CN106588994B - Phthalocyanine aryl ruthenium complex and its preparation method and application - Google Patents
Phthalocyanine aryl ruthenium complex and its preparation method and application Download PDFInfo
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- CN106588994B CN106588994B CN201610947733.5A CN201610947733A CN106588994B CN 106588994 B CN106588994 B CN 106588994B CN 201610947733 A CN201610947733 A CN 201610947733A CN 106588994 B CN106588994 B CN 106588994B
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- phthalocyanine
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- aryl ruthenium
- ruthenium complex
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- 239000012327 Ruthenium complex Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229960000935 dehydrated alcohol Drugs 0.000 claims abstract description 12
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 4
- 229910019891 RuCl3 Inorganic materials 0.000 claims abstract description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims abstract description 3
- 229910009112 xH2O Inorganic materials 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- -1 phthalocyanine aryl ruthenium complexes Chemical class 0.000 abstract description 10
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 208000007578 phototoxic dermatitis Diseases 0.000 description 2
- 231100000018 phototoxicity Toxicity 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses phthalocyanine aryl ruthenium complexes: shown in structural formula such as formula (I).The invention discloses the preparation methods of phthalocyanine aryl ruthenium complex, comprising: 1) by RuCl3·xH2O and γ-terpinene are dissolved in dehydrated alcohol, and reflux obtains formula (II) compound；2) it takes the bromo- phthalocyanine of β-one, 5- (2- hydroxyethyl) -2- bipyridine and potassium carbonate to be dissolved in DMF solution reaction, obtains formula (III) compound；3) formula (III) compound and formula (II) compound are dissolved in dehydrated alcohol, flowed back, n-hexane is added, precipitates crystal.The invention discloses the purposes of phthalocyanine aryl ruthenium complex.
Description
Technical field
The invention belongs to technical field of pharmaceuticals, it is related to a kind of phthalocyanine aryl ruthenium complex and its preparation method and application.
Background technique
Currently, cis-platinum has become in the world for one of most commonly used 3 kinds of drugs for the treatment of cancer, sell in the year in the U.S.
Volume reaches nearly 500,000,000 dollars.But the use of cis-platinum is there is also there is certain deficiency, it does not have inhibiting effect to certain tumours, and easily
Cross resistance is generated with other platinum preparations.In addition, there are many side effects for cis-platinum, such as renal toxicity, peripheral nerve toxicity, marrow poison
Property, haematics toxicity and emetic etc..Therefore, efficient, low toxicity and the new type antineoplastic medicine one without cross resistance are found
It is directly the research hotspot of researcher.
Aryl ruthenium complex since its toxicity is low, the high feature of anti-tumor activity and be concerned by people.Porphyrin
Object is closed to attract people's attention since it stablizes nontoxic property and its good luminescent properties.With porphyrins aryl ruthenium
Complex-bound obtains porphyrin and connects aryl ruthenium ruthenium compound, due to the synergistic effect of aryl ruthenium and porphyrin compound, can make it
Have phototoxicity on the basis of having good anti-tumor activity, achievees the effect that enhance its cell inhibitory activity.
Summary of the invention
It is excellent it is an object of the invention to solve at least the above problems and/or defect, and provide at least to will be described later
Point.
The present invention separately has a purpose to be to provide a kind of phthalocyanine aryl ruthenium complex.
A further object of the present invention is to provide a kind of preparation method of phthalocyanine aryl ruthenium complex.
It is a still further object of the present invention to provide the purposes of the phthalocyanine aryl ruthenium complex.
For this purpose, technical solution provided by the invention are as follows:
A kind of phthalocyanine aryl ruthenium complex, shown in the phthalocyanine aryl ruthenium complex structural formula such as formula (I):
The preparation method of the phthalocyanine aryl ruthenium complex, includes the following steps:
1) RuCl for being 37% by ruthenium weight content3·xH2The γ-terpinene that O and purity are 95% is dissolved in dehydrated alcohol
In, it is heated to reflux stirring, precipitation is stood and obtains formula (II) compound；
2) the bromo- phthalocyanine of β-one, 5- (2- hydroxyethyl) -2- bipyridine and potassium carbonate is taken to be dissolved in DMF solution, nitrogen protection
After lower 80 DEG C of reactions, stands precipitation and obtain formula (III) compound；
3) formula (III) compound and formula (II) compound are dissolved in dehydrated alcohol, heating stirring reflux, after the reaction was completed
Solution evaporates surplus 2ml liquid, and 30ml n-hexane is added, and red crystals, as product are precipitated.
Preferably, in the phthalocyanine-aryl ruthenium compound preparation method, in step 1), dosage of each component are as follows:
The RuCl3·xH2O is 0.366g, and the γ-terpinene is 3ml, and the dehydrated alcohol is 10ml；
The mixing time that is heated to reflux is 6 hours.
Preferably, in the phthalocyanine-aryl ruthenium compound preparation method, in step 2), dosage of each component are as follows:
The bromo- phthalocyanine of β-one is 0.1g, and 5- (2- the hydroxyethyl) -2- bipyridine is 0.06g, and the potassium carbonate is 0.20g,
The DMF solution is 10ml；
It is reacted 8 hours in lower 80 DEG C of the nitrogen protection.
Preferably, in the phthalocyanine-aryl ruthenium compound preparation method, in step 3), dosage of each component are as follows:
Formula (III) compound is 30mg, and formula (II) compound is 12mg, and the dehydrated alcohol is 8ml；
The heating stirring return time is 6 hours.
The purposes of the phthalocyanine aryl ruthenium complex is prepared using the phthalocyanine aryl ruthenium complex for treating ovary
The drug of cancer.
The present invention is include at least the following beneficial effects:
Organometallic ruthenium compound of the invention can be used for preparing the drug for the treatment of cancer, can be made into injection, tablet, ball
Agent, the form use of capsule, suspending agent or emulsion.
The preparation method of organometallic ruthenium compound of the present invention is simple, and raw material is easy to get, and has advantage at low cost.
Further advantage, target and feature of the invention will be partially reflected by the following instructions, and part will also be by this
The research and practice of invention and be understood by the person skilled in the art.
Specific embodiment
The present invention will be further described in detail below with reference to the embodiments, to enable those skilled in the art referring to specification
Text can be implemented accordingly.
It should be appreciated that such as " having ", "comprising" and " comprising " term used herein do not allot one or more
The presence or addition of a other elements or combinations thereof.
Embodiment 1
A kind of phthalocyanine aryl ruthenium complex, shown in the structural formula such as formula (I) of the phthalocyanine aryl ruthenium complex:
Structural formula:
2) physicochemical property: formula (I) compound is red crystals, soluble easily in water and organic solvent, nuclear magnetic resonance spectroscopy number
According to for1H NMR:(ppm,CDCl3) δ=1.28 (6H, d, J=6.1Hz), 2.38 (3H, s), 3.95 (2H, m, J=5.9Hz),
3.15 (1H, m, J=5.9Hz), 4.35 (2H, d, J=5.9Hz), 6.70-7.90 (22H, m, J=5.8Hz), 8.42-8.60
(4H, m, J=5.7Hz).
Embodiment 2
The preparation method of formula (I) compound, comprising the following steps:
1) RuCl for being 37% by 0.366g ruthenium weight content3·xH2The γ-terpinene that O and 3ml purity is 95% is dissolved in
10ml dehydrated alcohol is heated to reflux stirring 6 hours, stands precipitation and obtains formula (II) compound.
2) the bromo- phthalocyanine of 0.1g β-one, 0.05g 5- (2- hydroxyethyl) -2- bipyridine are weighed, 0.22g potassium carbonate is dissolved in
10ml DMF solution stands precipitation and obtains formula (III) compound after nitrogen protection lower 80 DEG C of reactions 8 hours.
3) formula of 30mg (III) compound and 12mg formula (II) compound are dissolved in 8ml dehydrated alcohol, heating stirring reflux 6
Hour, solution is evaporated surplus 2ml liquid after the reaction was completed, 30ml n-hexane is added, red crystals, as product are precipitated.
Embodiment 3
Using MTT method, vitro cytotoxicity measurement is carried out.The organometallic ruthenium compound and ovum that embodiment 1 is obtained
Nest cancer A2780 cell strain is distinguished action time 72 hours, and the results are shown in Table 1.
Medium effective concentration (IC of 1 organometallic ruthenium compound of table to tumor cell line50)
| Cell strain | A2780 (is protected from light) | A2780 (illumination) |
| IC50(μmol/mL) | 8.3±1.2 | 1.0±0.1 |
Show formula of the invention (I) compounds on ovarian cancer A2780 cell by the experiment of tumor cell in vitro inhibitory activity
Strain has significant inhibiting effect, and its inhibiting effect is remarkably reinforced under visible light illumination.
It can be seen from the results above that organometallic ruthenium compound of the invention shows the change through anticancer experiment in vitro
Closing object has strong anti-tumor activity and preferable cell phototoxicity.The present invention provides to research and develop new anti-tumor drug
New thinking.
Module number and treatment scale described herein are for simplifying explanation of the invention.To phthalocyanine virtue of the invention
The application of base ruthenium complex and its preparation method and application, modifications and variations are apparent to one skilled in the art
's.
Although the embodiments of the present invention have been disclosed as above, but its is not only in the description and the implementation listed
With it can be fully applied to various fields suitable for the present invention, for those skilled in the art, can be easily
Realize other modification, therefore without departing from the general concept defined in the claims and the equivalent scope, the present invention is simultaneously unlimited
In specific details and embodiment shown and described herein.
Claims (6)
1. a kind of phthalocyanine aryl ruthenium complex, which is characterized in that shown in the phthalocyanine aryl ruthenium complex structural formula such as formula (I):
2. the preparation method of phthalocyanine aryl ruthenium complex as described in claim 1, which comprises the steps of:
1) RuCl for being 37% by ruthenium weight content3·xH2The γ-terpinene that O and purity are 95% is dissolved in dehydrated alcohol, is added
Hot return stirring stands precipitation and obtains formula (II) compound；
2) the bromo- phthalocyanine of β-one, 5- (2- hydroxyethyl) -2- bipyridine and potassium carbonate is taken to be dissolved in DMF solution, 80 under nitrogen protection
DEG C reaction after, stand be precipitated obtain formula (III) compound；
3) formula (III) compound and formula (II) compound are dissolved in dehydrated alcohol, heating stirring reflux, after the reaction was completed solution
Surplus 2ml liquid is evaporated, 30ml n-hexane is added, red crystals, as product are precipitated.
3. phthalocyanine as claimed in claim 2-aryl ruthenium compound preparation method, which is characterized in that in step 1), each group
Divide dosage are as follows: the RuCl3·xH2O is 0.366g, and the γ-terpinene is 3ml, and the dehydrated alcohol is 10ml；
The mixing time that is heated to reflux is 6 hours.
4. phthalocyanine as claimed in claim 2-aryl ruthenium compound preparation method, which is characterized in that in step 2), each group
Divide dosage are as follows: the bromo- phthalocyanine of β-one is 0.1g, and it is 0.06g, the carbonic acid that 5- (2- the hydroxyethyl) -2-, which connects two pyridines,
Potassium is 0.20g, and the DMF solution is 10ml；
It is reacted 8 hours in lower 80 DEG C of the nitrogen protection.
5. phthalocyanine as claimed in claim 2-aryl ruthenium compound preparation method, which is characterized in that in step 3), each group
Divide dosage are as follows: formula (III) compound is 30mg, and formula (II) compound is 12mg, and the dehydrated alcohol is 8ml；
The heating stirring return time is 6 hours.
6. the purposes of phthalocyanine aryl ruthenium complex described in claim 1, which is characterized in that cooperated using the phthalocyanine aryl ruthenium
Object prepares the drug for treating oophoroma.
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| CN201610947733.5A CN106588994B (en) | 2016-10-26 | 2016-10-26 | Phthalocyanine aryl ruthenium complex and its preparation method and application |
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| CN106588994B true CN106588994B (en) | 2019-02-22 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
| CN101851256A (en) * | 2010-04-30 | 2010-10-06 | 广东药学院 | Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof |
-
2016
- 2016-10-26 CN CN201610947733.5A patent/CN106588994B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008090526A1 (en) * | 2007-01-26 | 2008-07-31 | Universite De Neuchatel | Organometallic compounds |
| CN101851256A (en) * | 2010-04-30 | 2010-10-06 | 广东药学院 | Ruthenium (II) porphyrin complex connected by flexible carbon chain and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| Tagging (Arene)ruthenium(II) Anticancer Complexes with Fluorescent Labels;Fabio Zobi et al;《Eur. J. Inorg. Chem.》;20070503;第2783-2796页 |
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Effective date of registration: 20191114 Address after: 210000 No.1, Xiushan Middle Road, Lishui Economic Development Zone, Nanjing City, Jiangsu Province Patentee after: NANJING ADVANCED BIOMATERIALS AND PROCESS EQUIPMENT RESEARCH INSTITUTE Co.,Ltd. Address before: 530001 Nanning Normal University, 175 Mingxiu East Road, Nanning City, Guangxi Zhuang Autonomous Region Patentee before: Nanning Normal University |