JP2001247597A - Method of producing formed article - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a DNA into which an aromatic compound among a wide aromatic compound range has efficiently been introduced at a high introduction rate in good introduction purity, and to provide a method of producing a DNA formed article. SOLUTION: This method for producing the DNA into which an aromatic compound has been introduced, is haracterized by having (D a process for mixing an organic solvent solution containing an aromatic compound with a DNA aqueous solution and (2) a process for separating precipitates produced in the process (1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a deoxyribonucleic acid (hereinafter abbreviated as DNA) molded product, and more particularly to a method for producing a DNA molded product in which an aromatic compound is introduced into DNA. It is.

[0002]

2. Description of the Related Art DNA is an organic compound possessed by all living things on the earth, and has a molecular structure in which two polynucleotide chains are spirally wound. There are four types of nucleobases that are constituent molecules of nucleotide chains: adenine, thymine, guanine, and cytosine. These nucleobases protrude inward from each other in a plane perpendicular to the center, forming so-called Watson-Crick base pairs. Thus, DNA has a characteristic chemical structure, and can be said to be a functional polymer material that interacts with various substances with extremely high specificity and selectivity. So, DNA
Attempts have been made to apply as a natural polymer material to functional materials. For example, it has been attempted to introduce an aromatic compound such as an organic dye into DNA and use it as a functional material, and it is already known that an aromatic compound such as an organic dye is introduced into DNA. .

[0003] Japanese Patent Application Laid-Open No. 61-6885 discloses DNA
It is stated that a complex is obtained by placing an aqueous solution in a mortar, adding a solid, water-insoluble pigment thereto, and grinding the solution to color the aqueous solution, and separating the colored liquid. Since this method is a so-called solid-liquid reaction, D
The introduction rate of the aromatic compound into NA is slow, the introduction rate is low, and the apparatus is limited for industrial implementation.

[0004] J. J. Am. Chem. Soc. , 1
18 (44), 1067 (1996);
No. 1-119270 discloses that a DNA-Na salt aqueous solution is mixed with an aqueous solution of a quaternary ammonium salt having a long-chain alkyl group, and the resulting precipitate is centrifuged and freeze-dried to obtain the obtained DNA-quaternary ammonium salt. Dissolve the salt complex in a non-aqueous organic solvent and cast to produce a film,
A method is described in which this DNA film is immersed in an aqueous solution of a dye or a methanol solution for 24 hours to obtain a DNA film in which a dye has been introduced into DNA. In this method, the solvent that can be used to introduce a dye into DNA is limited to one that does not dissolve the DNA film, that is, water or methanol, and it is required that the solubility of the aromatic compound is high. Aromatic compounds are limited. When the DNA film is immersed in the aromatic compound solution, the DNA film may be deteriorated or collapsed. There is also a problem that the processing steps are long and the processing time of each step is long, so that it is difficult to employ industrially.

[0005] Further, Polymer Preprin
ts, Japan, 48 (3), 368 (1999),
And JP-A-11-119270, DNA-
An aqueous solution of a Na salt and an aqueous solution of a quaternary ammonium salt having a long-chain alkyl group are mixed, and the generated precipitate is separated by filtration and dried.
A method is described in which the obtained DNA-quaternary ammonium salt complex is dissolved in a non-aqueous solvent, a dye is added thereto, left overnight, and then cast to obtain a film having a dye introduced into DNA. In this method, in addition to the desired mode of introduction, aromatic compounds simply attached to the DNA are mixed, and a step for removing the aromatic compounds is required. There is also a problem that the processing steps are long and the processing time of each step is long.

As described above, conventionally, the purpose of studying the introduction mode of a certain limited aromatic compound such as a dye or the study of the limited function expression has been aimed at, and efficient or industrial aromatic compounds have been proposed. From the viewpoint of a method for producing a group-compound-introduced DNA film, it was extremely insufficient. In addition, there is no report on the production of a DNA fiber into which an aromatic compound has been introduced.

[0007] Furthermore, in order to introduce an aromatic compound into DNA and use it as a functional material, the purity of the introduced aromatic compound becomes a problem. That is, the method of introducing an aromatic compound into DNA includes forming a complex between a phosphate residue of DNA and a cationic group of the aromatic compound, and inserting an aromatic compound between nucleic acid base pairs of DNA (referred to as intercalation). Has been considered). When a DNA and an aromatic compound are mixed, the removal of the aromatic compound is required because the aromatic compound simply attached to the DNA is mixed in addition to the introduction of the aromatic compound into the DNA. The method for obtaining a DNA molded product with good quality is not sufficient.

[0008]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a method of efficiently producing a DNA and a DNA molded article into which an aromatic compound has been introduced at a high rate of introduction into DNA. is there. It is a further object of the present invention to provide a method for producing a DNA and a DNA molded article having only a small amount of an attached aromatic compound, that is, having a high introduced purity.

[0009]

Means for Solving the Problems The present inventors have made intensive studies and as a result, have been able to solve the above-mentioned conventional problems.

That is, the present invention provides (1) a step of mixing an organic solvent solution containing an aromatic compound and an aqueous solution of deoxyribonucleic acid, and (2) a step of separating the precipitate formed in the step (1). And a method for producing a deoxyribonucleic acid into which an aromatic compound has been introduced.

Further, the present invention provides (1) a step of mixing an organic solvent solution containing an aromatic compound, an aqueous solution of deoxyribonucleic acid, and an organic cationic substance, and (2) a step of mixing in the step (1). A method for producing a deoxyribonucleic acid into which an aromatic compound has been introduced, the method comprising a step of separating the precipitate formed.

Further, the present invention provides (1) a step of mixing an organic solvent solution containing an aromatic compound and an aqueous solution of deoxyribonucleic acid, and (2) a step of separating the precipitate formed in the step (1) to solidify. And (3) a step of molding the solid content into a desired shape. A method for producing a molded article having an aromatic compound introduced into deoxyribonucleic acid, the method comprising:

Further, the present invention provides (1) a step of mixing an organic solvent solution containing an aromatic compound, an aqueous solution of deoxyribonucleic acid, and an organic cationic substance; and (2) a step of mixing in the step (1). A method for producing a molded article in which an aromatic compound is introduced into deoxyribonucleic acid, comprising: a step of separating a precipitate to obtain a solid content; and (3) a step of molding the solid content into a desired shape. Is provided.

Further, the present invention provides a method for producing a molded article in which an aromatic compound is introduced into deoxyribonucleic acid, wherein the molded article is molded into a film or a fiber. It is.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION Deoxyribonucleic acid (DNA) The DNA used in the present invention is not particularly limited. Examples of the raw material include salmon, trout, herring, mackerel, cod fish milt (sperm), and bovine mammary gland. Is mentioned. The molecular weight and the purity may be appropriately selected according to the use and the target physical properties.

Aromatic Compound The aromatic compound used in the present invention is not particularly limited, but when classified according to the structure, for example, a monocyclic aromatic compound, a condensed polycyclic aromatic compound, a heterocyclic compound, a condensed heterocyclic compound and the like can be used. And various functional groups may be bonded. Also, when classified according to their functions, there are non-linear optical materials, photochromic materials, liquid crystal materials, light control materials, conductive materials, antibacterial materials, ultraviolet absorbing materials, visible light absorbing materials, infrared absorbing materials, functional dye materials, and the like. .

Specific examples of these compounds include, for example, nitrobenzene, 4-nitroaniline, 3-nitroaniline, 2-nitroaniline, 2,4-dinitroaniline, 2-chloro-4-nitroaniline, 2-bromoaniline −
4-nitroaniline, 2-methyl-4-nitroaniline, N, N-dimethyl-4-nitroaniline, 4-cyanoaniline, 4-cyano-N, N-dimethylaniline,
4-aminoacetophenone, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, 1,2-
Diiodobenzene, toluene, 4-nitrotoluene, 4
-Cyanotoluene, 4-nitroanisole, 4-cyanoanisole, 2-fluoronitrobenzene, 3-fluoronitrobenzene, 4-fluoronitroaniline, 4-
Nitro-trans-stilbene, 4-amino-trans-stilbene, 4-dimethylamino-trans-stilbene, 4-chloro-trans-stilbene, 4-chloro-4'-nitro-trans-stilbene, 4-chloro-
4′-dimethylamino-trans-stilbene, 4-cyano-4′-dimethylamino-trans-stilbene,
4-cyano-4′-methoxy-trans-stilbene,
4-methyl-4'-nitro-trans-stilbene, 4
-Amino-4'-nitro-trans-stilbene, 4-
Dimethylamino-4′-nitro-trans-stilbene, 4-[(1-methyl-4- (1H) -pyridinylidene) ethylidene] 2,5-cyanohexadien-1-one, 4-dimethylamino-β-nitrostyrene Methyl-N- (2,4-dinitrophenyl) alaninate, trans-4-azastilbene, 1- (4-cyanophenyl) -4- (4-dimethylaminophenyl) -buta-
1,3-diene, 1- (4-dimethylaminophenyl)
-4-nitrobuta-1,3-diene, 2- (4-thianomethylenecyclohexa-2,5-dienylidene) -imidazolidene, 3-ethyl-2- [2- (4-oxo-
2,5-cyclohexadienylidene) ethylidene]-
2,3-dihydrobenzothiazole, 2- [6- (4-
Carboxyphenylamino) hexa-2,4-dienylidene] -3-ethyl-2,3-dihydroxybenzothiazole,

Azobenzene, spiropyran, fulgide,
Diarylethene, phenoxynaphthacenequinone, thioindigo, malachito green, spirooxazine compounds, cyclophane compounds, phenylenevinylene compounds, stilbenzene compounds, nitrobenzene compounds, styrene compounds, pyridone compounds, azobenzene compounds, phthalocyanines Compounds, fexinaphthacene compounds,

C.I.Direct Yellow 12,
Sea Eye Direct Yellow 28, Sea Eye
Direct Yellow 44, C.I.Direct.
Yellow 142, C.I.Direct Orange 6, C.I.Direct Orange 26, C.I.Direct Orange 39, C.I.Direct Orange 107, C.I.Direct Red 2, C.I. Eye direct red 31, sea eye direct red 79, sea eye direct
Red 81, C.I.Direct Red 247,
C.I.Direct Green 59, C.I.
Direct Green 85,

2,6-di-tert.-butylphenol (hereinafter, tert.-butyl is abbreviated as t-butyl), 2,6-di-tert-butyl-p-cresol,
2,6-di-t-butyl-4-methylphenol, 2,
6-di-t-butyl-4-ethylphenol, 2,4-
Dimethyl-6-t-butylphenol, 4,4′-methylenebis (2,6-di-t-butylphenol), 4,
4'-bis (2,6-di-t-butylphenol),
4,4'-bis (2-methyl-6-t-butylphenol), 2,2'-methylenebis (4-methyl-6-t-
Butylphenol), 2,2′-methylenebis (4-ethyl-6-t-butylphenol), 4,4′-butylidenebis (3-methyl-6-t-butylphenol),
4,4'-isopropylidenebis (2,6-di-t-butylphenol), 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (4-methyl-6 Nonylphenol), 2,
2′-isobutylidenebis (4,6-dimethylphenol), 2,6-bis (2′-hydroxy-3′-tert-butyl-5′-methylbenzyl) -4-methylphenol,

3-tert-butyl-4-hydroxyanisole, 2-tert-butyl-4-hydroxyanisole,
(4-hydroxy-3,5-di-t-butylphenyl)
Stearyl propionate, 3- (4-hydroxy-3,
5-di-t-butylphenyl) oleyl propionate,
Dodecyl 3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, 3- (4-hydroxy-
Decyl 3,5-di-t-butylphenyl) propionate, octyl 3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrakis {3- (4
-Hydroxy-3,5-di-t-butylphenyl) propionyloxymethyldimethane, 3- (4-hydroxy-3,5-di-t-butylphenyl) propionic acid glycerin monoester, 3- (4-hydroxy −3,5-
Ester of di-t-butylphenyl) propionic acid with glycerin monooleyl ether, butylene glycol 3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, 3- (4-hydroxy-
3,5-di-t-butylphenyl) propionic acid thiodiglycol ester, 4,4′-thiobis (3-methyl-6-t-butylphenol), 4,4′-thiobis (2-methyl-6-t -Butylphenol), 2,2 ′
-Thiobis (4-methyl-6-t-butylphenol), 2,6-di-t-butyl-α-dimethylamino-
p-cresol, 2,6-di-t-butyl-4- (N,
N'-dimethylaminomethylphenol),

Bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, tris {(3,5-di-tert-butyl-4-hydroxyphenyl) propionyl-oxyethyl} isocyanurate, tris (3 , 5-
Di-tert-butyl-4-hydroxyphenyl) isocyanurate, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, bis {2-methyl-4- (3 -N-alkylthiopropionyloxy) -5-t-butylphenyl disulfide,
1,3,5-tris (4-t-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, tetraphthaloyludi (2,6-dimethyl-4-t-butyl-3-hydroxybenzyl sulfide) ), 6- (4-
Hydroxy-3,5-di-t-butylanilino) -2,
4-bis (octylthio) -1,3,5-triazine,
2,2-thio- {diethyl-bis-3- (3,5-di-
t-butyl-4-hydroxyphenyl) propionate, N, N'-hexamethylenebis (3,5-di-t-
Butyl-4-hydroxy-hydrocinamide), 3,5-
Di-t-butyl-4-hydroxy-benzyl-phosphoric acid diester, bis (3-methyl-4-hydroxy-5-t
-Butylbenzyl) sulfide, 3,9-bis [1,
1-dimethyl-2- {β- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] -2,4,8,10-tetraoxaspiro [5
5] undecane, 1,1,3-tris (2-methyl-4
-Hydroxy-5-t-butylphenyl) butane, 1,
3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, bis {3,3′-bis- (4′-hydroxy-3′-t) −
Butylphenyl) butyric acid glycol ester, 2,2-bis (p-hydroxyphenyl) propane (bisphenol A),

1-naphthylamine, phenyl-1-naphthylamine, p-octylphenyl-1-naphthylamine, p-nonylphenyl-1-naphthylamine, p-dodecylphenyl-1-naphthylamine, phenyl-2-
Naphthylamine

N, N'-diisopropyl-p-phenylenediamine, N, N'-diisobutyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-di-β-naphthyl- p-phenylenediamine, N-phenyl-N'-isopropyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, N-1,3-dimethylbutyl-N'-phenyl-p-phenylene Diamine, dioctyl-p-phenylenediamine, phenylhexyl-p
-Phenylenediamine, phenyloctyl-p-phenylenediamine

Dipyridylamine, diphenylamine,
p, p'-di-n-butyldiphenylamine, p, p '
-Di-t-butyldiphenylamine, p, p'-di-t
-Pentyldiphenylamine, p, p'-dinonyldiphenylamine, p, p'-didecyldiphenylamine,
p, p′-didodecyldiphenylamine, p, p′-distyryldiphenylamine, p, p′-dimethoxydiphenylamine, 4,4′-bis (4-α, α-dimethylbenzoyl) diphenylamine, p-isopropoxydiphenylamine, Dipyridylamine,

Fluoran dyes, cyanine dye borates, polymethine dyes, azurenium dyes, pyridone monoazo dyes, quinophthalone dyes, tricyanostyryl dyes, anthraquinone monoazo dyes, heterocyclic monoazo dyes, and other azo dyes Dye, indoaniline dye, phthalocyanine dye, naphthalocyanine dye,
Indium naphthol-based metal complexes, porphine, quinizarin, 8-oxyquinoline aluminum complex, quinacridone-based dyes, dicyanomethylene-based dyes, symmetric bisazomethine-based dyes, quinone-based dyes, nitrogen-containing heteroaromatic dyes such as ethidium bromide, And triphenylmethane dyes such as crystal violet.

In the present invention, in order to obtain a DNA and a DNA molded product having a high purity of the aromatic compound, the aromatic compound preferably has low water solubility and is soluble in an organic solvent. However, a DNA and a DNA molded article into which an aromatic compound has been introduced, or a DN into which an aromatic compound has been introduced
It is necessary that the complex of the A-cationic substance does not dissolve in the organic solvent. Complexes of DNA and a DNA molded article into which an aromatic compound has been introduced, or a DNA-cationic substance into which an aromatic compound has been introduced,
Aromatic compounds separated as precipitates and not introduced into DNA can be removed by washing with an organic solvent.

The organic solvent Therefore, the organic solvent used in the present invention can be prepared by dissolving the aromatic compound, the aromatic compound is introduced DNA and DNA moldings, or an aromatic compound is introduced DNA
-The complex of the cationic substance is preferably insoluble and can be appropriately selected, but a solvent having a relatively low polarity is preferable, and ethers such as diethyl ether, dipropyl ether, benzyl ethyl ether, dioxane, and tetrahydrofuran; acetone, methyl ethyl ketone, Ketones such as cyclohexanone; esters such as ethyl formate, methyl acetate, and ethyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethane, trichloroethane, tetrachloroethane, dichloroethylene, trichloroethylene, and tetrachloroethylene; hexane, heptane, cyclohexane, and toluene And hydrocarbons such as xylene.

In the present invention, DNA for an organic solvent is used.
The concentration and the use ratio of the aromatic compound are not particularly limited, but the concentration is preferably 0.1 to 10% by weight in the total amount of the DNA and the aromatic compound in the solution, and the use ratio is the introduction of the aromatic compound into the DNA. Although it depends on the possible amount and the target introduction rate, it is preferable that the aromatic compound be at most 3 moles per two phosphorus atoms in DNA.

Organic Cationic Substance In the present invention, when the DNA into which the aromatic compound has been introduced is difficult to form as a precipitate, or when the aromatic compound is to be introduced by intercalation instead of complex, the organic cationic substance is used. Is effective when added. The organic cationic substance used in the present invention is not particularly limited, but is preferably an amine or a quaternary ammonium salt, and is separable as a precipitate from the aqueous-organic solvent of the DNA into which the aromatic compound has been introduced, and the aromatic compound The selection is made in consideration of the effect of improving the introduction rate, the introduction mode of the aromatic compound, and the physical properties of the molded product such as the produced DNA film or DNA fiber. Specifically, trimethylbenzyl ammonium salt,
Benzylammonium salts such as triethylbenzylammonium salt, benzalkonium salt and benzethonium chloride;
Alkylpyridinium salts such as laurylpyridinium salts and laurylpicolinium salts; imidazolinium salts; tetramethylammonium salts, tetraethylammonium salts;
Aliphatic quaternary ammonium salts such as tetrabutylammonium salt, lauryltrimethylammonium salt, myristyltrimethylammonium salt, oleyltrimethylammonium salt, stearyltrimethylammonium salt, dilauryldimethylammonium salt; trimethylphenylammonium salt; trimethyl (tetraoxadocosyl) ) Polyoxyalkylene ammonium salts such as ammonium salt and polyoxypropylene methyl diethyl ammonium salt; amphoteric surfactants such as carboxybetaine, aminocarboxylate, imidazolinium betaine and alkylamine oxide; polydimethyldiallylammonium salt and dimethyldiallyl And high-molecular cationic compounds such as copolymers of ammonium salts and acrylamide. The amount of the organic cationic substance added in the present invention is not particularly limited.
Preferably, it is molar.

In the step (1) of the present invention, heating and stirring DNA and an aromatic compound or an organic cationic substance at the time of mixing are preferable because the rate and rate of introduction of the aromatic compound into the DNA are improved. . The temperature at the time of mixing is preferably from 0 to 100 ° C, more preferably from 40 to 80 ° C.
° C. If the temperature is higher than this, the DNA may be denatured. The means for separating the precipitate in step (2) of the present invention is not particularly limited. For example, filtration and the like can be mentioned.

The term “compact” as used in the present invention refers to all materials utilizing a DNA complex into which an aromatic compound has been introduced.
Examples include DNA films and DNA fibers. When a film is formed, for example, the obtained extract is cast. At this time, if the organic solvent is removed under reduced pressure and / or heating, a film can be efficiently formed, and a transparent film can be easily obtained. The heating temperature is desirably 100 ° C. or less to prevent denaturation of the film. In the case of fibrillation, the organic solvent of the extract is distilled off under reduced pressure to obtain a solid content, which may be melt-spun in the same manner as ordinary synthetic fibers. The melting temperature varies depending on the type and amount of the introduced aromatic compound and the used organic cationic substance, but is preferably 60 to 150 ° C.
Is preferred. The DNA molded product (for example, D
The NA film or DNA fiber) can be subjected to a stretching treatment, an electric field orientation (polling) treatment or the like in order to align or regularly arrange the DNA itself or the introduced aromatic compound.

The DNA molded product (for example, D
The use of NA film or DNA fiber is not limited, but it is advantageous to use the feature that an aromatic compound is molecularly dispersed or oriented in DNA, such as a nonlinear optical material or a photochromic material. And electron / light-related materials such as polarizing materials and conductive materials, flame-retardant materials, optical isomer separation membranes, antibacterial materials, ultraviolet absorbing materials, visible light absorbing materials, and infrared absorbing materials.

[0034]

EXAMPLES The present invention will be further described below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, “%” in Examples is by weight.

Example 1 79 mg of salmon milt-derived DNA (P content: 7.7%, the same is used in the following Examples and Comparative Examples) was dissolved in 5 ml of distilled water. Separately, compound A86m having the following structural formula
g (0.2 mmol) was dissolved in 20 ml of chloroform and mixed with an aqueous DNA solution. The mixture was stirred at 55 ° C. and 500 rpm for 30 minutes. A precipitate was deposited with stirring.
The precipitate was filtered and the solid obtained was dissolved in 10 ml of a mixed solvent of water / ethanol / chloroform (0.05 / 1/4 vol ratio). This solution was transferred to a fluororesin dish, and the lower portion was heated (at a temperature of 90 ° C.) and dried under reduced pressure to obtain a DNA film into which an aromatic compound was introduced.

[0036]

Embedded image

Example 2 79 mg of DNA was dissolved in 10 ml of distilled water, and 53 mg (0.2 mmol) of monolauryltrimethylammonium chloride was dissolved.
l) and 79 mg of ethidium bromide made separately
(0.2 mmol) in 10 ml of chloroform was added, and the mixture was stirred at room temperature (25 ° C.) and 500 rpm for 2 hours. A precipitate was deposited with stirring. The precipitate was separated by filtration and the solid content obtained was mixed with 10 ml of a mixed solvent of water / ethanol / chloroform (0.05 / 1/4 vol ratio).
Was dissolved. This solution was transferred to a fluororesin dish, and the lower portion was heated (at a temperature of 90 ° C.) and dried under reduced pressure to obtain a DNA film into which an aromatic compound was introduced.

Example 3 79 mg of DNA was dissolved in 10 ml of distilled water, and 53 mg (0.2 mmol) of monolauryltrimethylammonium chloride was dissolved.
l) and 0.2 mmol of an aromatic compound prepared separately
(A variety of aromatic compound names and addition amounts are described in Table 1) in 10 ml of chloroform.
The mixture was stirred at 0 rpm for 30 minutes. A precipitate was deposited with stirring. The solid content obtained by filtering this precipitate was separated into water / ethanol / chloroform (0.05 / 1/4 vol.).
Ratio) dissolved in 10 ml of mixed solvent. This solution was transferred to a fluororesin dish, and the lower portion was heated (at a temperature of 90 ° C.) and dried under reduced pressure to obtain a DNA film into which an aromatic compound was introduced. A half of the obtained DNA film was taken, and the film was immersed and washed in 40 ml of acetone, and the solid content was filtered off and dried under reduced pressure to remove an aromatic compound simply attached to the DNA. The aromatic compound content was measured.

Comparative Example 1 79 mg of DNA was taken in a mortar and dissolved with 10 ml of distilled water. 0.2 mmol of aromatic compound was added to this aqueous DNA solution.
(The names and amounts of various aromatic compounds are described in Table 1), and the mixture was ground for about 1 hour. This was centrifuged at 5000 G for 10 minutes to obtain a supernatant. Add 10 ml of this supernatant to 1
After mixing with 10 ml of a 0% aqueous polyvinyl alcohol solution, the mixture was transferred to a fluororesin petri dish and reduced pressure at 40 ° C. for 24 hours.
This was left for a time to obtain a DNA film.

Comparative Example 2 3 g of DNA was dissolved in 100 ml of distilled water. 2.2 g (8.4 g) of monolauryltrimethylammonium chloride was added thereto.
mmol), and the resulting solid was filtered off and freeze-dried to obtain a DNA-lipid complex. This DNA-
After dissolving 132 mg of the lipid complex in 10 ml of a mixed solvent of ethanol-chloroform (1: 4 vol ratio), the solution was transferred to a fluororesin dish, and allowed to stand at room temperature for 1 day to obtain DN.
A film was obtained. Next, 0.2 mmol of the aromatic compound
(The names of various aromatic compounds and the amounts added are described in Table 1.) This DN was added to a solution in which 10 ml of distilled water was dissolved or dispersed.
The A film was immersed and allowed to stand at room temperature for one day to obtain a DNA film in which an aromatic compound was introduced into the DNA-lipid complex.

Comparative Example 3 DNA-lipid complex 132 obtained in Comparative Example 2
mg and 0.2 mmol of the aromatic compound (the names and amounts of various aromatic compounds described in Table 1) were dissolved in 10 ml of a mixed solvent of ethanol-chloroform (1: 1 vol ratio), and the solution was transferred to a fluororesin petri dish, and the mixture was stirred at room temperature. For 1 day to obtain a DNA film into which the aromatic compound was introduced. Obtained DN
Take half of the A film and remove the film with 40 ml of acetone to remove only the attached aromatic compounds in the DNA.
After immersion washing, the solid content was separated by filtration and dried under reduced pressure, and the obtained solid content was measured for the aromatic compound content.

Measurement of introduction ratio of aromatic compound into DNA The DNA film into which the aromatic compound was introduced and the solid content obtained in Examples and Comparative Examples were subjected to water-ethanol (1:
(1 vol ratio) After dissolving in a mixed solvent, appropriately diluting the mixture, measuring the amount of aromatic compound in the solution with an ultraviolet-visible spectrophotometer (UV-2200, manufactured by Shimadzu Corporation), and measuring the amount of aromatic compound introduced into the DNA film. I asked. Note that the amount of the aromatic compound introduced into the DNA film is expressed as a relative value (mol%) with 100 when 1 mol of the aromatic compound is introduced per two phosphorus atoms in the DNA, The results are shown in Table 1.

[0043]

[Table 1]

[0044]

According to the present invention, there is provided a method for producing a DNA and a DNA molded product capable of efficiently and efficiently introducing a wide range of aromatic compounds at a high rate of introduction into a DNA at a high introduction rate.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Tetsuya Ikeshima 7-35 Higashi Oku, Arakawa-ku, Tokyo Asahi Denka Kako Co., Ltd. (72) Hideo Kawasaki 7-35 Higashi Oku, Arakawa-ku, Tokyo Asahi Denka Kogyo Co., Ltd. F-term (reference) 4C057 AA30 BB05 DD03 MM04

Claims (5)

[Claims] 1. A method comprising: (1) a step of mixing an organic solvent solution containing an aromatic compound with an aqueous solution of deoxyribonucleic acid; and (2) a step of separating a precipitate formed in the step (1). A method for producing a deoxyribonucleic acid into which a characteristic aromatic compound has been introduced. (2) a step of mixing an organic solvent solution containing an aromatic compound, an aqueous solution of deoxyribonucleic acid, and an organic cationic substance; and (2) a step of forming a precipitate formed in the step (1). A method for producing deoxyribonucleic acid into which an aromatic compound has been introduced, comprising a step of separating. (1) a step of mixing an organic solvent solution containing an aromatic compound and an aqueous solution of deoxyribonucleic acid,
(2) a step of obtaining a solid content by separating the precipitate formed in the above (1) step, and (3) a step of molding the solid content into a desired shape. A method for producing a molded article into which an aromatic compound has been introduced. 4. A step of (1) mixing an organic solvent solution containing an aromatic compound, an aqueous solution of deoxyribonucleic acid, and an organic cationic substance, and (2) separating a precipitate formed in the step (1). And (3) forming the solid content into a desired shape by a method for producing a molded product in which an aromatic compound is introduced into deoxyribonucleic acid. 5. The method for producing a molded article in which an aromatic compound is introduced into deoxyribonucleic acid according to claim 3, wherein the molded article is molded into a film or a fiber.