethacrylate, glycerol methacrylate and the like as main components.
  • the silicone hydrogel lens is a hydrous contact lens containing at least one or more of silicon-containing (meth) acrylate compounds, silicon-containing macromonomers and the like as main components.
  • the glucose detector of the present invention can be directly used as a lens shape.
  • the glucose detector of the present invention prepared in advance can be incorporated at the time of manufacturing the contact lens.
  • the glucose detector of the present invention can be prepared and incorporated on a contact lens prepared in advance.
  • the monomer composition containing the photopolymerization initiator is filled in a mold corresponding to the shape of the desired ophthalmic lens material, and then the mold composition is irradiated with light.
  • Polymerization may be performed by irradiation.
  • the material of the mold used for polymerization by light irradiation is not particularly limited as long as it is a material that can transmit light necessary for polymerization and curing, and general-purpose resins such as polypropylene, polystyrene, nylon, and polyester are preferable. It may be. By molding and processing these materials, a mold having a desired shape can be obtained.
  • the glucose detection method of the present invention includes a polymer that is composed of at least a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer represented by the chemical formula (1), and whose turbidity changes depending on the amount of glucose present.
  • a glucose detector is used to detect glucose based on a change in turbidity of the polymer. This turbidity change of the polymer may be caused by the action of the boronic acid group of the boronic acid-containing monomer and glucose.
  • the glucose can be detected by immersing the above-described glucose detector in a solution to be detected and measuring the turbidity T. In addition, turbidity can also be confirmed visually.
  • the glucose concentration and content can be detected in addition to the presence or absence of glucose by the turbidity T or turbidity change TCR described above. Further, for example, not only visual observation of turbidity but also a method of quantifying glucose by polymerizing the polymer of the present invention on an electrode and detecting an electrical signal (conductivity, etc.) can be employed.
  • the action of the boronic acid group and glucose can be effectively utilized by changing the physical properties of the polymer, and glucose can be detected.
  • the reason why such an effect is obtained is that, for example, by combining a hydrophilic monomer, a hydrophobic monomer, and a boronic acid-containing monomer represented by the chemical formula (1) into a polymer, the hydrophilicity in the polymer chain can be obtained. It is presumed that the side chain of the monomer or hydrophobic monomer affects the boron atom of the boronic acid group and can be stabilized with a tetrahedral structure.
  • This glucose detector is preferably used for an ophthalmic member, for example, an ophthalmic lens such as a contact lens.
  • This compounded solution was poured into a mold and irradiated with ultraviolet light (UV, 365 nm) for 30 minutes at room temperature to be polymerized.
  • UV light UV, 365 nm
  • the polymer was taken out from the mold, cut into a circle with a diameter of 6 mm, and then immersed in ethanol to extract unpolymerized monomers and the solvent. Thereafter, the polymer was immersed in a phosphate buffer solution containing 1 M glucose for 12 hours or more, and a photograph of the polymer was taken. Thereafter, each polymer was transferred to a phosphate buffer solution, and a photograph of the polymer was taken again after 3-4 minutes.
  • UV light ultraviolet light
  • any one of the hydrophilic monomers AA, HEA, and DMAA, the hydrophobic monomer N-phenylacrylamide (NPA), and the boronic acid-containing monomer 3APB have an arbitrary mixing ratio (see Table 2). Except for the above, the same steps as in Experimental Example 1 were performed, and the obtained polymers were referred to as Experimental Examples 37 and 38. Note that the LogPow value of each monomer is 0.51 for 3APB, -0.65 for AA, 0.04 for HEA, 0.17 for DMAA, 0.17 for EA, according to the calculated value by the online software ALGOPS2.1. 1.24, NPA is 1.67.
  • Hydrophilic / hydrophobic balance value HHB is LogPow value of hydrophilic monomer Li, Hydromonomer content rate Mi (mol%), Hydrophobic monomer LogPow value Lo, Hydrophobic monomer content rate Mo (mol%)
  • the LogPow value of the boronic acid-containing monomer was Lb, and the content of the boronic acid-containing monomer was Mb (mol%), and the above formula (1) was used for calculation.
  • each content rate is a content rate with respect to the total amount (mol) of a hydrophilic monomer, a hydrophobic monomer, and a boronic acid containing monomer.
  • Turbidity Turbidity is measured using ImageJ, which is image processing software in the public domain, and the gray value is measured from the photograph to be measured, the gray value of the sample is Gs, and the gray value of the background where the sample is placed is Gb. Calculated according to (2).
  • T turbidity
  • TCR turbidity Change Ratio
  • Tables 1 and 2 also show the results of visual confirmation of turbidity T (+) and turbidity change TCR.
  • Turbidity T (+) is A (T ⁇ 1.2; visually colorless and transparent), B (1.2 ⁇ T ⁇ 1.5; turbidity that can be visually confirmed), C ( T>1.5; turbidity that can be clearly confirmed visually).
  • the turbidity change TCR is a turbidity change when immersed in a phosphate buffer solution containing 1 M glucose and then immersed in a phosphate buffer solution not containing glucose.
  • A (TCR ⁇ 2.0; change in turbidity that can be clearly confirmed visually)
  • B (1.2 ⁇ TCR ⁇ 2.0; change in turbidity that can be visually confirmed)
  • C (TCR ⁇ 1.2; It was evaluated as a change in turbidity that could hardly be confirmed visually.
  • the hydrophilic / hydrophobic balance value HHB was in the range of 25 to 75, more preferably in the range of 33 to 69.
  • the molar ratio Mi / Mb is preferably in the range of 3.2 to 7.6, and the molar ratio Mo / Mb is preferably in the range of 5 to 11.4.
  • the hydrophilic / hydrophobic balance value HHB was preferably in the range of 41 to 56.
  • the molar ratio Mi / Mb is preferably in the range of 5 to 7.5
  • the molar ratio Mo / Mb is preferably in the range of 1.5 to 4 and hydrophilic.
  • the hydrophobic balance value HHB was preferably in the range of 33 to 57.
  • the molar ratio Mi / Mb is preferably in the range of 4.5 to 5
  • the molar ratio Mo / Mb is preferably in the range of 4 to 4.5
  • the hydrophilic / hydrophobic balance value HHB is 63. A range of 69 or less was preferred.
  • Example 42 A polymer in which the polymer of the present invention was incorporated in a contact lens was produced, and this was designated as Experimental Example 42.
  • the polymer of Experimental Example 26 soaked in a phosphate buffer solution containing 1 M glucose was placed in the center of the lens mold, and 2 mol containing 2,2-methoxy-2-aminophenylacetophenone and MBA were added from above.
  • -A monomer solution of hydroxyethyl methacrylate (HEMA) was injected. Thereafter, ultraviolet light (UV, 365 nm) was irradiated at room temperature for 30 minutes for polymerization.
  • the contact lens was removed from the lens mold and immersed in a phosphate buffer solution containing 1M glucose.
  • T (+) was 1.2
  • T ( ⁇ ) was 3.7.
  • the turbidity change TCR was 3.1, and good glucose responsiveness was obtained in a contact lens mainly composed of HEMA.
  • the glucose detector of the present invention can be used in the field of detecting glucose and can be used for applications such as contact lenses.

Abstract

L'invention concerne un détecteur de glucose qui contient un polymère qui est constitué au moins d'un monomère hydrophile, d'un monomère hydrophobe et d'un monomère contenant de l'acide boronique. La turbidité du polymère est modifiée par l'action d'un groupe acide boronique du monomère contenant de l'acide boronique et du glucose, et le glucose est détecté sur la base de la modification de la turbidité. L'invention concerne également un procédé de détection de glucose qui utilise ce détecteur de glucose et détecte du glucose sur la base de modifications de la turbidité du polymère provoquées par l'action d'un groupe acide boronique sur le monomère contenant de l'acide boronique et du glucose.
PCT/JP2015/072700 2015-08-10 2015-08-10 Détecteur de glucose et procédé de détection de glucose WO2017026044A1 (fr)

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CN115746196A (zh) * 2022-11-15 2023-03-07 电子科技大学长三角研究院(湖州) 一种异丙基甲基丙烯酰胺-氟基苯硼酸共聚葡萄糖响应微凝胶的制备方法及其应用

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WO2019221135A1 (fr) * 2018-05-15 2019-11-21 大阪有機化学工業株式会社 Composition de résine durcissable
JPWO2019221135A1 (ja) * 2018-05-15 2021-06-17 大阪有機化学工業株式会社 硬化性樹脂組成物
JP7368350B2 (ja) 2018-05-15 2023-10-24 大阪有機化学工業株式会社 硬化性樹脂組成物
WO2021053586A1 (fr) * 2019-09-18 2021-03-25 Alcon Inc. Inserts oculaires d'hydrogel mou conditionnés par voie humide
US11931454B2 (en) 2019-09-18 2024-03-19 Alcon Inc. Wet-packed soft hydrogel ocular inserts
CN115746196A (zh) * 2022-11-15 2023-03-07 电子科技大学长三角研究院(湖州) 一种异丙基甲基丙烯酰胺-氟基苯硼酸共聚葡萄糖响应微凝胶的制备方法及其应用

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