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Fluorescent Micro Sphere^ U.S [111 4,413,070 [451 Nov. I, 3983 [54] PQLYACRQLEIN MICRQSPHERES 4,210,565 7/1980 Emrnons ............................. 526/315 4,230,772 10/1980 Swift et al. .......................... 526/315 [75] Inventor: Alan Rembaum, Pasadena, Calif. 4,267,091 5/1981 Geelhaar et al. ................... 526/315 [73] Assignee: California Institute of Technology, OTHER PUBLICATIONS Pasadena, Calif. “Characteristics of Fine Particles” Chemical Engineer- [21] Appl. No.: 248,899 ing, Jun. 11, 1962, p. 207. E221 Filed: Mar. 30, 1981 Primary Examiner-Wilbert J. Briggs, Sr. Assistant Examiner-A. H. Koeckert [51] Int. (3.3 .......................... C08F 2/54; C08F 16/34 Attorney, Agent, or Firm-Marvin E. Jacobs [52] U.S. Cl. ............................... 523/223; 204A59.21; 435/180; 526/315; 526/303.1; 252/301.36; [571 ABSTRACT 252/62.54; 424/82; 525/377; 525/380; 525/382 Microspheres of acrolein homopolymers and co- [58] Field of Search ........................ 526/315; 523/223; polymer with hydrophillic comonomers such as meth- 435/180 acrylic acid and/or hydroxyethylmethacrylate are pre- 1561 References Cited pared by cobalt gamma irradiation of dilute aqueous solutions of the monomers in presence of suspending U.S. PATENT DOCUMENTS agents, especially alkyl sulfates such as sodium dodecyl 3,105,801 10/1963 Bell et al. ............................ 204/154 sulfate. Amine or hydroxyl modification is achieved by 3,819,555 6/1974 Kaufman ............................. 526/315 forming adducts with diamines or alkanol amines. Car- 3,936,423 2/1976 Randazzo ............................ 526/315 boxyl modification is effected by oxidation with perox- 3,957,741 5/1978 Rembaum ...................... 204/159.15 ides. Pharmaceuticals or other aldehyde reactive mate- 3,988,505 10/1976 Evans et al. ........................ 526/315 rials can be coupled to the microspheres. The micro- 4,016,127 4/1977 Larsson et al. ..................... 526/315 4,035,316 7/1977 Rernbaum ........................... 526/225 spheres directly form antibody adducts without ag- 4,138,383 2/1979 Rernbaurn ........................... 526/227 glomeration. 4,157,323 6/1979 Yen et al. .............................. 422/68 4,191,838 3/1980 Merger et al. ...................... 526/315 16 Claims, 4 Drawing Figures Y ALDEHYDE MICROSPHERE c-0 + NH2-FLUOROCHROME H2N- (CH$+-OH I iYDROXYALKYLAMINE t NH2-PHARMACEUTICAL I 1 I-OXIDIZING AGENT CH=N-R-NRz I POLYAMINE HO- C POLYCARBOXY L PHARMACEUTICAL-N-HC 43W MICROSPHERE fCH=N-(CH&-OH PHARMACEUTICAL ADDUCT / $CH=NOH ANTIBODY-N=HC+ ) POLYOXIMES IMMUNO REAGENT - FLUOROCHROME-N=HC~ FLUORESCENT MICRO SPHERE^ U.S. Patent NOV. 1, 1983 Sheet 1 of 2 9 4 70 6000 v) B 0 [L I- :4000 a - [L A- w l- t W B Q_ 2000 Q HEMA + ACROLEIN t --4--HEMAtBAM+MAtACROLEIN 0 ALDEHYDE MICROSPH 1 CHzN-R-NRz P OLYA MI NE P HAR MACE UTI CA L- N = H C MICROSPHERE PHARM ACEUTI CAL ADDUCT ANT i BODY - N = HC 4 IMMUNO REAGENT I FLUOROCHROME-N=HC FLUORESCENT MICROSPHERE akllt Nov. 1, 1983 Sheet 2 of 2 28 "I CARBOXYL \ ALI II 100 90 80 70 60 ! MOLE To ACROLEIN -POLYACROLEIN MICROSPHERES --*--CONTROL 3 494 3,070 1 tive charge onto the particles are likely to prevent non- POLYACROLEIN MICROSPHERES specific binding to cell surfaces and to provide carboxyl groups to which a variety of biochemical molecules can ORIGIN OF THE INVENTION be covalently bonded using the carbodiimide method. The invention described herein was made in the per- 5 The derivatization procedure is unnecessarily com- formance of work under a NASA contract and is sub- plex and requires an additional step to prepare the bead ject to the provisions of Section 305 of the National surface for covalently binding to proteins such as anti- Aeronautics and Space Act of 1958, Public Law 83-568 bodies, lectins and the like or other molecules such as (72 Stat. 435; 42 USC 2457). DNA, hormones and the like. Therefore, the method of lo derivatization of acrylic microbeads is tedious and TECHNICAL FIELD availability is limited. Monomeric glutaraldehyde has The present invention relates to the synthesis of been used as a biochemical reagent to covalently bond polyacrolein microspheres, functional derivatives proteins such as immunoglobulins to ferritin polymeric thereof, fluorescent and magnetic variations thereof, microspheres and other small particles which were then Protein ConJWates thereof and to the use of the COnJU- l5 utilized to map receptors on cell membranes. However, gates in biological and chemical research and testing. the reaction mechanism of proteins with glutaraldehyde BACKGROUND OF THE PRIOR ART is difficult to ascertain since its structure is still not clear and it has been reported to be in equilibrium with cyclic The isolation and characterization of cell membranes and hydrated forms. ~h~ reaction is difficult to carry and their components is essential for an understanding 2o out and frequently gives unsatisfactory results. of the role in which surface membranes play in regulat- Direct protein bonding polyglutaraldehyde or co- ing a wide variety Of and immunological polymers therefore disclosed in copending application activities. The present techniques used for this purpose Ser. Nos, 21,988, now Pat. No. 4,267,235 and are not quite satisfactory. u.s. 21,989, now US. Pat. No. 4,267,234, both filed Mar. 19, Knowledge of the nature, number and distribution of 25 specific receptors on cell surfaces is of central impor- 1979 prepared by solution polymerization in aqueous tance for an understanding of the molecular basis under- basic medium. In contrast to monomeric glutaralde- lying such biological phenomena as cell-cell recognition hyde~ the polymers contain conjugated in development, cell communication and regulation by groups. This imparts stability to the Schiff s bases hormones and chemical transmitters, and differences in 30 formed after reaction with proteins and, further, since normal and tumor cell surfaces. In previous studies, the the hydrophilic PolYglutaraldehYde has relatively 10% localization of antigens and carbohydrate residues on chains extending from the surface into the surrounding the surface of cells, notably red blood cells and lympho- aqueous medium, the heterogeneous reaction with pro- cytes, has been determined by bonding antibodies or tein is facilitated. lectins to such molecules as ferritin, hemocyanin or 35 Polyglutaraldehyde (PGL) microspheres can be di- peroxidase which have served as markers for transmis- rectly prepared by suspension polymerization with stir- sion electron microscopy. With advances in high reso- ring in presence of surfactant or by precipitation from lution scanning electron microscopy (SEM), however, solution containing surfactant. Magnetic, high density the topographical distribution of molecular receptors or electron dense microspheres can be prepared by On the surfaces of cell and tissue specimens can be 40 coating metal particles or by suspension polymerization readily determined by similar histochemical techniques of glutaraldehyde in presence of a suspension of finely using newly developed markers resolvable by SEM. divided metal or metal oxide. It has been determined Recently, commercially available Polystyrene latex that the PGL microspheres exhibit some degree of non- particles have been utilized as immunologic markers for specific binding to cells. M~~~~~~~,though cross- use in the SEM technique. The SWface of such polysty- 45 linking occurs during the homopolymerization of glum rene particles is hydrophobic and hence certain types of taraldehyde, the polymer can be dissolved in highly macromolecules such as antibodies are absorbed on the polar solvents. surface under carefully controlled conditions. How- A process for polymerizing unsaturated aldehydes ever, such particles stick non-specifically to many sur- such acrolein is disclosed in U.S. Pat. No. 3,105,801. faces and molecules and this seriously limits their broad 50 The process comprises adding a small amount of acid or application. an acid-acting material to an aqueous solution contain- The preparation of small, stable spherical Poly-Hema particles which are biocompatib~e, i.e., do not interact ing Or Other unsaturated and exposing non-specifically with cells or other biological the acidic medium to high energy ionizing radiation to nents and which contain functional groups to which 55 form high weight polymer in the form Of specific proteins and other biochemical molecules can light powders having non-uniform shapes and sizes. The be covalently bonded is disclosed in U.S. pat. No, polymers were not utilized as such but are dissolved in 3,957,741. aqueous alkaline sulfur dioxide solution to form water smaller, evenly shaped acrylic microspheres soluble derivatives which are used as coatings or sizings are disclosed in U.S. Pat. No. 4,138,383. Microspheres 60 for paper, cloth, fibers and the like. Bell et a1 also dis- having a density differing from that of cell membranes cusses the copolymerization Of acrolein with a wide are disclosed in U.S. Pat. No. 4,035,316 and fluorescen- variety of ethylenically unsaturated ~O~XXXSsuch as tacrylic copolymer microspheres are disclosed in Ser. ethylene diamine, pyridine or acrylic acids or esters, No. 718,104 filed Aug. 27, 1976. vinyl halides, etc. in amounts from 0.1 to 60%, prefera- The hydroxyl groups can be activated by cyanogen 65 bly from 1% to 25% by weight of the monomer mix- bromide for covalent bonding of proteins and other ture. chemicals containing amino groups to the polymeric The monomer mixture can contain other agents such bead. Methacrylic acid residues which impart a nega- as stabilizing, suspending as emulsifying agents. Radia- 4,413,070 3 4 tion accelerators such as halides or metal salts may be magnetic coatings or s. The microspheres of the added to the reaction mixture. invention provide a le, simple 'method to label Though the polyacroleins prepared by Bell et a1 have cells for research or analysis. a high degree of available aldehyde function, there was The microspheres of the invention can also be utilized no recognition of the use of such material as a biological 5 as a substrate to bind containing func- reagent.
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