Surface-bound fluorescent polymers and related methods of synthesis and use

• US 5,480,723 A
• Filed: 05/17/1994
• Issued: 01/02/1996
• Est. Priority Date: 04/08/1985
• Status: Expired due to Term

• Current Assignee: Optical Sensors Incorporated
• Original Assignee: Optical Sensors Incorporated
• Inventors: Walt, David R., Klainer, Stanley M., Gottlieb, Amos J.
• Primary Examiner(s): Sellers, Robert E.
• Assistant Examiner(s): MOORE, MARGARET G
• Application Number:
  US08/243,961
• Time in Patent Office: 595 Days
• Field of Search: 427/157, 428/500, 428/441, 526/268, 526/270, 526/312, 252/301.32, 252/301.35, 252/408.1, 252/700
• US Class Current: 428/441
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: G01N 2021/6432 Quenching
• CPC Class Codes: G01N 2021/6484 Optical fibres
• CPC Class Codes: G01N 2021/772 Tip coated light guide
• CPC Class Codes: G01N 21/6428 Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" in vivo A61B5/00; immunoassay G01N33/53
• CPC Class Codes: G01N 21/7703 using reagent-clad optical fibres or optical waveguides using measurement of total internal reflection or attenuated total reflection G01N21/552; optical fibres or waveguides per se G02B
• CPC Class Codes: G01N 21/81 Indicating humidity
• CPC Class Codes: G01N 33/552 Glass or silica
• CPC Class Codes: Y10T 428/31645 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers

Abstract

A fiber optic sensing device for measuring a chemical or physiological parameter of a body fluid or tissue is provided. To one end of the fiber is attached a polymer including a plurality of photoactive moieties selected from the group consisting of chromophores and lumophores, the photoactive moieties spaced apart so as to minimize chemical or physical interaction therebetween while optimizing the density of photoactive moieties. In one embodiment, a polymer chain is covalently bound to photoactive moieties through functional groups such as esters, amides, or the like. In a second embodiment, a polymer chain is inherently fluorescent and is formed from at least one monomeric unit. These devices are particularly useful as pH and oxygen sensors.

Claims

1. A surface-bound fluorescent polymer prepared by the process comprising copolymerizing a monomeric fluorescent species having the structure ##STR18## with acrylamide in the presence of a catalyst and in the presence of a glass surface having free NH₂ groups activated with acryloyl chloride.

2. A process for preparing a surface-bound fluorescent polymer, comprising copolymerizing a monomeric fluorescent species having the structure ##STR19## with acrylamide in the presence of a glass surface having free NH₂ groups activated with acryloyl chloride.

3. A surface-bound fluorescent polymer prepared by the process comprising:

(a.) treating a glass surface having free NH₂ groups with succinic anhydride, to produce acid glass in which the free NH₂ groups have been replaced with surface --NH(CO)CH₂ CH₂ COOH groups;

(b.) preparing acid chloride glass by converting the surface --NH(CO)CH₂ CH₂ COOH groups to surface --NH(CO)CH₂ CH₂ COCl moieties;

(c.) treating said acid chloride glass with N-hydroxysuccinimide, to produce NHS glass having surface ##STR20## groups;

(d.) treating the NHS glass with triethylenetetramine, to provide aminoalkyl glass having surface ##STR21## groups;

(e.) activating the aminoalkyl glass with acryloyl chloride to provide an activated surface having surface-bound acrylamide groups; and

(f.) copolymerizing a fluorescent species having the structure ##STR22## with acrylamide in the presence of a catalyst and in the presence of the activated surface.

4. A process for preparing a surface-bound fluorescent polymer, comprising:

(a.) treating a glass surface having free NH₂ groups with succinic anhydride, to produce acid glass in which the free NH₂ groups have been replaced with surface --NH(CO)CH₂ CH₂ COOH groups;

(b.) preparing acid chloride glass by converting the surface --NH(CO)CH₂ CH₂ COOH groups to surface --NH(CO)CH₂ CH₂ COCl moieties;

(c.) treating said acid chloride glass with N-hydroxysuccinimide, to produce NHS glass having surface ##STR23## groups;

(d.) treating the NHS glass with triethylenetetramine, to provide aminoalkyl glass having surface ##STR24## groups;

(e.) activating the aminoalkyl glass with acryloyl chloride to provide an activated surface having surface-bound acrylamide groups; and

(f.) copolymerizing a fluorescent species having the structure ##STR25## with acrylamide in the presence of a catalyst and in the presence of the activated surface.