CN107226817A - A kind of pyropheophorbide-a methyl ether compound and preparation method and application - Google Patents
A kind of pyropheophorbide-a methyl ether compound and preparation method and application Download PDFInfo
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- CN107226817A CN107226817A CN201610176244.4A CN201610176244A CN107226817A CN 107226817 A CN107226817 A CN 107226817A CN 201610176244 A CN201610176244 A CN 201610176244A CN 107226817 A CN107226817 A CN 107226817A
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- pyropheophorbide
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- KPMNNVDYGPYSSS-CFJSMKAVSA-N CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(O)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C(C)OC)c(C)c1[nH]2 Chemical compound CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(O)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C(C)OC)c(C)c1[nH]2 KPMNNVDYGPYSSS-CFJSMKAVSA-N 0.000 description 1
- NDYXBZGJXUUPIS-DBQFSCIFSA-N CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(OC)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C(C)OC)c(C)c1[nH]2 Chemical compound CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(OC)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C(C)OC)c(C)c1[nH]2 NDYXBZGJXUUPIS-DBQFSCIFSA-N 0.000 description 1
- RYLBYBPLWNFWPG-KYWUBCJDSA-N CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(OC)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C=C)c(C)c1[nH]2 Chemical compound CCC(C(/C=C(/C(C)=C1C(C2)=O)\NC1=C2C([C@@H](CCC(OC)=O)C1C)=N/C1=C1)=N2)=C(C)/C2=C/c2c(C=C)c(C)c1[nH]2 RYLBYBPLWNFWPG-KYWUBCJDSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0076—PDT with expanded (metallo)porphyrins, i.e. having more than 20 ring atoms, e.g. texaphyrins, sapphyrins, hexaphyrins, pentaphyrins, porphocyanines
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Abstract
The present invention relates to a kind of pyropheophorbide-a methyl ether compound and preparation method and application, the compound has following structures (I)：
Description
Technical field
The present invention relates to photosensitive drug and photodynamic therapy field, more particularly to a kind of pyropheophorbide-a methyl ether
Compound and preparation method and application.
Background technology
Photodynamic therapy (PDT) is that one kind treats tumour, macular degeneration, actinic keratoma, nevus flammeus, point
The new method of the diseases such as sharp condyloma.Since entering clinical research from 1970s, PDT has achieved order in clinical treatment
The achievement that people attractes attention, there is selectivity good, toxic side effect be small because of it, favorable repeatability, safety, minimal invasive, can concertedness etc. it is excellent
Point is shown one's talent, and shows huge potentiality and powerful vitality.
The principle of photodynamic therapy is that sensitising agent enters after body, is optionally gathered in blood circulation in target tissue,
Then shone directly into using the laser of certain wavelength on tumor tissues, become unstable by ground state after sensitiser absorption photon energy
Fixed excitation state, the sensitising agent in excitation state reacts with surrounding molecular, produces free radical (such as single line of high oxidation activity
State oxygen), target cell is acted on, causes cell metabolism disorderly, target cell is killed.
In optical dynamic therapy, photosensitive drug (also referred to as sensitising agent or photo-dynamical medicine) is used as the carrier of energy, reaction
Bridge and play conclusive effect.First generation sensitising agent is with first sensitising agent in Holland's listing in 1993
Photofrin II are representative, and it is the mixture of the complicated hematoporphyrin derivative of composition, it is difficult to carries out quality control, produced
Journey poor repeatability.For preparation structure it is single, be easy to carry out the new drug of quality control, people carry out to chlorophyll and its derivative
Compared with in-depth study, be therefrom found that chemical constitution is clear and definite, constituent is single, red light district absorb stronger photo-dynamical medicine he
Draw pool fragrant (Talaporfin), in the treatment for being widely used in various tumor diseases, achieve significant social benefit with
Economic benefit.But talaporfin is remained in some shortcomings, extremely difficult, production cost height, price height etc., influence popularization are such as prepared
Promote.
The content of the invention
To overcome talaporfin to prepare the shortcomings of extremely difficult, production cost is high, price is high, we are to chlorophyll and its spread out
Biology has conducted intensive studies, by substantial amounts of exploration work, has designed and synthesized pyropheophorbide-a methyl ether chemical combination
Thing, completes the present invention.
The present invention relates to a kind of pyropheophorbide-a methyl ether compound and preparation method thereof and purposes.
Technical scheme is summarized as follows：
Pyropheophorbide-a methyl ether compound has following structures (I)：
The preparation method of pyropheophorbide-a methyl ether compound, comprises the following steps：
By porphyrin compound (II) (its synthetic method reference literature Photochemistry and Photobiology,
1996,64 (1)：194-204) dissolved with methanol, add the acetic acid solution of the hydrogen bromide containing 30-35%, heating stirring；Then depressurize
Concentration；Methanol is added into residue, room temperature continues to stir；Then isolated compound (III).Compound obtained above
(III) it is dissolved in organic solvent, adds alkali, stir at room temperature.Adjust pH value of solution；Extraction；Washing, collects organic phase；Organic phase
Column chromatography for separation is carried out after concentration, compound (I) is obtained.
In the step, it is DMF, Isosorbide-5-Nitrae-two that formula (II), which prepares organic solvent used during formula (III),
The ring of oxygen six, dimethyl sulfoxide (DMSO), acetonitrile, acetone, tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE), glycol dimethyl ether, ethylene glycol two
Any one in ether, ethylene glycol di-n-butyl ether etc. or any a variety of mixture.
In the step, it is diisopropyl ethyl amine, triethylamine, pyridine, sodium that formula (III), which prepares alkali used during formula (I),
Hydrogen, potassium carbonate, sodium carbonate, saleratus, sodium acid carbonate, potassium hydrogen phosphate, dibastic sodium phosphate, potassium hydroxide, sodium hydroxide, hydroxide
Lithium, sodium formate, sodium acetate, sodium methoxide, caustic alcohol, potassium ethoxide, normal propyl alcohol sodium, normal propyl alcohol potassium, sodium isopropylate, potassium isopropoxide, uncle
Any one in butanol potassium, sodium tert-butoxide etc. or any a variety of mixture or its aqueous solution；Reaction time is 8~18h.
In the step, filler when formula (II) prepares formula (III) used in column chromatography for separation is silica gel, and eluent is two
Chloromethanes：The mixed solution (1: 30~30: 1) of petroleum ether.
In the step, it is methanol, ethanol, ethylene glycol, acetic acid second that formula (III), which prepares organic solvent used during formula (I),
Ester, acetone, dichloromethane, acetonitrile, tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE), glycol dimethyl ether, ethylene glycol diethyl ether, second
Any one in glycol di-n-butyl ether etc. or any a variety of mixture.
In the step, filler when formula (III) prepares formula (I) used in column chromatography for separation is silica gel, and eluent is two
Chloromethanes: the mixed solution (100: 1~5: 1) of methanol.
A kind of pyropheophorbide-a methyl ether compound of the present invention can be yellow as light power diagnosis and treatment tumour, retina
The medicine of the diseases such as spot denaturation, actinic keratoma, nevus flammeus, condyloma acuminatum.
Embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limitation the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, people in the art
Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited
Scope.
[embodiment 1]
1st, 3- (1- methoxy ethyls) -3- goes the preparation method of vinyl pyropheophorbide-a
230mg (0.4mmol) Methyl Pyropheophorbides 20ml methanol is dissolved, 5mL brominations containing 30-35% are added
The acetic acid solution of hydrogen, 3 hours are reacted at 40 DEG C.It is concentrated under reduced pressure, 10mL methanol is added into residue, room temperature continues to stir 8
Hour.2M LiOH solution 20mL are added, are stirred at room temperature 5 hours.AcOH is added into reaction solution, pH to 5-6 is adjusted；Add
60mL CH2Cl2Extractive reaction liquid；Organic phase is washed with saturated common salt.Organic phase is collected, anhydrous magnesium sulfate is dried, filtering；Will filter
Liquid is concentrated；Gained residue is subjected to column chromatography (methylene chloride/methanol=30/1), dark brown product 212mg, yield is obtained
79.4%.1H NMR (400MHz, CDCl3)：δ 9.70,9.50,8.56 (each s, 1H, meso-H), 5.89 (q, J=13.1,
6.5Hz, 1H, 3a-H), 5.33-5.10 (dd, 2H, 132- H), 4.52-4.50 (m, 1H, 17-H), 4.35-4.33 (m, 1H, 18-
H), 3.71 (q, J=7.3Hz, 2H, 8a-H), 3.66 (s, 3H, 3-OCH3), 3.58 (s, 3H, 12-CH3), 3.42 (s, 3H, 2-
CH3), 3.29 (s, 3H, 7-CH3), 2.72-2.69 (m, 2H, 17b-H), 2.67-2.63 (m, 2H, 17a-H), 2.15 (d, J=
4.5Hz, 3H, 3b-CH3), 1.85 (d, J=7.1Hz, 3H, 18-CH3), 1.73 (t, J=7.4Hz, 3H, 8b-CH3), -1.66
(s, 2H, NH) .MS (MALDI-TOF) m/z：566.2750[M+H+] .UV-Vis (DMSO), λ max (nm)：421,509,532,
613,669.
2nd, the light power antiproliferative of human esophagus cancer cell (Eca-109) is tested
Subject cell：Human esophagus cancer cell (Eca-109)
Test medicine：Pyropheophorbide-a methyl ether (hereinafter referred to as sensitising agent 1).Aseptically the medicine is dissolved in
Minimum Tween-80, with normal saline dilution to 0.2mg/mL solution for standby；Hematoporphyrin monomethyl ether (Shanghai elder generation brightness medical sci-tech
Co., Ltd), compound method is with sensitising agent 1.
Light source：XD-650AB type lasers.
Laser power instrument：SD2490 type laser power measurement instrument.
The effect experiment of light power anti-tumour cell proliferative：
After cell pancreatin in exponential phase is digested, cell suspension is resuspended into complete medium；Then will be swollen
Oncocyte is inoculated in 96 orifice plates, per the μ l of hole 100, is placed in 37 DEG C of 5%CO2Different photosensitive of concentration is added after incubator culture, 24h
Agent；12h changes fresh culture into, then carries out illumination (power 25mW/cm2, wavelength 650nm, light dosage 16J/cm2)；After 24h
Carry out MTT detections.Culture terminates the MTT that preceding 4h adds 10 μ l 5mg/ml, and suction is abandoned after nutrient solution plus 100 μ l DMSO are terminated instead
Should, ELIASA 570nm detection OD values.Experiment is in triplicate.Experimental result is shown in Table 1, as a result shows that sensitising agent 1 is thin to human esophagus cancer
Born of the same parents (Eca-109) have significant light power antiproliferative effect.
The sensitising agent 1 of table 1 is to human esophagus cancer cell (Eca-109) inhibited proliferation
3rd, the optical dynamic therapy of human esophagus cancer cell in nude mouse (Eca-109) transplantable tumor is tested
Animal subject：BABL/c nude mouses, 15~20g of average weight (Shanghai Slac Experimental Animal Co., Ltd.)
Test medicine：Pyropheophorbide-a methyl ether (hereinafter referred to as sensitising agent 1).Aseptically the medicine is dissolved in
Minimum Tween-80, with normal saline dilution to 0.2mg/mL solution for standby；Hematoporphyrin monomethyl ether (Shanghai elder generation brightness medical sci-tech
Co., Ltd), compound method is with sensitising agent 1.
Light source：XD-650AB type lasers.
Laser power instrument：SD2490 type laser power measurement instrument.
Human esophagus cancer cell (Eca-109) transplantable tumor Photodynamic polymer is tested：
In mouse anterior part of chest subcutaneous vaccination Eca-109 cells under aseptic condition, when tumour length is to 5~7mm of diameter, choose
Well-grown, the nude mice without ulcer, the hemispherical single tumour of tool, are grouped, every group 8, tail vein note at random by brood same sex
Administration is penetrated, and using drug solvent as blank control, Temoporfin is made into same concentrations solution as positive control, after administration
3h is 180mW/cm with power density2Laser (wavelength 650mm, light dosage 100J/cm2) radiation tumour；14 days after illumination, place
Dead mouse, peels off tumour, claims knurl weight, calculates inhibiting rate.
Tumor control rate %=(C-T)/C × 100%
In formula, T：The average knurl weight of administration group；C：The average knurl weight of control group.
Experimental result is shown in Table 2, and sensitising agent 1 has significant light power inhibitory action to tumour.
Inhibition of the sensitising agent 1 of table 2 to tumour
* P ＜ 0.05 and blank control.
Claims (8)
1. a kind of pyropheophorbide-a methyl ether compound, it is characterized in that with following structures (I)：
。
2. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 1, its feature includes as follows
Step：
Porphyrin compound (II) is dissolved with methanol, the acetic acid solution of the hydrogen bromide containing 30-35%, heating stirring is added；Then subtract
Pressure concentration, methanol is added into residue, and room temperature continues to stir；Then isolated compound (III).Chemical combination obtained above
Thing (III) is dissolved in organic solvent, is added alkali, is stirred at room temperature.Adjust after pH value of solution, extract, organic phase is collected in washing.Have
Machine carries out column chromatography for separation after mutually concentrating, and obtains compound (I).
。
3. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 2, it is characterised in that：Institute
State in step, it is DMF, Isosorbide-5-Nitrae-dioxane, two that formula (II), which prepares organic solvent used during formula (III),
Methyl sulfoxide, acetonitrile, acetone, tetrahydrofuran, ethanol, methyl tertiary butyl ether(MTBE), glycol dimethyl ether, ethylene glycol diethyl ether, second two
Any one in alcohol di-n-butyl ether equal solvent or any a variety of mixture.
4. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 2, it is characterised in that：Institute
State in step, when formula (III) prepares formula (I) alkali used be diisopropyl ethyl amine, triethylamine, pyridine, sodium hydrogen, potassium carbonate,
Sodium carbonate, saleratus, sodium acid carbonate, potassium hydrogen phosphate, dibastic sodium phosphate, potassium hydroxide, sodium hydroxide, lithium hydroxide, sodium formate,
Sodium acetate, sodium methoxide, potassium methoxide, caustic alcohol, potassium ethoxide, normal propyl alcohol sodium, normal propyl alcohol potassium, sodium isopropylate, potassium isopropoxide, the tert-butyl alcohol
Any one in potassium, sodium tert-butoxide etc. or any a variety of mixture or its aqueous solution；Reaction time is 6~16h.
5. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 2, it is characterised in that：Institute
State in step, filler when formula (II) prepares formula (III) used in column chromatography for separation is silica gel, and eluent is dichloromethane: first
The mixed solution (1: 30~30: 1) of alcohol.
6. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 2, it is characterised in that：Institute
State in step, it is methanol, ethanol, ethylene glycol, ethyl acetate, acetone, two that formula (III), which prepares organic solvent used during formula (I),
Chloromethanes, acetonitrile, tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE), glycol dimethyl ether, ethylene glycol diethyl ether, the positive fourth of ethylene glycol two
Any one in ether etc. or any a variety of mixture.
7. a kind of preparation method of pyropheophorbide-a methyl ether compound according to claim 2, it is characterised in that：Institute
State in step, filler when formula (III) prepares formula (I) used in column chromatography for separation is silica gel, and eluent is dichloromethane: methanol
Mixed solution (100: 1~5: 1).
8. a kind of pyropheophorbide-a methyl ether compound described in claim 1 can be yellow as light power diagnosis and treatment tumour, retina
The medicine of the diseases such as spot denaturation, actinic keratoma, nevus flammeus, condyloma acuminatum.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610176244.4A CN107226817A (en) | 2016-03-25 | 2016-03-25 | A kind of pyropheophorbide-a methyl ether compound and preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265465A (en) * | 2018-11-07 | 2019-01-25 | 陈志龙 | A kind of novel pyropheophorbide-a derivative and the preparation method and application thereof |
| CN114315842A (en) * | 2022-01-20 | 2022-04-12 | 上海先辉医药科技有限公司 | Novel carbonic anhydrase IX targeted photosensitizer and application thereof in medical field |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384743A (en) * | 2015-11-12 | 2016-03-09 | 中国人民解放军第二军医大学 | Pyropheophorbide-a ether amino acid derivative as well as preparation method and application thereof |
-
2016
- 2016-03-25 CN CN201610176244.4A patent/CN107226817A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105384743A (en) * | 2015-11-12 | 2016-03-09 | 中国人民解放军第二军医大学 | Pyropheophorbide-a ether amino acid derivative as well as preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| BARBARA W. HENDERSON ET AL.: "An in Vivo Quantitative Structure-Activity Relationship for a Congeneric Series of Pyropheophorbide Derivatives as Photosensitizers for Photodynamic Therapy", 《CANCER RESEARCH》 * |
| R. VANYU"R ET AL.: "Prediction of Tumoricidal Activity and Accumulation of Photosensitizers in Photodynamic Therapy Using Multiple Linear Regression and Artificial Neural Networks", 《PHOTOCHEMISTRY AND PHOTOBIOLOGY》 * |
| ZHI MENG ET AL.: "Amino acid derivatives of pyropheophorbide-a ethers as photosensitizer: Synthesis and photodynamic activity", 《CHINESE CHEMICAL LETTERS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265465A (en) * | 2018-11-07 | 2019-01-25 | 陈志龙 | A kind of novel pyropheophorbide-a derivative and the preparation method and application thereof |
| CN109265465B (en) * | 2018-11-07 | 2021-09-28 | 陈志龙 | Novel pyropheophorbide a derivatives and preparation method and application thereof |
| CN114315842A (en) * | 2022-01-20 | 2022-04-12 | 上海先辉医药科技有限公司 | Novel carbonic anhydrase IX targeted photosensitizer and application thereof in medical field |
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