WO2022157547A1 - Couche électrofilée active pour filtration de l'adn - Google Patents

Couche électrofilée active pour filtration de l'adn Download PDF

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Publication number
WO2022157547A1
WO2022157547A1 PCT/IB2021/050524 IB2021050524W WO2022157547A1 WO 2022157547 A1 WO2022157547 A1 WO 2022157547A1 IB 2021050524 W IB2021050524 W IB 2021050524W WO 2022157547 A1 WO2022157547 A1 WO 2022157547A1
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Prior art keywords
polymer
gemini surfactant
preparing
solution
base polymer
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PCT/IB2021/050524
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English (en)
Inventor
Somaye Akbari
Sepideh PAKPOUR
Rasul SHABANLOO
Marjan MIRSALEHI
Frank K. KO
Abbas SADEGHZADEH MILANI
Addi BAHI
Bogumil E. BRYCKI
Kajatan PYRZYNSKI
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Somaye Akbari
Pakpour Sepideh
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Priority to PCT/IB2021/050524 priority Critical patent/WO2022157547A1/fr
Publication of WO2022157547A1 publication Critical patent/WO2022157547A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/10—Processes for the isolation, preparation or purification of DNA or RNA
    • C12N15/1003—Extracting or separating nucleic acids from biological samples, e.g. pure separation or isolation methods; Conditions, buffers or apparatuses therefor
    • C12N15/1017—Extracting or separating nucleic acids from biological samples, e.g. pure separation or isolation methods; Conditions, buffers or apparatuses therefor by filtration, e.g. using filters, frits, membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D39/00—Filtering material for liquid or gaseous fluids
    • B01D39/14—Other self-supporting filtering material ; Other filtering material
    • B01D39/16—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres
    • B01D39/1607—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres the material being fibrous
    • B01D39/1623—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres the material being fibrous of synthetic origin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/0007—Electro-spinning
    • D01D5/0015—Electro-spinning characterised by the initial state of the material
    • D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
    • D01D5/0038—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion the fibre formed by solvent evaporation, i.e. dry electro-spinning
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D01F1/103—Agents inhibiting growth of microorganisms
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
    • D01F6/625—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters derived from hydroxy-carboxylic acids, e.g. lactones
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/02—Types of fibres, filaments or particles, self-supporting or supported materials
    • B01D2239/025—Types of fibres, filaments or particles, self-supporting or supported materials comprising nanofibres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/04—Additives and treatments of the filtering material
    • B01D2239/0414—Surface modifiers, e.g. comprising ion exchange groups
    • B01D2239/0428—Rendering the filter material hydrophobic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/04—Additives and treatments of the filtering material
    • B01D2239/0442—Antimicrobial, antibacterial, antifungal additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/06—Filter cloth, e.g. knitted, woven non-woven; self-supported material
    • B01D2239/0604—Arrangement of the fibres in the filtering material
    • B01D2239/0631—Electro-spun
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
    • B01D2239/10—Filtering material manufacturing

Definitions

  • the present disclosure relates to electrospun nanofibrous webs and methods for preparing nanofibrous webs. Particularly, the present disclosure relates to electrospun nanofibrous layers for DNA filtration.
  • Tian et al. (Analytical Biochemistry 2000, 283 (2), 175) disclose a solid phase extraction method, in which silica resin is utilized for adsorption and desorption of DNA in a chaitropic salt solution.
  • Wolfe et al. Electrode et al. (Electrophoresis 2002, 23 (5), 727), Breadmore et al. (Analytical Chemistry 2003, 75 (8), 1880), Cady et al. (Sensors and Actuators B-Chemical 2005, 107 (1), 332), and Wu et al.
  • an active electrospun layer for DNA separation may include a polymer scaffold.
  • An exemplary polymer scaffold may include at least one of aromatic and aliphatic polyester polymers, such as lactic acid / glycolic acid copolymer.
  • An exemplary active electrospun layer for DNA separation may further include an amine-terminated dendritic polymer that may be embedded within the polymer scaffold.
  • An exemplary amine-terminated dendritic polymer may include at least one of polyamidoamine, polypropylene imine, and polyethylene imine.
  • An exemplary active electrospun layer for DNA separation may further include a cationic gemini surfactant.
  • an exemplary amine-terminated dendritic polymer has a concentration of 5 wt.% to 30 wt.% based on total weight of the polymer scaffold.
  • an exemplary cationic gemini surfactant has a concentration of 0.01 wt.% to 0.1 wt.% based on total weight of the polymer scaffold.
  • an exemplary method may include preparing a base polymer solution by dissolving a base polymer in a first solvent, preparing a base polymer/ gemini surfactant solution by mixing a gemini surfactant with the base polymer solution, preparing an amine-terminated dendritic polymer solution by dissolving an amine-terminated dendritic polymer in a second solvent, preparing a spinning solution by dispersing the amine-terminated dendritic polymer solution into the base polymer/ gemini surfactant solution, and preparing the active electrospun layer by electrospinning the spinning solution.
  • preparing an exemplary base polymer/ gemini surfactant solution may include mixing a first amount of the gemini surfactant with the base polymer solution.
  • the first amount may include between 0.01 wt.% and 0.1 wt.% based on total weight of the base polymer solution.
  • preparing an exemplary amine-terminated dendritic polymer solution may include dissolving a first amount of the amine-terminated dendritic polymer in the second solvent.
  • the first amount may include between 5 wt.% and 30 wt.% based on total weight of the base polymer.
  • preparing the base polymer/ gemini surfactant solution may include mixing a first amount of the gemini surfactant with the base polymer solution, an exemplary gemini surfactant may include a cationic gemini surfactant.
  • preparing the amine-terminated dendritic polymer solution may include dissolving at least one of polyamidoamine, polypropylene imine, and polyethylene imine in the second solvent.
  • an exemplary first solvent and an exemplary second solvent may be similar.
  • An exemplary first solvent may include at least one of chloroform, dichloromethane, dimethylformamide and an exemplary second solvent may include at least one of dimethylformamide, methanol, ethanol, propanol.
  • preparing the active electrospun layer may include electrospinning the spinning solution at an electrospinning distance between 15 cm and 20 cm and at a voltage between 20 kV and 25 kV.
  • preparing an exemplary active electrospun layer may include electrospinning an exemplary spinning solution.
  • the exemplary spinning solution may include 5 to 20 wt.% of the base polymer, 0.01 to 0.1 wt.% of the gemini surfactant, and 5 to 30 wt.% of the dendritic polymer.
  • the present disclosure is directed to a method for DNA filtration.
  • An exemplary method may include preparing an exemplary nanofibrous filter and forcing an exemplary DNA sample through the exemplary nanofibrous filter.
  • An exemplary nanofibrous filter may include a polymer scaffold, where the polymer scaffold may include at least one of aromatic and aliphatic polyester polymers, such as lactic acid / glycolic acid copolymer, an amine -terminated dendritic polymer embedded within the polymer scaffold, where the amine-terminated dendritic polymer may inlcude at least one of polyamidoamine, polypropylene imine, and polyethylene imine, and a cationic gemini surfactant.
  • aromatic and aliphatic polyester polymers such as lactic acid / glycolic acid copolymer
  • an amine -terminated dendritic polymer embedded within the polymer scaffold
  • the amine-terminated dendritic polymer may inlcude at least one of polyamidoamine, polypropylene imine, and polyethylene imine, and a cationic gemini surfactant.
  • FIG. 1 illustrates a structural representation of a fourth generation of Polyamidoamine (PAMAM) dendritic polymer, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 2 illustrates a structure of a cationic gemini surfactant, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 3 illustrates a flowchart of a method for preparing a positively-charged dendrimer/gemini surfactant membrane, consistent with one or more exemplar embodiments of the present disclosure
  • FIG. 4 illustrates an electrospinning apparatus, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 5 illustrates Fourier-transform infrared (FTIR) spectra of nanofibrous layers prepared utilizing different spinning solutions, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 6 illustrates a bar chart of water and oil contact angles for nanofibrous layers prepared utilizing different spinning solutions, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 7 illustrates surface arrangement of gemini surfactants on a PLLA surface, consistent with one or more exemplary embodiments of the present disclosure
  • FIG. 8 illustrates a table reporting DNA separation results, consistent with one or more exemplary embodiments of the present disclosure.
  • FIG. 9 illustrates a schematic representation of an exemplary interaction between an exemplary PLLA/gemini surfactant/PAMAM nanofibrous filter and an exemplary DNA sample, consistent with one or more exemplary embodiments of the present disclosure.
  • the present disclosure relates to exemplary embodiments of an electrospun nanofibrous article or membrane, a method for fabrication an electrospun nanofibrous membrane, and a method for utilizing an electrospun nanofibrous membrane for removing floating and free nucleic acids, such as antibiotic-resistant DNA from fluid media such as drinking water.
  • An exemplary electrospun nanofibrous membrane may include a positively charged dendrimer/gemini surfactant membrane.
  • Dendrimers are artificial macromolecules that are characterized by tree-like topological structures, highly branched structures of great regularity with empty spaces between the branches, compact shapes, and large numbers of reactive end groups.
  • an exemplary highly branched structure may refer to a macromolecule structure with a high degree of branching originated from a core region.
  • Examples of highly branched dendritic macromolecules may include, but are not limited to, dendrimers, hyperbranched polymers, dendrigraft polymers, and core- shell dendrimers.
  • An exemplary dendrimer may include a core, hyperbranched arms extending from the core with repeated units, and surface functional groups.
  • Exemplary surface functional groups may be located on an outermost layer of an exemplary dendrimer in a multivalent fashion and may significantly influence the physical and chemical properties of the dendrimer. Due to the abundance of hollow spaces between interior branches, an exemplary dendritic structure may host a wide variety of nonpolar or charged guest molecules into its hollow spaces or pockets by hydrophobic/hydrogen-bond interactions. Furthermore, due to the abundance of surface functional groups, an exemplary dendritic structure may host a wide variety of nonpolar or charged guest molecules on its surface by electrostatic interactions.
  • FIG. 1 illustrates a structural representation of a fourth generation of Polyamidoamine (PAMAM) dendritic polymer 10, consistent with one or more exemplary embodiments of the present disclosure.
  • PAMAM dendritic polymer 10 may include a core region 12 and extended branches 14 originated from core region 12.
  • extended branches 14 may be terminated by amie functional groups 16, hence, PAMAM dendritic polymer is an amine-terminated dendritic polymer.
  • An exemplary functional group of an exemplary dendrimer for example amine functional groups 16 of PAMAM dendritic polymer 10 may act as a reactive site, which may be capable of attracting and binding to guest molecules of interest.
  • hollow spaces between exemplary branches of an exemplary dendrimer for example, hollow spaces between extended branches 14 of PAMAM dendritic polymer 10 may act as cages or spaces in which a guest molecule of interest may be encaged or encapsulated.
  • a gemini surfactant may include two monomeric surfactant molecules that may be covalently linked by a spacer.
  • Two polar head groups of the aforementioned monomeric surfactant molecules may be cationic, anionic or nonionic. For example, double quaternary ammonium salts are among cationic gemini surfactant. These polar head groups may determine the classification and properties of surfactants.
  • FIG. 2 illustrates a structure of a cationic gemini surfactant 20, consistent with one or more exemplary embodiments of the present disclosure.
  • a cationic gemini surfactant such as cationic gemini surfactant 20 may include at least two hydrophobic chains, such as hydrophobic chains 22 and two hydrophilic quaternary ammonium groups such as hydrophilic quaternary ammonium groups 24 connected by a spacer group, such as spacer 26.
  • hydrophobic chains 22 may include linear or branched hydrocarbon chains. Hydrophobic chains 22 may further be functionalized with heteroatoms, such as fluorine, or may contain various functional groups, such as esters, or amide groups.
  • An exemplary spacer group, such as spacer 26 may be hydrophobic, like a polymethylene chain or may be hydrophilic, like polymethylene with ether or hydroxyl groups. From a structural point of view an exemplary spacer group, such as spacer 26 may be rigid, such as an aromatic spacer or may be flexible, like a polymethylene chain. Methyl groups within a cationic gemini surfactant may be substituted with another functional groups, for example, hydroxyethyl or deoxy-D-glucitol. The neutral charge of the surfactant molecule may be retained, by the presence of counterions, which usually are halide anions.
  • hydrophilic quaternary ammonium groups such as hydrophilic quaternary ammonium groups 24 and hydrophobic parts, such as hydrophobic chains 22 may be responsible for special properties of cationic gemini surfactants in solutions, such as adsorption on the surfaces and interfaces and formation of self-assembly aggregates.
  • the structure must be optimized by modification of HLB of the cationic gemini surfactants. This can be obtained by introduction of balanced polar or hydrophilic functional groups to substituents or to the spacer group. Hydrophilicity may be increased by insertion of hydroxyl, ester, ether, amide etc. groups. To increase lipophilicity, hydrocarbon chains longer than 12 methylene groups, or aromatic rings may be introduced to the substituents or to the spacer group. To increase biodegradability of cationic gemini surfactants, amide, ester or sugar groups may also be introduced to the substituents or to the spacer group.
  • the gemini alkylammonium salts show unique interfacial properties in aqueous solution.
  • Critical micelle concentration (CMC) of gemini alkylammonium salts is usually two orders lower than the CMC for corresponding monomeric surfactants.
  • CMC Critical micelle concentration
  • the effectiveness of cationic gemini surfactants in lowering surface tension is also much better than their monomeric counterparts.
  • the values of C20 (surfactant concentration at which the surface tension is lowered by 20 mN/m), are dozen times smaller for gemini surfactants compared to monomeric surfactants.
  • double quaternary ammonium salts may form many morphological structures in solution, like spherical, ellipsoidal, rod shape and worm-like micelles as well as vesicles and helical or tubular forms. This may lead to cationic gemini surfactants to have unique detergent, dispersion and solubilizing properties.
  • the gemini alkylammonium compounds further show a very high antimicrobial activity against microorganisms, like Gram positive bacteria, Gram negative bacteria, viruses, molds and yeasts.
  • the mechanism of biocidal activity of quaternary ammonium salts is based on the adsorption of the ammonium cation on the bacterial cell surface, diffusion through the cell wall and then binding and disruption of cytoplasmic membrane. Damage of the membrane results in the release of potassium ions and other cytoplasmatic constituents, leading to the death of the cell.
  • the minimal inhibitory concentrations (MIC) of gemini surfactants against microorganisms are even three orders of magnitude lower in comparison to MIC values of monomeric surfactants.
  • the gemini surfactants may further function as very efficient corrosion inhibitors, due to the presence of two positively charged nitrogen atoms and a large molecular surface.
  • Antimicrobial resistance continues to be one of the most serious global public health threats. Recently, it has been evidenced that free nucleic acids (NAs) are abundantly present in the effluent of wastewater treatment after bacterial die-off. These free DNAs contain trace amounts of antibiotic resistant DNAs which are often reintroduced to the water supply chains, potentially resulting in the spread of AMR via horizontal gene transfer in the receiving environment.
  • the global resistome include dispersion of free antibiotic -resistant DNAs in sewage into environments such as soil, fresh water, sea sediments and animals. Antibiotic -resistant DNAs may also be up-taken by human body through drinking water, contaminated food, crops, etc.
  • An exemplary positively charged dendrimer/gemini surfactant membrane may function as an effective barrier for removal of free DNAs including antibiotic -resistant DNAs.
  • An exemplary positively charged dendrimer/gemini surfactant membrane may be utilized as a filter in wastewater and drinking water treatment pipelines.
  • An exemplary positively charged dendrimer/gemini surfactant membrane may prohibit further dispersion of resistant genes into environments and contribute to counteracting the AMR global public health threats.
  • an isoelectric point (Ip) of a virion depends on the amino acid composition of the protein capsid. At pH values above the Ip, viruses have a net negative charge, but below the Ip, their charge is positive. Consequently, at higher pH values, an exemplary positively charged dendrimer/gemini surfactant membrane may adsorb viruses.
  • a synergetic effect between amine-terminated dendrimers and cationic gemini surfactants present in the structure of an exemplary positively charged dendrimer/gemini surfactant membrane may be utilized for both virus removal and antibiotic-resistant DNA filtration.
  • Exemplary methods and techniques disclosed herein are directed to exemplary embodiments of an exemplary fabrication method for preparing an exemplary positively charged dendrimer/gemini surfactant membrane.
  • An exemplary fabrication method may include preparing an exemplary spinning solution including an exemplary base polymer, an exemplary gemini surfactant, and an exemplary dendritic polymer.
  • An exemplary fabrication method may further include forming an exemplary nanofibrous membrane by electrospinning the exemplary spinning solution.
  • an exemplary fabrication method may include simultaneous electrospinning of an exemplary base polymer and an exemplary dendritic polymer in the presence of a gemini surfactant.
  • such simultaneous electrospinning of an exemplary base polymer and an exemplary dendritic polymer in the presence of a gemini surfactant may allow for the presence of the exemplary gemini surfactant within the exemplary nanofibrous membrane.
  • the synergetic effect between amine-terminated dendrimers and cationic gemini surfactants present in the structure of an exemplary positively charged dendrimer/gemini surfactant membrane may make the exemplary positively charged dendrimer/gemini surfactant membrane an effective filter for both virus removal and antibiotic -resistant DNA filtration.
  • FIG. 3 illustrates a flowchart of a method 30 for preparing a positively-charged dendrimer/gemini surfactant membrane, consistent with one or more exemplar embodiments of the present disclosure.
  • method 30 may include a step 32 of preparing a polymer solution by dissolving a base polymer in a first solvent, a step 34 of preparing a polymer/surfactant solution by mixing a gemini surfactant with the polymer solution, a step 36 of preparing an amine-terminated dendritic polymer solution by dissolving an amine-terminated dendritic polymer in a second solvent, a step 38 of preparing a spinning solution by dispersing the amine-terminated dendritic polymer solution into the polymer/surfactant solution, and a step 310 of preparing the positively-charged dendrimer/gemini surfactant membrane by electrospinning the spinning solution to obtain the scented nanofibrous layer.
  • step 32 may include preparing the polymer solution by dissolving a base polymer such as aromatic and aliphatic polyester polymers, such as lactic acid / glycolic acid copolymer, or combinations thereof in a suitable first solvent for the first polymer, where the first solvent may be one of chloroform, dichloromethane, dimethylformamide, and mixtures thereof.
  • the polymer solution may have a polymer-to-solvent concentration between 5 (w/v) % and 20 (w/v) %.
  • step 34 of preparing the polymer/surfactant solution may include mixing a gemini surfactant, such as hexamethylene- l,6-bis(N,N-dimethyl-N- dodecylammonium bromide), 3 -oxapentylene -l,5-bis(N,N-dimethyl-N-dodecylammonium bromide), 3 -azapentylene -l,5-bis(N,N-dimethyl-N-dodecylammonium bromide), or combinations thereof with the polymer solution.
  • a gemini surfactant such as hexamethylene- l,6-bis(N,N-dimethyl-N- dodecylammonium bromide), 3 -oxapentylene -l,5-bis(N,N-dimethyl-N-dodecylammonium bromide), 3 -azapentylene -l,5-bis(N
  • the gemini surfactant may have a concentration between 0.01 (w/v) % and 0.1 (w/v) % based on the total volume of the polymer solution.
  • mixing a gemini surfactant with the polymer solution may aid in emulsifying an exemplary mixture of an exemplary polymer solution and an exemplary dendritic polymer solution that may be mixed with the exemplary polymer solution in the following steps.
  • mixing a gemini surfactant with the polymer solution may further enhance the virus removal and DNA filtration capabilities of an exemplary positively-charged dendrimer/gemini surfactant membrane.
  • step 36 of preparing the amine-terminated dendritic polymer solution may include dissolving the amine-terminated dendritic polymer in the second solvent in an amount such that the amine-terminated dendritic polymer may have a concentration between 5 wt. % and 30 wt. % based on the weight of the first polymer.
  • dissolving the amine-terminated dendritic polymer in the second solvent may include adding the amine-terminated dendritic polymer to the second solvent while being stirred by a stirrer such as a mechanical stirrer, a sonicator, or other similar homogenizers.
  • dissolving the amine-terminated dendritic polymer in the second solvent may include adding the amine-terminated dendritic polymer to at least one of dimethylformamide, methanol, ethanol, propanol, and mixtures thereof.
  • dissolving the amine-terminated dendritic polymer in the second solvent may include adding at least one of a hyperbranched polymer, a dendrigraft polymer, a dendrimer, or mixtures thereof in the second solvent.
  • the first solvent and the second solvent may be similar.
  • step 38 may include preparing the spinning solution by dispersing the amine-terminated dendritic polymer solution into the polymer/surfactant solution, such that the spinning solution may include the base polymer with a concentration between 5 (w/v) % and 20 (w/v) % in the first solvent, the gemini surfactant with a concentration between 0.01 wt. % and 0.1 wt. % based on the weight of the first polymer, and the amine-terminated dendritic polymer with a concentration between 5 wt. % and 30 wt. % based on the weight of the first polymer.
  • step 310 may include electrospinning the spinning solution in an electrospinning apparatus to obtain the positively-charged dendrimer/gemini surfactant membrane.
  • the electrospinning may be carried out with different flow rates at different spray-to-collector distances.
  • electrospinning the spinning solution may be carried out at a nozzle-to-collector distance between 15 cm and 20 cm at a voltage between 20 kV and 25 kV, and with a flow rate of between 0.5 cm 3 hr -1 and 1 cm 3 hr -1 .
  • step 312 may include electrospinning the spinning solution in a needleless electrospinning apparatus to obtain the positively-charged dendrimer/gemini surfactant membrane.
  • FIG. 4 illustrates an electrospinning apparatus 40, consistent with one or more exemplary embodiments of the present disclosure.
  • apparatus 40 may include an electrospinning nozzle 42 that may be utilized for injecting an exemplary spinning solution and a collector 44 placed in front of nozzle 42 at a distance 48.
  • distance 48 may be adjustable.
  • a power supply system 410 connected to both nozzle 42 and collector 44 may apply a predetermined potential difference between a tip 46 of nozzle 42 and collector 44.
  • collector 44 may be grounded.
  • step 310 of preparing the positively-charged dendrimer/gemini surfactant membrane may include electrospinning of the spinning solution onto a collector, such as collector 44 from an electrospinning nozzle such as nozzle 42 with a flow rate between 0.5 cm 3 hr -1 and 1 cm 3 hr -1 .
  • Collector 44 may be positioned at distance 44.
  • distance 48 may be between 15 cm and 20 cm from tip 46 of electrospinning nozzle 42.
  • a power supply system such as power supply system 410 may apply a voltage between 20 kV and 25 kV between nozzle tip 46 and collector 44.
  • a nanofibrous layer of poly(L-Lactic acid) (PLLA)/gemini surfactant/polyamidoamine (PAMAM) was prepared utilizing a synthesis method similar to method 30 of FIG. 3.
  • PLLA poly(L-Lactic acid)
  • PAMAM polyamidoamine
  • CHCI3 chloroform
  • DMF N,N-dimethylformide
  • a PLLA/gemini surfactant solution was prepared by mixing a gemini surfactant with the PLLA solution.
  • a second generation PAMAM solution was prepared by dissolving a second generation PAMAM polymer in a solvent system containing chloroform (CHCI3) and N,N-dimethylformide (DMF) with a CHCI3: DMF ratio of 85:15 v/v.
  • a spinning solution was prepared by dispersing the second generation PAMAM solution into PLLA/gemini surfactant solution.
  • the spinning solution included 10 wt.% of PLLA, 0.01 wt.% of the gemini surfactant, and 10 wt.% of the second generation PAMAM polymer based on the total weight of the spinning solution.
  • the prepared spinning solution was electrospun in an electrospinning system with a feeding rate of approximately 0.5 ml/h, an electrospinning distance of approximately 18 cm, and a voltage of approximately 20 kV.
  • the electrospinning process was carried out at 18-20 °C utilizing an electrospinning nozzle with an inner diameter of 0.4 mm and a cylindrical collector rotating at 2000 rpm.
  • three other samples were prepared under similar electrospinning conditions as described above.
  • a first sample was prepared using a spinning solution containing only a 10 wt.% polymer solution of PLLA in a solvent system containing chloroform (CHCI3) and N,N-dimethylformide (DMF) with a CHCI3: DMF ratio of 85:15 v/v
  • second sample was prepared using a spinning solution including a PLLA/gemini surfactant solution containing 10 wt.% of PLLA and 0.01 wt.% of the gemini surfactant.
  • a third sample was prepared using a spinning solution including PLLA with a concentration of 10 wt.% and a second generation PAMAM polymer with a concentration of 10 wt.% based on the total weight of the spinning solution.
  • the first sample is referred to herein as PLLA sample
  • the second sample is referred to herein as PLLA/gemini surfactant sample
  • the third sample is referred to herein as PLLA/PAMAM sample.
  • FIG. 5 illustrates Fourier-transform infrared (FTIR) spectra 50 of nanofibrous layers prepared utilizing different spinning solutions, consistent with one or more exemplary embodiments of the present disclosure.
  • FTIR spectra 50 of nanofibrous layers include an FTIR spectrum 52 of PLLA sample, an FTIR spectrum 54 of PLLA/gemini surfactant sample, an FTIR spectrum 56 of PLLA/PAMAM sample, and an FTIR spectrum 58 of PLLA/gemini surfactant/PAMAM sample.
  • FIG. 6 illustrates a bar chart 60 of water and oil contact angles for nanofibrous layers prepared utilizing different spinning solutions, consistent with one or more exemplary embodiments of the present disclosure.
  • Bar chart 60 includes water contact angle bar 62a and oil contact angle bar 62b for PLLA/PAMAM sample, water contact angle bar 64a and oil contact angle bar 64b for PLLA sample, water contact angle bar 66a and oil contact angle bar 66b for PLLA/gemini surfactant/PAMAM sample, and water contact angle bar 68a and oil contact angle bar 68b for PLLA/gemini surfactant sample.
  • PLLA/PAMAM sample shows the highest wettability due to the presence of amin functional end groups within the structure of the PLLA/PAMAM sample. It is further evident that, PLLA/gemini surfactant sample has the lowest wettability due to the long hydrophobic tail and surface arrangement of the gemini surfactant.
  • FIG. 7 illustrates surface arrangement of gemini surfactants 70 on PLLA surface 72, consistent with one or more exemplary embodiments of the present disclosure.
  • PLLA surface 72 has a negative charge, therefore, when PLLA is exposed to gemini surfactants 70, gemini surfactants 70 may tend to turn form the positive heads of gemini surfactants 70 towards PLLA surface 72.
  • hydrophobic tails are positioned outward, the wettability of the sample decreases.
  • synthesized nanofibrous layers of PLLA /gemini surfactant/PAMAM were utilized in a spin filter of a DNA capturing kit.
  • PLLA /gemini surfactant/PAMAM nanofibrous filter, PLLA nanofibrous filter, PLLA/gemini surfactant nanofibrous filter, and PLLA/PAMAM nanofibrous filter as-synthesized in Example 1, referred to hereinafter as nanofibrous filters were placed in a number of spin filter tubes. Each spin filter tube was centrifuged at 13500 rpm for 30 seconds to make sure that each nanofibrous filter was properly disposed within each respective spin filter tube.
  • FIG. 8 illustrates a table 80 reporting DNA separation results, consistent with one or more exemplary embodiments of the present disclosure. As discussed in the preceding paragraph, four different DNA separation set-ups were utilized for evaluating the performances of the nanofibrous filters synthesized in Example 1.
  • the DNA separation set-up, in which, a PLLA nanofibrous filter was utilized within the spin filter of the DNA separation kit is referred to as set-up “B” in table 80.
  • the DNA separation set-up, in which, a PLLA/gemini surfactant nanofibrous filter was utilized within the spin filter of the DNA separation kit is referred to as set-up “C” in table 80.
  • the DNA separation set-up, in which, a PLLA/PAMAM nanofibrous filter was utilized within the spin filter of the DNA separation kit is referred to as set-up “D” in table 80.
  • the DNA separation set-up, in which, a PLLA/gemini surfactant/PAMAM nanofibrous filter was utilized within the spin filter of the DNA separation kit is referred to as set-up “E” in table 80.
  • FIG. 9 illustrates a schematic representation of an exemplary interaction between an exemplary PLLA/gemini surfactant/PAMAM nanofibrous filter and an exemplary DNA sample, consistent with one or more exemplary embodiments of the present disclosure.
  • interactions among PAMAM dendritic polymer 92, gemini surfactant 94, PLLA 96, and DNA sample 98 is illustrated in this figure. It may be evident that in an exemplary PLLA/gemini surfactant/PAMAM nanofibrous filter, an exemplary gemini surfactant is not only functioning as a surfactant, but the synergetic effect of simultaneous presence of an exemplary gemini surfactant and an exemplary amine terminated dendrimer may allow for an efficient DNA removal.

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Abstract

L'invention concerne une couche électrofilée active pour séparation de l'ADN, pouvant comprendre un échafaudage polymère. Un exemple d'échafaudage polymère peut comprendre un polymère de polyester aromatique et/ou un polymère de polyester aliphatique. Un exemple de couche électrofilée active pour séparation de l'ADN peut comprendre en outre un polymère dendritique à terminaison amine, pouvant être incorporé dans l'échafaudage polymère. Un exemple de polymère dendritique à terminaison amine peut comprendre une polyamidoamine, une polypropylène-imine, et/ou une polyéthylène-imine. Un exemple de couche électrofilée active pour séparation de l'ADN peut comprendre en outre un tensioactif géminé cationique.
PCT/IB2021/050524 2021-01-23 2021-01-23 Couche électrofilée active pour filtration de l'adn WO2022157547A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9168231B2 (en) * 2010-12-05 2015-10-27 Nanonerve, Inc. Fibrous polymer scaffolds having diametrically patterned polymer fibers
US20160303517A1 (en) * 2015-01-30 2016-10-20 California Institute Of Technology Dendrimer particles and related mixed matrix filtration membranes, compositions, methods, and systems
US10532330B2 (en) * 2011-08-08 2020-01-14 California Institute Of Technology Filtration membranes, and related nano and/or micro fibers, composites, methods and systems

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9168231B2 (en) * 2010-12-05 2015-10-27 Nanonerve, Inc. Fibrous polymer scaffolds having diametrically patterned polymer fibers
US10532330B2 (en) * 2011-08-08 2020-01-14 California Institute Of Technology Filtration membranes, and related nano and/or micro fibers, composites, methods and systems
US20160303517A1 (en) * 2015-01-30 2016-10-20 California Institute Of Technology Dendrimer particles and related mixed matrix filtration membranes, compositions, methods, and systems

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