DE19811963A1 - Luminescent receptors useful for specific determination of sugars, especially glucose - Google Patents
Luminescent receptors useful for specific determination of sugars, especially glucoseInfo
- Publication number
- DE19811963A1 DE19811963A1 DE1998111963 DE19811963A DE19811963A1 DE 19811963 A1 DE19811963 A1 DE 19811963A1 DE 1998111963 DE1998111963 DE 1998111963 DE 19811963 A DE19811963 A DE 19811963A DE 19811963 A1 DE19811963 A1 DE 19811963A1
- Authority
- DE
- Germany
- Prior art keywords
- luminescent
- ligand
- boronic acid
- transition metal
- polypyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims description 4
- 239000008103 glucose Substances 0.000 title claims description 4
- 235000000346 sugar Nutrition 0.000 title claims 3
- 150000008163 sugars Chemical class 0.000 title claims 2
- 239000003446 ligand Substances 0.000 claims abstract description 13
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000005620 boronic acid group Chemical group 0.000 claims abstract 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004424 polypyridyl Polymers 0.000 claims abstract 3
- 229910001428 transition metal ion Inorganic materials 0.000 claims abstract 3
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 claims abstract 2
- HUBWRAMPQVYBRS-UHFFFAOYSA-N 1,2-phenylenebis(dimethylarsane) Chemical compound C[As](C)C1=CC=CC=C1[As](C)C HUBWRAMPQVYBRS-UHFFFAOYSA-N 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 2
- -1 bipyrazine Chemical compound 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- HKOAFLAGUQUJQG-UHFFFAOYSA-N 2-pyrimidin-2-ylpyrimidine Chemical compound N1=CC=CN=C1C1=NC=CC=N1 HKOAFLAGUQUJQG-UHFFFAOYSA-N 0.000 claims 2
- 238000004020 luminiscence type Methods 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGUWACLYDSWXRZ-UHFFFAOYSA-N (2-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C=O DGUWACLYDSWXRZ-UHFFFAOYSA-N 0.000 description 1
- SMPJZGCAUYUJJE-UHFFFAOYSA-N 4'-methyl-2,2'-bipyridine-4-carboxaldehyde Chemical group CC1=CC=NC(C=2N=CC=C(C=O)C=2)=C1 SMPJZGCAUYUJJE-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YHOMCUREJOXFPI-UHFFFAOYSA-N formylboronic acid Chemical compound OB(O)C=O YHOMCUREJOXFPI-UHFFFAOYSA-N 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 108010070004 glucose receptor Proteins 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- G01N33/66—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood sugars, e.g. galactose
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Diabetes (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
In einem 100 ml Rundkolben werden unter Stickstoff 11.3 ml einer 33% Lösung von Methylamin in absolutem Ethanol mit 30 ml absolutem Methanol versetzt. Danach wird eine Lösung von 12 ml einer 2.5 mol/l HCl in absolutem Methanol und 2.78 g 4-Formyl-4'-methyl-(2.2'-bipyridyl) A1 hergestellt nach B.M. Peek et al., Int. J. Peptide Protein Res., 34, (1991), 114-123 hinzugefügt. Zuletzt werden noch 630 mg NaBH3CN in kleinen Portionen unter Rühren hinzugefügt wonach das Gemisch drei Tage bei Raumtemperatur gerührt wird.11.3 ml of a 33% solution of methylamine in absolute ethanol are mixed with 30 ml of absolute methanol in a 100 ml round-bottomed flask under nitrogen. A solution of 12 ml of a 2.5 mol / l HCl in absolute methanol and 2.78 g of 4-formyl-4'-methyl- (2,2'-bipyridyl) A1 is then prepared according to BM Peek et al., Int. J. Peptide Protein Res., 34, (1991), 114-123. Finally, 630 mg of NaBH 3 CN are added in small portions with stirring, after which the mixture is stirred for three days at room temperature.
Die reduktive Aminierung wird durch das Zutropfen von konzentrierter HCl, die den Überschuß von NaBH3CN zerstört, gestoppt. Die Zugabe von HCl wird bis zu pH 1 fortgesetzt wobei die Farbe der Lösung von schwarz nach rot umschlägt. Nach 2 h wird vom entstandenen, leuchtend braunen Nebenprodukt abfiltriert und die Lösungsmittel abrotiert, wobei ein grünlicher, wäßriger Rückstand verbleibt, der mit 90 ml (3 × 30 ml) Ether ausgeschüttelt wird. Die wäßrige Phase wird danach auf pH 9-10 mit fester KOH eingestellt. Hier ist es sehr wichtig, daß nur soviel festes KOH genommen wird, daß sich kein rotes Öl bildet. Die Lösung wird mit NaCl gesättigt und danach mit 100 ml (5 × 20 ml) Ether extrahiert. Nach Einrotieren und Trocknen erhält man ein gelblich-braunes Öl als Rohprodukt. (DC auf Silica Platten mit Butanol : Acetonitril : conc. NH3 = 2 : 2 : 1; Rf: 0.92-0.73 Produkt; 0.65, 0.52 and 0.49 Verunreinigung). Zur Reinigung wird das Amin durch die Zugabe von 6 ml 2.5 mol/l HCl in absolutem Methanol in das Hydrochlorid übergeführt. Die Mischung wird kurz unter Rückfluß erhitzt und danach schnell abgekühlt.The reductive amination is stopped by the dropwise addition of concentrated HCl, which destroys the excess NaBH 3 CN. The addition of HCl is continued up to pH 1, the color of the solution changing from black to red. After 2 h, the bright brown by-product formed is filtered off and the solvents are spun off, leaving a greenish, aqueous residue which is shaken out with 90 ml (3 × 30 ml) of ether. The aqueous phase is then adjusted to pH 9-10 with solid KOH. It is very important here that only so much solid KOH is used that no red oil forms. The solution is saturated with NaCl and then extracted with 100 ml (5 × 20 ml) of ether. After spinning in and drying, a yellowish brown oil is obtained as a crude product. (TLC on silica plates with butanol: acetonitrile: conc. NH 3 = 2: 2: 1; R f : 0.92-0.73 product; 0.65, 0.52 and 0.49 contamination). For purification, the amine is converted into the hydrochloride by adding 6 ml of 2.5 mol / l HCl in absolute methanol. The mixture is briefly heated under reflux and then quickly cooled.
Das Hydrochlorid A2 wird aus einer Mischung von 10 ml Cyclohexan, 10 ml
Ethylacetat und 45 ml 2-Propanol umkristallisiert und das Produkt 3 Tage über
P2O5 getrocknet.
Ausbeute: 1.15 g eines lachsfarbenen hygroskopischen Pulvers, C13H16N3Cl
(249.74 g/mol),
Rf-Wert: (Silicagel; Butanol : Acetonitril : conc. NH3 = 2 : 2 : 1) 0.85
Schmp.: 215°C
IR (KBr): ν [cm-1] = 3300 (s), 3050 (w), 2920 (s), 2760 (s), 1600 (s), 1560 (m),
1460 (m), 1380 (m), 1250 (w), 1100 (w), 1030 (w), 820 (s)
1H-NMR (250 MHz, DMSO-d6):
The hydrochloride A2 is recrystallized from a mixture of 10 ml of cyclohexane, 10 ml of ethyl acetate and 45 ml of 2-propanol and the product is dried over P 2 O 5 for 3 days.
Yield: 1.15 g of a salmon-colored hygroscopic powder, C 13 H 16 N 3 Cl (249.74 g / mol),
R f value: (silica gel; butanol: acetonitrile: conc. NH 3 = 2: 2: 1) 0.85
Mp: 215 ° C
IR (KBr): ν [cm -1 ] = 3300 (s), 3050 (w), 2920 (s), 2760 (s), 1600 (s), 1560 (m), 1460 (m), 1380 (m ), 1250 (w), 1100 (w), 1030 (w), 820 (s)
1 H-NMR (250 MHz, DMSO-d 6 ):
In einem 50 ml Rundkolben werden unter Stickstoffatmosphäre 1.0 g der obigen
Verbindung A2 und 600 mg 2-Formyl-boronsäure (Wyto et al., J. Org.
Chem., 57, 1015-1018 (1982)) in 18 ml absolutem Methanol gelöst. Danch werden
unter Rühren portionsweise 250 mg NaBH3CN hinzugefügt und die Suspension 3
Tage bei Raumtemperatur gerührt, worauf das Lösungsmittel abgezogen und der
Rückstand in möglichst wenig Toluol and Acetonitril (1 : 1) (v/v) gelöst wird. Die
Reinigung des Produktes erfolgt durch eine säulenchromatographische Trennung
auf basischem Aluminiumoxid (33 g). Zuerst wird der Amin-substituierte Bipyridyl-
Ligand mit Toluol: Acetonitril 1 : 1 eluiert (DC (Al2O3, Toluol : Aceton : conc. NH3 =
10 : 10 : 1), Rf: 0.73-0.52). Danach wird ein mit einem Gradienten von
Tol : Ac = 40 : 60, 30 : 70, usw. bis zu reinem Acetonitril der Bipyridyl-Ligand (DC (Al2O3, Toluol
Aceton : conc. NH3 = 10 : 10 : 1), Rf: 0.41-0.21) und am Schluß die Formyl
boronsäure eluiert. Nach dem Einrotieren der Fraktionen erhält man den Liganden
als farblose Substanz.
Ausbeute: 319.5 mg (0.92 mmol, 23%). Schmp: 98°C. Rf-Wert: (Al2O3, Toluol
Aceton : conc. NH3 = 10 : 10 : 1) 0.41-0.21.
IR (KBr): ν [cm-1] = 3390 (m), 3060 (w), 3010 (w), 2920 (w), 2850 (w), 1600 (s),
1560 (m), 1460 (m), 1440 (m), 1380 (s, B-O), 1350 (m), 1300 (w), 1270 (w), 1220
(w), 1155 (w), 1030 (w), 990 (w), 820 (m), 750 (m), 670 (w)
1H-NMR (400 MHz, DMSO-d6, D2O Austausch)
1.0 g of the above compound A2 and 600 mg of 2-formylboronic acid (Wyto et al., J. Org. Chem., 57, 1015-1018 (1982)) are dissolved in 18 ml of absolute methanol in a 50 ml round-bottom flask under a nitrogen atmosphere . Then 250 mg of NaBH 3 CN are added in portions with stirring and the suspension is stirred for 3 days at room temperature, whereupon the solvent is stripped off and the residue is dissolved in as little toluene and acetonitrile (1: 1) (v / v) as possible. The product is purified by column chromatography on basic aluminum oxide (33 g). First, the amine-substituted bipyridyl ligand is eluted with toluene: acetonitrile 1: 1 (TLC (Al 2 O 3 , toluene: acetone: conc. NH 3 = 10: 10: 1), R f : 0.73-0.52). Then the bipyridyl ligand (TLC (Al 2 O 3 , toluene acetone: conc. NH 3 = 10: 10: 1) with a gradient of Tol: Ac = 40: 60, 30: 70, etc. to pure acetonitrile ), R f : 0.41-0.21) and finally the formyl boronic acid eluted. After spinning in the fractions, the ligand is obtained as a colorless substance.
Yield: 319.5 mg (0.92 mmol, 23%). Mp: 98 ° C. R f value: (Al 2 O 3 , toluene acetone: conc. NH 3 = 10: 10: 1) 0.41-0.21.
IR (KBr): ν [cm -1 ] = 3390 (m), 3060 (w), 3010 (w), 2920 (w), 2850 (w), 1600 (s), 1560 (m), 1460 (m ), 1440 (m), 1380 (s, BO), 1350 (m), 1300 (w), 1270 (w), 1220 (w), 1155 (w), 1030 (w), 990 (w), 820 (m), 750 (m), 670 (f)
1 H-NMR (400 MHz, DMSO-d 6 , D 2 O exchange)
140.7 mg Ru(bipy)2Cl2.H2O (Aldrich) werden in 4 ml Methanol gelöst und mit 100
mg des obigen Liganden 3A gelöst in 1 ml Wasser versetzt. Die Mischung wird 5
Stunden unter Rückfluß gekocht, abgekühlt und von einem dunkelbraunen
Rückstand abfiltriert. Die Verbindung wird durch Zugabe von 2.5 g NH4PF6 in 10
ml Wasser als orange-farbene Festsubstanz aus dem Filtrat ausgefällt.
Ausbeute: 242.7 mg (83%), oranges Pulver, C40H38BF12P2N7O2Ru (1050 g/mol)
Schmelzpunkt: 180°C
Massenspektrum: (FAB, GC-MS) 761, [Ru(bpy)2(A3)2+]
140.7 mg of Ru (bipy) 2 Cl 2 .H 2 O (Aldrich) are dissolved in 4 ml of methanol and 100 mg of the above ligand 3A dissolved in 1 ml of water are added. The mixture is refluxed for 5 hours, cooled and filtered off from a dark brown residue. The compound is precipitated from the filtrate by adding 2.5 g of NH 4 PF 6 in 10 ml of water as an orange-colored solid.
Yield: 242.7 mg (83%), orange powder, C 40 H 38 BF 12 P 2 N 7 O 2 Ru (1050 g / mol)
Melting point: 180 ° C
Mass spectrum: (FAB, GC-MS) 761, [Ru (bpy) 2 (A3) 2+ ]
Änderung des Lumineszenzspektrums der Probe A4 mit zunehmender Konzentration an Glucose. Anregungswellenlänge 460 nm, pH-Wert 11.0, Messung nach 2 Min. Inkubation bei 90°C. Change in the luminescence spectrum of sample A4 with increasing Concentration of glucose. Excitation wavelength 460 nm, pH 11.0, Measurement after 2 min. Incubation at 90 ° C.
Claims (3)
wobei
- - A, B bzw. C für zwei- bzw. dreizähnige Polypyridyl-Liganden und deren Abkömmlinge, wie z. B. Bipyridin, Bipyrazin, Bipyrimidin, Phenanthrolin, Terpyridyl u.s.w. stehen, wobei zumindest ein Ligand eine oder mehrere Boronsäurefunktion der oben abgebildeten Art trägt.
- - Me für ein Übergangsmetall-Ion wie Ru2+, Os2+, Re⁺, Cu2+, oder Fe2+ steht.
in which
- - A, B or C for bidentate or tridentate polypyridyl ligands and their derivatives, such as. B. bipyridine, bipyrazine, bipyrimidine, phenanthroline, terpyridyl, etc., where at least one ligand carries one or more boronic acid function of the type shown above.
- - Me stands for a transition metal ion such as Ru 2+ , Os 2+ , Re⁺, Cu 2+ , or Fe 2+ .
- - Me für ein Übergangmetall-Ion wie Ru2+, Os2+, Re⁺, Cu2+, oder Fe2+ steht.
- - Me stands for a transition metal ion such as Ru 2+ , Os 2+ , Re⁺, Cu 2+ , or Fe 2+ .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998111963 DE19811963A1 (en) | 1998-03-19 | 1998-03-19 | Luminescent receptors useful for specific determination of sugars, especially glucose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998111963 DE19811963A1 (en) | 1998-03-19 | 1998-03-19 | Luminescent receptors useful for specific determination of sugars, especially glucose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19811963A1 true DE19811963A1 (en) | 1999-09-23 |
Family
ID=7861457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1998111963 Withdrawn DE19811963A1 (en) | 1998-03-19 | 1998-03-19 | Luminescent receptors useful for specific determination of sugars, especially glucose |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19811963A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009091357A (en) * | 2000-12-05 | 2009-04-30 | Regents Of The Univ Of California | Optical determination of glucose utilizing boronic acid adduct |
-
1998
- 1998-03-19 DE DE1998111963 patent/DE19811963A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009091357A (en) * | 2000-12-05 | 2009-04-30 | Regents Of The Univ Of California | Optical determination of glucose utilizing boronic acid adduct |
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