US20090214618A1 - Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications - Google Patents

Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications Download PDF

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US20090214618A1
US20090214618A1 US11/887,041 US88704106A US2009214618A1 US 20090214618 A1 US20090214618 A1 US 20090214618A1 US 88704106 A US88704106 A US 88704106A US 2009214618 A1 US2009214618 A1 US 2009214618A1
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nitric oxide
group
particle
releasing
releasing particle
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Mark H. Schoenfisch
Jae Ho Shin
Nathan Stasko
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University of North Carolina at Chapel Hill
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University of North Carolina at Chapel Hill
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Assigned to UNIVERISTY OF NORTH CAROLINA AT CHAPEL HILL, THE reassignment UNIVERISTY OF NORTH CAROLINA AT CHAPEL HILL, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SCHOENFISCH, MARK H., SHIN, JAE HO, STASKO, NATHAN
Assigned to NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT reassignment NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT CONFIRMATORY LICENSE (SEE DOCUMENT FOR DETAILS). Assignors: UNIVERSITY OF NORTH CAROLINA CHAPEL HIL
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Assigned to THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL reassignment THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL CORRECTIVE ASSIGNMENT TO CORRECT THE SPELLING OF ASSIGNEE NAME RECORDED INCORRECTLY AS THE "UNIVERISTY" OF NORTH CAROLINA AT CHAPEL HILL PREVIOUSLY RECORDED ON REEL 019944 FRAME 0902. ASSIGNOR(S) HEREBY CONFIRMS THE SPELLING OF ASSIGNEE NAME IS THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL. Assignors: SCHOENFISCH, MARK H., SHIN, JAE HO, STASKO, NATHAN
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Definitions

  • the interior region further comprises an organic linker selected from the group consisting of a labile linker responsive to changes in pH, a labile linker sensitive to electromagnetic radiation, a labile linker susceptible to degradation by enzymatic action, a hydrophobic linker, an amphiphilic linker, and combinations thereof.
  • an organic linker selected from the group consisting of a labile linker responsive to changes in pH, a labile linker sensitive to electromagnetic radiation, a labile linker susceptible to degradation by enzymatic action, a hydrophobic linker, an amphiphilic linker, and combinations thereof.
  • the NO donor is selected from the group consisting of a diazeniumdiolate, a nitrosamine, a hydroxylamine, a nitrosothiol, a hydroxylamine, and a hydroxyurea.
  • the NO donor is covalently bound to one of the interior region, the exterior region, the core, or to combinations thereof.
  • the NO donor is encapsulated in one of the interior region, the exterior region, the core, or to combinations thereof.
  • the NO donor is associated with part of the particle via a non-covalent interaction selected from the group consisting of Van der Waals interactions, electrostatic forces, hydrogen bonding, or combinations thereof.
  • the organic linker comprises a functional group capable of conferring an on/off state of nitric oxide release to the nitric oxide-releasing particle, wherein the functional group is selected from the group consisting of an ester, a hydrazone, an acetal, a thiopropionate, a photolabile moiety, and an amino acid sequence subject to enzymatic degradation.
  • the NO-releasing particle has a diameter of from between about 1 nm and about 1000 nm. In some embodiments, the particle has a metallic cluster core and the diameter of the particle is from between about 1 nm and about 5 nm. In some embodiments the particle has a co-condensed silica network core and has a diameter of between about 2 nm and about 10 ⁇ m.
  • the presently disclosed subject matter provides a method or a formulation for delivering nitric oxide to a subject.
  • the method comprises administering an effective amount of a NO-releasing particle to the subject, said particle comprising a NO donor, an exterior region, and an interior region having a volume, the volume of the interior region at least partially filled by a core selected from:
  • FIG. 1 is a schematic representation of a nitric oxide (NO)-releasing particle comprising a core CR, an interior region IR, a linker LK having a labile portion LP, a nitric oxide (NO) donor NO and an exterior EP.
  • NO nitric oxide
  • FIG. 2 is a synthesis scheme for preparing the presently disclosed NO-releasing monolayer protected cluster (MPC) gold nanoparticles.
  • FIG. 5A is a schematic representation of the synthesis of NO-releasing co-condensed silica particles using a “post-charging” method, wherein amino groups from aminoalkoxysilanes are reacted with NO gas after co-condensation in a silica network.
  • FIG. 5B is a schematic representation of the synthesis of NO-releasing co-condensed silica particles using a “pre-charging” method, wherein aminoalkoxysilanes are reacted with NO gas prior to co-condensation to form a silica network.
  • FIG. 6A is the structure of N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAP3).
  • FIG. 6B is the structure of (aminoethylaminomethyl)phenethyltrimethoxysilane (AEMP3).
  • FIG. 9B shows the structure of TECOFLEX® polyurethane, wherein n and n′ are integers.
  • FIG. 13 is a plot showing nitric oxide release profiles from monolayer protected cluster (MPC) gold nanoparticles derivatized with various diamines.
  • Line a is the nitric oxide release profile of underivatized MPC gold nanoparticles.
  • Line b is the nitric oxide release profile from MPC gold nanoparticles derivatized with 14% ethylenediamine.
  • Line c shows the nitric oxide release profile from MPC gold nanoparticles derivatized with 21% ethylenediamine.
  • Line d shows the nitric oxide release profile from MPC gold nanoparticles derivatized with 21% ethylenediamine.
  • Line e shows the nitric oxide release profile from MPC gold nanoparticles derivatized with 21% diethylenetriamine.
  • Line f shows the nitric oxide release profile from MPC gold nanoparticles derivatized with 21% hexanediamine.
  • FIG. 14 is a schematic representation showing the release of nitric oxide from functionalized monolayer protected cluster (MPC) gold nanoparticles.
  • FIG. 15 is a schematic representation of the chemical structure of polypropylenimine hexadecaamine dendrimer (DAB-Am-16).
  • FIG. 21C is a plot of % surface coverage of co-condensed amine ligands versus AEAP3 content loaded during the synthesis of AEAP3-modified silica composites.
  • FIG. 27 is a graph showing the cytotoxicity of control (dark squares) and NO-releasing MAP3 co-condensed (open squares) silica nanoparticles on normal (T29, immortalized) cells as well as the cytotoxicity of control (dark circles) and NO-releasing MAP3 co-condensed (open circles) silica nanoparticles on tumor (A2780) cells.
  • FIG. 30A is a photograph showing colonies of P. aeruginosa that formed on nutrient agar plates after incubation with sterile phosphate buffered solution (PBS) at 37° C.
  • PBS sterile phosphate buffered solution
  • cancers include, but are not limited to, skin cancers, connective tissue cancers, adipose cancers, breast cancers, lung cancers, stomach cancers, pancreatic cancers, ovarian cancers, cervical cancers, uterine cancers, anogenital cancers, kidney cancers, bladder cancers, colon cancers, prostate cancers, central nervous system (CNS) cancers, retinal cancer, blood, and lymphoid cancers.
  • skin cancers connective tissue cancers, adipose cancers, breast cancers, lung cancers, stomach cancers, pancreatic cancers, ovarian cancers, cervical cancers, uterine cancers, anogenital cancers, kidney cancers, bladder cancers, colon cancers, prostate cancers, central nervous system (CNS) cancers, retinal cancer, blood, and lymphoid cancers.
  • connective tissue cancers include, but are not limited to, connective tissue cancers, adipose cancers, breast cancers, lung cancers, stomach cancers, pancreatic
  • semiconductor nanocrystal and “quantum dot” are used interchangeably herein to refer to semiconductor nanoparticles comprising an inorganic crystalline material that is luminescent (i.e., that is capable of emitting electromagnetic radiation upon excitation), and including an inner core of one or more first semiconductor materials that is optionally contained within an overcoating or “shell” of a second semiconductor material.
  • a semiconductor nanocrystal core surrounded by a semiconductor shell is referred to as a “core/shell” semiconductor nanocrystal.
  • the surrounding shell material can optionally have a bandgap energy that is larger than the bandgap energy of the core material and can be chosen to have an atomic spacing close to that of the core substrate.
  • Suitable semiconductor materials for the core and/or shell include, but are not limited to, materials comprising a first element selected from Groups 2 and 12 of the Periodic Table of the Elements and a second element selected from Group 16. Such materials include, but are not limited to ZnS, ZnSe, ZnTe, CDs, CdSe, CdTe, HgS, HgSe, HgTe, MgS, MgSe, MgTe, CaS, CaSe, CaTe, SrS, SrSe, SrTe, BaS, BaSe, BaTe, and the like. Suitable semiconductor materials also include materials comprising a first element selected from Group 13 of the Periodic Table of the Elements and a second element selected from Group 15.
  • nitric oxide releasing or “nitric oxide donating” refer to methods of donating, releasing and/or directly or indirectly transferring any of the three redox forms of nitrogen monoxide (NO + , NO ⁇ , NO). In some cases, the nitric oxide releasing or donating is accomplished such that the biological activity of the nitrogen monoxide species is expressed at the intended site of action.
  • alkyl refers to C 1-20 inclusive, linear (i.e., “straight-chain”), branched, or cyclic, saturated or at least partially and in some cases fully unsaturated (i.e., alkenyl and alkynyl)hydrocarbon chains, including for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, octenyl, butadienyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, and allenyl groups.
  • “Higher alkyl” refers to an alkyl group having about 10 to about 20 carbon atoms, e.g., 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
  • “alkyl” refers, in particular, to C 1-8 straight-chain alkyls. In other embodiments, “alkyl” refers, in particular, to C 1-8 branched-chain alkyls.
  • aryl means a cyclic aromatic comprising about 5 to about 10 carbon atoms, e.g., 5, 6, 7, 8, 9, or 10 carbon atoms, and including 5- and 6-membered hydrocarbon and heterocyclic aromatic rings.
  • cyclic alkyl chain There can be optionally inserted along the cyclic alkyl chain one or more oxygen, sulfur or substituted or unsubstituted nitrogen atoms, wherein the nitrogen substituent is hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl, thus providing a heterocyclic group.
  • Representative monocyclic cycloalkyl rings include cyclopentyl, cyclohexyl, and cycloheptyl.
  • Multicyclic cycloalkyl rings include adamantyl, octahydronaphthyl, decalin, camphor, camphane, and noradamantyl.
  • carbonyl refers to the —(C ⁇ O)— group.
  • halo refers to fluoro, chloro, bromo, and iodo groups.
  • the NO releasing moiety or NO donor is engineered in such a fashion as not to disrupt the other particle descriptors while storing its quantity of NO until the appropriate targeting of the particle has occurred.
  • the NO release can be initiated thermally or via any of the degradation strategies for the labile portion of the linker as described herein below.
  • the NO donor can be any moiety capable of releasing NO, including N-diazeniumdiolates, nitrosamines, hydroxyl nitrosamines, nitrosothiols, hydroxylamines, hydroxyureas, metal complexes, organic nitrites and organic nitrates. See, Wang, P.
  • NO-releasing MPC gold nanoparticles provides for a range of biomedical and pharmaceutical applications including in vivo sensor design and topical creams to enhance wound healing and/or dilate blood vessels below the skin.
  • Inorganic-organic hybrid silica nanoparticles functionalized ceramic composites prepared from silicon dioxide, have been explored for applications spanning separation, biological labeling, diagnostics, and carrier systems for the controlled delivery of drugs, genes, and proteins. See Lai, C.-Y., et al., J. Am. Chem. Soc., 125, 4451-4459 (2003); Munoz, B., et al., Chem. Mater., 15, 500-503 (2003); Roy, I., et al., Proc. Natl. Acad. Sci, U.S.A., 102, 279-284 (2005); Trewyn, B. G., et al., Nano.
  • the alkoxysilane is a tetraalkoxysilane having the formula Si(OR) 4 , wherein R is an alkyl group.
  • R is an alkyl group.
  • the R groups can be the same or different.
  • the tetraalkoxysilane is selected tetramethyl orthosilicate (TMOS) or tetraethyl orthosilicate (TEOS).
  • the aminoalkoxysilane can be selected from N-(6-aminohexyl)aminopropyltrimethoxysilane (AHAP3); N-(6-aminoethyl)aminopropyltrimethoxysilane; (3-trimethoxysilylpropyl)di-ethylenetriamine (DET3); (aminoethylaminomethyl)phenethyltrimethoxysilane (AEMP3); [3-(methylamino)propyl]trimethoxysilane; N-butylamino-propyltrimethoxysilane; N-ethylaminoisobutyltrimethoxysilane; N-phenylamino-propyltrimethoxysilane; and N-cyclohexylaminopropyltrimethoxysilane.
  • the structures of representative suitable aminoalkoxysilanes are shown in FIG. 6 .
  • the co-condensed silica network comprises (i.e., is formed from the condensation of a solution containing) between about 10 mol % to about 99 mol % of tetraalkoxysilane; about 1 mol % to about 90 mol % of aminoalkoxysilane; about 0 mol % to about 20 mol % of fluorinated silane; about 0 mol % to about 20 mol % of cationic or anionic silane; and about 0 mol % to about 20 mol % of alkylsilane.
  • FIG. 7 shows the schematic representation of the synthesis of a mesoporous silica network using micelles as pore templates.
  • micelles can self-associate in a controlled solvent environment to form an ordered three-dimensional structure, such as a micellular rod, or an even more highly structured array of multiple rods.
  • Solutions containing mixtures of silanes can be introduced into the micelle solution and condensed, surrounding, but not penetrating, the micelle rods. Following condensation of the silane mixture, the micelles can be removed from the condensed silica via solvent extraction, leaving behind pores in the silica.
  • the presently disclosed silica chemistry is combined with hydroxylamine chemistry. In some embodiments, the presently disclosed silica chemistry is combined with hydroxyurea chemistry.
  • Controlled and/or targeted delivery techniques typically enhance the efficacy and/or safety of an active agent by controlling the rate and/or location of the release of the active agent.
  • the release of nitric oxide from the presently disclosed nitric oxide-releasing particles can be selectively turned on or turned off (i.e., triggered), as desired.
  • a labile group LP at position C can be degraded more quickly by environmental conditions to which particle P is subjected, in turn exposing NO donor NO located in interior IR of particle P to the same environmental conditions sooner.
  • Labile groups LP located more deeply in particle interior IR at positions A or B can, in some embodiments, provide for prolonged or delayed release kinetics.
  • the organic linker is a hydrophobic linker.
  • a hydrophobic linker can be choosen as an approach for protecting the NO donor, for example the diazeniumdiolate, and/or the labile linker from contact with water or protons when the particle is placed in an aqueous environment.
  • the length and exact chemical composition of a hydrophobic linker can, therefore, be used to control the NO-release kinetics.
  • the term hydrophobic can include groups that are strongly hydrophobic (i.e., have a very low dielectric constant) or are only somewhat hydrophobic (i.e., would allow water to slowly penetrate into the interior of the particle).
  • the exterior can comprise a polymeric layer, for example a hydrophilic polymer to impart improved aqueous solutility or a known biocompatible polymer.
  • the polymeric layer can be a biodegradable polymer, which can protect the NO donor from water for a period of time when used either in vivo or in vitro. Such a polymer coating can thereby affect the NO-release kinetics by allowing for continued NO-release over time as the polymer coating degrades.
  • Suitable polymers for functionalizing the exterior of the presently described particles include (poly)ethyleneoxide, (poly)urethanes, N-(2-hydroxypropyl)methacrylamide copolymes, and lactide/glycolide copolymers (e.g. PLGA).
  • additional funcitonalization of the particle enables targeting of specific cells, tissues, or organs.
  • the presently disclosed nitric oxide-releasing particles can be further modified by attaching selective recognition agents to the surface or exterior thereof.
  • selective recognition agents include, but are not limited to small molecule ligands; biomolecules, such as antibodies and antibody fragments; and other agents such as cytokines, hormones, carbohydrates, sugars, vitamins, and peptides.
  • a specific targeting moiety is not required in all cases.
  • the site specific targeting can also include a more passive approach, such as the enhanced permeability and retention effect (EPR) associated with tumor vasculature.
  • EPR enhanced permeability and retention effect
  • Site specific targeting can also be accomplished by the used of NO-release particles containing linkers that trigger release of the nitric oxide only upon contact with enzymes specific to a disease state or to a particular organ or tissue.
  • targeting can be accomplished via localized delivery of the particles, for example, topically directly to a wound, or through injection directly to a tumor site.
  • the targeting moiety can be designed around a tumor suppressor, a cytokine, a chemokine, a tumor specific receptor ligand, a receptor, an inducer of apoptosis, or a differentiating agent.
  • the targeting moiety can be developed to target a factor associated with angiogenisis.
  • the targeting moiety can be designed to interact with known angiogenisis factors such as vascular endothelial growth factor (VEGF). See Brannon-Peppas, L. and Blanchette, J. O., Advanced Drug Delivery Reviews, 56, 1649-1659 (2004).
  • VEGF vascular endothelial growth factor
  • Cytokines that can be targeted by the presently disclosed particles include, but are not limited to, IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-7, IL-8, IL-9, IL-10, ILA 1, IL-12, IL-13, IL-14, IL-15, TNF, GM-CSF, ⁇ -interferon and ⁇ -interferon.
  • Chemokines that can be used include, but are not limited to, M1P1 ⁇ , M1P1 ⁇ , and RANTES.
  • Enzymes that can be targeted include, but are not limited to, cytosine deaminase, hypoxanthine-guanine phosphoribosyltransferase, galactose-1-phosphate uridyltransferase, phenylalanine hydroxylase, glucocerbrosidase, sphingomyelinase, ⁇ -L-iduronidase, glucose-6-phosphate dehydrogenase, HSV thymidine kinase, and human thymidine kinase.
  • the ability of a particle to provide targeted delivery of NO is not limited to embodiments involving pendant targeting agents attached to the particle exterior.
  • Non exterior-associated characteristics of the particle also can be used for targeting.
  • the enhanced permeability and retention (EPR) effect is used in targeting.
  • the EPR effect is the selective concentration of macromolecules and small particles in the tumor microenvironment, caused by the hyperpermeable vasculature and poor lymphatic drainage of tumors.
  • the exterior of the particle can be coated with or conjugated to a hydrophilic polymer to enhance the circulation half-life of the particle and to discourage the attachement of plasma proteins to the particle.
  • the presently disclosed therapeutic compositions comprise an additional therapeutic agent in combination with the nitric oxide-releasing nanoparticles, wherein the additional therapeutic agent has additional desired therapeutic properties or enhances the therapeutic properties of the nitric oxide-releasing nanoparticles.
  • the additional therapeutic agent can be administered in the same or a different therapeutic composition.
  • the term “in combination” can refer to the administration of active agents in a single composition or in one or more separate compositions.
  • the compounds also can be formulated as a preparation for implantation or injection.
  • the compounds can be formulated with suitable polymeric or hydrophobic materials (e.g., as an emulsion in an acceptable oil) or ion exchange resins, or as sparingly soluble derivatives (e.g., as a sparingly soluble salt).
  • suitable polymeric or hydrophobic materials e.g., as an emulsion in an acceptable oil
  • ion exchange resins e.g., as sparingly soluble derivatives (e.g., as a sparingly soluble salt).
  • the compounds also can be formulated in rectal compositions (e.g., suppositories or retention enemas containing conventional suppository bases, such as cocoa butter or other glycerides), creams or lotions, or transdermal patches.
  • an effective amount is used herein to refer to an amount of the therapeutic composition (e.g., a composition comprising a nitric oxide-releasing particle) sufficient to produce a measurable biological response.
  • Actual dosage levels of active ingredients in an active composition of the presently disclosed subject matter can be varied so as to administer an amount of the active compound(s) that is effective to achieve the desired response for a particular subject and/or application.
  • the selected dosage level will depend upon a variety of factors including the activity of the composition, formulation, the route of administration, combination with other drugs or treatments, severity of the condition being treated, and the physical condition and prior medical history of the subject being treated.
  • a minimal dose is administered, and dose is escalated in the absence of dose-limiting toxicity to a minimally effective amount. Determination and adjustment of an effective dose, as well as evaluation of when and how to make such adjustments, are known to those of ordinary skill in the art of medicine.
  • the NO-releasing particles can be incorporated into polymeric films. Such incorporation can be through physically embedding the particles into polymer surfaces, via electrostatic association of particles onto polymeric surfaces, or by covalent attachment of particles onto reactive groups on the surface of a polymer. Alternatively, the particles can be mixed into a solution of liquid polymer precursor, becoming entrapped in the polymer matrix when the polymer is cured. Polymerizable groups can also be used to functionalize the exterior of the particles, whereupon, the particles can be co-polymerized into a polymer during the polymerization process.
  • DAB-C7-64 was charged at 5-atm nitric oxide for three days in the presence of NaOMe/MeOH. This procedure yielded 45 moles NO/mole dendrimer (35.6% conversion) and 1.48 ⁇ 10 ⁇ 7 moles NO released.
  • DAB-Ac-16 (Scheme 6) was charged at 5-atm nitric oxide for three days in the presence of NaOMe. This procedure yielded 0.039 moles NO/mole dendrimer (0.12% conversion) and 4.95 ⁇ 10 ⁇ 10 moles NO released.
  • DAB-Pro-16 (Scheme 7) was charged at 5-atm nitric oxide for three days in the presence of NaOMe. This procedure yielded 42 moles NO/mole dendrimer (130% conversion) and 1.92 ⁇ 10 ⁇ 7 moles NO released.
  • NO-releasing silica particles with a particle size ranging from about 200 nm to about 300 nm are prepared following the method described by Zhang, H., et al., J. Am. Chem. Soc., 125, 5015 (2003).
  • Tetraethyl orthosilicate (TEOS), tetramethylsilane (TMS), and sodium methoxide (NaOMe) were purchased from Fluka (Buchs, Switzerland).
  • Silanes including (aminoethylaminomethyl)phenethyltrimeth-oxysilane (AEMP3), N-(6-aminohexyl)aminopropyltrimethoxysilane (AHAP3), N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAP3), and N-[3-(trimeth-oxysilyl)propyl]diethylenetriamine (DET3) were purchased from Gelest (Tullytown, Pa., United States of America).
  • the size of silica nanoparticles was tunable by varying the type and concentration of aminoalkoxysilane used.
  • Contact mode atomic force microscope (AFM) images of silica spheres having different silane compositions are shown in FIGS. 20A-20E .
  • the diameter of control (TEOS only) silica particles was 250 ⁇ 20 nm.
  • Altering the TEOS solution to include 10 mol % AHAP3 decreased the diameter of the particles to 20 ⁇ 2 nm.
  • NO release characteristics including the total amount of NO (t[NO]), half-life of NO release (t 1/2 ), maximum flux of NO release ([NO] m ), and time necessary (t m ) to reach [NO] m were evaluated as a function of aminoalkoxysilane structure and amount. The results are summarized in Table 4, below.
  • A2780 ovarian epithelial tumor cells were treated with varying doses of control and NO-releasing AHAP3 silica (0.013-1.0 mg/mL) for 48 h.
  • the viability of the A2780 cells was reduced upon exposure to NO-releasing AHAP3 silica at low doses, and the proliferation of A2780 cells was almost completely inhibited by NO-releasing AHAP3 silica at a dose of 0.50 mg/mL [minimum inhibitory concentration (MIC) at ⁇ 5% survival; corresponding to 0.75 mM of NO].
  • the IC 50 dose (50% inhibitory concentration) of NO donor AHAP3 silica was 0.02 mg/mL (0.03 mM NO).
  • the inhibitory concentrations of the NO-releasing silica proved to be significantly lower than those of small molecule NO donors (e.g., MIC and IC 50 for PYRRO/NO were 4.4 and 2 mM NO, respectively).
  • control electrodes were also prepared: a control sensor having only a protecting layer and a GOx layer, and a sensor containing all four layers only prepared with silica nanoparticles that did not contain NO-donors.
  • the sensitivity of the various sensors was evaluated in PBS (0.05 M, pH 7.4) using an applied potential of +7 V vs. Ag/AgCl.
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US8282967B2 (en) 2012-10-09
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US20120021055A1 (en) 2012-01-26
US20140058124A1 (en) 2014-02-27
CA2606565A1 (fr) 2006-11-30
EP1888510A4 (fr) 2013-01-16
JP5753558B2 (ja) 2015-07-22
EP2669269B1 (fr) 2019-05-22
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US20160060279A1 (en) 2016-03-03
US20140005426A1 (en) 2014-01-02
US11691995B2 (en) 2023-07-04
US8962029B2 (en) 2015-02-24
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US9403851B2 (en) 2016-08-02
CA2912259C (fr) 2020-04-28
US20120034169A1 (en) 2012-02-09
US20150182543A1 (en) 2015-07-02
WO2006128121A2 (fr) 2006-11-30
US8956658B2 (en) 2015-02-17
AU2006249323A1 (en) 2006-11-30
AU2006249323B2 (en) 2012-08-30
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