CN103524504A - Guanine derivative as well as preparation method and application thereof - Google Patents
Guanine derivative as well as preparation method and application thereof Download PDFInfo
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- CN103524504A CN103524504A CN201210234339.9A CN201210234339A CN103524504A CN 103524504 A CN103524504 A CN 103524504A CN 201210234339 A CN201210234339 A CN 201210234339A CN 103524504 A CN103524504 A CN 103524504A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N2021/6417—Spectrofluorimetric devices
- G01N2021/6423—Spectral mapping, video display
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6443—Fluorimetric titration
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Abstract
The invention relates to a guanine derivative as well as a preparation method and application thereof. Three guanine derivatives are prepared. The inducibility and the affinity of the guanine derivatives to a G-quadruplex and an I-motif DNA (Deoxyribonucleic Acid) as well as the recognition capability to the structure are researched by means of fluorescence titration, TO competition and circular dichroism spectrum (CD). Compared with the prior art, the guanine derivatives prepared by the invention have the recognizing and stabilizing effects on telomere G-quadruplex and I-motif DNA; the combining capacity of the guanine derivatives with I-motif is remarkably stronger than that with G-quadruplex.
Description
Technical field
The present invention relates to a kind of, especially relate to a kind of guanine derivatives and preparation method thereof and and the effect of telomeric dna between application.
Background technology
Old and feeble and cancer is medical science two hang-ups, and the two and telomere and Telomerase have substantial connection.
Telomere is a kind of special nucleoprotein complex body of eukaryotic cell end of chromosome, and the tumor-necrosis factor glycoproteins of the rich G (guanine base) being repeated by one section of 5-8 base series connection is feature.The length of telomere plays an important role in cell carcinogenesis and aging, and its length is regulated by Telomerase.Telomerase is positioned at telomere end, is responsible for a kind of enzyme of the prolongation of telomere in cell, is basic nucleoprotein reversed transcriptive enzyme.The biological function of Telomerase is the telomere of synthetic end of chromosome.
The activity inhibited of Telomerase in normal human tissue is reactivated in tumour, makes it can maintain the length of telomere, participates in vicious transformation.Therefore, to suppress the research of telomerase activation, become cancer therapy drug action target spot.
Purine derivative is the very important Internmediate of anti viral medicine of a class, and the guanine derivatives of wherein take asks that in medicine the medicine that body makes has special effect to cancer, is the potential hypotoxic cancer therapy drug of highly selective.
Summary of the invention
Object of the present invention is exactly to provide a kind of guanine derivatives that telomeric dna is had to recognition capability, stabilizing power in order to overcome the defect that above-mentioned prior art exists, and studies the effect of itself and telomeric dna, thereby provides theoretical foundation for the screening of cancer therapy drug.
Object of the present invention can be achieved through the following technical solutions:
, it is characterized in that, this guanine derivatives connects phenyl ring, naphthalene nucleus and anthracene nucleus respectively on the 8th of guanine, and the structural formula of guanine derivatives is as follows respectively:
A preparation method for guanine derivatives, comprises the following steps:
(1) in pressure bottle, add aromatic aldehyde and 4,5,6-Triaminopyrimidine vitriol, using dimethyl sulfoxide (DMSO) as solvent, magnetic agitation is heated to 90 ℃ of reaction 24h;
(2) utilize underpressure distillation evaporate to dryness dimethyl sulfoxide (DMSO), the product then processing being obtained is placed in flask, adds methyl alcohol and 1.0g silica gel to mix sample, then decompression is spin-dried for methyl alcohol;
(3) step (2) is processed to the silica gel column chromatography separation for thick product obtaining, be then spin-dried for eluent, obtain powdery product and be product.
The mol ratio of the aromatic aldehyde described in step (1) and 4,5,6-Triaminopyrimidine vitriol is 1: 1.
Aromatic aldehyde described in step (1) is respectively phenyl aldehyde, 1-naphthaldehyde or 9-anthraldehyde.
Thick product in step (3) uses a dry method on a sample while crossing silicagel column, and wet method is crossed post.
Eluent described in step (3) is mixed by the volume ratio of 1: 2,1: 5 or 1: 10 respectively by methyl alcohol and methylene dichloride.
An application for guanine derivatives, this guanine derivatives has identification, stable, keying action to telomere G-tetra-serobilas and I-motif DNA.
Telomere G-tetra-serobilas and I-motifDNA that described telomere G-tetra-serobilas and I-motif DNA are people.
The application of guanine derivatives can be identified telomere G-tetra-serobilas and I-motifDNA by fluorometric assay, adds the guanine derivatives of I-motifDNA, and its fluorescence significantly reduces.
Guanine derivatives has fluorescent quenching phenomenon to telomere G-tetra-serobilas, replaces TO and is deposited in the position on DNA, with telomere G-tetra-serobila DNA, keying action occurs.
To the guanine derivatives of synthesized carried out hydrogen spectrum (
1h NMR) and electrospray ionization mass spectrum (ES-MS) characterize.Utilize the means such as fluorescence, TO competition, circular dichroism spectrum (CD) to detect designed synthetic guanine derivatives to the identification of G-tetra-serobilas and I-motif structure, stable, inducibility and combination.
Fluorescent spectrometry is the Main Means of research small molecules and nucleic acid interaction, fluorescent substance, under the exciting of exciting light, after excited state, can consume the minimum vibrations energy level that part energy is got back to the first excited electronic state by ground state transition, with the form emitted energy of photon, be fluorescence simultaneously.After small molecules Interaction with DNA, its vibrating mode is changed.We judge the power of small molecules Interaction with DNA according to the variation of fluorescence intensity.
Under normal temperature, do not have fluorescence material can with the competitive assay of thiazole orange (TO) study itself and DNA key and character.The fluorescence intensity of TO own is very weak, but adds after nucleic acid, and its fluorescence intensity increases greatly.When adding small molecules, by observing the process of fluorescent quenching, judge that small molecules and TO compete the size in conjunction with DNA ability.
Circle two Optical Chromatography can detect the existence that has or not optical rotatory substance, or in the more left and right mixture that revolves material, which kind of content is more, and the micromolecular CD spectrum of measuring after dialysis helps the interaction of determining small molecules and DNA to have or not isomery selectivity.G-tetra-serobilas and I-motif have special peak structure in circular dichroism spectrum.Add after small molecules, can make its absorption peak be moved and change its intensity.A kind of like this phenomenon has just had certain selectivity to change, and more easily distinguishes the configuration conversion of G-serobila and I-motif, the binding pattern of small molecules and DNA.
Compared with prior art, guanine derivatives prepared by the present invention has identification, stabilization to telomere G-tetra-serobilas and I-motifDNA, the binding ability of guanine derivatives and I-motif is the binding ability of strong and G-tetra-serobilas obviously, thereby provides theoretical foundation for the screening of cancer therapy drug.
Accompanying drawing explanation
Fig. 1 be the present invention obtain in potassium ion buffered soln, the fluorometric titration curve that guanine derivatives 1 and G-tetra-serobilas (a) and I-motif (b) act on;
Fig. 2 be the present invention obtain in sodium ion buffered soln, the fluorometric titration curve that guanine derivatives 1 and G-tetra-serobilas (a) and I-motif (b) act on;
Fig. 3 be the present invention obtain in potassium ion buffered soln, the fluorometric titration curve that guanine derivatives 2 and G-tetra-serobilas (a) and I-motif (b) act on;
Fig. 4 be the present invention obtain in sodium ion buffered soln, the fluorometric titration curve that guanine derivatives 2 and G-tetra-serobilas (a) and I-motif (b) act on;
Fig. 5 be the present invention obtain in potassium ion buffered soln, the fluorescence spectrum figure of guanine derivatives 3 and TO competition G-tetra-serobilas;
Fig. 6 be the present invention obtain in sodium ion buffered soln, the fluorescence spectrum figure of guanine derivatives 3 and TO competition G-tetra-serobilas;
Fig. 7 be the present invention obtain in potassium ion buffered soln, guanine derivatives 1 and DNAC
3t(A
2c
3t)
3circular dichroism titration curve figure;
Fig. 8 be the present invention obtain in potassium ion buffered soln, guanine derivatives 2 and DNAC
3t(A
2c
3t)
3circular dichroism titration curve figure;
Fig. 9 be the present invention obtain in potassium ion buffered soln, guanine derivatives 3 and DNAC
3t(A
2c
3t)
3circular dichroism titration curve figure.
Embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is described in detail.
Embodiment 1
Synthesizing of guanine derivatives 1
In 100ml pressure bottle, add phenyl aldehyde (286.5mg, 2.7mmol), 4,5,6-Triaminopyrimidine vitriol (646mg, 2.7mmol) and 30ml dimethyl sulfoxide (DMSO), magnetic agitation is heated to 90.React 24 hours, obtain burgundy solution.With vacuum distillation apparatus solvent dimethyl sulfoxide (DMSO) evaporate to dryness.Product is poured in 50ml round-bottomed flask and added a small amount of methyl alcohol and 0.5g silica gel to mix sample, and decompression is spin-dried for methyl alcohol.Thick silica gel column chromatography separation (dry method loading, wet method is crossed post) for product, eluent ethanol/methylene (1: 2), obtains orange powder guanine derivatives 1.
Productive rate: 62%,
1h-NMR (DMSO-d
6, TMS, 400MHz): 10.65 (1H, br), 10.10 (1H, br), 8.02 (1H, d), 7.47 (1H, m), 7.22 (1H, s), 7.10 (1H, s), 6.97 (1H, s), 6.38 (2H, s)
Embodiment 2
Synthesizing of guanine derivatives 2
In 100ml pressure bottle, add 1-naphthaldehyde (366.7mg, 2.7mmol), 4,5,6-Triaminopyrimidine vitriol and 30ml dimethyl sulfoxide (DMSO), magnetic agitation is heated to 90.React 24 hours, obtain purplish red solution.With vacuum distillation apparatus solvent dimethyl sulfoxide (DMSO) evaporate to dryness.Product is poured in 50ml round-bottomed flask and added a small amount of methyl alcohol and 1.0g silica gel to mix sample, and decompression is spin-dried for methyl alcohol.Thick silica gel column chromatography separation (dry method loading, wet method is crossed post) for product, eluent ethanol/methylene (1: 5), obtains yellow powder guanine derivatives 2.
Productive rate: 70%,
1h-NMR (DMSO-d
6, TMS, 400MHz): 11.73 (1H, br), 8.43 (1H, d), 8.22 (1H, d), 8.10 (1H, d), 7.91 (1H, d), 7.70 (3H, m), 7.40 (2H, br)
Embodiment 3
Synthesizing of guanine derivatives 3
In 100ml pressure bottle, add 9-anthraldehyde (556.8mg, 2.7mmol), 4,5,6-Triaminopyrimidine vitriol and 30ml dimethyl sulfoxide (DMSO), magnetic agitation is heated to 90 ° of reactions 24 hours, obtains purplish red solution.With vacuum distillation apparatus solvent dimethyl sulfoxide (DMSO) evaporate to dryness.Product is poured in 50ml round-bottomed flask and added a small amount of methyl alcohol and 1.5g silica gel to mix sample, and decompression is spin-dried for methyl alcohol.Thick silica gel column chromatography separation (dry method loading, wet method is crossed post) for product, eluent ethanol/methylene (1: 10), obtains darkorange powder guanine derivatives 3.
Productive rate: 85%,
1h-NMR (DMSO-d
6, TMS, 400MHz): 11.54 (1H, br), 8.28 (1H, d), 7.77 (2H, d), 7.64 (3H, m), 7.08 (2H, br)
Embodiment 4
The effect of guanine derivatives and telomeric dna
Guanine derivatives and telomere G-tetra-serobilas and the interactional fluorometric assay of I-motifDNA
The preparation of buffered soln
Buffered soln is prepared with high purity water.
High purity water obtains with the automatic triple distillation water generator of SZ97.
Damping fluid 1:100mM KCl, 10mM Tris, pH=7
Damping fluid 2:100mM NaCl, 10mM Tris, pH=7
Damping fluid 3:100mM KCl, 10mM Tris, pH=5.5
Damping fluid 4:100mM NaCl, 10mM Tris, pH=5.5
Determining of guanine derivatives and DNA concentration
1. guanine derivatives concentration determines
Guanine derivatives 1:B-8-gua
Guanine derivatives 2:1-Naphth-8-gua
Guanine derivatives 3:9-An-8-gua
Taking certain mass small molecules dissolves with high purity water and damping fluid 1,2,3,4 respectively
The processing of 2.DNA and concentration are determined
1) rich G single stranded DNA
Get the rich G single stranded DNA of certain mass, be dissolved in high purity water, put into 4 ℃ of refrigerators and keep 24h, standby.
Concentration is determined: with ultraviolet spectrophotometer, measure DNA at the absorbance A of 260nm
260.Molar extinction coefficient is 2.285 * 105m
3cm
-1, DNA concentration [DNA]=K * A
260/ 2.285 * 10
5(k is extension rate), unit is mol L
-1.
2) rich G-tetra-helical dnas
Get the rich G single stranded DNA of certain mass, be dissolved in buffered soln 1 or buffered soln 2, be heated to seal to 90 ℃, and keep 5 minutes.Then naturally cool to room temperature, put into 4 ℃ of refrigerators and keep 24 hours, standby.
Concentration is determined: with ultraviolet spectrophotometer, measure DNA at the absorbance A of 260nm
260.Molar extinction coefficient is 2.285 * 105m
3cm
-1, DNA concentration [DNA]=K * A
260/ 2.285 * 10
5(k is extension rate), unit is mol L
-1.
3) I-motif structure
The rich C single stranded DNA of getting certain mass, is dissolved in buffered soln 3 or buffered soln 4, puts into 4 ℃ of refrigerators and keeps 24 hours, standby.
Concentration is determined: concentration is determined: with ultraviolet spectrophotometer, measure DNA at the absorbance A of 260nm
260.Molar extinction coefficient is 2.285 * 105m
3cm
-1, DNA concentration [DNA]=K * A
260/ 2.285 * 10
5(k is extension rate), unit is mol L
-1.
Base derivative 1,2 and G-tetra-serobilas and the interactional fluorometric assay of I-motifDNA
Instrument: Hitachi FP 7000 fluorophotometers
Instrument parameter: excitation wavelength: 300nm, slit width: (10,10), voltage: 500V
Sweep limit: 320-550nm
Guanine derivatives 1,2 is dissolved in buffered soln 1,2,3 and 4, is mixed with the solution that concentration is 4 μ M.With microsyringe, in sample pool, add the G-quadruplex of 5 μ L and the DNA storing solution of I-motif, with liquid-transfering gun repeatedly compressing mix, after 5 minutes, measure.Repeatedly, toward the DNA storing solution that adds same volume in sample pool, observe fluorescence intensity change.Until continuous 4 titration fluorescence intensities stop titration after all unchanged, its result as Figure 1-4.
Result shows: after adding I-motifDNA, fluorescence significantly reduces, and adds after G-tetra-serobila DNA, and fluorescence does not occur noticeable change or only has the reduction of a little.Illustrate that the key of guanine derivatives and I-motif and ability are obviously better than key and the ability with G-tetra-serobilas.
The TO competitive assay of base derivative 3
Instrument: Hitachi FP 7000 fluorophotometers
Instrument parameter: excitation wavelength: 480nm, slit width: (10,10), voltage: 500V
Sweep limit: 500-650nm
Preparation contains TO, the solution of G-tetra-serobilas, and in sample pool, add 5 μ L concentration is guanine derivatives 3 solution of 200 μ M at every turn, by liquid-transfering gun compressing repeatedly, mix, after 5 minutes, detect fluorescent quenching situation, so repeatedly, drip 13-15 time, its result is as shown in Fig. 5-6.
Result shows: 3 couples of G-of guanine derivatives, tetra-serobila DNA have good quenching phenomenon, illustrate that guanine derivatives 3 can replace TO, with DNA, keying action occurs.
The CD spectrometry of guanine derivatives
Instrument: JASCO-J715 circular dichroism spectrometer.
Instrument parameter: bandwidth 2nm, step-length 1nm, data point reading duration 0.5s, light path 1cm
Sweep limit: 200-400nm
Spectral scan is used quartz to compare ware.Buffering baseline measures in same cuvette, from measure sample spectrum, deducts, and each specimen multiple scanning 3 times, is averaged and is worth last spectrogram, and data analysis is carried out in software Origin 8.0.In titration experiments, the concentration of fixed dna, the concentration of base derivative increases progressively by a certain percentage, mixes after approximately 5 minutes, carries out spectral scan, and its result is as Figure 7-8.
Result shows: when guanine derivatives 1,2,3 join in I-motif DNA, along with the intensity of the increase CD signal of guanine derivatives concentration also increase gradually and positive absorption peak red shift to 290nm, the red shift of negative absorption peak is to 260nm.This illustrates that these 3 kinds of guanine derivatives all can make the structure of I-motif DNA occur significantly to change, and impel and form more stable structure.
Claims (10)
1. a guanine derivatives, is characterized in that, this guanine derivatives connects phenyl ring, naphthalene nucleus or anthracene nucleus respectively on the 8th of guanine, and the structural formula of guanine derivatives is as follows respectively:
2. a preparation method for guanine derivatives as claimed in claim 1, is characterized in that, the method comprises the following steps:
(1) in pressure bottle, add aromatic aldehyde and 4,5,6-Triaminopyrimidine vitriol, using dimethyl sulfoxide (DMSO) as solvent, magnetic agitation is heated to 90 ℃ of reaction 24h;
(2) utilize underpressure distillation evaporate to dryness dimethyl sulfoxide (DMSO), the product then processing being obtained is placed in flask, adds methyl alcohol and 1.0g silica gel to mix sample, then decompression is spin-dried for methyl alcohol;
(3) step (2) is processed to the silica gel column chromatography separation for thick product obtaining, be then spin-dried for eluent, obtain powdery product and be product.
3. the preparation method of guanine derivatives according to claim 2, is characterized in that, the mol ratio of the aromatic aldehyde described in step (1) and 4,5,6-Triaminopyrimidine vitriol is 1: 1.
4. according to the preparation method of the guanine derivatives described in claim 2 or 3, it is characterized in that, the aromatic aldehyde described in step (1) is respectively phenyl aldehyde, 1-naphthaldehyde or 9-anthraldehyde.
5. the preparation method of guanine derivatives according to claim 2, is characterized in that, the thick product in step (3) uses a dry method on a sample while crossing silicagel column, and wet method is crossed post; Described eluent is mixed by the volume ratio of 1: 2,1: 5 or 1: 10 respectively by methyl alcohol and methylene dichloride.
6. an application for guanine derivatives as claimed in claim 1, is characterized in that, this guanine derivatives has identification, stable, keying action to telomere G-tetra-serobilas and I-motifDNA.
7. the application of guanine derivatives according to claim 6, is characterized in that, telomere G-tetra-serobilas and I-motifDNA that described telomere G-tetra-serobilas and I-motifDNA are people.
8. the application of guanine derivatives according to claim 6, is characterized in that, the application of guanine derivatives can be identified telomere G-tetra-serobilas and I-motifDNA by fluorometric assay, adds the guanine derivatives of I-motifDNA, and its fluorescence significantly reduces.
9. the application of guanine derivatives according to claim 6, it is characterized in that, guanine derivatives has fluorescent quenching phenomenon to telomere G-tetra-serobilas, illustrates that described guanine derivatives can replace TO and be deposited in the position on DNA, with telomere G-tetra-serobila DNA, keying action occurs.
10. the application of guanine derivatives according to claim 6, it is characterized in that, guanine derivatives makes the CD signal of I-motifDNA occur significantly to strengthen and red shift, illustrate that described guanine derivatives all can make the structure of I-motifDNA occur obviously to change, and forms more stable structure.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105823764A (en) * | 2016-03-17 | 2016-08-03 | 同济大学 | Calix[4]arene adenine derivative-oxidized graphene compound, preparation method and applications thereof |
-
2012
- 2012-07-06 CN CN201210234339.9A patent/CN103524504A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| QING DAI, ET AL.: "Efficient Syntheses of C8-Aryl Adducts of Adenine and Guanine Formed by Reaction of Radical Cation Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons with DNA", 《J. ORG. CHEM.》 * |
| 买尔哈巴.吾买尔等: "碱基衍生物对端粒酶的抑制作用研究", 《中国化学会第28届学术年会》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105823764A (en) * | 2016-03-17 | 2016-08-03 | 同济大学 | Calix[4]arene adenine derivative-oxidized graphene compound, preparation method and applications thereof |
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