IL44165A - Method for fluorescently labelling a material with a furanone derivative and products formed by reacting such a material with the furanone derivative - Google Patents
Method for fluorescently labelling a material with a furanone derivative and products formed by reacting such a material with the furanone derivativeInfo
- Publication number
- IL44165A IL44165A IL44165A IL4416574A IL44165A IL 44165 A IL44165 A IL 44165A IL 44165 A IL44165 A IL 44165A IL 4416574 A IL4416574 A IL 4416574A IL 44165 A IL44165 A IL 44165A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- phenyl
- compound
- lower alkyl
- labeled
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 32
- 238000002372 labelling Methods 0.000 title claims description 22
- 150000002241 furanones Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 17
- 235000018102 proteins Nutrition 0.000 claims description 17
- 102000004169 proteins and genes Human genes 0.000 claims description 17
- 108090000623 proteins and genes Proteins 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 241000700605 Viruses Species 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 235000001014 amino acid Nutrition 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- BLWINLJDTOJSRU-UHFFFAOYSA-N 2-methoxy-2,4-diphenylfuran-3-one Chemical compound O=C1C(OC)(C=2C=CC=CC=2)OC=C1C1=CC=CC=C1 BLWINLJDTOJSRU-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 241000588722 Escherichia Species 0.000 claims description 3
- 241001464384 Hymenolepis nana Species 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- BEAWFNYWFJIVNJ-UHFFFAOYSA-N 2,4-diphenyl-2-phenylmethoxyfuran-3-one Chemical compound O=C1C(C=2C=CC=CC=2)=COC1(C=1C=CC=CC=1)OCC1=CC=CC=C1 BEAWFNYWFJIVNJ-UHFFFAOYSA-N 0.000 claims description 2
- 241000588724 Escherichia coli Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010186 staining Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 for example Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000427 antigen Substances 0.000 description 10
- 102000036639 antigens Human genes 0.000 description 10
- 108091007433 antigens Proteins 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007850 fluorescent dye Substances 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 241000304886 Bacilli Species 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000242722 Cestoda Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002081 enamines Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- UCYQBFGYQFAGSO-UHFFFAOYSA-N 3-hydroxy-3h-furan-2-one Chemical compound OC1C=COC1=O UCYQBFGYQFAGSO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 125000005594 diketone group Chemical group 0.000 description 3
- 238000001215 fluorescent labelling Methods 0.000 description 3
- 150000003948 formamides Chemical class 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000001900 immune effect Effects 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000606701 Rickettsia Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241000223996 Toxoplasma Species 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- DQFBYFPFKXHELB-UHFFFAOYSA-N chalcone Chemical class C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 108010074605 gamma-Globulins Proteins 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 210000003593 megakaryocyte Anatomy 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MXWINGMFLTWYNW-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-2-ethoxy-4-(1h-indol-3-yl)furan-3-one Chemical compound O1C=C(C=2C3=CC=CC=C3NC=2)C(=O)C1(OCC)C1=CC=C(OC)C=C1OC MXWINGMFLTWYNW-UHFFFAOYSA-N 0.000 description 1
- OGMPVRFBLUQXTL-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-methoxy-4-phenylfuran-3-one Chemical compound O=C1C(OC)(C=2C=CC(Cl)=CC=2)OC=C1C1=CC=CC=C1 OGMPVRFBLUQXTL-UHFFFAOYSA-N 0.000 description 1
- PVLHOQYRRHGSDM-UHFFFAOYSA-N 2-ethoxy-2,4-diphenylfuran-3-one Chemical compound O=C1C(OCC)(C=2C=CC=CC=2)OC=C1C1=CC=CC=C1 PVLHOQYRRHGSDM-UHFFFAOYSA-N 0.000 description 1
- YWYHAVDJDQIRDR-UHFFFAOYSA-N 2-methoxy-4-(4-nitrophenyl)-2-phenylfuran-3-one Chemical compound O=C1C(OC)(C=2C=CC=CC=2)OC=C1C1=CC=C([N+]([O-])=O)C=C1 YWYHAVDJDQIRDR-UHFFFAOYSA-N 0.000 description 1
- LANZJCCSVOKIDQ-UHFFFAOYSA-N 2-methoxy-4-naphthalen-2-yl-2-phenylfuran-3-one Chemical compound O1C=C(C=2C=C3C=CC=CC3=CC=2)C(=O)C1(OC)C1=CC=CC=C1 LANZJCCSVOKIDQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000186046 Actinomyces Species 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 241000606125 Bacteroides Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000589968 Borrelia Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- 108010074051 C-Reactive Protein Proteins 0.000 description 1
- 102100032752 C-reactive protein Human genes 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 101710188971 Catalase-3 Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001112696 Clostridia Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000004381 Complement C2 Human genes 0.000 description 1
- 108090000955 Complement C2 Proteins 0.000 description 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- 208000000655 Distemper Diseases 0.000 description 1
- 235000003550 Dracunculus Nutrition 0.000 description 1
- 241000316827 Dracunculus <angiosperm> Species 0.000 description 1
- 206010062714 Dysglobulinaemia Diseases 0.000 description 1
- 208000006586 Ectromelia Diseases 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000009123 Fibrin Human genes 0.000 description 1
- 108010073385 Fibrin Proteins 0.000 description 1
- 241000239183 Filaria Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000007212 Foot-and-Mouth Disease Diseases 0.000 description 1
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000228402 Histoplasma Species 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 108010003272 Hyaluronate lyase Proteins 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- 208000002979 Influenza in Birds Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000222722 Leishmania <genus> Species 0.000 description 1
- 241000589902 Leptospira Species 0.000 description 1
- 206010024503 Limb reduction defect Diseases 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 208000016604 Lyme disease Diseases 0.000 description 1
- 201000005505 Measles Diseases 0.000 description 1
- 208000005647 Mumps Diseases 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000010359 Newcastle Disease Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 208000031845 Pernicious anaemia Diseases 0.000 description 1
- 108010047386 Pituitary Hormones Proteins 0.000 description 1
- 102000006877 Pituitary Hormones Human genes 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 102000013566 Plasminogen Human genes 0.000 description 1
- 108010051456 Plasminogen Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710119112 Prolactin-2 Proteins 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 206010037151 Psittacosis Diseases 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- 241001085826 Sporotrichum Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 108010055044 Tetanus Toxin Proteins 0.000 description 1
- 208000003217 Tetany Diseases 0.000 description 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 1
- 241000223997 Toxoplasma gondii Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- 241000589884 Treponema pallidum Species 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 208000004062 Tumor Virus Infections Diseases 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 241000244002 Wuchereria Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000003460 anti-nuclear Effects 0.000 description 1
- 230000003497 anti-pneumococcal effect Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007640 basal medium Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000003618 borate buffered saline Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 208000014058 canine distemper Diseases 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960004407 chorionic gonadotrophin Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 206010016235 fasciolopsiasis Diseases 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000001914 gastric parietal cell Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 102000006602 glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 1
- 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 229940072221 immunoglobulins Drugs 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 231100000381 nephrotoxic Toxicity 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 201000000901 ornithosis Diseases 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229940118376 tetanus toxin Drugs 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 210000002993 trophoblast Anatomy 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/04—Determining presence or kind of microorganism; Use of selective media for testing antibiotics or bacteriocides; Compositions containing a chemical indicator therefor
- C12Q1/12—Nitrate to nitrite reducing bacteria
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- General Engineering & Computer Science (AREA)
- Pathology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cell Biology (AREA)
- Biophysics (AREA)
- Toxicology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Genetics & Genomics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33801973A | 1973-03-05 | 1973-03-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
IL44165A0 IL44165A0 (en) | 1974-05-16 |
IL44165A true IL44165A (en) | 1977-06-30 |
Family
ID=23323052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL44165A IL44165A (en) | 1973-03-05 | 1974-02-07 | Method for fluorescently labelling a material with a furanone derivative and products formed by reacting such a material with the furanone derivative |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS5443571B2 (xx) |
AT (1) | AT332545B (xx) |
AU (1) | AU473159B2 (xx) |
BE (1) | BE811825A (xx) |
CA (1) | CA1022483A (xx) |
CH (1) | CH602905A5 (xx) |
DD (1) | DD111374A5 (xx) |
DE (1) | DE2407899C3 (xx) |
ES (1) | ES423853A1 (xx) |
FR (1) | FR2221728B1 (xx) |
GB (1) | GB1433093A (xx) |
IL (1) | IL44165A (xx) |
IT (1) | IT1015815B (xx) |
NL (1) | NL156509B (xx) |
NO (1) | NO750485L (xx) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1573212A (en) * | 1976-04-15 | 1980-08-20 | Technicon Instr | Immunoassay for gentamicin |
DE2965740D1 (en) * | 1978-11-10 | 1983-07-28 | Hoffmann La Roche | Method for the determination of an amino acid or an amino sulfonic acid |
KR102385099B1 (ko) | 2017-06-30 | 2022-04-12 | 주식회사 만도 | 전자식 브레이크 시스템 및 제어 방법 |
-
1974
- 1974-02-07 IL IL44165A patent/IL44165A/en unknown
- 1974-02-07 AU AU65340/74A patent/AU473159B2/en not_active Expired
- 1974-02-19 DE DE2407899A patent/DE2407899C3/de not_active Expired
- 1974-02-20 CH CH234074A patent/CH602905A5/xx not_active IP Right Cessation
- 1974-02-20 IT IT48594/74A patent/IT1015815B/it active
- 1974-02-27 NL NL7402645.A patent/NL156509B/xx not_active IP Right Cessation
- 1974-03-01 DD DD176901A patent/DD111374A5/xx unknown
- 1974-03-01 JP JP2348574A patent/JPS5443571B2/ja not_active Expired
- 1974-03-04 GB GB959274A patent/GB1433093A/en not_active Expired
- 1974-03-04 ES ES423853A patent/ES423853A1/es not_active Expired
- 1974-03-04 FR FR7407245A patent/FR2221728B1/fr not_active Expired
- 1974-03-04 AT AT174174A patent/AT332545B/de not_active IP Right Cessation
- 1974-03-04 BE BE141602A patent/BE811825A/xx unknown
- 1974-03-04 CA CA194,030A patent/CA1022483A/en not_active Expired
-
1975
- 1975-02-14 NO NO740485A patent/NO750485L/no unknown
Also Published As
Publication number | Publication date |
---|---|
NO750485L (xx) | 1974-09-06 |
AU473159B2 (en) | 1976-06-17 |
CH602905A5 (xx) | 1978-08-15 |
DD111374A5 (xx) | 1975-02-12 |
NL7402645A (xx) | 1974-09-09 |
NL156509B (nl) | 1978-04-17 |
DE2407899B2 (de) | 1978-02-16 |
JPS49134670A (xx) | 1974-12-25 |
JPS5443571B2 (xx) | 1979-12-20 |
FR2221728B1 (xx) | 1976-10-15 |
GB1433093A (en) | 1976-04-22 |
DE2407899A1 (de) | 1974-09-19 |
ATA174174A (de) | 1976-01-15 |
CA1022483A (en) | 1977-12-13 |
IL44165A0 (en) | 1974-05-16 |
DE2407899C3 (de) | 1978-09-28 |
BE811825A (fr) | 1974-09-04 |
AU6534074A (en) | 1975-08-07 |
FR2221728A1 (xx) | 1974-10-11 |
IT1015815B (it) | 1977-05-20 |
ES423853A1 (es) | 1976-03-16 |
AT332545B (de) | 1976-10-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4018884A (en) | Fluorogenic materials and labeling techniques | |
US5145790A (en) | Reagents and method for detecting polychlorinated biphenyls | |
US5672478A (en) | Methods of use for and kits containing chemiluminescent compounds | |
EP0876428B1 (en) | SULFO BENZ e]INDOCYANINE FLUORESCENT DYES | |
EP0082636B1 (en) | Luminescent labelling materials and procedures | |
EP2045252B1 (en) | Derivatives of 1,2-dihydro-7-hydroxyquinolines containing fused rings | |
US5340716A (en) | Assay method utilizing photoactivated chemiluminescent label | |
US5352803A (en) | 5(6)-methyl substituted fluorescein derivatives | |
US5182214A (en) | Method for detection and determination of human serum albumin | |
US4886744A (en) | Fluorescent conjugates and biological diagnostic assay system | |
US4687747A (en) | Phenanthridinium ester as a labelling compound in luminometric immunoassay | |
GB2041921A (en) | Intermediates useful in the synthesis of chemiluminescent phthalhydrazidelabelled conjugates | |
CA2306752C (en) | Chemiluminescent reagent and chemiluminescent analysis using the same | |
US20200408739A1 (en) | Carbopyronone Compounds Useful as Diagnostic Adjuvants | |
US6180844B1 (en) | Composition containing fluorescence-generating substrate | |
US4045487A (en) | 1-Dimethylamino-2,4-diphenyl-1-butene-3,4-dione | |
US6002000A (en) | Chemiluminescent compounds and methods of use | |
US5756771A (en) | 5(6)-methyl substituted fluorescein derivatives | |
IL44165A (en) | Method for fluorescently labelling a material with a furanone derivative and products formed by reacting such a material with the furanone derivative | |
US3969373A (en) | Fluorogenic 2-oxy-3(2H)-furanone materials | |
EP0348494B1 (en) | Dioxetanes for use in assays | |
US4238589A (en) | Fluorogenic materials and labeling techniques | |
US4822878A (en) | Cyclic anhydride derivatives of chromophors | |
US4906749A (en) | Cyclic anhydride derivatives of chromophors | |
US4038289A (en) | Certain 2-hydroxy-2,4-diaryl-3-furanones |