WO2016088712A1 - Matériau formant un hydrogel - Google Patents

Matériau formant un hydrogel Download PDF

Info

Publication number
WO2016088712A1
WO2016088712A1 PCT/JP2015/083581 JP2015083581W WO2016088712A1 WO 2016088712 A1 WO2016088712 A1 WO 2016088712A1 JP 2015083581 W JP2015083581 W JP 2015083581W WO 2016088712 A1 WO2016088712 A1 WO 2016088712A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
hydrogel
forming material
formula
monopalmitin
Prior art date
Application number
PCT/JP2015/083581
Other languages
English (en)
Japanese (ja)
Inventor
松本　圭吾
Original Assignee
日産化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Priority to JP2016562445A priority Critical patent/JPWO2016088712A1/ja
Publication of WO2016088712A1 publication Critical patent/WO2016088712A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere

Definitions

  • the present invention relates to a hydrogel-forming material, and in particular, to a hydrogel-forming material that can form a hydrogel that can be re-formed even if it is made into a sol, and a hydrogel formed from the hydrogel-forming material.
  • Hydrogel is useful as a highly biocompatible gel because it uses water as a medium, and is used in a wide range of fields such as disposable diapers, cosmetics, and fragrances for daily necessities.
  • the conventional hydrogel includes a polymer gel formed by crosslinking a polymer chain to form a three-dimensional network structure, which forms a non-covalent bond with a medium such as water and swells.
  • the research on physical properties and development of applications of this polymer gel are based on natural polymer gels formed from polysaccharides such as agarose and proteins, and synthetic polymer gels such as acrylamide gels, in which polymer chains are crosslinked by chemical covalent bonds. Many have been made.
  • not only gels composed of the above-mentioned polymer compounds but also hydrogels composed of self-assembly of relatively low molecular weight organic compounds have been found and variously studied.
  • the low-molecular gelling agents that have been proposed so far are amphiphilic compounds in which a long-chain alkyl group, which is a hydrophobic part, and a hydrophilic part are combined.
  • the hydrophilic part is an amino acid (non-patent literature) 1), peptides (Patent Documents 1 and 2), sugars (Non-Patent Documents 2 and 3) or polyols (Non-Patent Document 4).
  • a low molecular gelling agent (Non-patent Document 5) utilizing the fact that a peptide composed of valine easily takes a ⁇ -sheet structure has been proposed.
  • the present invention has been made on the basis of the above circumstances, and the problem to be solved is to re-form the gel by allowing it to stand at room temperature even after the prepared hydrogel is made into a sol by shaking or the like. It is an object of the present invention to provide a hydrogel forming material.
  • the present inventors have found that when forming a hydrogel from a lipid peptide-type gelling agent comprising a low-molecular lipid peptide or a pharmaceutically usable salt thereof and water.
  • the present invention has found that by using a specific glycerin fatty acid ester, the resulting hydrogel can be re-formed by allowing it to stand at room temperature even after solification by shaking, etc. Was completed.
  • the present invention contains, as a first aspect, a lipid peptide-type gelling agent comprising at least one of a compound represented by the following formula (1) or a pharmaceutically usable salt thereof, water and monopalmitin.
  • the present invention relates to a hydrogel-forming material.
  • R 1 represents an aliphatic group having 9 to 23 carbon atoms
  • R 2 represents a hydrogen atom or an alkyl group having 1 or 2 carbon atoms as a branched chain having 1 to 4 carbon atoms.
  • R 3 represents a — (CH 2 ) n —X group, n represents a number of 1 to 4, and X represents an amino group, a guanidino group, a —CONH 2 group, or a nitrogen atom in the ring It represents a 5- or 6-membered cyclic group having 1 to 3 atoms, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)
  • R 2 represents a hydrogen atom, a methyl group, an i-propyl group, an i-butyl group or a sec-butyl group, and the hydrogel formation according to the first aspect or the second aspect Regarding materials.
  • R 3 represents a 4-aminobutyl group, a carbamoylmethyl group, a 2-carbamoylethyl group, a 4-imidazolmethyl group, or a 3-indolemethyl group.
  • the present invention relates to a hydrogel-forming material described in two aspects.
  • R 1 represents an aliphatic group having 11 to 23 carbon atoms
  • R 2 represents a hydrogen atom, a methyl group or an i-propyl group
  • R 3 represents 4-amino
  • the hydrogel-forming material according to the first aspect or the second aspect which represents a butyl group, a 4-imidazolemethyl group, or a 3-indolemethyl group.
  • the present invention relates to the hydrogel-forming material according to the fifth aspect, wherein R 2 represents a hydrogen atom and R 3 represents a 4-imidazolemethyl group in the formula (1).
  • hydrogel according to the seventh aspect wherein the hydrogel has a pH of 7 to 9.
  • the hydrogel-forming material of the present invention contains monopalmitin, it can form a gel again even when the hydrogel once formed is made into a sol state by shaking or the like and then allowed to stand at room temperature. Furthermore, since monopalmitin used is nonionic, the pH change of the obtained hydrogel is small.
  • the lipid peptide type gelling agent contained in the hydrogel-forming material of the present invention is a very safe artificial low molecular weight compound composed only of lipid and peptide, and monopalmitin is a general-purpose additive for foods. It is. That is, the hydrogel-forming material of the present invention has high biological safety, and is particularly useful in the above applications from the viewpoint of high safety required for cell culture substrates, medical materials, cosmetic materials, and the like. is there.
  • the hydrogel-forming material of the present invention is a material capable of forming a hydrogel by gelling water without using, for example, a conventionally proposed cross-linking agent required for the formation of a synthetic polymer gel. There is no problem of remaining unreacted substances such as unreacted crosslinking agent in the obtained hydrogel. Moreover, the hydrogel-forming material can form a hydrogel with an addition amount of the gelling agent of only about 20 mM, and has a low load when taken up in the environment or in vivo.
  • the hydrogel of this invention can be obtained by addition of a small amount of gelatinizers compared with the former as mentioned above, it can be said that it is a hydrogel with high safety
  • the present invention provides a hydrogel formation containing a lipid peptide type gelling agent comprising at least one of the compound represented by the formula (1) described in detail below or a pharmaceutically usable salt thereof, water and monopalmitin.
  • a lipid peptide type gelling agent comprising at least one of the compound represented by the formula (1) described in detail below or a pharmaceutically usable salt thereof, water and monopalmitin.
  • lipid peptide type gelling agent As the lipid peptide type gelling agent used in the present invention, a compound (lipid peptide) represented by the following formula (1) or a pharmaceutically usable salt thereof (a lipid part which is a hydrophobic part and a hydrophilic part) A low molecular compound having a peptide portion).
  • R 1 represents an aliphatic group having 9 to 23 carbon atoms, and preferably R 1 is a straight chain having 11 to 23 carbon atoms which may have 0 to 2 unsaturated bonds. An aliphatic group is desirable.
  • lipid moiety (acyl group) composed of R 1 and an adjacent carbonyl group examples include lauroyl group, dodecylcarbonyl group, myristoyl group, tetradecylcarbonyl group, palmitoyl group, margaroyl group, oleoyl group, and elideoyl group.
  • Linoleoyl group, stearoyl group, baccenoyl group, octadecylcarbonyl group, arachidyl group, eicosylcarbonyl group, behenoyl group, ercanoyl group, docosylcarbonyl group, lignoceyl group and nerbonoyl group, and the like are particularly preferable.
  • Examples include lauroyl group, myristoyl group, palmitoyl group, margaroyl group, stearoyl group, oleoyl group, elidoyl group, and behenoyl group.
  • R 2 contained in the peptide portion represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms that may have a branched chain of an alkyl group having 1 or 2 carbon atoms.
  • the alkyl group having 1 to 4 carbon atoms which can have the above alkyl group having 1 or 2 carbon atoms as a branched chain, has 1 to 4 carbon atoms in the main chain and 1 or 2 carbon atoms.
  • alkyl group that may have a branched chain as an alkyl group, and specific examples thereof include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec -Butyl group or tert-butyl group.
  • R 2 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which can have a branched chain having an alkyl group having 1 carbon atom, and more preferably a hydrogen atom.
  • An alkyl group having 1 to 3 carbon atoms which can have an alkyl group having 1 carbon atom as a branched chain is an alkyl group having 1 to 3 carbon atoms in the main chain and having an alkyl group having 1 carbon atom.
  • R 3 represents a — (CH 2 ) n —X group.
  • n represents a number from 1 to 4
  • X is an amino group, a guanidino group, a —CONH 2 group, or a 5-membered group having 1 to 3 nitrogen atoms as ring atoms.
  • a cyclic group or a 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring is represented.
  • X is preferably an amino group, guanidino group, carbamoyl group (—CONH 2 group), pyrrole group, imidazole group, pyrazole group or indole group, and more Preferably it is an imidazole group.
  • n is preferably 1 or 2, and more preferably 1.
  • the — (CH 2 ) n —X group is preferably an aminomethyl group, 2-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, carbamoylmethyl group, 2-carbamoylethyl group, 3- It represents a carbamoylbutyl group, 2-guanidinoethyl group, 3-guanidinobutyl group, pyrrolemethyl group, 4-imidazolemethyl group, pyrazolemethyl group, or 3-indolemethyl group, more preferably 4-aminobutyl group, carbamoylmethyl.
  • a lipid peptide particularly suitable as a lipid peptide-type gelling agent is a compound formed from the following lipid part and peptide part (amino acid assembly part).
  • amino acids alanine (Ala), asparagine (Asn), glutamine (Gln), glycine (Gly), histidine (His), isorosine (Ile), leucine (Leu), lysine (Lys), tryptophan (Trp) ), Valine (Val).
  • Lauroyl-Gly-His Lauroyl-Gly-Gln, Lauroyl-Gly-Asn, Lauroyl-Gly-Trp, Lauroyl-Gly-Lys, Lauroyl-Ala-His, Lauroyl-Ala-Gln, Lauroyl-Ala-Asn, Lauroyl- Ala-Trp, Lauroyl-Ala-Lys; Myristoyl-Gly-His, Myristoyl-Gly-Gln, Myristoyl-Gly-Asn, Myristoyl-Gly-Trp, Myristoyl-Gly-Lys, Myristoyl-Ala-His, Myristoyl-Ala- Gln, Myristoyl-Ala-Asn, Myristoyl-Ala-Trp, Myristoyl-Ala-Lys; Palmitoyl-Gly-His, Palmitoyl-Gly-Gln, Palmitoy
  • lauroyl-Gly-His lauroyl-Ala-His
  • myristoyl-Gly-His myristoyl-Ala-His
  • palmitoyl-Gly-His palmitoyl-Ala-His
  • stearoyl-Gly-His stearoyl-Ala -His.
  • the lipid peptide type gelling agent used in the present invention comprises at least one of the compound represented by the above formula (1) (lipid peptide) or a pharmaceutically usable salt thereof.
  • a compound can be used individually or in combination of 2 or more types.
  • the proportion of the lipid peptide-type gelling agent (the total amount when two or more lipid peptide-type gelling agents are used) is, for example, relative to the total volume of the hydrogel-forming material. 0.1 to 200 mmolar (mM, mol / m 3 ), preferably 0.5 to 100 mmolar, more preferably 1 to 50 mmolar.
  • the hydrogel-forming material of the present invention contains monopalmitin. Further, the hydrogel-forming material of the present invention can be used in combination with monopalmitin in combination with other glycerin fatty acid esters such as monocaprin, monolaurin, monomyristin, monostearin and monoolein, as long as the effects of the present invention are not impaired. it can.
  • the blending ratio of monopalmitin is, for example, 0.1 to 200 with respect to the total volume of the hydrogel-forming material.
  • Milli-molar preferably 0.5 to 100 mm-molar, more preferably 1 to 50 mm-molar.
  • the hydrogel-forming material of the present invention contains a lipid peptide-type gelling agent comprising at least one of the compound represented by the formula (1) or a pharmaceutically usable salt thereof, water and monopalmitin. is there.
  • the lipid peptide type gelling agent is easily dissolved and dispersed in water as a medium by heating at about 100 ° C., preferably with stirring. be able to. At this time, the heating and stirring time is usually about 20 to 90 minutes, although it varies depending on the type of lipid peptide gelling agent or additive used and the amount of them.
  • the hydrogel-forming material in the form of a solution in which the lipid peptide type gelling agent is in a dissolved / dispersed state is cooled at about room temperature (about 25 ° C.) and allowed to stand to obtain a hydrogel.
  • Hydrogels formed using the hydrogel-forming materials described above are also the subject of the present invention.
  • the resulting hydrogel is preferably a hydrogel having a pH of 7-9.
  • the hydrogel-forming material of the present invention particularly the low molecular weight compound (lipid peptide) represented by the above formula (1), is charged with water, dissolved and dispersed, and hydrophobic interaction and amide bond generated between alkyl chains. Intermolecular interactions such as hydrogen bonds that occur between them are self-organized using a driving force to form a molecular association state. The resulting molecular association state grows two-dimensionally to form a fibrous association. The fibrous aggregates are intertwined to form a three-dimensional network structure, and this three-dimensional network structure reduces the fluidity of water to form a hydrogel.
  • the hydrogel-forming material of the present invention uses a low-molecular gelling agent or monopalmitin composed of naturally-derived raw materials such as fatty acids and amino acids as the gelling agent. It is a material with excellent biological safety.
  • hydrogel of the present invention can be re-formed by making it into a sol by shaking or the like and then leaving it at room temperature again.
  • the hydrogel-forming material of the present invention is a material that is very advantageous in actual use such as repeated use, and a cell culture substrate, a biomolecule storage material such as cells and proteins, an external substrate, It can be used for materials in various fields such as medical materials, biochemical materials, cosmetic materials, food materials, contact lenses, disposable diapers, artificial actuators, and dryland agricultural materials.
  • reaction solution reached 60 ° C.
  • dropwise addition of 70.7 g (366 mmol) of sodium methoxide 28% methanol solution was started, and the addition was completed in 20 minutes.
  • the reaction was continued at about 60 ° C. for 1 hour.
  • the oil bath was removed and the mixture was allowed to cool to 25 ° C., it was separated into an upper layer mainly composed of cyclohexane and a lower layer mainly composed of methanol.
  • the lower layer of the reaction solution divided into two layers was collected in Meyer using a separatory funnel, a solution obtained by mixing 180 g of water and 420 g of methanol was added to the remaining upper layer, and the solution separated into two layers was allowed to stand again for 20 minutes.
  • the lower layer was collected by Meyer and mixed with the lower layer collected earlier.
  • This mixed solution was added to a mixed solution of 720 g of water, 780 g of methanol, and 36.5 mL (366 mmol) of 6N hydrochloric acid at 25 ° C. with stirring. After all the amount was added, the reaction solution was heated to 60 ° C. and stirred for 1 hour. Thereafter, the mixture was allowed to cool to 25 ° C., and the precipitated solid was collected by filtration and washed with 180 g of water. Next, 900 g of water and 1800 g of methanol were added to the obtained solid, and the mixture was heated and stirred at 60 ° C. for 1 hour.
  • Examples 1 and 2 and Reference Examples 1 and 2 N-palmitoyl-Gly-His monopalmitin-containing hydrogel-forming ability evaluation and re-formation evaluation test
  • N-palmitoyl-Gly-His prepared in the above synthesis example, the final final concentration of N-palmitoyl-Gly-His and monopalmitin in a mighty vial (No. 3, manufactured by Marum Corp.) is 20 mM (solvent: In addition, it was heated at 100 ° C. for 60 minutes with a dry bath Sahara 320 (manufactured by ASONE Co., Ltd.) and allowed to cool for one day.
  • N-palmitoyl-Gly-His monolaurin-containing hydrogel-forming ability evaluation and re-formation evaluation test N-palmitoyl-Gly-His prepared in the above synthesis example was added to Mighty vial (No.3, manufactured by Marem Co., Ltd.) with a total final concentration of N-palmitoyl-Gly-His and monolaurin of 20 mM (solvent: super In addition, it was heated at 100 ° C. for 60 minutes with a dry bath Sahara 320 (manufactured by ASONE Co., Ltd.) and allowed to cool for one day.
  • N-palmitoyl-Gly-His monomyristin-containing hydrogel-forming ability evaluation and re-formation evaluation test N-palmitoyl-Gly-His prepared in the above synthesis example was added to a final final concentration of 20 mM (solvent: N-palmitoyl-Gly-His and monomyristin) in a mighty vial (No. 3, manufactured by Marem Co., Ltd.). In addition, it was heated at 100 ° C. for 60 minutes with a dry bath Sahara 320 (manufactured by ASONE Co., Ltd.) and allowed to cool for one day.
  • the hydrogel-forming material of the present invention in which monopalmitin is mixed with N-palmitoyl-Gly-His forms a hydrogel and has a regeneration-forming ability.
  • a hydrogel-forming material containing monolaurin or monomyristin instead of monopalmitin formed a hydrogel under certain conditions, but the hydrogel did not have the ability to reform.
  • the gel was not formed only with glycerol fatty acid ester.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Inorganic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Materials For Medical Uses (AREA)
  • Peptides Or Proteins (AREA)

Abstract

L'invention vise à fournir, au moyen d'une composition simple, un matériau de formation d'hydrogel tel que, même après que l'hydrogel préparé ait été transformé en sol par l'intermédiaire d'une agitation, le gel peut se re-former par repos à la température ambiante. L'invention concerne un matériau de formation d'hydrogel contenant de l'eau, de la monopalmitine, et un agent gélifiant lipide-peptide comprenant au moins une substance parmi les composés représentés par la formule (1) et les sels pharmaceutiquement acceptables de ces derniers. (Dans la formule, R1 représente un groupe aliphatique en C9–23 ; R2 représente un atome d'hydrogène ou un groupe alkyle en C1–4 qui peut avoir un groupe alkyle en C1–2 sous la forme d'une chaîne ramifiée ; R3 représente un groupe –(CH2)n–X ; n représente un nombre entier de 1 à 4 ; et X représente un groupe amino, un groupe guanidino, un groupe -CONH2, un groupe cyclique de 5 ou 6 chaînons ayant d'1 à 3 atomes d'azote comme atomes au sein du cycle, ou un groupe hétérocyclique condensé formé à partir d'un cycle à 5 chaînons et d'un cycle à 6 chaînons.)
PCT/JP2015/083581 2014-12-05 2015-11-30 Matériau formant un hydrogel WO2016088712A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2016562445A JPWO2016088712A1 (ja) 2014-12-05 2015-11-30 ヒドロゲル形成材料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-247159 2014-12-05
JP2014247159 2014-12-05

Publications (1)

Publication Number Publication Date
WO2016088712A1 true WO2016088712A1 (fr) 2016-06-09

Family

ID=56091654

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/083581 WO2016088712A1 (fr) 2014-12-05 2015-11-30 Matériau formant un hydrogel

Country Status (2)

Country Link
JP (1) JPWO2016088712A1 (fr)
WO (1) WO2016088712A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018221445A1 (fr) * 2017-06-01 2018-12-06 国立大学法人神戸大学 Agent gélifiant

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011052613A1 (fr) * 2009-10-26 2011-05-05 日産化学工業株式会社 Préparation cosmétique et externe pour la peau, et instrument médical
WO2012063947A1 (fr) * 2010-11-12 2012-05-18 日産化学工業株式会社 Feuille de gel comprenant un agent gélifiant de type peptide lipidique et composé polymère
WO2014003015A1 (fr) * 2012-06-25 2014-01-03 日産化学工業株式会社 Liquide de dispersion et procédé de formation d'un hydrogel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011052613A1 (fr) * 2009-10-26 2011-05-05 日産化学工業株式会社 Préparation cosmétique et externe pour la peau, et instrument médical
WO2012063947A1 (fr) * 2010-11-12 2012-05-18 日産化学工業株式会社 Feuille de gel comprenant un agent gélifiant de type peptide lipidique et composé polymère
WO2014003015A1 (fr) * 2012-06-25 2014-01-03 日産化学工業株式会社 Liquide de dispersion et procédé de formation d'un hydrogel

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018221445A1 (fr) * 2017-06-01 2018-12-06 国立大学法人神戸大学 Agent gélifiant

Also Published As

Publication number Publication date
JPWO2016088712A1 (ja) 2017-10-12

Similar Documents

Publication Publication Date Title
JP5388848B2 (ja) 新規脂質トリペプチド性ヒドロゲル化剤及びヒドロゲル
JP5441693B2 (ja) 新規脂質ペプチド並びにヒドロゲル
JP5943211B2 (ja) ヒドロゲル形成材料
EP2664321B1 (fr) Instrument et préparation médicaux comprenant un peptide lipidique et de la gomme arabique
TWI605110B (zh) 新穎脂質二肽以及膠體
Yang et al. A versatile cyclic dipeptide hydrogelator: Self-assembly and rheology in various physiological conditions
WO2010106981A1 (fr) Matériau de base pour pulvérisation comprenant un agent gélifiant de faible poids moléculaire
JP2011037926A (ja) 長鎖オキシアミノポリオール型ゲル化剤およびゲル
JP6132107B2 (ja) ヒドロゲル形成材料
JP5510635B2 (ja) 脂質ヒスチジンゲル化剤
WO2016088712A1 (fr) Matériau formant un hydrogel
JP6440254B2 (ja) ゲル化剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15864333

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2016562445

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 15864333

Country of ref document: EP

Kind code of ref document: A1