WO1998022541A2 - Procede de revetement de substrats - Google Patents

Procede de revetement de substrats Download PDF

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Publication number
WO1998022541A2
WO1998022541A2 PCT/US1997/020389 US9720389W WO9822541A2 WO 1998022541 A2 WO1998022541 A2 WO 1998022541A2 US 9720389 W US9720389 W US 9720389W WO 9822541 A2 WO9822541 A2 WO 9822541A2
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WO
WIPO (PCT)
Prior art keywords
substrate
solution
nhs
polymeric material
coating
Prior art date
Application number
PCT/US1997/020389
Other languages
English (en)
Other versions
WO1998022541A3 (fr
Inventor
Mingdi Yan
Original Assignee
Ikonos Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ikonos Corporation filed Critical Ikonos Corporation
Priority to AU51735/98A priority Critical patent/AU5173598A/en
Publication of WO1998022541A2 publication Critical patent/WO1998022541A2/fr
Publication of WO1998022541A3 publication Critical patent/WO1998022541A3/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
    • H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
    • H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/06—Use of macromolecular materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/002—Processes for applying liquids or other fluent materials the substrate being rotated
    • B05D1/005—Spin 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/02—Methods for coating medical devices

Definitions

  • This invention concerns methods for chemically functionalizing and/or coating materials and devices made according to the methods .
  • Y is H, -OH, -SH, or NH 2 ; and (f) Z is S or an anhydride.
  • the coating material is a thiol (RSH) or a disulfide (-S-S-), then the substrate might be a semiconductor, such as gallium arsenide and cadmium sulfide, or a metal substrate wherein the metal is selected from the group consisting of gold, aluminum, copper and platinum. If the substrate is made from aluminum, then the coating material generally is a carboxylic acid or an anhydride. As with the embodiments discussed above, the coating material may be applied only to preselected portions of the substrate, and may be applied to form arrays.
  • Such exposure covalently attaches the crosslinked polymeric product to the substrate via nitrene addition to the molecular tether on the substrate surface.
  • a layer (or multiple layers) of non-crosslinked polymeric material is applied to the crosslinked polymeric material.
  • the non-crosslinked polymeric film does not covalently bond to the crosslinked polymeric layer.
  • FIG. 1 is a photograph of micron-sized patterns as observed under a fluorescence microscope (450-490 nm excitation wavelength; >510 nm emission) showing the surface modification of a polystyrene film as described in Example 4.
  • FIG. 2A is a photomicrograph of fluorescent protein formed by treating preformed polystyrene patterns with a PFPA compound (compound la in Scheme 1) followed by photolysis, then treating with N- (5- aminopentyl) biotinamide followed by fluorescein-avidin, as described in Example 5.
  • a “functionalized substrate” is a substrate to which one or more functional groups are covalently bonded according to the methods of the present invention.
  • a “functional group” is a group of one or more atoms bonded together in an organized way so as to have a desired chemical property. Certain functional groups can, when covalently bonded to a substrate surface, participate in one or more additional bonding reactions with either a similar functional group or a different type of functional group. Such bonding reactions can result in: (a) attachment to the functional groups of any of a variety of additional functional groups; or (b) coupling together (cross-linking) of the functionalized substrate molecules. Many other functional groups attachable to polymer molecules according to the present invention can confer altered chemical properties to the polymer molecules such as, but not limited to, making them labeled or tagged with a fluorescent, radioactive, immunologic, diagnostic or therapeutic markers.
  • the term "functionalized polymer” can concern either a functionalized polymeric substrate or a functionalized polymer molecule.
  • Functionalized polymer molecules comprise one or more functional groups covalently bonded to the polymer molecules according to the present invention.
  • the functionalizing reagent is preferably selected from a group consisting generally of: aryl azides, alkyl azides, alkenyl azides, alkynyl azides, acyl azides, and azidoacetyl derivatives, all capable of carrying a variety of substituents.
  • Halogen atoms are present to the maximum extent possible in the positions on the functionalizing reagent molecule adjacent the azide group. Best results are achieved when fluorine and/or chlorine atoms are the halogen atoms .
  • (a) carboxyl groups and various derivatives thereof such as , (but not necessarily limited to) : N- hydroxysuccinimide esters; N-hydroxybenztriazole esters; acid halides corresponding to the carboxyl group; acyl imidazoles; thioesters; p-nitrophenyl esters; alkyl, alkenyl, alkynyl and aromatic esters, including esters of biologically active (and optically active) alcohols such as cholesterol and glucose; various amide derivatives such as amides derived from ammonia, primary, and secondary amines and including biologically active (and optically active) amines such as epinephrine, dopa, enzymes, antibodies, and fluorescent molecules; (b) alcohol groups, either free or esterified to a suitable carboxylic acid which could be, for example, a fatty acid, a steroid acid, or a drug such as naprosin or aspirin;
  • PFPAs include (but are not limited to) the N-hydroxysuccinimide (NHS) ester A (also designated “NHS-PFPA”), the p_-nitrophenyl ester B, the 1-hydroxybenzotriazole ester C, the acyl imidazole D, the acid chloride E, the mixed anhydride F and the 2, 2, 2-trichloroethyl ester G:
  • Specialized molecules can be attached to a substrate surface (s) to potentiate the biocompatibility of substrates, control the wettability of the substrate surface (s), or to alter the ability of living cells to adhere to the substrate surface (s).
  • RNH 2 represents the amino group of N-biotinylhexylenediamine:
  • a glass disc was spin-coated with a solution of 5 wt % polystyrene (PS) in xylene to form a film on the disk about 0.5 ⁇ m. thick, as described in Cai et al . , Chem. Mater. 4:879-884 (1992).
  • PS polystyrene
  • the PS film was then spin-coated with a solution of 0.5 wt % of la or lb in nitromethane and baked at 60 °C for 20 minutes. The baking step removed residual solvent and likely facilitated the diffusion of surface-deposited PFPAs into the PS films.
  • the films 2a and 2b were incubated in a 50- ⁇ M solution of HRP in NaHC0 3 buffer (pH 8.2) at 25 °C for 3 hours, Brinkley, Bioconiugate Chem. 3_:2-13 (1992), followed by a thorough rinsing with phosphate buffer (pH 7.0) .
  • N-4-azido-2, 3 , 5, 6-tetrafluorobenzyl biotinamide (3) was performed as follows: To a solution of 33 mg (0.097 mmol) N-succinimidyl-D-biotin in 0.5 mL of DMS0-d 6 was added 27 mg (0.12 mmol) of 4-azido- 2, 3, 5, 6-tetrafluorobenzylamine. The resulting solution was maintained at room temperature for 0.5 hours ,- after which NMR revealed completion of the reaction. The solution was added dropwise into 10 mL water to form a precipitate.
  • the chemistry utilizes maleimide-containing PFPAs 1 and 2 which were previously used to map cysteine residues introduced into ATPase by mutation, yielding a photo-cross-linking yield as high as 50 percent.
  • maleimide-containing PFPAs 1 and 2 which were previously used to map cysteine residues introduced into ATPase by mutation, yielding a photo-cross-linking yield as high as 50 percent.
  • FIG. 4A features of 0.2 ⁇ m were resolved.
  • the smallest features (0.1 ⁇ m) were not resolved in this unoptimized experiment.
  • the sensitivity is about 10 to about 30 ⁇ C/cm 2 .
  • the P30T was prepared from 3-octylthiophene as reported in Cai et al . , id.
  • This Example is a control for Example 19.
  • a P30T film (without the active ester 1) was exposed to an electron beam (intensity 30 ⁇ C/cm 2 , line width 0.5 ⁇ m) , developed, then treated with amino- fluorescein 7 as described in Example 19.
  • the micron- sized patterns "drawn" on the control P30T film were identical to the patterns in Example 19.
  • FOG. 8C rhodamine excitation wavelength
  • FOG. 8D fluorescein excitation wavelength
  • the wafers were then spincoated with 0.5 percent NHS-PFPA in nitromethane at 1000 rpm, baked at 60°C for 25 minutes and then photolyzed at 254 nms for about 6 minutes .
  • the photolysis resulted in the formation of an azide, which then underwent a C-H insertion reaction at the benzyl carbon of the p-toluoyl moiety, thereby attaching the NHS-PFPA to the wafer.
  • silica wafers were cleaned with concentrated H 2 S0 4 , water and acetone and then dried. A solution was then formed comprising 2 octadecyltrichlorosilane (Aldrich) in about 20 milliliters of toluene. The pieces of silica were added to the solution and the resulting composition was then refluxed overnight. The silica wafers were then washed thoroughly with toluene and air-dried to obtain silica wafers modified with the octadecyldichlorosilane . The wafers were then spincoated with 0.5 percent
  • the wafers were then spotted with a solution comprising about 0.5 milligram of aminoacetamidofluorescein in pH 9 NaOH in 3 X 3 arrays using a pipette.
  • the solution comprising aminoacetamidofluorescein was left on the wafer for about 2 hours .
  • the wafers were then rinsed with pH 9 NaOH, then distilled water, followed by air drying. Analysis of the resulting product using fluorescence microscopy demonstrated that aminoacetamidofluorescein was attached to the wafer as expected.
  • a substrate made from gold is reacted with 10-thio- decylamine to form a gold substrate modified with a decylamine.
  • a solution of NHS-PFPA ester is then spincoated onto the gold substrate in a manner allowing for the NHS-PFPA ester to react with the amino group of the decylamine.
  • the gold substrate is spincoated with polypropylene, and photolyzed for about 5 minutes. This causes the formation of a nitrene from the azide, which then undergoes an insertion reaction with the polypropylene. .This results in the modification of the gold substrate with polypropylene .
  • EXAMPLE 39 This example describes the formation of arrays on the surface of a gold substrate.
  • a gold substrate is reacted with 1-decanethiol to form a gold substrate having a pendent C-10 carbon chain.
  • a solution of NHS- PFPA ester is then spincoated onto the gold substrate, followed by photolysis at 254 nm for about 5 minutes. This results in the formation of a nitrene from the azide group of the NHS-PFPA ester, which undergoes an insertion reaction with the pendent methyl group of the 1-decanthiol . This attaches the NHS-PFPA ester to the gold surface.
  • the gold substrate is then spotted with a solution of an oligonucleotide having a 5' amino group using a pipette or a mechanical spotting device.
  • the amino group reacts with the NHS-PFPA ester to form a gold substrate having an oligonucleotide attached thereto .
  • the amino group reacts with the NHS-PFPA ester to form a silver substrate having an oligonucleotide attached thereto.
  • EXAMPLE 50 This example describes the formation of preselected patterns of materials on the surface of an aluminum substrate.
  • An aluminum substrate is reacted with an decanoic acid in a manner that allows the carboxylic acid moiety to react with the aluminum.
  • a solution of an NHS-PFPA ester is then spincoated onto the aluminum substrate, followed by photolysis at 254 nm for about 5 minutes using a UV mask aligner.
  • a nitrene is formed from the azide group of the NHS-PFPA ester, which undergoes a C-H insertion reaction with the pendent alkyl group of the carbon chain. This attaches the NHS-PFPA ester to the aluminum surface in preselected patterns.
  • EXAMPLE 58 A substrate made from gold is reacted with octyl sulfide (Aldrich) to form a gold substrate having a pendent C-8 carbon chain.
  • a solution of NHS-PFPA ester is then spincoated onto the gold substrate, followed by photolysis at 254 nm for about 5 minutes. This results in the formation of a nitrene from the azide group of the NHS-PFPA ester, which undergoes an insertion and/or addition reaction with the pendent methyl group of the 1-octylthiol. This attaches the NHS-PFPA ester to the gold surface.
  • the gold substrate is then immersed in a solution of an oligonucleotide having a 5' amino group. The amino group reacts with the NHS-PFPA ester to form a gold substrate having an oligonucleotide attached thereto.
  • non-crosslinked polymeric films may be applied superposedly to the workpiece if thicker films are desired.
  • Examples 59 and 60 pertain to spincoating of non-crosslinked polypropylene onto a silicon wafer and a silicon well, respectively.
  • a solution was prepared comprising about 60 mg of polypropylene and about 10 ml of dry toluene.
  • the polypropylene may be analytical grade, industrial grade containing additives, or commercial polypropylene products.
  • the solution was degassed with N 2 for about 30 minutes.
  • the polypropylene/toluene solution was heated to about 100°C to between about 110°C until the polypropylene was substantially, completely dissolved.
  • the first layer comprises a polymeric material crosslinked with a functionalizing reagent such as, bis- PFPA.
  • a functionalizing reagent such as, bis- PFPA.
  • the crosslinked polymeric first layer is bonded to the workpiece by the molecular tether.
  • Such a reaction can be generally depicted as shown in Scheme 20:
  • a solution was prepared comprising about 66 mg of polypropylene dissolved in about 10 mL of degassed dry toluene at about 100°C-110°C. About 7.4 mg of bis-PFPA was added to the hot polypropylene solution. The hot solution was immediately spin-coated onto the wafer (previously heated on a spincoater stage) at about 2000 rpm, resulting in a thin, uniform film thereon.

Abstract

Cette invention se rapporte à des procédés de revêtement de substrats destinés à potentialiser la biocompatibilité du substrat. Ces procédés consistent à revêtir au moins une partie d'un substrat avec des matériaux de revêtement particulaires. Ces matériaux peuvent être réticulés et déposés sur un substrat. Dans une variante, ces matériaux de revêtement peuvent être liés par covalence aux substrats. Ces matériaux de revêtement peuvent fonctionnaliser le substrat ou former un revêtement biocompatible sur le substrat. Ces matériaux de revêtement peuvent également renfermer des groupes électrophiles ou nucléophiles qui permettent la réaction ultérieure des matériaux de revêtement avec des réactifs additionnels. Cette invention présente également des pièces usinées ayant un revêtement, conçues pour venir en contact avec des tissus corporels ou avec le sang. Ces pièces usinées peuvent être revêtues d'une première puis d'une seconde couche. Cette première couche comprend une attache moléculaire liée par covalence à la surface de la pièce. La seconde couche est liée à la pièce par la première couche et contient un agent bioactif. Cette invention présente également la possibilité de potentialiser la biocompatibilité de pièces usinés en revêtant ces pièces d'un film polymère non réticulé, qui est appliqué sur la surface du substrat et qui n'est ni réticulé ni lié par covalence à ladite surface. Cette invention se rapporte en outre à la formation de substrats à l'aide de couches multiples de films polymères réticulés, non réticulés, liés par covalence ou liés de façon non covalente.
PCT/US1997/020389 1996-11-08 1997-11-07 Procede de revetement de substrats WO1998022541A2 (fr)

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Application Number Priority Date Filing Date Title
AU51735/98A AU5173598A (en) 1996-11-08 1997-11-07 Method for coating substrates

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Application Number Priority Date Filing Date Title
US3071296P 1996-11-08 1996-11-08
US60/030,712 1996-11-08

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EP0989418A2 (fr) * 1998-09-23 2000-03-29 JOHNSON & JOHNSON VISION PRODUCTS, INC. Lentille à base de polymère de silicone mouillable
WO2001068158A1 (fr) * 2000-03-15 2001-09-20 Orbus Medical Technologies Inc. Revetement favorisant la fixation des cellules endotheliales
WO2002085537A2 (fr) * 2001-04-19 2002-10-31 General Electric Company Support revetu par centrifugation
US6818394B1 (en) 1996-11-06 2004-11-16 Sequenom, Inc. High density immobilization of nucleic acids
WO2007004995A1 (fr) * 2005-07-04 2007-01-11 National University Of Singapore Agent de réticulation de rayonnement
US7232688B2 (en) 1997-01-23 2007-06-19 Sequenom, Inc. Systems and methods for preparing and analyzing low volume analyte array elements
US7405034B2 (en) 2001-08-01 2008-07-29 State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Portland State University Polymeric structures, particularly microstructures, and methods for making same
US20100130380A1 (en) * 2005-06-17 2010-05-27 Kiyoshi Nokihara Biochip substrate and biochip
WO2013044942A1 (fr) * 2011-09-27 2013-04-04 Invatec S.P.A. Cathéter à ballonnet avec ballonnet polymère ayant une surface modifiée par une réaction de photoactivation et procédé de fabrication
JP2013524902A (ja) * 2010-04-19 2013-06-20 インヴァテック ソシエタ ペル アチオニ 光活性化高分子材料及びその医療機器作製への使用
TWI402235B (zh) * 2010-07-30 2013-07-21 Univ Nat Formosa Mixed self - assembled molecular structure with antibacterial properties and its preparation method
TWI404686B (zh) * 2010-12-30 2013-08-11 Univ Nat Formosa Preparation of Antibacterial Film
US9068953B2 (en) 2007-09-17 2015-06-30 Agena Bioscience, Inc. Integrated robotic sample transfer device
US9403141B2 (en) 2013-08-05 2016-08-02 Twist Bioscience Corporation De novo synthesized gene libraries
WO2016126882A1 (fr) * 2015-02-04 2016-08-11 Twist Bioscience Corporation Procédés et dispositifs pour assemblage de novo d'acide oligonucléique
US9669376B2 (en) 2000-10-30 2017-06-06 Agena Bioscience, Inc. Method and apparatus for delivery of submicroliter volumes onto a substrate
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US9895673B2 (en) 2015-12-01 2018-02-20 Twist Bioscience Corporation Functionalized surfaces and preparation thereof
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US10053688B2 (en) 2016-08-22 2018-08-21 Twist Bioscience Corporation De novo synthesized nucleic acid libraries
US10417457B2 (en) 2016-09-21 2019-09-17 Twist Bioscience Corporation Nucleic acid based data storage
US10696965B2 (en) 2017-06-12 2020-06-30 Twist Bioscience Corporation Methods for seamless nucleic acid assembly
US10844373B2 (en) 2015-09-18 2020-11-24 Twist Bioscience Corporation Oligonucleic acid variant libraries and synthesis thereof
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US11512347B2 (en) 2015-09-22 2022-11-29 Twist Bioscience Corporation Flexible substrates for nucleic acid synthesis
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US9522217B2 (en) 2000-03-15 2016-12-20 Orbusneich Medical, Inc. Medical device with coating for capturing genetically-altered cells and methods for using same
CA2563329C (fr) 2004-04-30 2016-01-26 Orbus Medical Technologies, Inc. Dispositif medical dote d'un revetement servant a capter des cellules modifiees genetiquement et methodes d'utilisation associees

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Cited By (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6818394B1 (en) 1996-11-06 2004-11-16 Sequenom, Inc. High density immobilization of nucleic acids
US7232688B2 (en) 1997-01-23 2007-06-19 Sequenom, Inc. Systems and methods for preparing and analyzing low volume analyte array elements
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