Conjugated gold nanoparticles
09587071 ยท 2017-03-07
Assignee
Inventors
- Duxin Sun (Ann Arbor, MI)
- Hongwei Chen (Ann Arbor, MI, US)
- Wei Qian (Ann Arbor, MI, US)
- Yong Che (Ann Arbor, MI, US)
- Masayuki Ito (Cupertino, CA, US)
- Hayley Paholak (Ann Arbor, MI, US)
- Kanokwan Sansanaphongpricha (Ann Arbor, MI, US)
Cpc classification
A61K47/50
HUMAN NECESSITIES
C08G65/48
CHEMISTRY; METALLURGY
A61K49/0065
HUMAN NECESSITIES
A61K47/60
HUMAN NECESSITIES
International classification
C08G65/48
CHEMISTRY; METALLURGY
A61K41/00
HUMAN NECESSITIES
Abstract
The present invention relates to methods, compositions, and kits for generating conjugated gold nanoparticles. In certain embodiments, the present invention provides methods of generating unsaturated conjugated gold nanoparticles by mixing naked gold nanoparticles with a first type of attachment molecules at a molar ratio such that the attachment molecules attach to the naked gold particles at a density level below the saturation level of the naked gold particles (e.g., at a saturation level of 1-99%). In some embodiments, a second type of attachment molecules (e.g., with the opposite charge as the first type of attachment molecules) are mixed with the unsaturated conjugated gold nanoparticles to generate double-conjugated gold nanoparticles (e.g., that are zwitterionic).
Claims
1. A composition comprising: conjugated gold nanoparticles, wherein each of said conjugated gold nanoparticles comprise: a) a gold nanoparticle comprising a gold surface, b) a first type of attachment molecules attached to said gold nanoparticle at a density level below the saturation level for said gold nanoparticle, wherein said first type of attachment molecules have the formula R1-polymer-R2, wherein R1 is a moiety having affinity for said gold surface of said gold nanoparticle, and wherein R2 is a functional group that allows attachment to other chemicals, and/or comprises a targeting ligand, and c) a second type of attachment molecules attached to said gold nanoparticle, wherein said second type of attachment molecules have the formula R3-polymer-R4, wherein R3 is a moiety having affinity for said gold surface of said gold nanoparticle, and wherein R4 is a functional group that allows attachment to other chemicals, and/or comprises a targeting ligand, and wherein either: A) said first type of attachment molecules possess a positive charge and said second type of attachment molecules possess a negative charge, or B) said first type of attachment molecules possess a negative charge and said second type of attachment molecules possess a positive charge, and wherein said conjugated gold nanoparticle posses a ratio of negative to positive attachment molecules of 900/100 to 700/300.
2. The composition of claim 1, wherein each of said conjugated gold nanoparticles further comprise: a third type of attachment molecules having the formula R5-polymer-R6, wherein R5 is a moiety having affinity for said gold surface of said gold nanoparticle, and wherein R6 is a functional group that allows attachment to other chemicals, and/or comprises a targeting ligand.
3. The composition of claim 1, wherein said R1 is the same or different on each of said first type of attachment molecules and is selected from the group consisting of: a thiol group, an amine group, a phosphine group, and a disulfide group.
4. The composition of claim 1, wherein said R3 is the same or different on each of said second type of attachment molecules and is selected from the group consisting of: a thiol group, an amine group, a phosphine group, and a disulfide group.
5. The composition of claim 1, wherein said polymer in said first type of attachment molecules comprises polyethylene glycol.
6. The composition of claim 1, wherein said polymer in said first type of attachment molecules is selected from the group consisting of: polyethyleneglycol (PEG), polyacrylamide, polydecylmethacrylate, polystyrene, dendrimer molecule, polycaprolactone (PCL), polylactic acid (PLA), poly(lactic-co-glycolic acid) (PLGA), polyglycolic acid (PGA), polyhydroxybutyrate (PHB), and the said polymer has degree of polymerization in the range from 1 unit to 100 units.
7. The composition of claim 1, wherein said polymer in said second type of attachment molecules comprises polyethylene glycol.
8. The composition of claim 1, wherein said polymer in said second type of attachment molecules is selected from the group consisting of: polyethyleneglycol (PEG), polyacrylamide, polydecylmethacrylate, polystyrene, dendrimer molecule, polycaprolactone (PCL), polylactic acid (PLA), poly(lactic-co-glycolic acid) (PLGA), polyglycolic acid (PGA), polyhydroxybutyrate (PHB), and the said polymer has degree of polymerization in the range from 1 unit to 100 units.
9. The composition of claim 1, wherein said R2 is selected from the group consisting of COOH, OCH3, and NH2.
10. The composition of claim 1, wherein said R4 is selected from the group consisting of COOH, OCH3, and NH2.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
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DETAILED DESCRIPTION
(9) Gold nanocolloids have attracted strong interest from scientists for over a century and are now being heavily investigated for their potential use in a wide variety of medical and biological applications. For example, potential uses include surface-enhanced spectroscopy, biological labeling and detection, gene-regulation, and diagnostic or therapeutic agents for treatment of cancer in humans. Their versatility in a broad range of applications stems from their unique physical, chemical, and surface properties, such as: (i) size- and shape-dependent strong optical extinction and scattering at visible and near infrared (NIR) wavelengths due to a localized surface plasmon resonance of their free electrons upon excitation by an electromagnetic field; (ii) large surface areas for conjugation to functional ligands; and (iii) little or no long-term toxicity or other adverse effects in vivo allowing their high acceptance level in living systems.
(10) These new physical, chemical, and surface properties, which are not available from either atomic or bulk counterparts, explain why gold nanocolloids have not been simply chosen as alternatives to molecule-based systems but as novel structures which provide substantive advantages in biological and medical applications.
(11) The prerequisite for most of intended biological and medical applications of gold nanoparticles is the further surface modification of the as-synthesized gold nanoparticles via conjugation of functional ligand molecules to the surface of the gold nanoparticles. The surface functionalization of gold nanoparticles for any biological or medical applications is crucial for at least two reasons. First is control over the interaction of the nanoparticles with their environment, which is naturally taking place at the nanoparticle surface. Appropriate surface functionalization is a key step to providing stability, solubility, and retention of physical and chemical properties of the nanoparticles in the physiological conditions. Second, the ligand molecules provide additional and new properties or functionality to those found inherently in the core gold nanoparticle. These conjugated gold nanoparticles bring together the unique properties and functionality of both the core material and the ligand shell for achieving the goals of highly specific targeting of gold nanoparticles to the sites of interest, ultra-sensitive sensing, and effective therapy.
(12) Nowadays, the major strategy for surface modification of gold nanoparticles include coating gold nanoparticles with polymer, for example PEG containing reactive functional groups, such as COOH and NH.sub.2, which are ready for the conjugation of targeting ligands. However, current strategy of coating gold nanoparticles with functional groups, such as COOH and NH.sub.2, often results in highly charged surfaces, which promote their binding to biomolecules in the biological systems through ionic interactions, causing nanoparticles to aggregate in biological environments and thus exhibit strong non-specific binding to various cells and tissues that is undesirable in many in vitro and in vivo applications.
(13) In the present invention, provided are methods which permits versatile and controllable surface modification of gold nanoparticles with both positive charged PEG and negative charged PEG (e.g., for addressing the issues and challenges described above) and provide methods to fabricate gold nanoparticles having minimum cellular uptake by macrophage cells via forming zwitterionic surface containing both positive and negative charges on the same gold nanoparticle. It is believed that, prior to the present invention, there was no way to conjugate a defined number of positive charged ligands and negative charged ligands onto the surface of gold nanoparticles to control the surface charge (or zeta potential) for optimizing their biomedical performance.
(14) As discussed above, the overwhelming majority of gold nanoparticles are prepared by the standard sodium citrate reduction reaction. This method allows for the synthesis of spherical gold nanoparticles with diameters ranging from 5 to 200 nanometers (nm) which are capped with negatively charged citrate ions. The capping controls the growth of the nanoparticles in terms of rate, final size, geometric shape and stabilizes the nanoparticles against aggregation by electrostatic repulsion.
(15) In contrast to the prior process of bottom-up fabrication using wet chemical processes, in certain embodiments, the gold nanoparticles used in the present invention are produced by a top-down nanofabrication approach. The top-down fabrication methods of the present invention start with a bulk material in a liquid and then break the bulk material into nanoparticles in the liquid by applying physical energy to the material. The physical energy can be mechanical energy, heat energy, electric field arc discharge energy, magnetic field energy, ion beam energy, electron beam energy, or laser beam energy including laser ablation of the bulk material. The present process produces a pure, bare colloidal gold nanoparticle that is stable in the ablation liquid. The ablation liquids comprise a plurality of solvents selected from but not limited to deionized water, methanol, ethanol, acetone, and dimethylformamide.
(16) The present invention is noted limited by the top-down nanofabrication approach used in the present invention. These methods involve the generation of the nanoparticles from the bulk material in the presence of the suspension medium. In one embodiment the process comprises a one step process wherein the application of the physical energy source, such as mechanical energy, heat energy, electric field arc discharge energy, magnetic field energy, ion beam energy, electron beam energy, or laser energy to the bulk gold occur in the suspension medium. The bulk source is placed in the suspension medium and the physical energy is applied thus generating nanoparticles that are immediately suspended in the suspension medium as they are formed. In another embodiment the present invention employs a two-step process including the steps of: 1) fabricating gold nanoparticle arrays on a substrate by using photo, electron beam, focused ion beam, nanoimprint, or nanosphere lithography as known in the art; and 2) removing the gold nanoparticle arrays from the substrate into the suspension liquid using one of the physical energy methods. Tabor, C., Qian, W., and El-Sayed, M. A., Journal of Physical Chemistry C, Vol 111 (2007), 8934-8941; Haes, A. J.; Zhao, J.; Zou, S. L.; Own, C. S.; Marks, L. D.; Schatz, G. C.; Van Duyne, R. P. Journal Of Physical Chemistry B, Vol 109 (2005), 11158. In both methods the colloidal gold is formed in situ by generating the nanoparticles in the suspension medium using one of the physical energy methods.
(17) In certain embodiments of the present invention, colloidal suspensions of gold nanoparticles are produced by pulsed laser ablation of a bulk gold target in deionized water as the suspension medium.
(18) In work conducted during the development of embodiments of the present invention, the following laser parameters were used to fabricate gold nanocolloids by pulsed laser ablation of a bulk gold target in acetone: pulse energy of 10 uJ (micro Joules), pulse repetition rate of 100 kHz, pulse duration of 700 femtoseconds, and a laser spot size on the ablation target of about 50 um (microns). For the preparation of Au nanocolloids a 16 mm (millimeter) long, 8 mm wide, and 0.5 mm thick rectangular target of Au from Alfa Aesar was used. For convenience, the Au target materials can be attached to a bigger piece of a bulk material such as a glass slide, another metal substrate, or a Si substrate.
(19) More generally, for the present invention the laser ablation parameters are as follows: a pulse duration in a range from about 10 femtoseconds to about 500 picoseconds, preferably from about 100 femtoseconds to about 30 picoseconds; the pulse energy in the range from about 1 J to about 100 J; the pulse repetition rate in the range from about 10 kHz to about 10 MHz; and the laser spot size may be less than about 100 m. The target material has a size in at least one dimension that is greater than a spot size of a laser spot at a surface of the target material.
(20) Work conducted during the development of embodiments of the present invention found that stable colloidal solution of gold nanoparticles with only partial surface modification could be fabricated. Also, the surface coverage amount of functional PEG molecules on the surface of the gold nanoparticles can be tuned to be any percent value between 0 and 100%.
(21) The high colloidal stability of laser-made AuNPs after PEGylation with different molar ratios is probably attributed to the highly negatively charged surface as displayed in
(22) The PEGylation process was further demonstrated by monitoring the change in particle size after PEGylation with increasing HS-PEG-COOH/AuNP molar ratios, as shown in
(23) The differential PEG-COOH chain density on AuNPs after PEGylation at varying molar ratios of HS-PEG-COOH/AuNP was detected by centrifuging the solutions and re-suspending the pellet of AuNPs. For molar ratios less than 100 the pellet could not be re-dispersed after centrifugation, as shown in
(24) Furthermore, surface modification was carried out on gold nanoparticles with HS-PEG-NH.sub.2 (thiolated positive charged PEG molecule terminated with amine group at its distal end).
(25) As the molar ratio of HS-PEG-NH.sub.2/AuNP increases from 50 to 300, the zeta potential of PEGylated AuNPs transforms from highly negative (44.9 mV) to slightly positive (+14.4 mV) as shown in
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(27) Based on controllable stable conjugation of HS-PEG-COOH molecules and HS-PEG-NH.sub.2 molecules on surface of gold nanoparticles described above with the surface coverage amount of HS-PEG-COOH molecules and HS-PEG-NH.sub.2 molecules on the surface of the gold nanoparticles can be tuned to be any percent value between 0 and 100%. As such, the present invention allows methods of fabricating gold nanoparticles with zwitterionic surface, which permits precisely control of number of both negative charged ligands and positive charged ligands bound onto surface of gold nanoparticles. In certain embodiments, this method comprises: performing surface modification of gold nanoparticles for forming zwitterionic surface by conjugation of both negative charged ligands and positive charged ligands onto surface of colloidal gold nanoparticles in a sequential manner. Exemplary steps include the follows; Step 1: the negative charged ligands are first mixed with said colloidal suspension of gold nanoparticles at room temperature for at least 30 minutes. Step 2: addition of positive charged ligands to colloidal suspension of gold nanoparticles also at room temperature. The total amount of negative charged ligand added to the said colloidal gold nanoparticles is no more than the minimum amount required to provide a monolayer of bound negative charged ligand to the total of colloidal gold nanoparticles based on a footprint of negative charged ligand bound on gold nanoparticles and total amount of positive charged ligand added to the colloidal gold nanoparticles is no more than the minimum amount required to bind to all free binding sites left on surface of colloidal gold nanoparticles after conjugation of negative charged ligands onto surface of colloidal gold nanoparticles. Step 3: after mixing, the mixture is kept undisturbed for 24 hours at room temperature to provide a sufficient amount of time for both positive charged ligands and negative charged ligands to be conjugated onto the surfaces of colloidal Au nanoparticles; and optionally, after step 2 and before step 3, adding to colloidal gold nanoparticles more said negative charged ligands to ensure saturation of said binding sites on surface of said colloidal gold nanoparticles for maximizing colloidal stability of said colloidal gold nanoparticles.
(28) As an example, work conducted during the development of embodiments of the present invention used the above method to fabricate gold nanoparticles with zwitterionic surface containing both HS-PEG-COOH molecules and HS-PEG-NH.sub.2 molecules. The schematic illustration of fabrication of gold nanoparticles with zwitterionic surface bearing both PEG-COOH molecules and PEG-NH.sub.2 molecules on their surface in a sequential manner is shown in
(29) In work conducted during the development of embodiments of the present invention, a series of colloidal solutions of gold nanoparticles with zwitterionic surface have been made using method as shown in the
(30) Next, non-specific uptake of obtained gold nanoparticles was tested with zwitterionic surface by macrophage cells. As shown in
(31) TABLE-US-00001 TABLE 1 Sample Name Zeta Potential (mV) COOH/NH2_150/0 48.2 COOH/NH2_150/100 34.9 COOH/NH2_150/300 17.1 COOH/NH2_150/500 2.4 COOH/NH2_150/700 13.6 COOH/NH2_150/900 24.3
(32) Table 1 shows the Zeta potential of gold nanoparticles with zwitterionic surface as function of number of PEG-COOH molecules and PEG-NH.sub.2 molecules bound onto surface of gold nanoparticles. The number of PEG-COOH per gold nanoparticle is fixed at 150 and the number of PEG-NH.sub.2 ranges from 0 to 900.
(33) Furthermore, these AuNPs with zwitterionic surface have significant less non-specific uptake than the control AuNPs decorated with a single type of PEG-R (i.e. OCH.sub.3, COOH, NH.sub.2). For instance, the double-charged AuNPs show a relative uptake ranging from 40% to 76% when compared to AuNP-PEG-OCH.sub.3, the control with the least uptake.
(34) Various chemical functional groups, such as thiol, amine, disulfide, and phosphine, possess a high affinity for the surface of gold nanoparticles. Thiol groups are considered to show the highest affinity for gold surfaces, approximately 200 kJ/mol, and therefore a majority of gold nanoparticle surface functionalization occurs through using ligand molecules having thiol groups which bind to surfaces of gold nanoparticles via a thiol-Au bond.
(35) In addition to PEG or poly(ethylene oxide) (PEO) polymer, other polymers having molecular weight in the range of from 200 Daltons to 100,000,000 Daltons selected from but not limited to poly(2-(methacryloyloxy)ethyl phosphorylcholine), poly(2-(dimethylamino)ethyl methacrylate), poly(acrylic acid), and poly(ethylene glycol) containing at least one functional group having an affinity for surface of said gold nanoparticles could also be used as functional ligand.
(36) In certain embodiments, the Au nanoparticles have the shape of a sphere, rod, prism, disk, cube, or core-shell structures, cages, and frames, wherein they have at least one dimension in the range of from 1 to 200 nm (e.g., 1 . . . 50 . . . 100 . . . 150 . . . or 200 nm). In addition, the method of surface modification described in this invention can be used for structures (e.g., nanostructures) which have outer surfaces that are only partially covered with gold.
(37) Thus, while only certain embodiments have been specifically described herein, it will be apparent that numerous modifications may be made thereto without departing from the spirit and scope of the invention. Further, acronyms are used merely to enhance the readability of the specification and claims. It should be noted that these acronyms are not intended to lessen the generality of the terms used and they should not be construed to restrict the scope of the claims to the embodiments described therein.
(38) It is intended that the invention not be limited by the specific embodiments and their variations and combinations as described herein-above.