US20060251725A1 - Nano-particles comprising cucurbituril derivatives, pharmaceutical composition containing the same, and process for the preparation thereof - Google Patents

Nano-particles comprising cucurbituril derivatives, pharmaceutical composition containing the same, and process for the preparation thereof Download PDF

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Publication number
US20060251725A1
US20060251725A1 US10/565,834 US56583406A US2006251725A1 US 20060251725 A1 US20060251725 A1 US 20060251725A1 US 56583406 A US56583406 A US 56583406A US 2006251725 A1 US2006251725 A1 US 2006251725A1
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United States
Prior art keywords
substituted
unsubstituted
organic solvent
nanoparticles
cucurbituril
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Abandoned
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US10/565,834
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English (en)
Inventor
Kimoon Kim
Sang Yong Jon
Young Jin Jeon
Dong Hyun Oh
Narayanan Selvapalam
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Pohang University of Science and Technology Foundation POSTECH
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Pohang University of Science and Technology Foundation POSTECH
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Assigned to POSTECH FOUNDATION reassignment POSTECH FOUNDATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JEON, YOUNG JIN, JON, SANG YONG, KIM, KIMOON, OH, DONG HYUN, SELVAPALAM, NARAYANAN
Publication of US20060251725A1 publication Critical patent/US20060251725A1/en
Priority to US12/175,980 priority Critical patent/US7829698B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • 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 relates to nanoparticles including a cucurbituril derivative. More particularly, the present invention relates to nanoparticles prepared by the aggregation of cucurbituril derivatives, a pharmaceutical composition including the nanoparticles, and preparation methods thereof.
  • a drug delivery system requires a drug carrier and formulation. Synthesis of various polymers used as such a drug carrier has been predominantly studied. A representative of these synthetic polymers is a biodegradable polymer.
  • a biodegradable polymer which is non-toxic in vivo such as polylactide (PLA), poly(lactide-co-glycolide) (PLGA), polyethyleneglycol (PEG), and poly(alkylcyanoacrylate), has been actively studied for a drug delivery system.
  • Cucurbituril was first reported by R. Behrend, E. Meyer, F. Rusche in 1905 ( Liebigs Ann. Chem. 1905, 339, 1). According to their report, the condensation of glycoluril and excess formaldehyde in the presence of hydrochloric acid (HCl) produces an amorphous solid. Dissolution of the amorphous solid in hot concentrated sulfuric acid and then dilution of the resultant solution with water produce a crystalline substance. However, they wrongly characterized this substance as C 10 H 11 N 7 O 4 .2H 2 O without revealing the structure of this substance.
  • HCl hydrochloric acid
  • WO 00/68232 discloses cucurbit[n]uril represented by Reference Diagram 1 below:
  • n is an integer of 4 to 12.
  • cucurbituril derivatives are compounds including unsubstituted glycoluril monomer units.
  • Cucurbituril is a macrocyclic compound and has a lipophilic cavity and two hydrophilic entrances at upper and lower portions.
  • lipophilic interactions occur in the cavity of cucurbituril, and hydrogen bonds, polar-polar interactions, and positive charge-polar interactions occur in the two entrances having six carbonyl groups. Therefore, cucurbituril has retention capacity for various compounds by very stable non-covalent bond with these compounds (see Table 1).
  • cucurbituril forms a complex, particularly, with a compound having an amino group or a carboxyl group by very stable non-covalent linkage. Based on such characteristics, studies about application of cucurbituril in various areas have been continuously conducted.
  • the present inventors reported a complex formation between oxaliplatin approved as an anticancer agent by the Food Drug Administration (FDA) and cucurbituril used as a drug delivery system by a stable non-covalent bond (PCT/KR02/01755). Furthermore, the present inventors reported an enhancement of DNA binding capacity by cucurbituril-containing pseudo-rotaxane and a use of a cucurbituril-based dendrimer as a gene delivery system [KR01-7169, Angew. Chem. Int. Ed., 2000 and 2001].
  • a self-assembled monolayer made of cucurbituril which is formed on a gold surface, has a reproducible and stable non-covalent binding capacity with proteins such as lysozyme and glucose oxidase (GOD).
  • proteins such as lysozyme and glucose oxidase (GOD).
  • cucurbituril cannot be used as a drug delivery system only for a single molecule drug having an amine group, an ammonium group, or a carboxyl group, but also for a protein or polypeptide drug.
  • cucurbituril has a low solubility and no active functional groups that can be easily substituted by various substituents, and thus, its utility is extremely limited.
  • cucurbituril is subsidiary to cyclodextrin which is an existing promising drug delivery system.
  • extensive studies about a use of cucurbituril as a drug delivery system have not been conducted.
  • the present invention was completed based on the above-described non-covalent binding properties of cucurbiturils and easy introduction of various substituents into cucurbituril derivatives.
  • the present invention provides nanoparticles including a cucurbituril derivative.
  • the present invention also provides a pharmaceutical composition in which a drug is loaded into the nanoparticles.
  • the present invention also provides a method of preparing the nanoparticles.
  • the present invention also provides a method of preparing the pharmaceutical composition.
  • nanoparticles prepared by the aggregation of cucurbituril derivatives of Formula 1 below and having a particle size of 1 to 1,000 nm:
  • X is O, S, or NH
  • a 1 and A 2 are respectively OR 1 and OR 2 , SR 1 and SR 2 , or NHR 1 and NHR 2 ;
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C 1 -C 30 , a substituted or unsubstituted alkenyl of C 2 -C 30 , a substituted or unsubstituted alkynyl of C 2 -C 30 , a substituted or unsubstituted carbonylalkyl of C 2 -C 30 , a substituted or unsubstituted thioalkyl of C 1 -C 30 , a substituted or unsubstituted alkylthiol of C 1 -C 30 , a substituted or unsubstituted alkoxy of C 1 -C 30 , a substituted or unsubstituted hydroxyalkyl of C 1 -C 30 , a substituted or unsubstituted alkylsilyl of C 1 -C 30 , a substituted or unsubstituted aminoal
  • n is an integer of 4 to 20.
  • a pharmaceutical composition in which a pharmaceutically active substance is loaded as a guest molecule into nanoparticles formed by the aggregation of cucurbituril derivatives of formula 1 above.
  • a method of preparing nanoparticles by the agglomeration of cucurbituril derivatives which includes: dissolving cucurbituril derivatives of Formula 1 in an organic solvent to obtain a reaction solution; adding water to the reaction solution followed by dispersing; distilling the dispersed solution in a temperature range from a boiling point of the organic solvent to 100° C. to remove the organic solvent; and cooling the resultant solution to room temperature.
  • a method of preparing a pharmaceutical composition in which a pharmaceutically active substance as a guest molecule is loaded into the above-prepared nanoparticles which includes: dissolving a cucurbituril derivative of Formula 1 and the pharmaceutically active substance in an organic solvent to obtain a reaction solution; adding water to the reaction solution followed by dispersing; distilling the dispersed solution in a temperature range from a boiling point of the organic solvent to 100° C. to remove the organic solvent; and cooling the resultant solution to room temperature.
  • FIG. 1 is a scanning electron microscopic image of nanoparticles prepared using octanesulfanylpropyloxycucurbit[12]uril according to a method of the present invention.
  • the present invention provides nanoparticles prepared by the aggregation of cucurbituril derivatives of formula 1 below and having cavities and a particle size of 1 to 1,000 nm:
  • X is O, S, or NH
  • a 1 and A 2 are respectively OR 1 and OR 2 , SR 1 and SR 2 , or NHR 1 and NHR 2 ;
  • R 1 and R 2 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C 1 -C 30 , a substituted or unsubstituted alkenyl of C 2 -C 30 , a substituted or unsubstituted alkynyl of C 2 -C 30 , a substituted or unsubstituted carbonylalkyl of C 2 -C 30 , a substituted or unsubstituted thioalkyl of C 1 -C 30 , a substituted or unsubstituted alkylthiol of C 1 -C 30 , a substituted or unsubstituted alkoxy of C 1 -C 30 , a substituted or unsubstituted hydroxyalkyl of C 1 -C 30 , a substituted or unsubstituted alkylsilyl of C 1 -C 30 , a substituted or unsubstituted aminoal
  • n is an integer of 4 to 20.
  • the nanoparticles may be formed by the aggregation of a biodegradable polymer in addition to the cucurbituril derivatives.
  • the additional use of the biodegradable polymer reduces the content of the cucurbituril derivative without an adverse effect and minimizes a potential side effect in the human body.
  • the biodegradable polymer include, but are not limited to, poly(lactide-co-glycolide) (PLGA), polyethyleneglycol (PEG), poly(alkylcyanoacrylate), poly- ⁇ -caprolactone, cellulose derivative, albumin, gelatin, alginate, and a mixture thereof.
  • the nanoparticles resulting from the aggregation of the cucurbituril derivatives of formula 1 can be used as a drug carrier.
  • the pharmaceutically active substance is loaded as a guest molecule into the cavities of the nanoparticles.
  • the pharmaceutically active substance may be an organic compound, a protein, or a gene.
  • organic compound examples include, but are not limited to, hydrocortisone, prednisolone, spironolactone, testosterone, megesterol acetate, danasole, progesterone, indomethacin, amphotericin B, and a mixture thereof.
  • the protein examples include, but are not limited to, human growth hormone, G-CSF (granulocyte colony-stimulating factor), GM-CSF (granulocyte-macrophage colony-stimulating factor), erythropoietin, vaccine, antibody, insulin, glucagon, calcitonin, ACTH (adrenocorticotropic hormone), somatostatin, somatotropin, somatomedin, parathyroid hormone, thyroid hormone, hypothalamus secretion, prolactin, endorphin, VEGF (vascular endothelial growth factor), enkephalin, vasopressin, nerve growth factor, non-naturally occurring opioid, interferon, asparaginase, alginase, superoxide dismutase, trypsin, chymotrypsin, pepsin, and a mixture thereof.
  • G-CSF granulocyte colony-stimulating factor
  • GM-CSF granulocyte-macrophag
  • a method of preparing the nanoparticles include: dissolving the cucurbituril derivative of Formula 1 in an organic solvent to obtain a reaction solution; adding water to the reaction solution followed by dispersing; distilling the dispersed solution in a temperature range from a boiling point of the organic solvent to 100° C. to remove the organic solvent; and cooling the resultant solution to room temperature.
  • a method of preparing the pharmaceutical composition in which the pharmaceutically active substance as a guest molecule is loaded into the nanoparticles includes: dissolving the cucurbituril derivative of Formula 1 and the pharmaceutically active substance in an organic solvent to obtain a reaction solution; adding water to the reaction solution followed by dispersing; distilling the dispersed solution in a temperature range from a boiling point of the organic solvent to 100° C. to remove the organic solvent; and cooling the resultant solution to room temperature.
  • a biodegradable polymer may be dissolved in the organic solvent, together with the cucurbituril derivative, to obtain the reaction solution.
  • the biodegradable polymer may be PLGA, PEG, poly(alkylcyanoacrylate), poly- ⁇ -caprolactone, cellulose derivative, albumin, gelatin, alginate, or a mixture thereof, but is not limited thereto.
  • the organic solvent is a solvent capable of solubilizing the cucurbituril derivative and may be chloroform, dimethylsulfoxide, dichloromethane, dimethylformamide, tetrahydrofuran, or a mixture thereof, but is not limited thereto.
  • water is used in a higher amount than the reaction solution.
  • water is used in an amount of more than about 10-fold of the volume of the reaction solution.
  • the reaction solution must be uniformly dispersed in water.
  • the dispersing is carried out by sonication with a sonicator.
  • the organic solvent is removed by distillation with heating above the boiling point of the organic solvent.
  • the reaction temperature is reduced to room temperature after the removal of the organic solvent, an emulsion is created.
  • Optical microscope, scanning electron microscope, or transmission electron microscope analysis reveals nanoparticles with a particle size of 1 to 1,000 nm.
  • the SEM image is shown in FIG. 1 .
  • the present invention provides nanoparticles formed by the aggregation of cucurbituril derivatives, a pharmaceutical composition in which a drug is loaded into the nanoparticles, and preparation methods thereof.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
US10/565,834 2003-07-26 2004-07-26 Nano-particles comprising cucurbituril derivatives, pharmaceutical composition containing the same, and process for the preparation thereof Abandoned US20060251725A1 (en)

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US12/175,980 US7829698B2 (en) 2003-07-26 2008-07-18 Nano-particles comprising cucurbituril derivatives, pharmaceutical composition containing the same, and process for the preparation thereof

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KR1020030051841A KR100554156B1 (ko) 2003-07-26 2003-07-26 쿠커비투릴 유도체가 응집되어 형성된 나노 입자, 그 나노입자에 약물이 담지된 약제학적 조성물, 및 이들의 제조방법
KR10-2003-0051841 2003-07-26
PCT/KR2004/001874 WO2005010004A1 (fr) 2003-07-26 2004-07-26 Nanoparticules comprenant des derives de cucurbiturile, composition pharmaceutique contenant ces nanoparticules, ainsi que leurs methodes de preparation

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US (2) US20060251725A1 (fr)
EP (1) EP1651651A4 (fr)
JP (1) JP4574615B2 (fr)
KR (1) KR100554156B1 (fr)
WO (1) WO2005010004A1 (fr)

Cited By (5)

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CN105561330A (zh) * 2016-01-25 2016-05-11 四川大学 一种人降钙素-葫芦脲复合制剂及其制备方法
CN112341641A (zh) * 2020-11-23 2021-02-09 南京工业大学 一种双网络颗粒凝胶及其制备方法
US20210130613A1 (en) * 2019-10-30 2021-05-06 Korea Institute Of Science And Technology Positively charged nanoparticles, use thereof, and preparation method thereof
CN113968906A (zh) * 2021-11-22 2022-01-25 四川大学 一种利用外壁季铵化葫芦脲赋予胶原持久抗菌功能的方法
US11576846B2 (en) * 2018-03-22 2023-02-14 Aqdot Limited Emulsion stabiliser

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KR20050102295A (ko) * 2004-04-21 2005-10-26 학교법인 포항공과대학교 리포좀 및 그 제조방법
KR100638516B1 (ko) * 2005-04-21 2006-11-06 학교법인 포항공과대학교 고분자 캡슐 및 그 제조방법
KR101118587B1 (ko) * 2009-08-17 2012-06-12 포항공과대학교 산학협력단 감응성 고분자 캡슐 및 그 제조방법
KR101201473B1 (ko) 2009-12-29 2012-11-15 포항공과대학교 산학협력단 자기 조립형 약물 및 세포 전달체의 제조 방법 및 이에 의해 제조된 자기 조립형 약물 및 세포 전달체
US10988618B2 (en) 2011-09-23 2021-04-27 Dystar Hilton Davis Corp. Self-assembled nano-structured particle and methods for preparing
PL2758037T3 (pl) 2011-09-23 2018-10-31 Emerald Hilton Davis, Llc Samoistnie złożona cząsteczka nanostrukturalna i sposób otrzymywania
US9101669B2 (en) 2012-01-31 2015-08-11 Postech Academy-Industry Foundation Self-assembed conjugate and use thereof
KR101404973B1 (ko) 2012-11-16 2014-06-10 포항공과대학교 산학협력단 쿠커비투릴을 이용한 인슐린 나노 섬유화 제어 방법
WO2017062622A1 (fr) * 2015-10-06 2017-04-13 Massachusetts Institute Of Technology Modification supramoléculaire de protéines
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GB2556619B (en) * 2016-08-24 2019-01-02 Aqdot Ltd Suspension compositions
CN111821472B (zh) * 2019-04-17 2021-11-19 中国科学院武汉物理与数学研究所 一种可以递送疏水性药物的超极化129Xe磁共振分子探针
JPWO2021172197A1 (fr) * 2020-02-26 2021-09-02

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CN105561330A (zh) * 2016-01-25 2016-05-11 四川大学 一种人降钙素-葫芦脲复合制剂及其制备方法
US11576846B2 (en) * 2018-03-22 2023-02-14 Aqdot Limited Emulsion stabiliser
US20210130613A1 (en) * 2019-10-30 2021-05-06 Korea Institute Of Science And Technology Positively charged nanoparticles, use thereof, and preparation method thereof
CN112341641A (zh) * 2020-11-23 2021-02-09 南京工业大学 一种双网络颗粒凝胶及其制备方法
CN113968906A (zh) * 2021-11-22 2022-01-25 四川大学 一种利用外壁季铵化葫芦脲赋予胶原持久抗菌功能的方法

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KR100554156B1 (ko) 2006-02-22
JP2007500185A (ja) 2007-01-11
JP4574615B2 (ja) 2010-11-04
KR20050013019A (ko) 2005-02-02
US7829698B2 (en) 2010-11-09
US20080279950A1 (en) 2008-11-13
EP1651651A4 (fr) 2008-09-17
WO2005010004A1 (fr) 2005-02-03
EP1651651A1 (fr) 2006-05-03

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