CN106467489A - The Specific probe of one class human carboxylatase 1 and its application - Google Patents
The Specific probe of one class human carboxylatase 1 and its application Download PDFInfo
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- CN106467489A CN106467489A CN201510515876.4A CN201510515876A CN106467489A CN 106467489 A CN106467489 A CN 106467489A CN 201510515876 A CN201510515876 A CN 201510515876A CN 106467489 A CN106467489 A CN 106467489A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- 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
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- 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
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/44—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving esterase
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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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
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- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/916—Hydrolases (3) acting on ester bonds (3.1), e.g. phosphatases (3.1.3), phospholipases C or phospholipases D (3.1.4)
- G01N2333/918—Carboxylic ester hydrolases (3.1.1)
Abstract
The present invention relates to the Specific probe of a class human carboxylatase 1 and its application.Such Specific probe is 4- hydroxyl or 4- alkoxynaphtalene acid imide N- butyryl methyl ester, and it can be used for detecting the quantitative determination of the presence or absence of hCE1 and its enzyme activity in different biological specimens.The idiographic flow of hCE1 enzyme activity determination is as follows：Selection naphthalimide N- butyryl methyl ester hydrolysis are probe reaction, select suitable concentration of substrate in linear reaction interval by the growing amount of its hydrolysis metabolite N- butanoic acid naphthalimide in the detection by quantitative unit interval detect various biological specimens (in vitro tissue, cell, blood plasma, in body and overall organ) in hCE1 enzyme substantial activity.The present invention cannot be only used for the qualitative assessment of hCE1 enzyme activity in separate sources biological specimen, can be additionally used in the inhibitor of external rapid screening hCE1 in addition by this probe reaction.
Description
Technical field
The invention belongs to technical field of pharmaceutical biotechnology and in particular to a class human carboxylatase 1 (hCE1) special
Property probe substrate and its application.
Background technology
As the characteristic indication thing of internal organs and tissue, hCE1 content in the liver of crowd is very high, its albumen table
The amount of reaching arranges top ten in liver distribution albumen.HCE1 is a kind of embrane-associated protein, is positioned endocytoplasmic reticulum
In【CANCER RESEARCH 1998；58:3627-32&Drug Metab.Pharmacokinet.2006；
21:173-85】, also can be secreted into extracellular simultaneously and enter blood circulation【Proteomics 2009；9:
3989–99】.The analytic metabolism reaction of hCE1 is the hydrolysis containing less alcohol radical and larger amide substrate for the catalysis.
Although, Various Tissues all detect the protein expression of hCE1, it is far high in human liver organization content
In other tissues.HCE1 participates in the metabolite clearance of multiple exogenous materials, such as medicine Oseltamivir, piperazine vinegar
Methyl ester etc..Meanwhile, hCE1 is maintaining human normal physiological function Function considerable effect, participates in
The transport of cholesterol in human body ester and free fatty and metabolic process, maintain lipid metabolism balance【Chemistry
&Biology,Vol.10,341–349,April,2003】.In Normal healthy individuals, hCE1 is except with higher
Content distribution in the cell of hepatic tissue, also have a small amount of hCE1 to be detected in blood plasma it is often more important that,
HCE1 in patients with hepatocellular carcinoma blood plasma is 2-5 times of healthy population, and therefore hCE1 is considered as that liver is thin
A kind of good potential serologic marker thing of born of the same parents' hepatocarcinoma early diagnosis【Proteomics 2009,9,
3989–3999】.Additionally, the damaged related patients with liver diseases of hepatocyte also has hCE1 and is released into blood, draw
Play hCE1 concentration in blood plasma to change, therefore, the mark that in blood plasma, hCE1 can damage as liver acute
Thing.There is very big individual variation in the distribution of hCE1, the expression of hCE1 enzyme and function itself can be subject to human body
Heredity, age, disease, sex, environment and the impact of the many factors such as thing of taking medicine altogether.Therefore, hCE1
The activity test method of enzyme has wide potential applicability in clinical practice, can be used for evaluating human body liver function abnormal,
Liver toxicity, hepatocarcinoma early diagnosiss, the assessment of liver function individuation and part that medicine and poisonous substance lead to
Personalization use of prodrug etc..Additionally, hCE1 is as the important albumen maintaining Human Lipid Metabolism balance,
Its inhibitor can use as blood lipid-lowering medicine, and hCE1 is also approved as important drug target by FDA.
The quick characterization method of hCE1 activity can also be used for new drug development early discovery and the assessment new and effective suppression of hCE1
Preparation.Therefore, develop efficient, the hCE1 activity test method of hypersensitive, high specific for clinical sample
The detection of middle hCE1 activity, and new drug high intension high flux screening is most important.
Content of the invention
For the problems referred to above, the invention provides a kind of specific probe bottom of human carboxylatase 1 (hCE1)
Thing and its application, it can generate the hydrolyzate N- butanoic acid naphthoyl Asia with fluorescence properties after hCE1 hydrolysis
Amine.This enzymatic reaction has selectivity height, metabolite easily detects, enzymatic activity and inhibitor activity are evaluated soon
Fast timesaving feature.
It is an object of the invention to provide the Specific probe of a class human carboxylatase 1 (hCE1) and its
Application, the hydrolyzate of such specific probe has good fluorescence properties it is easy to detect.Using this spy
Pin reaction can carry out quantitative assessment to the distribution of the hCE1 in multiple living things systems and function.
The specificity fluorescent probe substrate of the present invention one class human carboxylatase 1 (hCE1), the first of such substrate
Ester bond can be corresponding hydrolyzate by hCE1 specific for hydrolysis；This substrate is 4- hydroxyl or 4- alkoxynaphtalene
Acid imide N- butyryl methyl ester, under its general structure：
Wherein R is-H ,-CH3One of substituent group.
Present invention also offers a kind of application of the specificity fluorescent probe of hCE1, such substrate can be by hCE1
Specific recognition catalytic reaction life hydrolysis, by hydrolyzate N- butanoic acid naphthalene in the detection by quantitative unit interval
Imido growing amount can measure the hCE1 activity in different enzyme sources (single enzyme, tissue, cell, blood plasma)；
Described biological specimen can be recombinant expressed hCE1, the cellular preparations of human or animal, tissue preparation liquid
Or blood plasma and other common biological specimens.
Specifically assay method is：
Specifically assay method is：
1) using any compound shown in formula (1) as Specific probe in system；Concentration of substrate selects
1/10～10Km；；
2) in the conventional buffer such as PBS or Tris-HCl, reaction temperature between 20-60 DEG C,；Incubate
System pH of educating between 5.5～10.5,；
3) response time is 5-120min, is guaranteeing that the corresponding hydrolyzate of above substrate reaches quantitative limit and bottom
Terminating reaction when thing conversion ratio is less than 20%；
4) in the analytical unit time hydrolyzate growing amount as hCE1 activity evaluation criterion.
Concentration of substrate preferred K during single point assay in described concrete assay methodm, preferably 37 DEG C be peak optimization reaction when
Between, preferably pH 7.4 is peak optimization reaction pH.
The production rate of described substrate elimination factor or hydrolyzate is between 0.1%～20%.
Described probe substrate and its hydrolyzate are respectively provided with fluorescence properties, can realize product using fluorescence detector
And the rapid sensitive detection of substrate；Fluoroscopic examination condition is：Excitation wavelength 372nm, enters in 420～520nm
The detection of row fluorescence emission spectrum.
The present invention provide the specificity fluorescent probe of class hCE1 application, this Specific probe and its
Hydrolysis can be additionally used in the rapid screening of hCE1 inhibitor and the quantitative assessment of rejection ability.
Application, this Specific probe and the phase of the specificity fluorescent probe of class hCE1 that the present invention provides
Answer hCE1 Activity determination process will not be disturbed by living things system substrate and impurity, can be used for various organisms
The detection by quantitative of hCE1 enzyme activity in system.
The invention provides the application of described specificity fluorescent probe, this Specific probe is used for table of recombinating
Enzyme activity in the common biological specimens such as the hCE1 that reaches, the cellular preparations of human or animal, tissue preparation liquid, blood plasma
Quantitative determination, and using this probe reaction rapid screening hCE1 enzyme inhibitor.
HCE1 specific probe reaction according to the present invention has the advantage that：
1. high specific：Naphthalimide N- butyryl first ester type compound can be become one by hCE1 specific metabolic
Metabolite, i.e. the hydrolyzate of methyl ester bond fission, remaining hydrolytic enzyme of human body is all not involved in this reaction.
2. high sensitivity：Naphthalimide N- butyryl first ester type compound can be discharged N- by hCE1 fast hydrolyzing
Butanoic acid naphthalimide, and substrate is respectively provided with good fluorescence emission spectrum signature, available fluorescence inspection with product
Survey device and realize super sensitivity detection, it is to the Monitoring lower-cut of object up to pM level.
Brief description
Fig. 1 .N- butyryl methyl ester -4- hydroxyl -1,8 naphthalimide13C-NMR spectrogram；
Fig. 2 .N- butyryl methyl ester -4- hydroxyl -1,8 naphthalimide and the detection chromatogram of hydrolyzate；
The single enzyme screening test result of people's restructuring of Fig. 3 .N- butyryl methyl ester -4- methoxyl group -1,8 naphthalimide；
The hydrolysis rate difference to N- butyryl methyl ester -4- methoxyl group -1,8 naphthalimide for Fig. 4 .12 example HLM；
Fig. 5. the Chemical Inhibition spectrogram of human plasma hydrolyzing N-butyryl methyl ester -4- methoxyl group -1,8 naphthalimide；
Fig. 6 .N- butyryl methyl ester 4- ethyoxyl -1,8 naphthalimide measures the activity profile of hCE1 in different cells；
The synthetic route of Fig. 7 .N- butyryl methyl ester -4- methoxyl group -1,8 naphthalimide.
Specific embodiment
The following examples will be further described to the present invention, but not thereby limiting the invention.
Embodiment 1
The synthesis of N- butyryl methyl ester -4- methoxyl group -1,8 naphthalimide
4.2mmol 4-Aminobutanoicacid is added to the 50ml containing bromo- 1,8 naphthalene anhydrides of 1 gram of (3.61mmol) 4-
In ethanol solution, 70-80 DEG C after reaction overnight, adds 200ml water, separates out a large amount of solids, filters, very
Sky is dried to obtain bromo- 1, the 8- naphthalimide of buff white solid N- butanoic acid -4-, yield 80-90%.By 800mgization
Bromo- 1, the 8- naphthalimide of compound N- butanoic acid -4- and 2.54g potassium carbonate are placed in 100ml single port bottle, add 30
Ml methanol, 60-70 DEG C after reaction overnight, cooling, with the hydrochloric acid of 1M, pH is adjusted to acidity, separates out a large amount of
Yellow solid, filters, massive laundering, and vacuum drying obtains yellow solid N- butanoic acid -4- methoxyl group -1,8- naphthoyl
Imines, yield 80-90%.By 0.1g N- butanoic acid -4- methoxyl group -1,8- naphthalimide is dissolved in 15mL first
Alcohol, adds some of concentrated sulphuric acid.Reaction system is stirred at reflux 8 hours.After being cooled to room temperature, after vacuum drying
By silica column purification, eluent dichloromethane/methanol (10:1), vacuum obtains being dried to obtain 0.086g yellow
Solid, yield 82.1%.Compound is accredited as N- butyryl methyl ester -4- methoxyl group -1 through high resolution mass spectrum, nuclear-magnetism,
8- naphthalimide (Fig. 1, Fig. 7).
Embodiment 2
The selectivity of hCE1 in the single enzyme of external test people restructuring
(1) 198 μ l hCE1 metabolic response systems are prepared in advance, including the PBS (100 of pH 7.4
MM), each single enzyme (5 μ g/mL) of people's restructuring, shakes under the conditions of 37 DEG C and incubates 3 minutes in advance；
(2) add N- (4 butyric acid the methyl ester) -4- methoxyl group -1,8 that 2 μ l concentration are 5mM in reaction system
Naphthalimide initial action；
After (3) 15 minutes, add 200 μ l ice acetonitriles, after acutely shaking, terminating reaction；
(4) use High speed refrigerated centrifuge at 4 DEG C, under conditions of 20,000 × g, high speed centrifugation is after 20 minutes,
Take supernatant, carry out liquid phase-fluoroscopic examination (Liquid Detection wavelength 247nm；Fluoroscopic examination Ex=362nm,
Em=450nm) (Fig. 2)；Recombined human hCE1 specificity participates in its hydrolysis, and other esterases are all not involved in its water
Solution is it was demonstrated that such compound has extraordinary selectivity (Fig. 3).
Embodiment 4
The active level assessment of hCE1 in the hepatomicrosome of Different Individual source
(1) choose 12 individuals hepatomicrosomes (HLM) and be diluted to 100 μ g/mL, prepare hCE1 generation
Thank to reaction system, PBS (100mM) including pH 7.4, people's hepatomicrosome (1 μ g/mL),
Shake under the conditions of 37 DEG C and incubate 3 minutes in advance；
(2) add N- (4- butyryl the methyl ester) -4- methoxyl group -1,8 that 2 μ l concentration are 5mM in reaction system
Naphthalimide initial action；
After (3) 30 minutes, add 200 μ l ice acetonitriles, after acutely shaking, terminating reaction；
(4) use High speed refrigerated centrifuge at 4 DEG C, under conditions of 20,000 × g, high speed centrifugation is after 20 minutes,
Take supernatant, carry out liquid phase-fluoroscopic examination (Liquid Detection wavelength 247nm；Fluoroscopic examination Ex=362nm,
Em=450nm), obtained chromatographic peak area is substituted into and obtain 12 people's hepatomicrosomes (HLM) after standard curve
Metabolic rate (Fig. 4) to N- (4- butyryl methyl ester) -4- methoxyl group -1,8 naphthalimide.
Embodiment 5
The activity chemistry Inhibition test of hCE1 in human plasma sample
(1) hCE1 metabolic response system, the PBS (100mM) including pH 7.4, people are prepared
Plasma sample (10 μ L), different esterase specific inhibitor (1 μ L) are shaken under the conditions of 37 DEG C and are incubated 3 points in advance
Clock；
(2) add N- (4- butyryl the methyl ester) -4- methoxyl group that 1 μ l concentration is 10mM in reaction system
- 1,8 naphthalimide initial actions；
After (3) 60 minutes, add 200 μ l ice acetonitriles, after acutely shaking, terminating reaction；
(4) use High speed refrigerated centrifuge at 4 DEG C, under conditions of 20,000 × g, high speed centrifugation is after 20 minutes,
Take supernatant, carry out liquid phase-fluoroscopic examination (Liquid Detection wavelength 247nm；Fluoroscopic examination Ex=362nm,
Em=450nm), N- (4- butyryl methyl ester) -4- methoxyl group -1, hydrolysing activity energy in blood plasma for 8 naphthalimides
Enough significantly inhibited by carboxy-lesterase specific inhibitor BNPP, and other esterase inhibitor hydrolyzes to it and do not have
Significantly, it was demonstrated that N- (4- butyryl methyl ester) -4- methoxyl group -1,8 naphthalimides being capable of specificity inspection for inhibitory activity
Survey the activity (Fig. 5) of the hCE1 in human plasma.
Embodiment 6
The activity of hCE1 in quantitative determination five kinds of tumor cells of people
HCE1 metabolic response system cumulative volume is the PBS 100mM that 200 μ L include pH 7.4,
And the microsome 0.5mg/Ml that five kinds of tumor cells are prepared into, shake at 37 DEG C and incubate in advance 3 minutes, to reactant
N- (4- butyryl methyl ester) -4- ethyoxyl -1,8 naphthalimide that 2 μ l concentration are 5mM is added to initiate in system anti-
Should, after 35 minutes, add 200 μ l ice acetonitriles, after acutely shaking, terminating reaction, take supernatant carry out liquid phase-
Fluorescence analysiss, obtained chromatographic peak area are substituted into and obtain five kinds of tumor cell microsomes to N- (4- after standard curve
Butyryl methyl ester) -4- ethyoxyl -1,8 naphthalimide hydrolysis rate (Fig. 6).
Claims (8)
1. a class human carboxylatase 1 Specific probe it is characterised in that：The methyl ester key of such substrate can quilt
HCE1 specific for hydrolysis is corresponding hydrolyzate；This substrate is 4- hydroxyl or 4- alkoxynaphtalene acid imide N-
Butyryl methyl ester, its general structure is as follows：
Wherein R is-H ,-CH3Or any one in the alkyl substituent such as ethyl.
2., according to the application of the human carboxylatase 1 specificity fluorescent probe of a class described in claim 1, its feature exists
In：Such substrate, can be by hydrolyzate in the detection by quantitative unit interval used as the specific probe of hCE1
The growing amount of N- butanoic acid naphthalimide is active to measure the hCE1 in different biological specimens.
3., according to the application of the human carboxylatase 1 specificity fluorescent probe of a class described in claim 2, its feature exists
In：Described biological specimen can be recombinant expressed hCE1, the cellular preparations of human or animal, tissue preparation liquid
Or blood plasma and other common biological specimens.
4. according to the application of human carboxylatase 1 specificity fluorescent probe a kind of described in claim 2 it is characterised in that：
Such substrate, can be by hydrolyzate N- fourth in the detection by quantitative unit interval used as the specific probe of hCE1
The growing amount of sour naphthalimide is active to measure the hCE1 in different biological specimens；Specifically assay method is：
1) using any compound shown in formula (1) as Specific probe in system；Concentration of substrate selects
1/10～10Km；；
2) in the conventional buffer such as PBS or Tris-HCl, reaction temperature between 20-60 DEG C,；Incubate
System pH of educating between 5.5～10.5,；
3) response time is 5-120min, is guaranteeing that the corresponding hydrolyzate of above substrate reaches quantitative limit and bottom
Terminating reaction when thing conversion ratio is less than 20%；
4) in the analytical unit time hydrolyzate growing amount as hCE1 activity evaluation criterion.
5., according to the application of a kind of human carboxylatase 1 specificity fluorescent probe described in claim 4, its feature exists
In：Concentration of substrate preferred K during single point assaym, preferably 37 DEG C is the peak optimization reaction time, and preferably pH 7.4 is
Peak optimization reaction pH.
6., according to the application of the human carboxylatase 1 specificity fluorescent probe of a class described in claim 4, its feature exists
In：The production rate of described hydrolyzate is between 0.1%～20%.
7., according to the application of a kind of human carboxylatase 1 specificity fluorescent probe described in claim 2, its feature exists
It is respectively provided with fluorescence properties in the Specific probe of described hCE1 and its hydrolyzate N- butanoic acid naphthalimide,
The rapid sensitive detection of product and substrate can be realized using fluorescence detector；Fluoroscopic examination condition is：Excitation wave
Long 372nm, carries out the detection of fluorescence emission spectrum in 420～520nm.
8., according to the application of a kind of human carboxylatase 1 specificity fluorescent probe described in claim 1, its feature exists
In：This Specific probe and its hydrolysis can be also used for rapid screening and the suppression of hCE1 inhibitor
The quantitative assessment of ability.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109810072A (en) * | 2019-03-11 | 2019-05-28 | 大连医科大学 | It is a kind of detect fatty amide hydrolase fluorescence probe and its application |
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