EP1037707A1 - Plaque de microtitrage pourvue d'un revetement - Google Patents

Plaque de microtitrage pourvue d'un revetement

Info

Publication number
EP1037707A1
EP1037707A1 EP98962684A EP98962684A EP1037707A1 EP 1037707 A1 EP1037707 A1 EP 1037707A1 EP 98962684 A EP98962684 A EP 98962684A EP 98962684 A EP98962684 A EP 98962684A EP 1037707 A1 EP1037707 A1 EP 1037707A1
Authority
EP
European Patent Office
Prior art keywords
microtiter plate
coating
para
xylylene
parylene
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP98962684A
Other languages
German (de)
English (en)
Inventor
James Thomson
Jan Ter Wiel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Packard Bioscience BV
Original Assignee
Packard Bioscience BV
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 Packard Bioscience BV filed Critical Packard Bioscience BV
Publication of EP1037707A1 publication Critical patent/EP1037707A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • B05D1/60—Deposition of organic layers from vapour phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01L—CHEMICAL OR PHYSICAL LABORATORY APPARATUS FOR GENERAL USE
    • B01L3/00—Containers or dishes for laboratory use, e.g. laboratory glassware; Droppers
    • B01L3/50—Containers for the purpose of retaining a material to be analysed, e.g. test tubes
    • B01L3/508—Containers for the purpose of retaining a material to be analysed, e.g. test tubes rigid containers not provided for above
    • B01L3/5085—Containers for the purpose of retaining a material to be analysed, e.g. test tubes rigid containers not provided for above for multiple samples, e.g. microtitration plates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N35/00—Automatic analysis not limited to methods or materials provided for in any single one of groups G01N1/00 - G01N33/00; Handling materials therefor
    • G01N35/02—Automatic analysis not limited to methods or materials provided for in any single one of groups G01N1/00 - G01N33/00; Handling materials therefor using a plurality of sample containers moved by a conveyor system past one or more treatment or analysis stations
    • G01N35/028—Automatic analysis not limited to methods or materials provided for in any single one of groups G01N1/00 - G01N33/00; Handling materials therefor using a plurality of sample containers moved by a conveyor system past one or more treatment or analysis stations having reaction cells in the form of microtitration plates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2465/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/02—Devices for withdrawing samples
    • G01N1/10—Devices for withdrawing samples in the liquid or fluent state

Definitions

  • This invention relates to a microtiter plate and to a method for applying a coating thereto.
  • Microtiter plates have long been widely used aids in a laboratory. They are part of the standard equipment in laboratories where analyses are carried out . There are numerous examples of such analyses in the world of pharmaceutical, biological and clinicomedical research.
  • microtiter plates are often used for carrying out chemical, biochemical and/or enzymatic reactions.
  • immunoassays too, whether or not using radioactive labels, microtiter plates are frequently used. They are useful especially for carrying out various test reactions for the quantitation of substances to be analyzed. Such test reactions may be, for instance, luminescence or fluorescence reactions, or assays of radioactivity using scintillation counting (LSC) .
  • LSC scintillation counting
  • the material of which it is made should be chemically resistant and inert to a sufficient extent.
  • the first microtiter plates were made of ceramic materials, such as porcelain or glass, which are still eminently satisfactory in many cases .
  • microtiter plates as such are eminently suitable for this purpose, it has been found difficult to form ceramic microtiter plates whose wells are small enough. In other words, ceramic materials are less suitable for making microtiter plates on which analyses or reactions are to be performed where the volume of test or reaction mixture is very small.
  • An example of a field where it is desired to perform reactions on a very small scale is the so-called combinatorial chemistry.
  • This technique currently enjoys much interest, in particular on the part of the pharmaceutical industry. In this technique, a large number of substances are synthesized in an automated manner. The thus obtained substances can subsequently be tested for certain properties (in an automated manner) .
  • microtiter plates having wells of very small dimensions, which wells are regularly shaped and are regularly spaced apart.
  • microtiter plates are manufactured which have 384 wells to 1536 wells.
  • a microtiter plate having a great multiplicity of wells is sometimes referred to as nanoplate, since in such a case the volume of a single well is only a few nanoliters. It has been found that forming such microtiter plates from porcelain is extremely difficult. By way of alternative, often a polymeric material is used for manufacturing these microtiter plates.
  • the material of a microtiter plate must satisfy high standards.
  • the material must have the desired reflective properties - or it must be readily possible to impart these properties to the material, for instance by addition of a color - so that the microtiter plate can be used in LSC and fluorescence or luminescence measurements .
  • the material must have such mechanical properties as to enable both easy handling (stiffness) and ready and accurately reproducible manufacture.
  • the material while maintaining mechanical properties, should be resistant to the influence of both increased and lowered temperatures, since the conditions under which it must be possible to use the microtiter plates vary widely.
  • the material as already noted hereinabove in more general terms, must be resistant to the influence of various chemical compounds and solvents.
  • microtiter plates can be manufactured simply and accurately in the desired form. It is difficult, however, to find a polymeric material that not only has the required mechanical properties but also has sufficient resistance to low and high temperatures and sufficient chemical resistance and inertness. Although the ceramic materials used heretofore are sufficiently resistant to influences of temperature and chemicals, ceramic material, as stated, is less suitable for manufacturing microtiter plates therefrom in a simple and reproducibly accurate manner.
  • U.S. Patent 5,544,218 discloses an alternative to a microtiter plate.
  • the document pertains to the problems that present themselves in handling very small samples for irradiation experiments. Because of the small amounts that are used as sample in such experiments, the exact position where the sample is provided is often difficult to define precisely, which may disturb the results of an irradiation experiment. It is proposed to solve this problem by providing a sample on a thin, elastic polymer film which is supported by a holder and in which wells are provided. The holder is provided with one or more orifices, over which the polymer film is fixed.
  • the polymer film may be made of different materials, such as polyimide, polyvinyl formal, polycarbonate, polypropylene and the like. It is an object of the invention to provide a microtiter plate of materials whereby the favorable properties of a ceramic and a polymeric material are combined. According to the invention, a microtiter plate is contemplated which is at least as inert and chemically resistant as a ceramic microtiter plate, but which is made of a material from which nanoplates can be manufactured in an accurate manner.
  • this object can be achieved by applying a specific coating to a plastic microtiter plate. Accordingly, this invention relates to a plastic microtiter plate provided with a coating which comprises a para-xylylene polymer.
  • Microtiter plates according to the invention satisfy the above-mentioned requirements, that is, the material is suitable for making therefrom microtiter plates having wells of a volume of from a few nanoliters to a few milliliters, while further being eminently chemically resistant and inert and having good reflective properties. Measurements which, as part of a particular analysis, are performed on substances in wells of a microtiter plate according to the invention, are not adversely affected by the presence of the coating. By virtue of the coating, the chemical resistance of the microtiter plate is so high that the material of which the microtiter plate is made does not disturb the measurements unacceptably .
  • a microtiter plate is understood to mean a support, which support is provided with a matrix of receiving cavities or wells.
  • Fig. 1 shows an example of a microtiter plate. Both the support and the receiving cavities may vary in dimensions. Conventional dimensions vary from about 10-15 x 6-9 cm. A widely used standard dimension is 127.85 x 85.65 mm. Depending on the desired application of the microtiter plate, dimensions may deviate from those mentioned. The thickness of a microtiter plate is not critical . The number of receiving cavities will depend on the desired magnitude of the volume. Conventional numbers range from 12 to 3456 and, for practical purposes, are mostly multiples of four. By way of illustration, it may be mentioned that the wells of a plate having 24 wells each have a volume of 1.5 ml, while the wells of an equally large plate having 1536 wells each have a volume of a few nanoliters.
  • Suitable materials of which a microtiter plate according to the invention may be made are all plastics having such properties that a microtiter plate having the desired number of regularly shaped wells can be manufactured. Further, the plastic should be sufficiently stiff, so that the microtiter plate can be readily handled. Both homopolymers and copolymers can be used. Suitable examples comprise vinyl polymers, such as styrene polymers and copolymers of styrene, polyvinyl chloride or polymethyl methacrylate, polyethylene terephthalate, polycarbonates, polyaryl ethers, polyether esters, polyether ketones, polyetherester ketones, polyurethanes , and mixtures thereof. Preferred are polystyrene, polyacrylates, polyvinyl chloride, polyamides and Barex ® (a polyacrylonitrile copolymer) .
  • polystyrene Particularly preferred is polystyrene. It has been found that microtiter plates of polystyrene combine the properties already mentioned, such as thermal stability, stiffness and dimensional reproducibility, with good miscibility with colors, such as titanium oxide, to obtain desired reflective properties. Moreover, the use of polystyrene is also appealing from the point of view of economy.
  • the coating should in any case be applied to the surface in the wells 1 (see Fig. 1) . It is preferred that the coating is further present on the entire side where the openings of the receiving cavities are located, i.e. the upper side 3. Under certain circumstances, it may additionally be desirable that the coating is further applied to the sides of the plate 2, 4, 6, 7.
  • the coating which, according to the invention, is applied to a microtiter plate, comprises a para-xylylene polymer, such as Parylene ® .
  • a microtiter plate on which a coating comprising a para-xylylene polymer has been applied has been found to exhibit exceedingly good chemical resistance and inertness. This makes it possible to expose the microtiter plate to a large variety of chemicals and solvents.
  • the properties of a microtiter plate can be optimized by providing particular functional groups, as desired, on the surface of the coating comprising a para-xylylene polymer.
  • the coating can be applied, as desired, in varying thicknesses, ranging from 0.1 to more than 50 ⁇ . Further, the coating can very simply be applied uniformly over the microtiter plate. This holds especially when the coating is based on a para-xylylene polymer, which is a preferred embodiment of the invention. Even in the case of very thin coating layers, the coating is pin-hole free, so that there is no risk of crack formation in the coating, and complex geometric shapes can be coated.
  • An additional advantage is that a coating comprising a para-xylylene polymer is sufficiently transparent, so that the reflective properties of the plastic of which the microtiter plate according to the invention is made are retained.
  • parylene coatings are known per se .
  • the material is used because of its low water permeability. Moisture- and water-sensitive microelectronic equipment can be protected with a parylene coating film.
  • U.S. Patent 4,225,647 discloses the use of para-xylylene polymers for applying a protective film to various objects, such as art objects, coins, car parts, fishing gear, and the like. This typically involves the protection of surfaces that are subject to corrosion or mechanical wear.
  • U.S. Patent 5,380,320 to coat articles used for medical purposes, such as catheters and cannulae, with parylene. The reason is that the material, in addition to being electrically insulating, has eminent biocompatibility .
  • a microtiter plate according to the invention can be used in applications where living cells play a role, as in so-called homogeneous bioassays. It has been found that in such an application, no disadvantageous binding of cells to the microtiter plate according to the invention occurs. This is sometimes referred to, in this connection, as cellular, non-adhesive functionality. If desired, this functionality can be reversed by cold surface plasma modification, which enables a choice between the desired properties, cellular adhesion or cellular non-adhesion. In a comparable manner, the possibility for a microtiter plate according to the invention to bind other biomolecules, such as proteins, can be controlled.
  • Para-xylylene polymers that are particularly suitable for the use according to the invention are polymers satisfying the formula (I) :
  • R', R' ', X and X' independently represent a hydrogen atom or a halogen atom. It is preferred for a coating on a microtiter plate according to the invention to comprise parylene C ® , parylene N ® , parylene D ® or parylene AF-4 ® .
  • Parylene C is a polymer of the formula (I), wherein X', R' and R' ' are all hydrogen and X represents a chlorine atom.
  • Parylene N is a polymer of the formula (I) , wherein X, X' , R' and R' ' are all hydrogen.
  • Parylene D is a polymer wherein R' and R' ' are both hydrogen and X and X' both represent a chlorine atom.
  • Parylene AF-4 is a polymer wherein X and X' both represent a hydrogen atom and R' and R' ' both represent a fluorine atom.
  • This invention further relates to a method for applying a coating which comprises a para-xylylene polymer to a microtiter plate.
  • a coating is applied utilizing a gas phase deposition process.
  • Such a process is known from U.S. Patents 3,288,728 and 3,342,754 and has as advantages that a uniform coating film of uniform thickness is realized and that the use of a solvent is avoided. It is possible, using this method, to coat surfaces not accessible for a coating applied in the liquid phase, without the various surfaces being connected to each other. This last is meant to say that it is undesired that the wells of the microtiter plate are wholly or partly filled up by the application of a coating .
  • the first step for applying a coating to a microtiter plate comprises bringing a para-xylylene dimer into the gas phase.
  • the nature of the para-xylylene dimer is selected on the basis of the nature of the eventual para-xylylene polymer.
  • the selected dimer is heated to about 120-180°C, preferably 140-160°C, at a pressure of 75 to 200 Pa, preferably 100-150 Pa.
  • the product obtained in the first step is pyrolyzed. This can be done in a suitable manner at a temperature of between 600 and 750°C, preferably between 650 and 700°C, and a pressure of 30 to 100 Pa, preferably 50-75 Pa. After this step, para-xylylene in monomeric form is obtained.
  • the third step comprises the actual deposition of the para-xylylene polymer on the microtiter plate. This deposition is carried out at a temperature of 20-50°C, preferably 25-40°C, and a pressure of 5-20 Pa, preferably
  • the thickness of the coating film to be deposited can be controlled by selecting a suitable residence time of the microtiter plate in the deposition chamber, i.e., the space in which the deposition is carried out. Given a particular desired thickness, those skilled in the art will be able to determine a suitable residence time on the basis of their knowledge.
  • the three steps for applying a coating comprising a para-xylylene polymer is carried out in three different reaction chambers.
  • this invention further relates to the use of a microtiter plate which has been provided with a coating in the above-described manner, in carrying out chemical, biochemical, biological, clinical or pharmaceutical analyses.
  • the invention relates to the use of the microtiter plate in carrying out test reactions, such as luminescence or fluorescence reactions, or in assays of radioactivity, for instance using scintillation counting (LSC) .
  • test reactions such as luminescence or fluorescence reactions
  • assays of radioactivity for instance using scintillation counting (LSC) .
  • LSC scintillation counting
  • Radioactive material for instance tritiated hexadecane
  • TopCount This is an instrument capable of measuring luminescence and radioactivity in the form of a light in microtiter plates. When the surface of the plate is affected, fewer counts (cpm) are registered over time.
  • Example I Coating a microtiter plate
  • Example II Comparison of the influence of a scintillation liquid on the light yield in a microtiter plate with a parylene coating and without parylene coating.
  • TopSeal A Packard Instrument, Downers Grove, 111., USA
  • Top Count microplate scintillation counter At set times (see Table A) , the plate was measured.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Clinical Laboratory Science (AREA)
  • Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Automatic Analysis And Handling Materials Therefor (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

L'invention concerne une plaque de microtitrage en plastique pourvue d'un revêtement composé d'un polymère de para-xylylène, ainsi qu'un procédé servant à appliquer ce revêtement à une plaque de microtitrage en plastique. Elle concerne également l'utilisation de cette plaque de microtitrage afin d'exécuter des analyses chimiques, biochimiques, biologiques, cliniques ou pharmaceutiques.
EP98962684A 1997-12-12 1998-12-11 Plaque de microtitrage pourvue d'un revetement Withdrawn EP1037707A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL1007781 1997-12-12
NL1007781A NL1007781C2 (nl) 1997-12-12 1997-12-12 Microtiterplaat.
PCT/NL1998/000711 WO1999030823A1 (fr) 1997-12-12 1998-12-11 Plaque de microtitrage pourvue d'un revetement

Publications (1)

Publication Number Publication Date
EP1037707A1 true EP1037707A1 (fr) 2000-09-27

Family

ID=19766176

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98962684A Withdrawn EP1037707A1 (fr) 1997-12-12 1998-12-11 Plaque de microtitrage pourvue d'un revetement

Country Status (3)

Country Link
EP (1) EP1037707A1 (fr)
NL (1) NL1007781C2 (fr)
WO (1) WO1999030823A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6274320B1 (en) 1999-09-16 2001-08-14 Curagen Corporation Method of sequencing a nucleic acid
GB2357288A (en) * 1999-12-13 2001-06-20 Ortho Clinical Diagnostics Solid phase carrier coated with a polymer for adsorbing macromolecules
AU2002329170B2 (en) * 2001-01-29 2005-07-07 Honeywell International Inc. Method for depositing a barrier coating on a polymeric substrate and composition comprising said barrier coating
US6586048B2 (en) * 2001-04-05 2003-07-01 Honeywell International Inc. Method for depositing a barrier coating on a polymeric substrate and composition comprising said barrier coating
EP1260542B1 (fr) * 2001-05-16 2007-03-07 Kishimoto Sangyo Co., Ltd. Feuille mince de polymère, méthode de fabrication, liant pour biopuce, biopuce et son procédé de fabrication
US6977138B2 (en) 2001-07-24 2005-12-20 Massachusetts Institute Of Technology Reactive polymer coatings
WO2004069849A2 (fr) 2003-01-29 2004-08-19 454 Corporation Amplification d'acides nucleiques par emulsion de billes
US7785862B2 (en) 2005-04-07 2010-08-31 454 Life Sciences Corporation Thin film coated microwell arrays
US7682816B2 (en) * 2005-04-07 2010-03-23 454 Life Sciences Corporation Thin film coated microwell arrays and methods of using same
DE102005022045A1 (de) * 2005-05-09 2006-11-16 Rwth Aachen Fermentationsverfahren und Anordnung zu dessen Durchführung
US7909928B2 (en) 2006-03-24 2011-03-22 The Regents Of The University Of Michigan Reactive coatings for regioselective surface modification
US7947148B2 (en) 2006-06-01 2011-05-24 The Regents Of The University Of Michigan Dry adhesion bonding
US8399047B2 (en) 2007-03-22 2013-03-19 The Regents Of The Univeristy Of Michigan Multifunctional CVD coatings
WO2009019452A1 (fr) * 2007-08-03 2009-02-12 Enigma Diagnostics Limited Récipient de réaction
GB0715170D0 (en) 2007-08-03 2007-09-12 Enigma Diagnostics Ltd Reaction vessel

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US3429739A (en) * 1964-10-01 1969-02-25 Union Carbide Corp Fibrous materials coated with linear p-xylylene polymers
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AU669754B2 (en) * 1992-12-18 1996-06-20 Becton Dickinson & Company Barrier coating
CH687592A5 (de) * 1993-10-18 1997-01-15 Eidgenoess Munitionsfab Thun Mehrgefaessanordnung zur Instrumental-Analyse.
US5466947A (en) * 1994-03-18 1995-11-14 Bio-Rad Laboratories, Inc. Protective overlayer for phosphor imaging screen
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Also Published As

Publication number Publication date
NL1007781C2 (nl) 1999-06-15
WO1999030823A1 (fr) 1999-06-24

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