WO2014121819A1 - Particules de nanodiamand fonctionnalisées avec du folate, procédé pour leur préparation et leur utilisation - Google Patents

Particules de nanodiamand fonctionnalisées avec du folate, procédé pour leur préparation et leur utilisation Download PDF

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Publication number
WO2014121819A1
WO2014121819A1 PCT/EP2013/052261 EP2013052261W WO2014121819A1 WO 2014121819 A1 WO2014121819 A1 WO 2014121819A1 EP 2013052261 W EP2013052261 W EP 2013052261W WO 2014121819 A1 WO2014121819 A1 WO 2014121819A1
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WO
WIPO (PCT)
Prior art keywords
nanodiamond particles
folate
nanodiamond
particles
modified
Prior art date
Application number
PCT/EP2013/052261
Other languages
English (en)
Inventor
Viktoryia LAPINA
Joerg Opitz
Alexander BOROBEY
Tatjana PAVICH
Juergen Schreiber
Vladimir Belyi
Original Assignee
Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
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Application filed by Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. filed Critical Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.
Priority to PCT/EP2013/052261 priority Critical patent/WO2014121819A1/fr
Publication of WO2014121819A1 publication Critical patent/WO2014121819A1/fr

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54313—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being characterised by its particulate form
    • G01N33/54346—Nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0052—Small organic molecules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
    • A61K49/0069—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the agent being in a particular physical galenical form
    • A61K49/0089—Particulate, powder, adsorbate, bead, sphere
    • A61K49/0091—Microparticle, microcapsule, microbubble, microsphere, microbead, i.e. having a size or diameter higher or equal to 1 micrometer
    • A61K49/0093—Nanoparticle, nanocapsule, nanobubble, nanosphere, nanobead, i.e. having a size or diameter smaller than 1 micrometer, e.g. polymeric nanoparticle
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Definitions

  • the present invention refers to a method for preparing folate functionalized nanodiamond particles in which the nanodiamond particles are coupled with a folate linker.
  • Such nano-particles are used in the field of biomedicine for selective delivery to active proliferated cells for their imaging and tracking in nano-scale range.
  • Nano-diamonds are imagining as new and promising cellular biomarkers with high potential. It is known from the prior art that nano-diamond particles have a suitable surface for biological activation and functionalization (J. Opitz, A. Pohl, J. Schreiber, M. Mkandawire, U. Krause-Buchhoiz, G. Roedel, W. Pompe, T. Gubarevich, V.
  • the cell- membrane folate receptor is a potential molecular target for tumor selective drug delivery, including various folate-chelate conjugates for diagnostic imaging (US 7, 598, 335).
  • nanodiamond particles with the features of claim 1 and nanodiamond particles with the features of claim 11 are provided.
  • Claim 15 a use according to the present invention are described.
  • a method for preparing folate functionalized nanodiamond particles comprising the following steps:
  • the nanodiamond particles are provided by detonation of 2- methyl-l,3,5-trinitrobenzene (TNT) and l,3,5-trinitroper-hydro-l,3,5-triazine (RDX).
  • TNT 2- methyl-l,3,5-trinitrobenzene
  • RDX l,3,5-trinitroper-hydro-l,3,5-triazine
  • the Afunctional linker preferably and amine, more preferably selected from the group consisting of N-tert-butoxycarbonyl-l,6-hexane-diamine, tert-butyi N-(6- aminohexyl)-carbamate, tert-butyl N-(5-aminopentyl)-carbamate, tert-butyl N-(3- aminopropyi)-carbamate, tert-butyl N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)- carbamate, and its mixtures.
  • the coupling of the at least one folate with the Afunctional linker is performed by the following steps: - providing a suspension of the at least one folate in an organic solvent, preferably selected from the group consisting of dimethylsulfoxide, pyridine, dimethyl formamide and its mixtures,
  • nanodiamond particles are ozonised by the following steps: providing a suspension of the nanodiamond particles in an alkaline water solution, preferably comprising sodium hydroxide, - feeding ozone into the solution, acidulation of the solution, preferably by adding hydrochloric acid, and isolating the modified nanodiamond particles by centrifugation.
  • the nanodiamond particles are oxidised by liquid phase oxidation, preferably with organic acids, inorganic acids, potassium permanganate, manganese dioxide, chromium (VI) compounds, halogens and its compounds, dimethyl sulfoxide, and its mixtures, and/or by gas phase oxidation, pref- erably a mixture of 0 2 + N 2 (4 -20% 0 2 ), C0 2 +K 2 C0 3 , H 2 0 +K 2 C0 3 and/or 0 3 .
  • the folate are preferably selected from the group consisting of folic acid, folic acid modified by l-ethyl-3-(3-dimethy!amino-propyl)-carboimide and N ' -hydroxy- succinimide.
  • the nanodiamond particles can be provided as a polydispersion of single nanodiamond particles and its aggregates. It is further preferred that at least a part of the nanodiamond particles comprise optically active structures, preferably nitrogen vacancy centres in the core of diamond particles and various fluorescence species in the diamond shell, preferably admixtures of metals Cu, Ti, Cr, Si, Zn, AL, M n, Fe and their compounds as oxides, oxy- organic compounds and salts.
  • nanodiamond particles with a functionalized surface comprising at least one folate are provided.
  • Such particle is conjugated with the folates via a chemical bonding wherein the density of the folate groups is at least one group per particle.
  • the nanodiamortd particles comprise optically active structures which are located on the surface and/or within the core of the particles, preferably nitrogen vacancy centres in the core of diamond particles or various fluorescence species in the diamond shell, preferably admixtures of metals Cu, Ti, Cr, Si, Zn, AL, Mn, Fe and their compounds as oxides, oxy- organic compounds and salts or modified by fluorescence organic dyes on surface shell.
  • the nanodiamond particles are preferably polycrystalline and/or microcrystalline.
  • Nanodiamond particles according to the present invention can be used as fluorescent marker for cells, in particular tumor cells, or as fluorescent tracking marker in tumor cells and active-proliferated cells.
  • These particles can be used as a nanoscale biomarker for cancer or chronic inflammatory diseases or as tracking imaging agent, e.g. to visualize the process of cancer tumors.
  • the present invention uses raw of the unique features of nanodiamond particles, including the nanoscale sizing, large chemically active surface area to mass ratio, surface modification, long-term photo stability, and fluorescence blinking and bleaching.
  • the present invention uses the fluorescence of the nanodiamond particles conjugated with the folate.
  • the visualization of the nanodiamond particles can be done by fluorescence provided from nanodiamond particles or their aggregates.
  • the selective imaging of cancer or inflammatory cells is realized by the folate func- tionalized nanodiamond particles. It is an advantage of the present invention that the long-term imaging and tracking incomp!ex cellular cancer or inflammatory envi- ronments can be improved due to the exceptionally photostability without photo- bleaching and photoblinking of the inventive nanodiamond particles.
  • the own fluorescence properties of the nanodiamond particles enables the visualization of cancer cells and the folate enables the selective delivery of the particles to the cancer cells.
  • Fig. 1 shows fluorescence excitation spectra of ultradispurse diamonds (UDD)for different wavelengths.
  • Fig. 2a and 2b show structural setup of the nanodiamond particles coupled with the folates. The synthesis of these structures is carried out in three stages:
  • Fig, 3 shows spectra of fluorescence excitation for folic acid, nanodiamond particles and nanodiamond particles coupled with folic acid.
  • Ultradisperse diamonds obtained by explosive synthesis are known to be elementary particles with the size of 4-6 nm and surrounded by the coating of various non-diamond forms of carbon.
  • carboxyl group situated on the UDD particle.
  • UDD cleaned by the method ⁇ method of back titration contains one carboxyl group for 5000-6000 carbon units, that is, in our opinion, is not effective at conjugate synthesis.
  • the increasing content of carboxyl groups can be made by additional oxidation of lower degrees of carbon as hydroxyl, carbonyl and isolated double bindings; and also thanks to hidden forms of carboxy!
  • Ozonization of UDD suspension with the concentration of 5 g per 1 liter of water was made on the set-up for obtaining ozone with the flow speed of 10-15 ml per second and content of ozone in gas mixture of 3-5 %.
  • the ozone was obtained of air mixture, cleaned by series connection of Tischenko bottles: starting with the concentrated sulfuric acid and then with dry granulated caustic soda.
  • 0.1 g of caustic soda was added and while mixing through the bubble tube there was passing the current of ozone for 2 hours ⁇ excess is more than in 300 times). Additional oxidation was made by adding 30 ml of 30% hydrogen peroxide and holing the mixture during 1 hour.
  • ND-FA complex is fine-dispersed dry powder of grayish-yellow color with the characteristic spectral properties.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biomedical Technology (AREA)
  • Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nanotechnology (AREA)
  • Veterinary Medicine (AREA)
  • Hematology (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Urology & Nephrology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Microbiology (AREA)
  • Cell Biology (AREA)
  • Carbon And Carbon Compounds (AREA)

Abstract

La présente invention concerne un procédé pour préparer des particules de nanodiamand fonctionnalisées avec du folate dans lequel les particules de nanodiamand sont couplées à un liant folate. De telles nanoparticules sont utilisées dans le domaine de la biomédecine pour une libération sélective dans les cellules ayant proliféré actives en vue de leur imagerie et suivie à l'échelle nanoscopique.
PCT/EP2013/052261 2013-02-06 2013-02-06 Particules de nanodiamand fonctionnalisées avec du folate, procédé pour leur préparation et leur utilisation WO2014121819A1 (fr)

Priority Applications (1)

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PCT/EP2013/052261 WO2014121819A1 (fr) 2013-02-06 2013-02-06 Particules de nanodiamand fonctionnalisées avec du folate, procédé pour leur préparation et leur utilisation

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PCT/EP2013/052261 WO2014121819A1 (fr) 2013-02-06 2013-02-06 Particules de nanodiamand fonctionnalisées avec du folate, procédé pour leur préparation et leur utilisation

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104495836A (zh) * 2014-11-26 2015-04-08 河南晶锐超硬材料有限公司 一种金刚石微粉的处理方法
WO2017096106A3 (fr) * 2015-12-02 2018-03-01 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Nanodiamants fluorescents comme marqueurs de référence pour microscopie et imagerie par fluorescence
CN107865970A (zh) * 2016-09-27 2018-04-03 中国科学院理化技术研究所 一种以纳米金刚石为载体的多功能靶向给药体系的构建及其应用
JP2019533005A (ja) * 2016-09-06 2019-11-14 デビナ・ダイアグノスティクス・インコーポレイテッドＤｅｂｉｎａ Ｄｉａｇｎｏｓｔｉｃｓ， Ｉｎｃ． ナノダイヤモンド粒子及び関連する装置及び方法
EP3987313A4 (fr) * 2019-06-18 2023-10-18 Debina Diagnostics, Inc. Compositions et articles comprenant des particules de (nano)diamant

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US7598335B2 (en) 2006-08-01 2009-10-06 Kaohsiung Medical University Folate-receptor-targeting iron oxide nanoparticles coated with poly(ethylene glycol)
US20110008447A1 (en) * 2009-07-13 2011-01-13 National Chiao Tung University Carrier comprising nanodiamond

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WO2000066090A1 (fr) * 1999-05-04 2000-11-09 Biotech Australia Pty Limited Amplification du ciblage a mediation folate de cellules tumorales a l'aide de nanoparticules
US7598335B2 (en) 2006-08-01 2009-10-06 Kaohsiung Medical University Folate-receptor-targeting iron oxide nanoparticles coated with poly(ethylene glycol)
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104495836A (zh) * 2014-11-26 2015-04-08 河南晶锐超硬材料有限公司 一种金刚石微粉的处理方法
WO2017096106A3 (fr) * 2015-12-02 2018-03-01 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Nanodiamants fluorescents comme marqueurs de référence pour microscopie et imagerie par fluorescence
JP2019533005A (ja) * 2016-09-06 2019-11-14 デビナ・ダイアグノスティクス・インコーポレイテッドＤｅｂｉｎａ Ｄｉａｇｎｏｓｔｉｃｓ， Ｉｎｃ． ナノダイヤモンド粒子及び関連する装置及び方法
EP3510381A4 (fr) * 2016-09-06 2020-07-29 Debina Diagnostics, Inc. Particules de nanodiamant, dispositifs et procédés associés
US11085920B2 (en) 2016-09-06 2021-08-10 Debina Diagnostics, Inc. Nanodiamond particles and related devices and methods
CN107865970A (zh) * 2016-09-27 2018-04-03 中国科学院理化技术研究所 一种以纳米金刚石为载体的多功能靶向给药体系的构建及其应用
CN107865970B (zh) * 2016-09-27 2021-04-02 中国科学院理化技术研究所 一种以纳米金刚石为载体的多功能靶向给药体系的构建及其应用
EP3987313A4 (fr) * 2019-06-18 2023-10-18 Debina Diagnostics, Inc. Compositions et articles comprenant des particules de (nano)diamant

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