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WO2015106329A1 - Nanotubes de carbone à liaison aux macromolécules limitée par revêtement avec de l'albumine (racnt-bsa) - Google Patents

Nanotubes de carbone à liaison aux macromolécules limitée par revêtement avec de l'albumine (racnt-bsa) Download PDF

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Publication number
WO2015106329A1
WO2015106329A1 PCT/BR2015/000003 BR2015000003W WO2015106329A1 WO 2015106329 A1 WO2015106329 A1 WO 2015106329A1 BR 2015000003 W BR2015000003 W BR 2015000003W WO 2015106329 A1 WO2015106329 A1 WO 2015106329A1
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WO
WIPO (PCT)
Prior art keywords
bsa
racnt
carbon nanotubes
restricted
albumin
Prior art date
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Ceased
Application number
PCT/BR2015/000003
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English (en)
Portuguese (pt)
Inventor
Eduardo Costa DE FIGUEIREDO
Adriano Francisco BARBOSA
Pedro Orival LUCCAS
Valéria Maria Pereira BARBOSA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
UNIVERSIDADE FEDERAL DE ALFENAS-UNIFAL-MG
Fundacao de Amparo a Pesquisa do Estado de Minas Gerais FAPEMIG
Original Assignee
UNIVERSIDADE FEDERAL DE ALFENAS-UNIFAL-MG
Fundacao de Amparo a Pesquisa do Estado de Minas Gerais FAPEMIG
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Publication of WO2015106329A1 publication Critical patent/WO2015106329A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/34—Size-selective separation, e.g. size-exclusion chromatography; Gel filtration; Permeation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
    • B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
    • B01J20/289—Phases chemically bonded to a substrate, e.g. to silica or to polymers bonded via a spacer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
    • B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
    • B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • B01J20/3274—Proteins, nucleic acids, polysaccharides, antibodies or antigens
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/158—Carbon nanotubes
    • C01B32/168—After-treatment
    • C01B32/174—Derivatisation; Solubilisation; Dispersion in solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/20—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
    • B01D15/206—Packing or coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Definitions

  • the subject of the invention relates to carbon nanotubes restricted to binding of macromolecules by means of external coating with bovine serum albumin (RACNT-BSA) restricted access carbon nanotube capped bovine serum albumin.
  • Carbon nanotubes are surrounded by a layer of bovine serum albumin, chemically crosslinked, forming a protective cap.
  • RACNT-BSA bovine serum albumin
  • the proteins in the sample do not bind to the sorbent due to the protection of the outer layer of albumin.
  • Even the low molecular weight analytes can diffuse in the middle of the albumin layer and bind to the nanotubes.
  • the material developed is of synthetic origin and can be used as a solid reagent for preconcentration / selective extraction of low molecular weight analytes in protein samples, thus avoiding the need to perform prior procedures for the decomposition of the sample matrix.
  • the CNTs are cylindrical in shape like graphite sheets rolled in the shape of a straw, and may have one or several layers, diameter from 4 to 30 nm and length of 1 ⁇ .
  • the properties of the CWT the high chemical and physical stability and, especially, the high surface area, favorable conditions in adsorption processes are mentioned (Byszewski, P., Lange, H., Huczko, A., Be nke, FJ of Physics Chemistry Solide., 11 (1997) 1679).
  • the excellent adsorptive properties of the CNTs are attributed to the hexagonal arrangement of the carbon atoms in the graphite sheet, which gives strong interaction of atoms and molecules higher than those observed in activated carbon.
  • These materials are widely used in sorption processes, for the solid phase extraction of various analytes and as a chromatographic column filling. However, all applications are restricted to aqueous solutions. When the analytes are found in medium with high concentration of macromolecules (eg whole blood, plasma, serum, food samples, etc.), the material does not present selectivity and retains large amount of proteins on its external surface, causing loss of selectivity, decrease in their useful life and risk of analytical column degradation when the analysis is conducted by solid phase and chromatographic extraction techniques.
  • macromolecules eg whole blood, plasma, serum, food samples, etc.
  • RAM Restricted access materials
  • silica-based sorbents and provided with pores where the various low molecular weight molecules are capable of binding.
  • such materials have their outer surface modified with hydrophilic binders to the point of chemically making the binding of undesired macro-molecules present in the matrix chemically unviable (Sad ⁇ lek P., Satinsky D., Solich P., Anal. Chem., 26 (2007) 375- 384.).
  • RAMs have been used in the direct extraction of organic analytes in protein fluids such as blood, plasma, serum, etc. Examples of applications of restricted access materials in analytical methods have been observed for the extraction of organic compounds using chromatographic columns and pre-column chromatography.
  • RAMs were already employed in commercial chromatography columns containing silica, C18, C8 and MIP (molecular printing polymers) (EP2156182; O2008148547; US20040191537; US200281050; WO2002101362; EP135721; EP1053021; WO1999039739; PI1020120153394).
  • CNTs are highly adsorptive materials, which are not very selective and have an undesirable ability to retain macromolecules, making their direct application in the extraction of analytes in protein fluids impossible.
  • CNT capable of eliminating macromolecules there are no reports in the literature of CNT capable of eliminating macromolecules, and these materials are promising in the direct separation / extraction / preconcentration of organic and inorganic analytes into protein fluids.
  • the main object of the invention is to describe the method of obtaining and using a CNT restricted to macromolecule binding (RACNT-BSA).
  • CNTs were coated / encapsulated by a layer of chemically cross-linked serum bovine albumin.
  • Direct extraction of cadmium into human blood serum followed by atomic absorption analysis is described as a model in that patent.
  • any other inorganic or organic analytes can be extracted from protein fluids using the RACNT-BSA. To date, there are no reports in databases on the technology developed.
  • RACNT-BSA has the potential for wide use and commercialization in industries and laboratories that work with analyzes of metals and organic compounds in biological fluids, and can be packaged in any extraction system that uses solid sorbents, with the great advantage of being possible the injection directly from protein fluids without any previous deproteinization step.
  • the aim of the present invention is the development and use of carbon nanotubes restricted to binding to macromolecules by coating with albumin (RACNT-BSA), and which are capable of directly extracting analytes present in protein matrices without the prior need of decomposition of the matrix by slow procedures such as microwave decomposition, dry route, humid route, etc. These materials are capable of eliminating about 100% of the macromolecules present in protein fluids undergoing extraction.
  • the principle of elimination of the macromolecules comes from the physico-chemical nature of the sorbent, since the immobilization of the BSA on the surface of the CNT blocks the CNT binding sites preventing binding of the same to the proteins of the sample.
  • RACNT-BSA has a long shelf-life, proven by maintaining its performance even after about 300 consecutive extractions of human serum samples for cadmium analysis. In terms of cost, the production of 1 g of RACNT-BSA requires about R $ 150.00. It is noteworthy that in the RACNT-BSA proposed in this application for patent protection does not resemble the patents reported on CTN. Brief Description of the Figures
  • Figure 1 Representative scheme of RACNT-BSA synthesis. (1) CNT, (2) reagents responsible for functionalization, (3) functionalisation reaction, (4) functionalized CNTs, (5) BSA (bovine serum albumin), (6) CNT coating step, (7 and 8 ) RACNT-BSA.
  • BSA bovine serum albumin
  • RACNT-BSA single or multiple-walled CNTs can be coated either directly or after a functionalization reaction.
  • Unmodified CNTs exhibit supportive characteristics and are mainly used for extraction / preconcentration of organic compounds.
  • the functionalization of the material provides better characteristics.
  • the CNTs can be functionalized with different organic molecules using covalent or non-covalent binding strategies (Antonio V. Herrera-Herrera et al., Analytica Chimica Acta, 734 (2012) 1).
  • the main functionalisations are:
  • the reagents used are: NH 3 . H 2 O / H 2 O 2 ; H 2 SO 4 / H 2 0 2 ; HNO 3 ; KMNO 4 ; 2CH 2 0 7; HNO 3 / 3 ⁇ 40 2 .
  • This functionalization initially involves the oxidation of CNTs and subsequent reaction with amines, such as: ethylenediamine (EDA) (Z. Zang, Z. Hu, Z. Li, Q. He, X. Chang, J. Hazard, Mater, 172 (2009) 958); Tris (2 ' aminoethyl) amine (TAA) (Y. Cui, S. Liu, Z.-J. Hu, X.-H. Liu, H. W .; Gao, Microchim. Acta 174 (2011) 107); 2- aminobenzothiazole (ABT) (R. Li, X. Ang., Z. Li. 2. Zang. Z. Hu. D. Li. Z.
  • Another way of functionalizing CNTs can be obtained by the use of N 2 induced plasma.
  • This technique allows the formation of ⁇ - C * and - CN * groups in CNTs which can then react with other organic compounds and receive other functional groups.
  • This technique aims to replace the previous stage of oxidation, used in other functionalisations of the CNT, to present higher efficiency since the oxidation stage can degrade the CNT.
  • the main modifications with this technique involve the use of polyacrylamide (PAAM), poly (N, N-dimethylacrylamide) PDMA (D. Shao, X. Ren, J. Hu, Y. Chen, X. Wang, Colloids Surf., A 360 (2010) 74); (VP) (X. Ren, D. Shao, G. Zhao, G. Sheng, J.
  • the functionalized CTNs were then coated with BSA (Menezes M.L., Felix G, J. Liq. Chromatogr RT, 21 (1998) 2863; Lima VV, Cassiano NM, Cass Q.B., Qu ⁇ mica Nova, 29 (2006) 72), and it is important to emphasize that any other type of CNT functioned for being subjected to this coating process.
  • BSA Melezes M.L., Felix G, J. Liq. Chromatogr RT, 21 (1998) 2863; Lima VV, Cassiano NM, Cass Q.B., Qu ⁇ mica Nova, 29 (2006) 72
  • a volume of 1 to 50 mL of an aqueous solution of sodium borohydride of 0.05 to 5% (w / v) were percolated by the cartridge for the purpose of reducing the imines (originating from the previous reaction) to amines which are more chemically stable moieties, thereby conferring chemical stability on the material.
  • the RACNT-BSA was washed in abundance with water to remove the remaining reagents from the coating process.
  • a column of 2 to 7 mm internal diameter by 5 cm in length was filled with RACNT-BSA and coupled in a chromatographic system to the analytical column.
  • 25 ⁇ l of an aqueous BSA standard 44 mg.mL- 1 (the same human blood serum protein concentration) were injected through the column and the resulting peak (detected at 254 nm) was compared to the peak obtained from the injection of the same BSA standard on the system without the column. It was verified that there was practically no albumin retention in the RACNT-BSA (with recovery of 101 ⁇ 1%), indicating that the coating satisfactorily prevented the binding of proteins on the CNT surface.
  • the RACNT-BSA-containing column was then coupled at the position of the sampling loop on a manual switch injector employed in the flow preconcentration system, eluted straight to a heated nickel tube atomic absorption equipment (TS-FF-AAS, from thermospray flame furnace atomic absorption spectrometry).
  • TS-FF-AAS heated nickel tube atomic absorption equipment
  • the system was optimized and validated for cadmium extraction in serum and human blood plasma.
  • the method was efficient in the direct analysis (without the need of any preliminary step of sample preparation) of cadmium, with limit of quantification of 0.8 ug / L>.
  • the material besides allowing the direct extraction of cadmium, still presented high preconcentration power (preconcentration factor of 5.7).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

La présente invention concerne l'élaboration d'un sorbant solide de nanotubes de carbone à liaison aux macromolécules limitée par revêtement avec de l'albumine (RACNT-BSA). Ce matériau est un extracteur / pré-concentrateur permettant d'éliminer 100% des macromolécules pendant les procédés d'extraction dans des liquides protéiques, supprimant ainsi la nécessité de décomposition de la matrice organique avant les analyses. Son obtention est simple et présente de faibles coûts de production, sa performance en termes de sélectivité et de capacité d'élimination de macromolécules étant supérieure à celle des sorbants disponibles sur le marché. Il possède une longue vie utile (environ 300 extractions) avec un grand potentiel de commercialisation.
PCT/BR2015/000003 2014-01-16 2015-01-16 Nanotubes de carbone à liaison aux macromolécules limitée par revêtement avec de l'albumine (racnt-bsa) Ceased WO2015106329A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BR102014001074-2A BR102014001074B1 (pt) 2014-01-16 2014-01-16 Nanotubos de carbono restritos à ligação com macromoléculas por meio de recobrimento com albumina (racnt-bsa)
BR102014001074-2 2014-01-16

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106442668A (zh) * 2016-09-28 2017-02-22 北京农学院 一种碳纳米管修饰电极的制备方法
CN109350996A (zh) * 2018-12-15 2019-02-19 浙江省食品药品检验研究院 一种石墨化多壁碳纳米管固相萃取柱及其应用
CN111389352A (zh) * 2020-02-28 2020-07-10 中国矿业大学(北京) 改性多壁碳纳米管及其制备方法和去除水中镍离子的方法

Citations (4)

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US6641793B2 (en) * 1998-10-02 2003-11-04 University Of Kentucky Research Foundation Method of solubilizing single-walled carbon nanotubes in organic solutions
BRPI1004450A2 (pt) * 2010-05-31 2012-02-22 Univ Minas Gerais método e sistema para purificação e funcionalização de nanotubos de carbono via radiação microondas
US20120234204A1 (en) * 2011-03-17 2012-09-20 Bayer Materialscience Ag Vapor phase functionalization of carbon nanotubes
WO2012168899A1 (fr) * 2011-06-10 2012-12-13 Commissariat A L'energie Atomique Et Aux Energies Alternatives Procédé de fonctionnalisation sélective de nanotubes de carbone monoparois

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BRPI1004450A2 (pt) * 2010-05-31 2012-02-22 Univ Minas Gerais método e sistema para purificação e funcionalização de nanotubos de carbono via radiação microondas
US20120234204A1 (en) * 2011-03-17 2012-09-20 Bayer Materialscience Ag Vapor phase functionalization of carbon nanotubes
WO2012168899A1 (fr) * 2011-06-10 2012-12-13 Commissariat A L'energie Atomique Et Aux Energies Alternatives Procédé de fonctionnalisation sélective de nanotubes de carbone monoparois

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LIMA, V.V. ET AL.: "Desenvolvimento de colunas cromatográficas de meios de acesso restrito proteina-imobilizada e suas avaliações para análise de fármacos com injeção direta de plasma humano.", QUIM. NOVA, vol. 29, no. 1, 2006, pages 72 - 78, XP055212994 *
OGBODU, R. O. ET AL.: "Effect of bovine serum albumin and single walled carbon nanotube on the photophysical properties of zinc octacarboxy phthalocyanine.", SPECTROCHIMICA ACTA PART A, vol. 121, 25 October 2013 (2013-10-25), pages 81 - 87, XP055212997 *
ZANG, Z. ET AL.: "Synthesis, characterization and application of ethylenediamine-modified multiwalled carbon nanotubes for selective solid-phase extraction and preconcentration of metal ions.", JOURNAL OF HAZARDOUS MATERIALS, vol. 172, 2009, pages 958 - 963, XP026719940 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106442668A (zh) * 2016-09-28 2017-02-22 北京农学院 一种碳纳米管修饰电极的制备方法
CN109350996A (zh) * 2018-12-15 2019-02-19 浙江省食品药品检验研究院 一种石墨化多壁碳纳米管固相萃取柱及其应用
CN111389352A (zh) * 2020-02-28 2020-07-10 中国矿业大学(北京) 改性多壁碳纳米管及其制备方法和去除水中镍离子的方法

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BR102014001074B1 (pt) 2021-12-28
BR102014001074A8 (pt) 2017-12-26

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