US20040126897A1 - Colorimetric sensors constructed of diacetylene materials - Google Patents

Colorimetric sensors constructed of diacetylene materials Download PDF

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US20040126897A1
US20040126897A1 US10/325,801 US32580102A US2004126897A1 US 20040126897 A1 US20040126897 A1 US 20040126897A1 US 32580102 A US32580102 A US 32580102A US 2004126897 A1 US2004126897 A1 US 2004126897A1
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sensor
alkylene
independently
receptor
analyte
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Ryan Prince
David Hays
Angela dillow
G. Bommarito
John Battiste
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3M Innovative Properties Co
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3M Innovative Properties Co
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Assigned to 3M INNOVATIVE PROPERTIES COMPANY reassignment 3M INNOVATIVE PROPERTIES COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BATTISTE, JOHN L., BOMMARITO, G. MARCO, DILLOW, ANGELA K., HAYS, DAVID S., PRINCE, RYAN B.
Priority to US10/738,573 priority patent/US7364918B2/en
Priority to TW092135981A priority patent/TW200502550A/zh
Priority to DE60314290T priority patent/DE60314290T2/de
Priority to MXPA05006445A priority patent/MXPA05006445A/es
Priority to EP03813810A priority patent/EP1579210B1/en
Priority to PCT/US2003/040714 priority patent/WO2004057331A1/en
Priority to DK03813810T priority patent/DK1579210T3/da
Priority to AT03813810T priority patent/ATE364176T1/de
Priority to CA2510030A priority patent/CA2510030C/en
Priority to JP2004562334A priority patent/JP4402597B2/ja
Priority to AU2003301171A priority patent/AU2003301171B8/en
Priority to BR0317472-7A priority patent/BR0317472A/pt
Priority to CN200380107097A priority patent/CN100578226C/zh
Priority to ES03813810T priority patent/ES2286511T3/es
Publication of US20040126897A1 publication Critical patent/US20040126897A1/en
Priority to ZA200505741A priority patent/ZA200505741B/en
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • G01N33/521—Single-layer analytical elements
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81—Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • Y10S530/812—Peptides or proteins is immobilized on, or in, an organic carrier

Definitions

  • the present invention relates to a technique for detection of analytes using observable spectral changes in polydiacetylene assemblies. More specifically, this invention relates to a colorimetric sensor comprising polydiacetylene assemblies and a method of using the sensor to detect an analyte.
  • Diacetylenes are typically colorless and undergo addition polymerization, either thermally or by actinic radiation. As the polymerization proceeds, these compounds undergo a contrasting color change to blue or purple. When exposed to external stimuli such as heat, physical stress or a change of solvents or counterions, polydiacetylenes exhibit a further color changes produced by distortion of the planar backbone conformation. Polydiacetylene assemblies are known to change color from blue to red with an increase in temperature or changes in pH due to conformational changes in the conjugated backbone as described in Mino, et al., Langmuir, Vol. 8, p. 594, 1992; Chance, et al., Journal of Chemistry and Physics , Vol.
  • Synthesis of both the receptors and the polydiacetylene membranes can be complicated and difficult.
  • the polydiacetylene membranes can exhibit insufficient color change upon binding with an analyte, requiring other substances for promoting the structural change or enhancing analytical equipment to observe the color change.
  • the present invention provides a calorimetric sensor to detect the presence of analytes by spectral changes (color changes visible to the naked eye or with a calorimeter) that occur as a result of the specific binding of the analytes to polydiacetylene assemblies.
  • the polydiacetylene assemblies indicate the presence of an analyte in a simple yet highly sensitive manner.
  • the present invention provides a colorimetric sensor comprising a receptor and the polymerization reaction product comprising at least one compound of the formula
  • R 3 , R 8 , R 13 , R 21 , R 24 , R 31 and R 33 are independently alkyl;
  • R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently alkylene;
  • R 6 , R 15 , R 18 , and R 26 are independently alkylene, alkenylene, or arylene;
  • R 9 is alkylene or —NR 34 —;
  • R 10 , R 12 , R 27 , and R 29 are independently alkylene or alkylene-arylene;
  • R 11 and R 28 are independently alkynyl;
  • R 17 is an ester-activating group;
  • R 23 is arylene;
  • R 30 is alkylene or —NR 4 —;
  • R 34 , and R 36 are independently H or C 1 -C 4 alkyl; p is 1-5; and n is 1-20; and where R 1 and R 2 are
  • test kit whose reliability is relativity stable in a wide range of environmental conditions, and when the analyte is mixed with a number of other materials.
  • FIG. 1 shows a schematic representation of a colorimetric sensor of the present invention.
  • FIG. 2 shows a schematic representation of a calorimetric sensor array of the present invention.
  • FIG. 3 shows a schematic representation of a colorimetric sensor for contacting the sensor with an analyte.
  • FIG. 4 shows a schematic representation of a foldable colorimetric sensor for contacting the sensor with an analyte.
  • FIG. 5 shows a schematic representation of a colorimetric sensor of the present invention with one type of analyte delivery.
  • FIG. 6 shows a schematic representation of a calorimetric sensor array of the prevent invention with one type of analyte delivery.
  • FIG. 7 is a phase diagram showing the colors of the coated and dried polydiacetylene film as a function of the contact angle of the substrate.
  • FIG. 8 is a phase diagram showing the colors of the coated and dried polydiacetylene film as a function of the surface tension of the substrate.
  • the present invention provides a colorimetic sensor comprising diacetylenic materials and a method of using the sensor to detect an analyte. While the present invention is not so limited, an appreciation of various aspects of the invention will be gained through a discussion of the examples provided below.
  • alkyl refers to a straight or branched chain or cyclic monovalent hydrocarbon radical having a specified number of carbon atoms. Alkyl groups include those with one to twenty carbon atoms. Examples of “alkyl” as used herein include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, isobutyl, and isopropyl, and the like. It is to be understood that where cyclic moieties are intended, at least three carbons in said alkyl must be present. Such cyclic moieties include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • alkylene refers to a straight or branched chain or cyclic divalent hydrocarbon radical having a specified number of carbon atoms. Alkylene groups include those with one to fourteen carbon atoms. Examples of “alkylene” as used herein include, but are not limited to, methylene, ethylene, trimethylene, tetramethylene and the like. It is to be understood that where cyclic moieties are intended, at least three carbons in said alkylene must be present. Such cyclic moieties include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene and cycloheptylene.
  • alkenylene refers to a straight or branched chain or cyclic divalent hydrocarbon radical having a specified number of carbon atoms and one or more carbon—carbon double bonds. Alkenylene groups include those with two to eight carbon atoms. Examples of “alkenylene” as used herein include, but are not limited to, ethene-1,2-diyl, propene-1,3-diyl, and the like.
  • arylene refers to divalent unsaturated aromatic carboxylic radicals having a single ring, such as phenylene, or multiple condensed rings, such as naphthylene or anthrylene.
  • Arylene groups include those with six to thirteen carbon atoms. Examples of “arylene” as used herein include, but are not limited to, benzene-1,2-diyl, benzene-1,3-diyl, benzene-1,4-diyl, naphthalene-1,8-diyl, and the like.
  • alkylene-arylene refers to an alkylene moiety as defined above bonded to an arylene moiety as defined above.
  • alkylene-arylene examples include, but are not limited to, —CH 2 -phenylene, —CH 2 CH 2 -phenylene, and —CH 2 CH 2 CH 2 -phenylene.
  • alkynyl refers to a straight or branched chain or cyclic monovalent hydrocarbon radical having from two to thirty carbons and at least one carbon-carbon triple bond.
  • alkynyl as used herein include, but are not limited to, ethynyl, propynyl and butynyl.
  • analyte(s) refers to any material that can be detected by the sensor of the present invention. Such materials include, but are not limited to small molecules, pathogenic and non-pathogenic organisms, toxins, membrane receptors and fragments, volatile organic compounds, enzymes and enzyme substrates, antibodies, antigens, proteins, peptides, nucleic acids, and peptide nucleic acids.
  • bacteria refers to all forms of microorganisms considered to be bacteria including cocci, bacilli, spirochetes, sheroplasts, protoplasts, etc.
  • receptor refers to any molecule with a binding affinity for an analyte of interest.
  • Receptor includes, but is not limited to, naturally occurring receptors such as surface membrane proteins, enzymes, lectins, antibodies, recombinant proteins, etc.; synthetic proteins; nucleic acids; c-glycosides; carbohydrates; gangliosides; and chelating agents.
  • the terms “assembly”, or “self-assembly”, refers to any self-ordering of diacetylene molecules prior to polymerization. J. Israelachvili, Intermolecular and Surface Forces (2 nd Ed.), Academic Press, New York (1992), pp. 321-427.
  • SAMs self-assembling monolayer(s)
  • transducer describes a material capable of turning a recognition event at the molecular level into an observable signal.
  • the present invention provides a calorimetric sensor comprising novel polydiacetylene assemblies incorporated with a receptor for detection of an analyte.
  • the polydiacetylene assemblies are polymerized compounds of the formula
  • R 3 , R 4 , R 13 , R 21 , R 24 , R 31 and R 33 are independently alkyl;
  • R 4 , R 5 , R 7 , R 14 , R 16 , R 19 , R 20 , R 22 , R 25 , and R 32 are independently alkylene;
  • R 6 , R 15 , R 18 , and R 26 are independently alkylene, alkenylene, or arylene;
  • R 9 is alkylene or —NR 34 —;
  • R 10 , R 12 , R 27 , and R 29 are independently alkylene or alkylene-arylene;
  • R 11 and R 28 are independently alkynyl;
  • R 17 is an ester-activating group;
  • R 23 is arylene;
  • R 30 is alkylene or —NR 36 —;
  • R 34 , and R 36 are independently H or C 1 -C 4 alkyl;
  • p is 1-5; and n is 1-20; and where R 1 and R
  • R 1 when R 1 is alkyl examples include C 1 -C 20 alkyl, C 6 -C 18 alkyl, and C 12 -C 16 alkyl. Additional examples of R 1 when R 1 is alkyl include dodecyl and hexadecyl.
  • R 3 examples include C 1 -C 20 alkyl, and C 6 -C 18 alkyl. Additional examples of R 3 include undecyl and pentadecyl.
  • R 4 examples include C 1 -C 14 alkylene, and C 1 -C 4 alkylene. Additional examples of R 4 include methylene (—CH 2 —), trimethylene, (—CH 2 CH 2 CH 2 —), and tetramethylene (—CH 2 CH 2 CH 2 CH 2 —).
  • R 5 examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene. Additional examples of R 5 include ethylene (—CH 2 CH 2 —), and trimethylene (—CH 2 CH 2 CH 2 —).
  • R 6 when R 6 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene. Additional examples of R 6 when R 6 is alkylene include ethylene (—CH 2 CH 2 —), and trimethylene (—CH 2 CH 2 CH 2 —). Examples of R 6 when R 6 is alkenylene include C 2 -C 8 alkenylene, and C 2 -C 4 alkenylene. An additional example of R when R 6 is alkenylene includes ethenylene (—C ⁇ C—). Examples of R 6 when R is arylene include C 6 -C 13 arylene, and phenylene. An additional example of R 6 when R 6 is arylene is benzene-1,2-diyl.
  • R 7 examples include C 1 -C 14 alkylene, and C 2 -Cg alkylene. Additional examples of R 7 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), heptamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), octamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), and nonamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 8 examples include Ct-C 1-6 alkyl, and C 1 -C 8 alkyl. Additional examples of R 8 include butyl, pentyl and hexyl.
  • R 9 is independently alkylene or —NR 34 —, where R 34 is H or C 1 -C 4 alkyl;
  • R 9 when R 9 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene, such as methylene (—CH 2 —) for example.
  • R 10 when R 10 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 8 alkylene. Additional examples of R 10 when R 10 is alkylene include methylene (—CH 2 —), ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), —C(CH 3 ) 2 —, and —CH((CH 2 ) 14 CH 3 )—. Examples of R 10 when R 10 is alkylene-arylene include (C 1 -C 14 alkylene)-arylene, and (C 1 -C 14 alkylene)-phenylene. An additional example of R 10 when R 10 is alkylene-arylene includes —CH 2 -phenylene.
  • R 11 examples include C 2 -C 30 alkynyl, and C 20 -C 25 alkynyl. Additional examples of R 11 include C 2 -C 30 alkynyl having at least two carbon-carbon triple bonds (—C ⁇ C—), and C 20 -C 25 alkynyl having at least two carbon-carbon triple bonds. Further examples of R 11 include C 22 alkynyl having at least two carbon-carbon triple bonds, C 24 alkynyl having at least two carbon-carbon triple bonds.
  • R 11 include —(CH 2 ) 8 —C ⁇ C—C ⁇ C—(CH 2 ) 9 CH 3 , and —(CH 2 ) 8 —C ⁇ C—C ⁇ C—(CH 2 ) 11 CH 3 .
  • R 12 when R 12 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 8 alkylene. Additional examples of R 12 when R 12 is alkylene include methylene (—CH 2 —), ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), —C(CH 3 ) 2 —, and —CH((CH 2 ) 14 CH 3 )—. Examples of R 12 when R 12 is alkylene-arylene include (C 1 -C 14 alkylene)-arylene, and (C 1 -C 14 alkylene)-phenylene. An additional example of R 12 when R 12 is alkylene-arylene includes —CH 2 -phenylene.
  • R 13 examples include C 1 -C 4 alkyl, such as methyl for example.
  • R 14 examples include C 1 -C 4 alkylene, such as ethylene (—CH 2 CH 2 —) for example.
  • R 15 when R 15 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene. Additional examples of R 15 when R 15 is alkylene include ethylene (—CH 2 CH 2 —), and trimethylene (—CH 2 CH 2 CH 2 —). Examples of R 15 when R 15 is alkenylene include C 2 -C 8 alkenylene, and C 2 -C 4 alkenylene. An additional example of R 15 when R 15 is alkenylene includes ethenylene (—C ⁇ C—). Examples of R 15 when R 15 is arylene include C 6 -C 13 arylene, and phenylene. An additional example of R 15 when R 15 is arylene is benzene-1,4-diyl.
  • R 16 examples include C 1 -C 14 alkylene, and C 2 -C 9 alkylene. Additional examples of R 16 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), heptamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), octamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), and nonamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 17 examples include groups that activate the neighboring ester group toward acyl transfer.
  • ester activating groups include pentafluorophenol, pentachlorophenol, 2,4,6-trichlorophenol, 3-nitrophenol, N-hydroxysuccinimide, N-hydroxyphthalimide and those disclosed in M. Bodanszky, “Principles of Peptide Synthesis,” (Springer-Verlag 1984), for example.
  • An additional example of R 17 is 2,5-dioxo-1-pyrrolidinyl.
  • R 18 when R 18 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene. Additional examples of R when R 18 is alkylene include ethylene (—CH 2 CH 2 —), and trimethylene (—CH 2 CH 2 CH 2 —). Examples of R 18 when R 18 is alkenylene include C 2 -C 8 alkenylene, and C 2 -C 4 alkenylene. An additional example of R 18 when R 18 is alkenylene includes ethenylene (—C ⁇ C—). Examples of R 18 when R 18 is arylene include C 6 -C 13 arylene, and phenylene. An additional example of R 18 when R 18 is arylene is benzene-1,2-diyl.
  • R 19 examples include C 1 -C 14 alkylene, and C 2 -C 9 alkylene. Additional examples of R 19 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), heptamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), octamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), and nonamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 20 examples include C 1 -C 14 alkylene, C 1 -C 9 alkylene, and C 1 -C 4 alkylene. Additional examples of R 20 include methylene (—CH 2 —), ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), heptamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), octamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), and nonamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 21 when R 21 is alkyl examples include C 1 -C 20 alkyl, C 6 -C 18 alkyl, and C 10 -C 17 alkyl. Additional examples of R 21 when R 21 is alkyl include decyl, undecyl, tridecyl, tetradecyl, pentadecyl, heptadecyl.
  • R 22 examples include C 1 -C 14 alkylene, and C 2 -C 9 alkylene. Additional examples of R 22 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), and tetramethylene.
  • R 23 examples include C 6 -C 13 arylene, and phenylene.
  • An additional example of R 23 when R 23 is arylene is benzene-1,4-diyl.
  • R 24 examples include C 1 -C 20 alkyl, and C 6 -C 18 alkyl. Additional examples of R 24 include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and dodecyl.
  • R 25 examples include C 1 -C 14 alkylene, and C 2 -C 9 alkylene. Additional examples of R 25 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), heptamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), octamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —), and nonamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 26 when R 26 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene. Additional examples of R 26 when R 26 is alkylene include ethylene (—CH 2 CH 2 —), and trimethylene (—CH 2 CH 2 CH 2 —). Examples of R 26 when R 26 is alkenylene include C 2 -C 8 alkenylene, and C 2 -C 4 alkenylene. An additional example of R 26 when R 26 is alkenylene includes ethenylene (—C ⁇ C—). Examples of R when R is arylene include C 6 -C 13 arylene, and phenylene. An additional example of R 26 when R 26 is arylene is benzene-1,2-diyl.
  • R 27 when R 27 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 8 alkylene. Additional examples of R 27 when R 27 is alkylene include methylene (—CH 2 —), ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), —C(CH 3 ) 2 —, and —CH((CH 2 ) 1-4 CH 3 )—. Examples of R 27 when R 27 is alkylene-arylene include (C 1 -C 14 alkylene)-arylene, and (C 1 -C 14 alkylene)-phenylene. An additional example of R 27 when R 27 is alkylene-arylene includes —CH 2 -phenylene.
  • R 28 examples include C 2 -C 30 alkynyl, and C 20 -C 25 alkynyl. Additional examples of R 28 include C 2 -C 30 alkynyl having at least two carbon-carbon triple bonds (—C ⁇ C—), and C 20 -C 25 alkynyl having at least two carbon-carbon triple bonds. Further examples of R 28 include C 22 alkynyl having at least two carbon-carbon triple bonds, C 24 alkynyl having at least two carbon-carbon triple bonds.
  • R 28 include —(CH 2 ) 8 —C ⁇ C—C ⁇ C—(CH 2 ) 9 CH 3 , and —(CH 2 ) 8 —C ⁇ C—C ⁇ C—(CH 2 ) 11 CH 3 .
  • R 29 when R 29 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 8 alkylene. Additional examples of R 29 when R 29 is alkylene include methylene (—CH 2 —), ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), —C(CH 3 ) 2 —, and —CH((CH 2 ) 1 C 14 CH 3 )—. Examples of R 29 when R 29 is alkylene-arylene include (C 1 -C 14 alkylene)-arylene, and (C 1 -C 14 alkylene)-phenylene. An additional example of R 29 when R 29 is alkylene-arylene includes —CH 2 -phenylene.
  • R 30 is independently alkylene or —NR 36 —, where R 36 is H or C 1 -C 4 alkyl;
  • R 30 when R 30 is alkylene examples include C 1 -C 14 alkylene, and C 1 -C 3 alkylene, such as methylene (—CH 2 —) for example.
  • R 31 examples include C 1 -C 16 alkyl, and C 1 -C 8 alkyl. Additional examples of R 31 include butyl, pentyl and hexyl.
  • R 32 examples include C 1 -C 14 alkylene, and C 2 -Cg alkylene. Additional examples of R 32 include ethylene (—CH 2 CH 2 —), trimethylene (—CH 2 CH 2 CH 2 —), tetramethylene (—CH 2 CH 2 CH 2 CH 2 —), pentamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 —), and hexamethylene (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).
  • R 33 examples include C 1 -C 20 alkyl, C 6 -C 18 alkyl, and C 10 -C 16 alkyl. Additional examples of R 33 include dodecyl, tetradecyl, hexadecyl, and octadecyl.
  • Compounds of the present invention also include those where p can be 1 or 2 and n can be 1-20, 3-17, 6-14, or 9-11.
  • the invention is inclusive of the compounds described herein including isomers, such as structural isomers and geometric isomers, salts, solvates, polymorphs and the like.
  • Diacetylenes of the Formula XXIII can be prepared as outlined in Scheme 1 where n is typically 1 to 4 and m is typically 10 to 14.
  • Compounds of formula XXIII can be prepared via oxidation from compounds of formula XXII by reaction with a suitable oxidizing agent in a suitable solvent such as DMF for example.
  • suitable oxidizing agents include Jones reagent and pyridinium dichromate for example. The aforesaid reaction is typically run for a period of time from 1 hour to 48 hours, generally 8 hours, at a temperature from 0° C. to 40° C., generally from 0° C. to 25° C.
  • Compounds of formula XXII can be prepared from compounds of formula XXI by reaction with a suitable acid chloride.
  • suitable acid chlorides include any acid chloride that affords the desired product such as lauroyl chloride, 1-dodecanoyl chloride, 1-tetradecanoyl chloride, 1-hexadecanoyl chloride, and 1-octadecanoyl chloride for example.
  • Suitable solvents include ether, tetrahydrofuran, dichloromethane, and chloroform, for example.
  • the aforesaid reaction is typically run for a period of time from 1 hour to 24 hours, generally 3 hours, at a temperature from 0° C. to 40° C., generally from 0° C. to 25° C., in the presence of a base such as trialkylamine or pyridine base.
  • Compounds of formula XXI are either commercially available (e.g. where n is 1-4) or can be prepared from compounds of the formula XVIII via compounds XIX and XX as outlined in Scheme I and disclosed in Abrams, Suzanne R.; Shaw, Angela C. “Triple-bond isomerizations: 2- to 9-decyn-1-ol,” Org. Synth . (1988), 66, 127-31 and Brandsma, L. “Preparative Acetylenic Chemistry,” (Elsevier Pub. Co.: New York, 1971), for example.
  • Diacetylenic compounds as disclosed herein can also be prepared by reacting compounds of formula XXII with an anhydride such as succinic, glutaric, or phthalic anhydride in the presence of a suitable solvents such as toluene.
  • anhydride such as succinic, glutaric, or phthalic anhydride
  • the aforesaid reaction is typically run for a period of time from 1 hour to 24 hours, generally 15 hours, at a temperature from 50° C. to 125° C., generally from 100° C. to 125° C.
  • the diacetylenic compounds as disclosed herein self assemble in solution to form ordered assemblies that can be polymerized using any actinic radiation such as, for example, electromagnetic radiation in the UV or visible range of the electromagnetic spectrum.
  • Polymerization of the diacetylenic compounds result in polymerization reaction products that have a color in the visible spectrum less than 570 nm, between 570 nm and 600 nm, or greater than 600 nm depending on their conformation and exposure to external factors.
  • polymerization of the diacetylenic compounds disclosed herein result in meta-stable blue phase polymer networks that include a polydiacetylene backbone. These meta-stable blue phase polymer networks undergo a color change from bluish to reddish-orange upon exposure to external factors such as heat, a change in solvent or counterion, if available, or physical stress for example.
  • Polymerization products of some of the diacetylenic compounds disclosed herein can exhibit a reversible color change and/or a three state color change.
  • the resulting blue-phase polymer network can change color to a reddish-orange state upon exposure to heat, a change in solvent or counterion, or physical stress.
  • This reddish-orange polymer network can then change color to a yellowish-orange state upon further exposure to heat, a change in solvent or counterion, or physical stress.
  • polymer networks disclosed herein can cycle between these reddish-orange and yellowish-orange states in a reversible manner.
  • the ability of the diacetylenic compounds and their polymerization products disclosed herein to undergo a visible color change upon exposure to physical stress make them ideal candidates for the preparation of sensing devices for detection of an analyte.
  • the polydiacetylene assemblies formed from the disclosed diacetylene compounds can function as a transducer in biosensing applications.
  • the structural requirements of a diacetylenic molecule for a given sensing application are typically application specific.
  • Features such as overall chain length, solubility, polarity, crystallinity, and presence of functional groups for further molecular modification all cooperatively determine a diacetylenic molecule's ability to serve as a useful sensing material.
  • the structure of the diacetylenic compound should be capable of forming a stable dispersion in water, polymerizing efficiently to a colored material, incorporating appropriate receptor chemistry for binding to an analyte, and transducing that binding interaction by means of a color change.
  • the diacetylenic compounds of the present invention possess the capabilities described above and can be easily and efficiently polymerized into polydiacetylene assemblies that undergo the desired color changes. Additionally, the diacetylenic compounds allow for the incorporation of large excesses of unpolymerizable material, such as a receptor described below, while still forming a stable, polymerizable solution.
  • the disclosed diacetylenic compounds can be synthesized in a rapid high-yielding fashion, including high-throughput methods of synthesis.
  • the presence of functionality in the backbones of the diacetylenic compounds, such as heteroatoms for example, provides for the possibility of easy structural elaboration in order to meet the requirements of a given sensing application.
  • the diacetylenic compounds can be polymerized into the desired polydiacetylene backbone containing network by adding the diacetylene to a suitable solvent, such as water for example, sonicating the mixture, and then irradiating the solution with ultraviolet light, typically at a wavelength of 254 nm.
  • the calorimetric sensors of the present invention comprising the disclosed diacetylene compounds can serve as the basis for the colorimetric detection of a molecular recognition event in solution or coated on a substrate.
  • a molecular recognition device can be prepared by adding a receptor to the diacetylene monomer system either prior to or after polymerization. Upon polymerization or thereafter, the receptor is effectively incorporated within the polymer network such that interaction of the receptor with an analyte results in a visible color change due to the perturbation of the conjugated ene-yne polymer backbone.
  • the receptor is physically mixed and dispersed among the polydiacetylene assemblies.
  • the receptor is covalently bonded to the polydiacetylene assemblies.
  • useful receptors include, but are not limited to surface membrane proteins, enzymes, lectins, antibodies, recombinant proteins, etc.; synthetic proteins; nucleic acids; c-glycosides; carbohydrates; gangliosides; and chelating agents.
  • the receptor is a phospholipid.
  • the receptor is a glycerol incorporated into the diacetylene assembly by known methods such as that discussed in Alcaraz, Marie-Lyne; Peng, Ling; Klotz, Phillipe; Goeldner, Maurice, J.Org.Chem. 1996, 61, 192-201.
  • the colometric sensors of the present invention formed from the disclosed diacetylene compounds are amenable to a variety of applications that demand cost-effective, stable, accurate, consistent and quick diagnostics outside the laboratory setting. Applications include point-of-care testing, home testing diagnostics, military and industrial detection of air —or water-borne pathogens and VOCs, and food processing.
  • a sensor comprising the polydiacetylene assemblies can be obtained without the need to form a film by the conventional LB (Langmuir-Blodgett) process before transferring it onto an appropriate support.
  • the polydiacetylene assemblies can be formed on a substrate using the known LB process as described in A. Ulman, An Introduction to Ultrathin Organic Films , Academic Press, New York (1991), pp. 101-219.
  • the present invention provides biosensing capabilities in a disposable adhesive product.
  • the sensors are self-contained and do not require additional instrumentation to convey a measurable result.
  • use with other analytical instrumentation is possible to further enhance sensitivity, such as fluorescence with the fluorescent “red” phase developed after detection of the analyte.
  • the sensors function to provide a rapid screening device when the detection of a threshold presence of a specific analyte is desired.
  • the sensors of the present invention are disposable and relatively inexpensive.
  • the calorimetric sensor comprises a transducer formed from a receptor incorporated within the polydiacetylene assemblies in solution.
  • the solution can be provided in a simple vial system, with the analyte directly added to a vial containing a solution with the transducer specific to the analyte of interest.
  • the colorimetric sensor could comprise multiple vials in a kit, with each vial containing a transducer comprising polydiacetylenes assemblies with incorporated receptors particular to different analytes. For those applications in which the analyte cannot be added directly to the polydiacetylene transducer, a two-part vial system could be used.
  • One compartment of the vial could contain reagents for sample preparation of the analyte physically separated from the second compartment containing the transducer formed from the polydiacetylene assemblies. Once sample preparation is complete, the physical barrier separating the compartments would be removed to allow the analyte to mix with the transducer for detection.
  • the colorimetric sensor is a rapid indicator in a tape or label format as depicted in FIG. 1.
  • FIG. 1 shows a tape or label 10 coated with a pressure sensitive adhesive 20 and a transducer 30 coated on a substrate 40 .
  • Pressure sensitive adhesive 20 can affix tape or label 10 to a surface for direct detection of an analyte.
  • Pressure sensitive adhesive 20 is isolated from transducer 30 containing the polydiacetylene assemblies to potentially minimize adverse effects.
  • pressure sensitive adhesive 20 surrounds the transducer 30 located in the center of tape or label 10 . In an alternate embodiment (not shown), the pressure sensitive adhesive and the transducer are combined.
  • tape or label 10 will contain a transparent window on the side of tape or label 10 that does not contain pressure sensitive adhesive 20 .
  • the window would be centered under transducer 30 to allow the user to view the color change without removing the tape or label 10 from the surface containing the analyte.
  • the tape or label 110 is shown as array 111 composed of multiple transducers 112 , 113 , 114 , 115 , and 116 .
  • Each of transducers 112 , 113 , 114 , 115 , and 116 could be formed from the same or different polydiacetylene assemblies with each polydiacetylene assembly incorporating the same or different receptor.
  • array 111 can be designed to detect multiple analytes at various concentration levels.
  • tape or label 100 comprises a foldable substrate 101 with pressure sensitive adhesive 102 on one side of foldable substrate 101 , and transducer 103 placed on the opposing side of foldable substrate 101 facing pressure sensitive adhesive 102 .
  • the surface containing a target analyte could be contacted with pressure sensitive adhesive 102 to collect the sample.
  • the foldable substrate 101 would be folded to contact the pressure sensitive adhesive 102 to transducer 103 as shown in FIG. 4.
  • foldable substrate 101 could be perforated to allow separation of foldable substrate 101 into two or more parts, with one part containing pressure sensitive adhesive 102 and another part containing the transducer 103 . Both the foldable feature and/or the perforations of foldable substrate 101 allow the user to prevent the transducer from contacting the sample surface that contains the analyte for applications requiring that functionality.
  • foldable substrate 101 in FIG. 3 could also include multiple transducers as shown in FIG. 2 and described above. Further, foldable substrate 101 could include a transparent window on the side opposite transducer 103 for viewing any color change after foldable susbstrate 101 is folded to contact transducer 103 to pressure sensitive adhesive 102 .
  • FIGS. 5 and 6 Alternative embodiments are shown in FIGS. 5 and 6 that allow delivery of a fluid sample to the transducer via a microfluidic element such as those described in U.S. Pat. Nos. 6 , 375 , 871 and 6 , 451 , 191 .
  • tape or label 301 contains a microfluidic element 302 that delivers the analyte to the transducer 303 .
  • pressure sensitive adhesive could be supplied on tape or label 301 on the side opposite transducer 303 to allow the tape or label to be attached to a surface for storage or holding purposes such as attaching to a wall or container.
  • a microfluidic element 401 is provided on tape or label 402 .
  • Microfluidic element 401 delivers the analyte to multiple wells 403 , 404 , 405 , and 406 containing the same or different transducers.
  • Each of the transducers in multiple wells 403 , 404 , 405 , and 406 could be formed from the same or different polydiacetylene assemblies with each polydiacetylene assembly incorporating the same or different receptor.
  • multiple wells 403 , 404 , 405 , and 406 can be designed to provide detection for multiple analytes at various concentration levels.
  • kits could contain a vial for reagant storage and mixing of the analyte before contacting the calorimetric sensor coated on a two-dimensional substrate.
  • the kit could comprise a vial for reagent storage and analyte preparation, with a cap system containing the transducer of the present invention coated on a substrate.
  • the present invention also provides a method for analysis of an analyte, which comprises contacting the abovementioned colorimetric sensor with a solution sample or surface containing an analyte and utilizing an absorption measurement or a visual observation with the naked eye to detect color change in the colorimetric sensor.
  • the present invention provides a method for indirect detection of an analyte by selection of a probe with an affinity to bind with both the receptor incorporated into the polydiacetylene assemblies and the analyte.
  • the probe selected will demonstrate a competitive affinity with the analyte.
  • the probe will bind to the analyte rather than the receptor on the polydiacetylene backbone, resulting in no color change. If the analyte is absent, the probe will bind to the receptor incorporated on the polydiacetylene backbone, resulting in a color change from blue to red.
  • the probe can contact the transducer after the analyte contacts the transducer, or can be mixed with the analyte prior to the mixture contacting the transducer.
  • the probe can be contacted with the transducer in solution or coated on a substrate.
  • the probe will be any molecule with an affinity for both the target analyte and the receptor.
  • Possible probes for use in the present invention include membrane disrupting peptides such as alamethicin, magainin, gramicidin, polymyxin B sulfate, and melittin.
  • probe concentrations can be chosen to correspond to desired concentration levels of detection.
  • the method of indirect detection using the probe allows design of the system around the type and concentration of the probe for desired sensitivity in a given application. This allows the transducer to be universal to multiple analytes of interest. For example, a single transducer (polydiacetylene/receptor combination) could serve to detect multiple analytes by varying the probe in contact with the transducer in accordance with the probe's affinity for the analyte.
  • the substrates of the present invention can be characterized by contact angle measurements using milli-Q (Millipore) water and methylene iodide (Aldrich) probe liquids.
  • a goniometer from Rame-Hart is used to measure the contact angle that a drop of a probe liquid forms when placed on a substrate. Although the drop covers a macroscopic area of the substrate, the interaction of the liquid and the surface probes only the outermost 1-5 ⁇ ngstroms of the surface.
  • contact angle analysis provides an accurate and sensitive technique for characterizing surface energetics as discussed in A. Ulman, An Introduction to Ultrathin Organic Films , Academic Press, New York (1991), pp. 48-58.
  • the coating substrates used in the present invention can be considered to encompass two broad categories.
  • the first of these categories include highly flat substrates, such as evaporated gold on atomically flat silicon (111) wafers, atomically flat silicon (111) wafers, or float glass, which are bare and modified with self-assembling monolayers (SAMs) to alter their surface energy in a systematic fashion.
  • SAMs self-assembling monolayers
  • the second class of surfaces comprised surfaces with a highly textured topography that included many different classes of materials ranging from paper substrates to polymeric ink receptive coatings to structured polymeric films, microporous films, and membrane materials. Common characteristics amongst these substrates are the large surface roughness and/or porosity.
  • the measurements of contact angles and the determination of polar and dispersive surface energies from these contact angle measurements cannot be regarded as an equilibrium characterization of their true thermodynamic energies.
  • the contact angles indicate an “effective” or “practical” surface energy that can be used to classify these substrates for comparative purposes.
  • TABLE 1 summarizes the substrates coated with the polydiacetylene assemblies for use as a calorimetric sensor of the present invention.
  • the SAMs used to modify the substrate are listed with the substrate when used.
  • the substrate contact angles as measured with water and methylene iodide are shown, as well as the dispersive and polar components of the surface energy calculated by the Geometric Mean Method as shown in S. Wu; Polymer Interface and Adhesion ; Marcel Dekker, New York (1982).
  • the last column lists the color of the dry PDA coating.
  • FIGS. 6 and 7 show the phase diagram based on the colorimetric observations of the dried coatings and the contact angle analysis of the coated substrates.
  • FIG. 6 shows the resulting color of the coated substrate as a function of advancing contact angle of water versus advancing contact angle of methylene iodide.
  • FIG. 7 shows the resulting color of the coated substrate as a function of the polar component of the substrate surface energy versus the dispersive component of that surface energy as calculated by the Geometric Mean method from the advancing contact angles of water and methylene iodide as provided in S. Wu; Polymer Interface and Adhesion ; Marcel Dekker, New York (1982).
  • the surfaces for which the polydiacetylene coating remained in its initial blue color are identified by a filled-in circle on each plot.
  • the surfaces identified with a circle are those on which the initial “blue” phase transformed into the red phase upon drying.
  • the triangular points identify surfaces on which the dry coating showed a mixture of the blue and red phases.
  • the coated substrates exhibit advancing contact angles with methylene iodide below 50° as depicted in FIG. 6. This condition corresponds to substrates characterized by a dispersive component of their surface energy greater than 40 dynes/cm on FIG. 7. For applications requiring the retention of the original “blue” phase, topography and surface energy will impact the effectiveness of the transducer on the substrate in characteristics such as color contrast at detection and shelf-life.
  • substrates with these properties that have an advancing contact angle with water less than 90° result in dry coatings containing a mixture of the blue and red phases as depicted in FIG. 6.
  • This condition would correspond to surfaces in which the dispersive surface energy component could be less than 40 dynes/cm but with a polar surface energy component greater than at least 10 dynes/cm in FIG. 7.
  • CR Colorimetric response
  • Step 1 Preparation of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 10 CH 3
  • the solid was purified over silica gel (gradient from 25% to 50% by volume ethyl acetate in hexanes) to yield 570 milligrams of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 10 CH 3 as a white solid.
  • Step 2 Preparation of HO(O)C(CH 2 ) 3 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 10 CH 3
  • the solid was purified over silica gel eluting with 25/74/1 of ethyl acetate/hexanes/formic acid by volume to yield 0.21 grams of HO(O)C(CH 2 ) 3 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 10 CH 3 as a white solid.
  • Step 1 Preparation of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 12 CH 3
  • the solid was purified over silica gel (15% by volume of ethyl acetate in dichloromethane to 100% theyl acetate gradient) to yield 5.0 grams of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 12 CH 3 as a white solid.
  • Step 2 Preparation of HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 12 CH 3
  • the organic layer was separated, dried over MgSO 4 , filtered and the solvent was removed to yield a white solid.
  • the solid was purified over silica gel eluting with 10/89/1 of ethyl acetate/dichloromethane/formic acid by volume to yield 1.70 grams of HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(O)C(CH 2 ) 12 CH 3 as a white solid.
  • Step 1 Preparation of HO(CH 2 ) 5 C ⁇ C—C ⁇ C(CH 2 ) 5 OH
  • HO(CH 2 ) 5 C ⁇ CH was prepared by the KAPA-promoted isomerization of HOCH 2 C ⁇ C(CH 2 ) 3 CH 3 prepared according to Miller, J. G.; Oehlschlager, A. C. J.Org. Chem. 1984, 49, 2332-2338 or HO(CH 2 ) 2 C ⁇ C(CH 2 ) 2 CH 3 (commercially available from GFS Chemicals; Powell, Ohio).
  • Oxidative coupling of HO(CH 2 ) 5 C ⁇ CH was carried out in a glass reaction vessel by dissolving 6.95 grams HO(CH 2 ) 5 C ⁇ CH in pyridine/methanol (2.0 mL/6.2 mL) and adding 307 grams of CuCl followed by stirring in the presence of oxygen until all the starting material was consumed.
  • the reaction mixture was worked up with diethyl ether and 4N HCl, the combined organic layers were dried over MgSO 4 , filtered and concentrated. Recrystallization of the residue from 1/1 hexanes/tert-butyl methyl ether yielded 5.35 grams of HO(CH 2 ) 5 C ⁇ C—C ⁇ C(CH 2 ) 5 OH.
  • Step 2 Preparation of HO(CH 2 ) 5 C ⁇ C—C ⁇ C(CH 2 ) 5 O(O)C(CH 2 ) 10 CH 3
  • Step 3 Preparation of HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 5 C ⁇ C—C ⁇ C(CH 2 ) 5 O(O)C(CH 2 ) 10 CH 3
  • Example 18 Step 1 The same procedure described in Example 18 Step 1 was followed to prepare the diol HO(CH 2 ) 6 C ⁇ C—C ⁇ C(CH 2 ) 6 OH starting from 1-heptyne.
  • the remaining procedure for Example 18 was followed using the diol and acid chloride in Step 2 shown in Table 5 to give the compounds with the general structure HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 6 C ⁇ C—C ⁇ C(CH 2 ) 6 O(O)C(CH 2 ) b CH 3 (b is defined in Table 5).
  • Example 18 Step 1 The same procedure described in Example 18 Step 1 was followed to prepare the diol HO(CH 2 ) 7 C ⁇ C—C ⁇ C(CH 2 ) 7 OH staring from 1-octyne.
  • the remaining procedure for Example 18 was followed using the diol and acid chloride in Step 2 shown in Table 6 to give the compounds with the general structure HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 7 C ⁇ C—C ⁇ C(CH 2 ) 7 O(O)C(CH 2 ) b CH 3 (b is defined in Table 6).
  • Example 18 Step 1 The same procedure described in Example 18 Step 1 was followed to prepare the diol HO(CH 2 ) 9 C ⁇ C—C ⁇ C(CH 2 ) 9 OH staring from 1-decyne.
  • the remaining procedure for Example 18 was followed using the diol and acid chloride in Step 2 shown in Table 7 to give the compounds with the general structure HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 9 C ⁇ C—C ⁇ C(CH 2 ) 9 O(O)C(CH 2 ) b CH 3 (b is defined in Table 7).
  • Step 1 Preparation of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(CH 2 ) 11 CH 3
  • the oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexane gradient) to yield 606 milligrams of HO(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 12 ) 4 O(CH 2 ) 11 CH 3 as a white solid.
  • Step 2 Preparation of HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 12 ) 4 O(CH 2 ) 11 CH 3
  • the organic layer was separated, dried over MgSO 4 , filtered and the solvent was removed to yield a white solid.
  • the solid was purified over silica gel eluting with 10/89/1 of ethyl acetate/dichloromethane/formic acid by volume to yield HO(O)C(CH 2 ) 2 C(O)O(CH 2 ) 4 C ⁇ C—C ⁇ C(CH 2 ) 4 O(CH 2 ) 11 CH 3 as a white solid.
  • Example 6 A sample of 10.1 milligrams of the compound prepared in Example 6 was placed in a glass vessel and suspended in 5 milliliters of isopropanol. The mixture was heated to boiling and 10 milliliters of 70° C. water was added. The resulting solution was boiled until the temperature reached 95° C. indicating the nearly all of the isopropanol had boiled off. The solution was cooled to room temperature and then to 4° C. for 16 hours. A 2 milliliter aliquot of the solution was exposed 254 nanometer light for 10 minutes, producing a dark blue color indicative that polymerization had occurred.
  • the sample was then filtered through a 1.2 ⁇ m syringe filter, and polymerized by irradiating the sample beneath a 254 nm UV lamp (commercially available from VWR Scientific Products; West Chester, Pa.) at a distance of 3 cm for 10 minutes. Polymerization results in the observation of a distinct, bluish-purple color.
  • the detection property of the solution was determined by the addition of ⁇ 80 ⁇ L of a polymyxin B sulfate solution (10,050 units/mL) to the sample. This resulted in a rapid colorimetric response that could easily be determined visually as a change from blue to red and quantified by UV-vis spectroscopy as a shift from peak absorbance at 640 nm to a peak absorbance at 540 nm in spectra taken after one hour at room temperature.
  • the polymerized PDAIDMPC mixture prepared in Example 43 was coated onto a piece of a reverse-phase C-18 silica gel plate. The solution was spotted on the plate and allowed to dry at room temperature resulting in blue spots on the test plate. To test this solid state form of the sensor, a test solution (40 ⁇ L) of a polymyxin B sulfate (10,050 units/mL) was added to the sample spot. This resulted in an immediate ( ⁇ 15 seconds) color change from blue to pink. A control test using only milli-Q water (50 ⁇ L) showed no color change.
  • a mixture of diacetylene monomer from Example 6 and DMPC (6:4) was weighed into a vial and suspended in Tris buffer (2 mM, pH 8.5) to produce a 1 mM concentration solution and a polymerized detection solution was prepared as in Example 43.
  • the detection property of the solution was determined by the addition of ⁇ 50 ⁇ L of a 1 mM mellitin solution to the sample. This resulted in a rapid calorimetric response that could easily be determined visually as a change from blue to red and quantified by UV-vis spectroscopy as a shift from peak absorbance at 640 nm to a peak absorbance at 540 nm in spectra taken after one hour at room temperature.
  • a test plate was made using the polymerized detector solution of Example 45 using the same procedure as in Example 44. Several spots (40 ⁇ l each) of the polymerized solutions were placed onto a piece of a reverse-phase C-18 silica gel plate. The solutions were allowed to dry at room temperature resulting in blue spots. To test the substrates' ability to detect peptides, two samples containing 15 and 30 nanomoles of mellitin respectively were added to the different spots on the test plate. This resulted in an immediate ( ⁇ 15 seconds) color change from blue to red. Control samples of milli-Q water spotted on separate test spots showed no color change.
  • a detection solution was prepared as in Example 45.
  • the detection properties of the solutions were determined by the addition of ⁇ 50 ⁇ L of a 75 ⁇ M Phospholipase A2 solution to each of the samples. This resulted in a colorimetric response that could easily be determined visually as a change from blue to red and quantified by UV-vis spectroscopy as a shift from peak absorbance at 640 nm to a peak absorbance at 540 nm in spectra taken after one hour at room temperature.
  • Example 48 was repeated, except that to test the peptide-membrane interaction detection properties of the polymerized assemblies on the substrate, 50 ⁇ L of a polymyxin B sulfate solution (10,050 units/mL) was added to each of the spots on the test plate. This resulted in a splotchy appearance that reflected a CR less than 5% of color change depending on the preparation of the solution.
  • Test plates were made as in Example 46.
  • the solution was then probe sonicated using a Model XL2020 probe sonicator (commercially available from Misonix, Inc.; Farmington, N.Y.) for 1 minute at a power setting of 5, and placed into a 4° C. refrigerator overnight ( ⁇ 16 hours).
  • the sample was filtered through a 1.2 ⁇ m syringe filter and polymerization of a stirring solution was achieved by irradiating the sample beneath a 254 nm UV lamp at a distance of 3 cm for 20 minutes, resulting in the observation of a blue color.
  • a syringe several spots (40 ⁇ l each) of the polymerized solution were placed onto a piece of a reverse-phase C-18 silica gel plate. The spots were allowed to dry at room temperature resulting in blue spots.
  • a polymyxin B sulfate solution (10,050 units/mL) was added to a solution of human urine and a solution of human urine contaminated with E.
  • the samples were filtered through a 1.2 ⁇ m syringe filter and polymerization of a stirring solution was achieved by irradiating the sample beneath a 254 nm UV lamp at a distance of 3 cm for 60 seconds, resulting in the observation of an intense blue color.
  • a syringe several spots (40 ⁇ l each) of the polymerized solutions were placed onto a piece of a reverse-phase C-18 silica gel plate. The solutions were allowed to dry at room temperature resulting in blue spots.
  • a polymyxin B sulfate solution (5025 units/mL) was added to a solution of endotoxin free water and a solution of endotoxin free water contaminated with lipopolysaccharide. After allowing the samples to incubate for 30 minutes at 37° C., the samples were cooled to room temperature and 500 ⁇ L of each solution was placed onto a dried spot of the PDA/DMPC solution. After 15 minutes of gentle shaking, the liquid was removed and the plates were examined. This resulted in a calorimetric response that could easily be determined visually as a change from blue to red in the absence of lipopolysaccharide.
  • surfaces were prepared in the following manner for evaluation.
  • the gold surfaces were prepared by evaporation of gold onto a chromium primed polished silicon wafer.
  • the resulting surface was highly reflective with an rms surface roughness less than 15 ⁇ ngstroms as measured by Atomic Force Microscopy (AFM) using Nanoscope Command Reference Manual Version 4.42; Digital Instruments; Sections 12.5 and 12.6.
  • the gold surfaces were dusted prior to use using a dry nitrogen stream.
  • the glass surfaces were prepared by cleaning in an oxidizing bath (commercially available from Nochromix) overnight, followed by copious rinsing in milli-Q water until the rinse water could maintain a uniform sheet over the glass surface without de-wetting.
  • the glass surfaces were dusted prior to use using a dry nitrogen stream.
  • Silicon wafer surfaces were used as received and dusted prior to use using a dry nitrogen stream. Surfaces modified with SAMs were formed by immersion of the surface in a solution nominally 1 mM in SAM concentration. Either ethanol or chloroform were used as solvents. Immersion times were at least 24 hours, followed by extensive rinsing with the neat solvent used during self-assembly. The samples were then allowed to dry in a dry box overnight prior to the contact angle measurements.

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US10/325,801 US20040126897A1 (en) 2002-12-19 2002-12-19 Colorimetric sensors constructed of diacetylene materials
US10/738,573 US7364918B2 (en) 2002-12-19 2003-12-16 Colorimetric sensors constructed of diacetylene materials
TW092135981A TW200502550A (en) 2002-12-19 2003-12-18 Colorimetric sensors constructed of diacetylene materials
ES03813810T ES2286511T3 (es) 2002-12-19 2003-12-19 Sensores colorimetricos construidos de materiales de diacetileno.
AT03813810T ATE364176T1 (de) 2002-12-19 2003-12-19 Aus polydiacetylen hergestellte kolorimetrische sensoren.
JP2004562334A JP4402597B2 (ja) 2002-12-19 2003-12-19 ジアセチレン物質から構築される比色分析センサー
EP03813810A EP1579210B1 (en) 2002-12-19 2003-12-19 Colorimetric sensors constructed of diacetylene materials
PCT/US2003/040714 WO2004057331A1 (en) 2002-12-19 2003-12-19 Colorimetric sensors constructed of diacetylene materials
DK03813810T DK1579210T3 (da) 2002-12-19 2003-12-19 Kolorimetriske sensorer, som er konstrueret af diacetylenmaterialer
DE60314290T DE60314290T2 (de) 2002-12-19 2003-12-19 Aus polydiacetylen hergestellte kolorimetrische sensoren.
CA2510030A CA2510030C (en) 2002-12-19 2003-12-19 Colorimetric sensors constructed of diacetylene materials
MXPA05006445A MXPA05006445A (es) 2002-12-19 2003-12-19 Sensores colorimetricos construidos de materiales de diacetileno.
AU2003301171A AU2003301171B8 (en) 2002-12-19 2003-12-19 Colorimetric sensors constructed of diacetylene materials
BR0317472-7A BR0317472A (pt) 2002-12-19 2003-12-19 Sensor colorimétrico e método para detectar um analito, kit descartável para detectar a presença de um analito, método para detectar a presença de bactérias, e, artigo médico
CN200380107097A CN100578226C (zh) 2002-12-19 2003-12-19 由二乙炔材料构成的比色传感器
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