DE2127655C3 - Alkali salts and ammonium salt of thymolphthalein monophosphate, process for their preparation and their use for the determination of serum phosphatase - Google Patents
Alkali salts and ammonium salt of thymolphthalein monophosphate, process for their preparation and their use for the determination of serum phosphataseInfo
- Publication number
- DE2127655C3 DE2127655C3 DE19712127655 DE2127655A DE2127655C3 DE 2127655 C3 DE2127655 C3 DE 2127655C3 DE 19712127655 DE19712127655 DE 19712127655 DE 2127655 A DE2127655 A DE 2127655A DE 2127655 C3 DE2127655 C3 DE 2127655C3
- Authority
- DE
- Germany
- Prior art keywords
- monophosphate
- thymolphthalein
- salts
- serum
- magnesium
- 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.)
- Expired
Links
- JWBPMLSZYOGYFD-UHFFFAOYSA-N [4-[1-(4-hydroxy-2-methyl-5-propan-2-ylphenyl)-3-oxo-2-benzofuran-1-yl]-5-methyl-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C(=CC(OP(O)(O)=O)=C(C(C)C)C=2)C)=C1C JWBPMLSZYOGYFD-UHFFFAOYSA-N 0.000 title claims description 16
- 210000002966 serum Anatomy 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 13
- 150000003863 ammonium salts Chemical class 0.000 title claims description 9
- 150000001447 alkali salts Chemical class 0.000 title claims description 7
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 title claims 9
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 title claims 9
- 238000002360 preparation method Methods 0.000 title claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 11
- 150000004712 monophosphates Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- LDKDGDIWEUUXSH-UHFFFAOYSA-N Thymophthalein Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C LDKDGDIWEUUXSH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003729 cation exchange resin Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- -1 magnesium thymol Chemical compound 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229940023913 cation exchange resins Drugs 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 159000000011 group IA salts Chemical class 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 claims 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims 1
- 206010049933 Hypophosphatasia Diseases 0.000 claims 1
- 208000002720 Malnutrition Diseases 0.000 claims 1
- 239000005844 Thymol Substances 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 210000003445 biliary tract Anatomy 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 230000001071 malnutrition Effects 0.000 claims 1
- 235000000824 malnutrition Nutrition 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 208000015380 nutritional deficiency disease Diseases 0.000 claims 1
- 210000000963 osteoblast Anatomy 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229960000790 thymol Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000006228 supernatant Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Jung wird als Kat-oncnaustauscherharz mit dieser austauscherharz von der Lösung abgetrennt und dieJung, as a catalyst exchange resin, is separated from the solution with this exchange resin and the
tpeziellen Kigensciidft vorzugsweise ein chelatbildendes Lösung z. B. lyophilisiert.Special Kigensciidft preferably a chelating solution z. B. lyophilized.
Harz mit einer Matrix aus einem Styrol-Divinylbenzol- Die auf diese Weise zugänglichen Alkali- oder Am-Resin with a matrix of a styrene-divinylbenzene- The alkali or am-
Copolymerisat der allgemeinen Formel moniumsalze von Thymolphthalein-monophosphatCopolymer of the general formula monium salts of thymolphthalein monophosphate
S können zur Bestimmung der alkalischen Serumphos-S can be used to determine the alkaline serum phospho-
phatase entsprechend dem vorstehend angegebenenphatase according to the above
° Verfahren verwendet werden mit der Verbesserung,° Processes are used with the improvement,
CH, C daß die Menge des Thymolphthaiein-monophosphat-CH, C that the amount of thymolphthalein monophosphate
Oe X' salzes auf ein gewünschtes Optimum von etwa 3 mgO e X 'salts to a desired optimum of about 3 mg
R — N ίο pro Milliliter erhöht werden kann, wodurch dieR - N ίο per milliliter can be increased, thereby reducing the
, ° Genauigkeit der Bestimmung wesentlich verbessert, ° Accuracy of the determination significantly improved
CH2—C wird.CH 2 -C becomes.
O Das Beispiel erläutert die Erfindung.The example explains the invention.
15 50 g eines chelatbildenden Kationenaustauscher-15 50 g of a chelating cation exchanger
verwendet, in der R die Matrix aus d<*m Styrol-Divinyl- harzes in der Natriumform werden in einem 1-Literbenzol-Copolymerisat und X ein Alkali- oder Ammo- Becherglas mit 200 ml destilliertem Wasser versetzt, niumion bedeutet. Kationenaustauscher dieses Typs Man rührt 5 Minuten und läßt dann das Harz abfijnd im Handel erhältlich, z. B. der Kationenaus- setzen. Der Überstand wird verworfen. Der Grund tauscher Chelex 100® oder Dowex A-I®. Im allge- 20 für diesen Reinigungsschritt liegt darin, daß die vom «leinen liegen die Kationenaustauscherharze in der Hersteller gelieferten Kationenaustauscherharze, wie Matriumform vor. Die Matrix ist jedoch so beschaffen, Chelex 100® oder Dowex A-l®, in wäßriger Suspension daß der Kationenaustauscher auch in einer anderen einen pH-Wert aufweisen, der etwas über dem ge-Alkalikationenform vorliegen kann. Die Kationen- wünschten Bereich von 10,5 bis 10,6 liegt. Demgemäß »ustauscherharze liegen üblicherweise in Form von 25 wird das Harz wiederholt mit je 200 ml destilliertem kleinen Perlen vor, die durch ein Sieb der lichten Wasser gewaschen, bis der pH-Wen des Überstandes Maschenweite von 0,24 bis 0,14 mm gehen. den gewünschten Wert erreicht. Dann werden 10 g Die Umwandlung von Magnesiumthymolphthalein- Magnesiumthymolphthalein-monophosphatundTOOml monophosphat in ein Alkali- oder Ammoniumsalz destilliertes Wasser zugesetzt. Die entstandene Suspen-■wird nach dem Verfahren der Erfindung in der Praxis 30 sion wird :>o lange gerührt, bis sie fast klar ist, d. h. bis dadurch erreicht, daß man die Harzteilchen und das sich das Magnesiumthymolphthalein-monophosphat Magnesiumthymolphthalein-monophosphat in Wasser vollständig gelöst hat. Dazu muß etwa 4 Stunden oder tiispergiert. Die Temperatur des Wassers liegt Vorzugs- möglicherweise etwas länger gerührt werden. Man läßt weise bei Raumtemperaturen (etwa 10 bis 3O0C), und die Harzteilchen absetzen und dekantiert den Überlein pH-Wert liegt zwischen 4 und 12, vorzugsweise 35 stand. Das Harz wird mehrmals mit je 50 ml destillier-Ctwa 10,5 bis 10,6. Beim Arbeiten bei höheren Tempe- tem Wasser gewaschen, und die Waschwasser werden raturen und höheren pH-Werten fällt die Ausbeute mit dem dekantierten Überstand vereinigt. Im allgewegen der Hydrolyse des Magnesiumthymolphthalein- meinen reichen sechs Waschvorgänge aus. Auf jeden tnonophosphats. Die Dispersion wird gerührt, das Fall wird das Waschen abgebrochen, wenn sich der Magnesiumthymolphthalein-monophosphat geht all- 40 Überstand blau zu färben beginnt. Die gewonnene tnählich in Lösung. Die Magnesiumionen werden vom Lösung wird durch ein Filter von 0,45 μ. Porengröße Kationenaustauscherharz aufgenommen, während nitriert und das Filtrat lyophilisiert. Man erhält prakgleichzeilig Alkali- oder Ammoniumionen freigesetzt tisch reines Natriumsalz des Thymolphthalein-monowerden. Im allgemeinen wird das Kationenaustau- phosphats.used, in which R is the matrix of d <* m styrene-divinyl resin in the sodium form in a 1 liter benzene copolymer and X an alkali or ammo beaker with 200 ml of distilled water, means nium ion. Cation exchanger of this type. The mixture is stirred for 5 minutes and then the resin is allowed to settle and are commercially available, e.g. B. exposure to cations. The supernatant is discarded. The basic exchanger Chelex 100® or Dowex AI®. The general rule for this cleaning step is that the cation exchange resins supplied by the manufacturer, such as matrium form, are available from the linen. The matrix, however, is made in such a way, Chelex 100® or Dowex Al®, in aqueous suspension that the cation exchanger also has a pH value in another which can be slightly above the ge-alkali cation form. The desired cation range is from 10.5 to 10.6. Accordingly, exchange resins are usually in the form of 25, the resin is repeated with 200 ml of distilled small beads each, which are washed through a sieve in the clear water until the pH of the supernatant mesh size is 0.24 to 0.14 mm. reached the desired value. Then 10 g of the conversion of magnesium thymolphthalein-magnesium thymolphthalein monophosphate and 100 ml of monophosphate into an alkali or ammonium salt are added to distilled water. The resulting suspension ■ is sion according to the process of the invention:> o long stirred until it is almost clear, that is, until the resin particles and the magnesium thymolphthalein monophosphate are dissolved in water completely resolved. This takes about 4 hours or 30 minutes. The temperature of the water is preferred - it may be stirred a little longer. The mixture is left at room temperature (about 10 to 3O 0 C), and the resin particles to settle and decant the Überlein pH is between 4 and 12, preferably 35 stand. The resin is distilled several times with 50 ml each - about 10.5 to 10.6. When working at higher temperatures, water is washed and the wash water is ratured and the pH is higher, the yield is combined with the decanted supernatant. In general, the hydrolysis of magnesium thymolphthalein mean that six washing processes are sufficient. On any monophosphate. The dispersion is stirred, the case, the washing is stopped when the magnesium thymolphthalein monophosphate goes all the supernatant begins to turn blue. The extracted almost in solution. The magnesium ions are removed from the solution through a filter of 0.45 μ. Cation exchange resin pore size added while nitrated and the filtrate lyophilized. Alkali or ammonium ions are obtained almost at the same time, liberated from the pure sodium salt of thymolphthalein monowerden. In general, the cation exchange phosphate will be used.
scherharz in etwas größerer Menge, als sie für die 45 Tn analoger Weise können aus dem Kationenaus-shear resin in a slightly larger amount than can be obtained from the cation
stöchiometrische Reaktion erforderlich ist, eingesetzt. tauscherharz in der entsprechenden Alkalimetallionen-stoichiometric reaction is required, used. exchange resin in the corresponding alkali metal ion
Vorzugsweise wird das Kationenaustauscherharz in bzw. Ammoniumform die entsprechenden Alkali- bzw.The cation exchange resin in or ammonium form is preferably the corresponding alkali or
einer Menge verwendet, die zwei Äquivalenten ent- Ammoniumsalze des Thymolphthalein-monophosphatsused in an amount equal to two equivalents of the ent-ammonium salts of thymolphthalein monophosphate
spricht. Nach beendeter Umsetzung wird das Kationen- hergestellt werden.speaks. After the reaction has ended, the cation will be produced.
Claims (3)
Nach einem geeigneten Zeitabstand, z. B. 15 Minuten, Die Erfindung betrifft ferner ein Verfahren zur Herwird die Reaktion durch Erhöhung des pH-Wertes auf stellung der Alkalisalze und des Amnioniumsalzes von 11,0 bis 11,5 unterbrochen, und die optische Dichte 50 Ihymolphthalein-monophosphat, das dadurch gebei 600 ΐημ wird mittels eines Spektrophotometers ge- kennzeichnet ist, daß man ein Kationenaustauschermessen und mit einem Leerwert verglichen, der aus harz in der Alkali- oder Ammoniumsabform in vvaß-4,0 ml der gepufferten Substratlösung besteht. Bei der ngem Medium mit Magnesiumthymolphthalein-inono-Beendigungder Reaktion durch ErhöhungdespH-Wer- phosphat umsetzt.0.5 mg / ml magnesium thymolphthalein monophosphate The sodium salt is preferred. The alkali salts are used in a buffer of pH 10 at a temperature and the ammonium salt of thymolphthalein-mono of 37 ° C. When carrying out the Be 45 phosphate are suitable because of their increased solubility mood 0.1 ml of serum with 4, OmI buffered excellent as a substrate for the determination of the active substrate solution at 37 ; C incubated in a cuvette. Most alkaline serum phobphatase.
After a suitable time interval, e.g. B. 15 minutes, The invention also relates to a method for Herwird the reaction by increasing the pH to position the alkali salts and the amnionium salt from 11.0 to 11.5 interrupted, and the optical density 50 Ihymolphthalein-monophosphat, which thereby give 600 ΐημ is identified by means of a spectrophotometer that a cation exchanger is measured and compared with a blank value, which consists of resin in the alkali or ammonium impression in vvass-4.0 ml of the buffered substrate solution. When the medium with magnesium thymolphthalein-inono terminates the reaction by increasing the pH-werophosphate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4398370A | 1970-06-05 | 1970-06-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2127655A1 DE2127655A1 (en) | 1971-12-09 |
| DE2127655B2 DE2127655B2 (en) | 1973-09-06 |
| DE2127655C3 true DE2127655C3 (en) | 1974-04-04 |
Family
ID=21929916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712127655 Expired DE2127655C3 (en) | 1970-06-05 | 1971-06-03 | Alkali salts and ammonium salt of thymolphthalein monophosphate, process for their preparation and their use for the determination of serum phosphatase |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA924729A (en) |
| DE (1) | DE2127655C3 (en) |
| ES (1) | ES390893A1 (en) |
| FR (1) | FR2095945A5 (en) |
| GB (1) | GB1314792A (en) |
-
1971
- 1971-04-23 CA CA111187A patent/CA924729A/en not_active Expired
- 1971-05-05 ES ES390893A patent/ES390893A1/en not_active Expired
- 1971-05-07 GB GB1373471A patent/GB1314792A/en not_active Expired
- 1971-06-03 DE DE19712127655 patent/DE2127655C3/en not_active Expired
- 1971-06-04 FR FR7120359A patent/FR2095945A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1314792A (en) | 1973-04-26 |
| ES390893A1 (en) | 1973-07-01 |
| DE2127655A1 (en) | 1971-12-09 |
| DE2127655B2 (en) | 1973-09-06 |
| CA924729A (en) | 1973-04-17 |
| FR2095945A5 (en) | 1972-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: MILLIPORE CORP., BEDFORD, MASS., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DIPL.-PHYS. DR.RER.NAT. SCHMITT-NILSON, G., DIPL.-ING. DR.-ING. HAGEN, G., DR.PHIL. HIRSCH, P., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |