CN1600780A - Hypocrellin in cyclic ethylene diamine group, preparation method and usage - Google Patents
Hypocrellin in cyclic ethylene diamine group, preparation method and usage Download PDFInfo
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- CN1600780A CN1600780A CN 03134667 CN03134667A CN1600780A CN 1600780 A CN1600780 A CN 1600780A CN 03134667 CN03134667 CN 03134667 CN 03134667 A CN03134667 A CN 03134667A CN 1600780 A CN1600780 A CN 1600780A
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Abstract
The invention particularly relates to ethylenidemine bamboo parasitic fungus, its prepn. method and uses.
Description
Technical field
The invention belongs to the photosensitizers field, particularly cyclic ethylene diamine group Hypocrellin B and its production and use.
Background technology
Hypocrellin (Hypocrellin) is a kind of parasitical fungi from the arrow bamboo that parasitizes Yunnan Province of China one band---the photosensitizers of a kind of natural pigment class of extracting the red bamboo fungus (Hypocrella bambuase), belong to 3,10-dihydroxyl-4,9-perylene quinone derivative.Natural hypocrellin mainly contains two kinds of components: Hypocrellin A (HypocrellinA is called for short HA) and Hypocrellin B (HypocrellinB is called for short HB), and structure and atom numbering are as follows:
The productive rate that extracts hypocrellin from the exsiccant red bamboo fungus can reach 3-5%.Be the first element more than 95% wherein, but under alkaline condition, HA can dewater and be converted into HB.Document " structural changes of Hypocrellin A in alkalescence and neutral solution ", organic chemistry, 1989,9:252, Zhao Kaihong, Jiang Lijin are seen in the extraction of hypocrellin and the conversion from HA to HB.Structure and the existing several pieces of outstanding summaries of character about hypocrellin are delivered, as " structure and the character of the structure of hypocrellin, character, photochemical reaction and reaction mechanism (I)-hypocrellin ", Science Bulletin, 1990,35:1608, Jiang Lijin; " reaction of the structure of hypocrellin, character, photochemical reaction and reaction mechanism (II)-hypocrellin ", Science Bulletin, 1990,35:1681, Jiang Lijin; Lown, J.W.Photochemistry and photobiology of perylenequinones.Can.J.Chem., 1997,75:99; Diwu, Z.J., Lown, J.W.Hypocrellins and their uses inphotosensitization.Photochem.Photobiol., 1990,52:609; Diwu, Z.J.Novel therapeutic and diagnostic applications of hypocrellins andhypericin s.Photochem.Photobiol., 1995,61:529; Jiang Lijin, He Yuying; " optical physics, photochemistry and the photo bio of hypocrellin class photosensitizers " Science Bulletin, 2000,45:2019.Because hypocrellin and derivative thereof can produce a large amount of active oxygen (creating singlet oxygen by using behind irradiation, superoxide anion, hydroxyl radical free radical etc.), many cancer cells are had killing action, so, in the past the research of hypocrellin and derivative thereof mainly all was limited on the drug candidate as phototherapy, as Diwu, Z.J., Lown, J.W.Hypocrellins and their uses in photosensitization.Photochem.Photobiol., 1990,52:609; Diwu, Z.J., Lown, J.W.Phototherapeuticpotential of alternative photosensitizers to porphyrins.Pharmacol.Ther., 1994,63:1-35; Pang, S.Z., Qing, J.F., Yue, J.C., An, J.Y.Photosensitizing damage to morphology of Hela cells by bromide ofhypocrellinB (5-Br-HB) .Acta Biophys.Sin., 1994,10:651; Pleasure adds prosperous, Pang Suzhen, Zhang Manhua etc.; The plain modifier of hypocrellin second (thanomin) is studied for the light injury of ascites liver cancer cell; Acta Biophysica Sinica, 1994,10:485-492; Zhang, W.G., Ma, L.P., Wang, S.W., Zhang, M.H., Yang, H.Y., Zhao, H.X., Zhang, Z.Y.Antisensebcl-2 retrovirus vector increase the sensitivity of a human gastricadenocarcinoma cell line to photodynamic therapy.J.Photochem.Photobiol.B:Biol., 1998,44:21; Zhang, J., Cao, E.H., Li, J.F., Zhang, T.C., Ma, W.J.Photodynamic effects of hypocrellin A on threehuman malignant cell lines by inducing apoptotic cell death J.Photochem.Photobiol.B:Biol., 1998,43:106.
Summary of the invention
One of purpose of the present invention provides a kind of cyclic ethylene diamine group Hypocrellin B.
Two of purpose of the present invention provides a kind of cyclic ethylene diamine group Preparation of Hypocrellin B method.
Three of purpose of the present invention is that the cyclic ethylene diamine group Hypocrellin B is used for optical function material and device as photosensitizers.
Four of purpose of the present invention provides with respect to known Hypocrellin B class photosensitizers, the evaluation method of cyclic ethylene diamine group Hypocrellin B photosensitive property.
The structure of cyclic ethylene diamine group Hypocrellin B of the present invention and atom numbering are as follows:
The synthetic method of cyclic ethylene diamine group Hypocrellin B of the present invention, in the Hypocrellin B of raw material 200 weight parts, the method for preparing the cyclic ethylene diamine group Hypocrellin B is:
200 weight part Hypocrellin Bs are dissolved in 200～250 milliliters of new tetrahydrofuran (THF)s that steam, add 15～25 milliliters of quadrols; Stir under the lucifuge condition, control reaction temperature is between 50～55 degrees centigrade, reacts 12 hours stopped reaction; The pressure reducing and steaming solvent with 200 milliliters of chloroform dissolvings, is used the unnecessary quadrol of dilute hydrochloric acid flush away of 10～20 milliliters of 1wt% then, is neutral substantially until water layer; Boil off chloroform, get black solid; With 100 weight part re-crystallizing in ethyl acetate, obtain the cyclic ethylene diamine group Hypocrellin B, calculating productive rate with Hypocrellin B is 52～56%.
Cyclic ethylene diamine group Hypocrellin B of the present invention can be used as semi-conductor and is used for optical function material and device for photosensitive dose.
Semi-conductive photosensitization:
After the semi-conductor extinction, the electronics of valence band can be excited and transit on the conduction band, and positive hole appears in valence band, and electronegative electronics appears in conduction band, so just might form optical function material and device.
General semi-conductor is as inorganic titanium dioxide (TiO
2) and organically polystyrene support (PPV) can only absorb ultraviolet ray; (molar extinction coefficient is 10 and synthetic dyestuff (hereinafter to be referred as dyestuff) or natural pigment (hereinafter to be referred as pigment) have very strong absorption at visible region
4More than).As them as photosensitizers attached to semi-conductive surface, dyestuff or pigment strong absorption visible light and be excited, the photoelectron that produces is injected into semi-conductive conduction band, and the electronics on the semi-conductor valence band can be filled up dyestuff or the pigment positive hole that the back occurs that is excited, dyestuff or pigment are restored, and semi-conductor has then also produced charge separation as itself absorbs ultraviolet ray.Like this, just semi-conductive sensitization scope has been elongated visible light from ultraviolet ray.Here it is semi-conductive dyestuff or pigment photosensitization are referred to as dye sensitization or spectral sensitization again.
The testing method of photosensitizers photosensitive property of the present invention is characterized in that photosensitizers is coated on the electrically-conductive backing plate, directly measures the relative efficiency that the sensitizing agent photoelectron injects by direct-current biasing on electrically-conductive backing plate.
The test of sensitizing agent photosensitive property as shown in Figure 1, the size in electrode front is as shown in Figure 2.
Photosensitizers thin layer in the coating of the bottom of transparent conductive glass (electrode of photosensitizer layer one side is done on top) plates the electrode of 6 bar aluminum strips as the photosensitizer layer another side in photosensitizers bottom vacuum again.Between two electrodes, connect direct-current biasing and reometer (in case of necessity, can connect and go up sizeable resistance) so that the electric current of being surveyed is in the useful range of reometer.During irradiation, organically photosensitizer layer is not an isolator, though direct-current biasing is arranged in the circuit, does not have galvanic current through reometer yet.When halogen lamp light source during from back side illuminaton to photosensitizer layer, photosensitizers is excited, and can inject photoelectron to conductive glass.Under the direct-current biasing effect, just have the galvanic current reometer of flowing through.And the photosensitive property of sensitizing agent is good more, and under same light intensity, the photoelectron that is injected into conductive glass is just many more, and the photoelectric current under same direct-current biasing is also just big more.
Relative merits of the present invention and positively effect
(1) red bamboo fungus is the special product in China western part, natural pigment wherein-hypocrellin content is abundant, it is convenient to extract, change into the second element and Hypocrellin B is made the cyclic ethylene diamine group derivative all than being easier to from Hypocrellin A, be used for semi-conductive photosensitization, with respect to design, synthetic light-sensitive coloring agent, be the photosensitizers that a class is cheap, conveniently be easy to get.
(2) the cyclic ethylene diamine group Hypocrellin B is equivalent to have two alkanamine substituting groups, in the long wave direction stronger absorption is arranged, and stronger electron donation is also arranged, and these all help the raising of photosensitive property.
(3) photocell of real dye sensitization is illustrated in Fig. 3.In testing method of the present invention (Fig. 1 and Fig. 2),, directly measure the relative efficiency that various sensitizing agent photoelectrons inject without semiconductor layer.Advantage is to have avoided semi-conductive influence, prepares also more convenient; The limitation part is the absolute efficiency that can not obtain the sensitizing agent photosensitive semiconductor, and can only compare photosensitizers relative efficiency each other.So the parent that the present invention only is suitable for known or a series is a benchmark, the photosensitive relatively efficient of other photosensitizerss or derivative.
Description of drawings
Fig. 1. optoelectronic equipment side and test synoptic diagram in the embodiment of the invention.
Fig. 2. optoelectronic equipment front schematic view in the embodiment of the invention.
Fig. 3. traditional photocell synoptic diagram.
Fig. 4. the abosrption spectrogram of three kinds of photosensitizerss in the embodiment of the invention.
Reference numeral
1. halogen lamp 2. electrode 3. photosensitive dye layer 4. transparent conducting glass of aluminizing
5. direct-current biasing 6. reometers 7. 8. semiconductor layers, 9. ammeters at interval
Embodiment
The following examples are photosensitizers 1 with the parent Hypocrellin B, and the butylamine base Hypocrellin B that alkylamino radical of reference replaces is a photosensitizers 2, and are cyclic ethylene diamine group Hypocrellin B of the present invention photosensitizers 3.
Structure is as follows respectively:
Photosensitizers 1 photosensitizers 2 photosensitizerss 3
Embodiment 1
The reaction formula of preparation cyclic ethylene diamine group Hypocrellin B is as follows:
200 milligrams of Hypocrellin Bs are dissolved in 250 milliliters of new tetrahydrofuran (THF)s that steam, and add 20 milliliters of quadrols.Stir under the lucifuge condition, control reaction temperature is between 50-55 degree centigrade, reacts 12 hours.Stopped reaction, the pressure reducing and steaming solvent with the chloroform dissolving, is used dilute hydrochloric acid (1%) washing then, is neutral substantially until water layer.Boil off chloroform, get black solid.Use re-crystallizing in ethyl acetate, obtain quadrol base Hypocrellin B (photosensitizers 3), productive rate is 56%.
Removing quadrol is 15 milliliters, and other reaction conditions is with embodiment 1, and productive rate is 52%.
Removing quadrol is 25 milliliters, and other reaction conditions is with embodiment 1, and productive rate is 54%.
The spectrum property of photosensitizers:
Fig. 4 is the absorption spectrum of three kinds of photosensitizerss.Among the figure, photosensitizers is made into trichloromethane (chloroform) solution, and concentration is 6 * 10
-5Mol.
Can be summarized as following table from Fig. 4:
In the table, λ is a maximum absorption wavelength, and unit is nanometer (nm); Log (ε) is 10 system logarithmic value of molar extinction coefficient.
| Photosensitizers 1 | | | |||||||
| λ(nm) | 466 | ??548 | ??580 | ??463 | ??583 | ??621 | ??462 | ??555 | ??641 |
| log(ε) | 4.36 | ??3.70 | ??3.52 | ??4.06 | ??4.09 | ??4.10 | ??4.34 | ??4.43 | ??4.56 |
From Fig. 4 and last table as can be seen, replace with alkylamino radical after the methoxyl group of parent, with parent photosensitizers 1 relatively, photosensitizers 2, particularly photosensitizers 3 have been absorbed with significant reinforcement on the long wave direction, this is favourable to the photosensitive property that improves sensitizing agent.
Embodiment 5
The test of sensitizing agent photosensitive property:
Conductive glass is buied from group of SHENZHEN NANBO, and conductive layer is tin indium oxide (ITO).
Photosensitizers is made into chloroformic solution, and concentration is 10
-3Mol.Conductive glass is immersed the chloroformic solution of photosensitizers by height shown in Figure 2,5 minutes for the first time, the hydroxyl that allows the photosensitizers utilization expose fully is adsorbed onto on the metal ion of ITO, after taking out air-dry (about 3 minutes), immerse photosensitizers solution once more, take out air-dryly after about 2 minutes, can form hydrogen bond mutually and adhere to one deck again with hydroxyl and the carbonyl that exposes between the photosensitizers, repeat so again 3 times, amount to 5 times.Situation after finishing can be schematically as follows: (M+)-(O-HB=O) ... (H-O-HB=O) ... (H-O-HB=O) ... (H-O-HB=O) ... (H-O-HB=O) M+ represents the metal ion on the conductive glass conductive layer, the Hypocrellin B of the first layer (HB) is adsorbed on the metal ion with hydroxyl, expose outside carbonyl, with adsorption by hydrogen bond, the rest may be inferred between the hydroxyl of the HB of the second layer and the carbonyl of the first layer.The height of every layer of HB is about 0.12 nanometer, considers intermolecular hydrogen bond action, and total thickness is about 1 nanometer.Carefully clean the dyestuff at the sheet glass back side with wetted absorbent cotton, to absorbent cotton no longer till the staining.
The sheet glass of the good photosensitizers of dip-coating is put into vacuum plating unit, plate as shown in Figure 26 aluminium electrodes by template, thickness is about the 0.1-0.2 micron.Then ready-made sheet glass is put into and shown the test of carrying out photoelectric properties as the device of Fig. 1.The direct-current biasing of test set is adjustable, and data of the present invention are got the current density when being fixed as 0.6 volt, and unit is a microampere/square centimeter.Survey earlier dark current (because of organic dye layer is insulating basically, dark current should be too not big), the measurement of turning on light again deducts the dark current of background, is density of photocurrent value of the present invention.
Each sheet glass sheet should have 6 numerical value (under the individual cases, the aluminium electrode that is plated may with the conductive glass short circuit, dark current at this moment obviously increases, rejection of data need not).At least simultaneously do 3 at every turn,, 18 data should be arranged ideally, can obtain rational data about 15 generally speaking like this for a photosensitizers.Get the photosensitive property data of its arithmetical av as the survey sensitizing agent.
Embodiment 6
The example of sensitizing agent photosensitive property:
In following table first row, which piece sheet glass B represents, and L represents which the bar aluminium electrode on each piece sheet glass.As the data of the 2nd row the 2nd row is exactly to coat on the 1st sheet glass sheet of photosensitizers 1 by the 1st the density of photocurrent numerical value (unit is a microampere/square centimeter) that the aluminium electrode is measured.The 20th row of form is a number of removing the reasonable numerical value of short circuit, the 21st row be these numerical value adding and, the 22nd row is an arithmetical av, and the 23rd row just last column is that photosensitive property with parent Hypocrellin B (photosensitizers 1) is 100, the relative value of derivative photosensitive property.
| B-L | Photosensitizers 1 | | |
| 1-1 | 6.9 | 10.7 | 10.8 |
| 1-2 | 6.6 | 10.2 | 11.3 |
| 1-3 | 6.2 | 8.9 | |
| 1-4 | 7.6 | 10.9 | |
| 1-5 | 9.6 | 11.2 | |
| 1-6 | 7.4 | 10.0 | 10.7 |
| 2-1 | 7.7 | 11.1 | |
| 2-2 | 10.6 | 11.5 | |
| 2-3 | 6.3 | 9.8 | |
| 2-4 | 7.5 | 9.9 | 10.8 |
| 2-5 | 7.4 | 10.5 | 11.7 |
| 2-6 | 7.6 | 8.9 | 11.3 |
| 3-1 | 6.3 | ||
| 3-2 | 7.2 | 10.4 | 9.3 |
| 3-3 | 6.8 | 9.9 | |
| 3-4 | 7.1 | 10.3 | 10.2 |
| 3-5 | 7.8 | 10.7 | 10.6 |
| 3-6 | 11.0 | 11.0 | |
| | 15 | 15 | 14 |
| Add and total value | 106.4 | 152.7 | 151.1 |
| Arithmetical av | 7.1 | 10.2 | 10.8 |
| Relative photosensitive property | 100 | 144 | 152 |
As can be known from the above table, photosensitizers 2 (Hypocrellin Bs of 2 last alkylamino radical methoxyl group displacements) is better than parent photosensitizers 1 (Hypocrellin B), reason may be that the electron donation of alkylamino radical is stronger than the methoxyl group of parent, thereby the ability that photoelectron injects is also stronger; Also may be to absorb enhanced results on the long wave direction; Perhaps two kinds of factors have.
The photoelectric properties of photosensitizers 3 of the present invention are more better, may be owing to be equivalent to the cause that two alkylamino radicals replace; It may be the stronger cause of absorption spectrum; Perhaps two kinds of factors all have effect simultaneously.
Claims (3)
1. cyclic ethylene diamine group Hypocrellin B, it is characterized in that: the structure of described cyclic ethylene diamine group Hypocrellin B is:
2. cyclic ethylene diamine group Preparation of Hypocrellin B method as claimed in claim 1, it is characterized in that: in the Hypocrellin B of raw material 200 weight parts, the method for preparing the cyclic ethylene diamine group Hypocrellin B is:
200 weight part Hypocrellin Bs are dissolved in 200～250 milliliters of new tetrahydrofuran (THF)s that steam, add 15～25 milliliters of quadrols; Stir under the lucifuge condition, control reaction temperature is between 50～55 degrees centigrade, and pressure reducing and steaming solvent behind the stopped reaction with the chloroform dissolving, is used the unnecessary quadrol of dilute hydrochloric acid flush away of 1wt% then, is neutral substantially until water layer; Boil off chloroform, get black solid; With 100 weight part re-crystallizing in ethyl acetate, obtain quadrol base Hypocrellin B.
3. the purposes of a cyclic ethylene diamine group Hypocrellin B as claimed in claim 1, it is characterized in that: described cyclic ethylene diamine group Hypocrellin B is used for optical function material and device for photosensitive dose as semi-conductor.
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| WO2007016762A1 (en) * | 2005-08-10 | 2007-02-15 | Quest Pharmatech Inc. | Perylenequinone derivatives and uses thereof |
| CN101817790A (en) * | 2010-03-14 | 2010-09-01 | 阜阳师范学院 | Ethylene diamine-modified elsinochrome A derivative and preparation method thereof |
| CN102526055A (en) * | 2010-12-24 | 2012-07-04 | 北京工业大学 | Application of cyclohexanediamine hypocrelline B in photodynamic anti-tumor medicaments |
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| EP3366669A4 (en) * | 2015-10-21 | 2019-03-27 | Technical Institute of Physics and Chemistry of the Chinese Academy of Sciences | Monosubstituted or polysubstituted amphiphilic hypocrellin derivative, preparation method therefor, and uses thereof |
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| GB2442915A (en) * | 2005-08-10 | 2008-04-16 | Quest Pharmatech Inc | Perylenequinone derivatives and uses thereof |
| JP2009505968A (en) * | 2005-08-10 | 2009-02-12 | クウェスト・ファーマテック・インコーポレイテッド | Perylenequinone derivatives and uses thereof |
| GB2442915B (en) * | 2005-08-10 | 2009-12-16 | Quest Pharmatech Inc | Perylenequinone derivatives and uses thereof |
| WO2007016762A1 (en) * | 2005-08-10 | 2007-02-15 | Quest Pharmatech Inc. | Perylenequinone derivatives and uses thereof |
| US8758725B2 (en) | 2005-08-10 | 2014-06-24 | Quest Pharmatech Inc. | Perylenequinone derivatives and uses thereof |
| US8506931B2 (en) | 2005-08-10 | 2013-08-13 | Quest Pharmatech Inc. | Perylenequinone derivatives and uses thereof |
| US8454991B2 (en) | 2006-07-24 | 2013-06-04 | Quest Pharmatech Inc. | Method and device for photodynamic therapy |
| CN101817790A (en) * | 2010-03-14 | 2010-09-01 | 阜阳师范学院 | Ethylene diamine-modified elsinochrome A derivative and preparation method thereof |
| CN101817790B (en) * | 2010-03-14 | 2012-07-04 | 阜阳师范学院 | Ethylene diamine-modified elsinochrome A derivative and preparation method thereof |
| CN102526055B (en) * | 2010-12-24 | 2014-01-01 | 北京工业大学 | Application of cyclohexanediamine hypocrelline B in photodynamic anti-tumor medicaments |
| CN102526055A (en) * | 2010-12-24 | 2012-07-04 | 北京工业大学 | Application of cyclohexanediamine hypocrelline B in photodynamic anti-tumor medicaments |
| CN103570567A (en) * | 2012-07-23 | 2014-02-12 | 医影生物纳米技术(苏州)有限公司 | N,N-dimethylamino-3-N-propylamine substituted demethoxyl hypocrellin B, and salt and preparation method thereof |
| EP3366669A4 (en) * | 2015-10-21 | 2019-03-27 | Technical Institute of Physics and Chemistry of the Chinese Academy of Sciences | Monosubstituted or polysubstituted amphiphilic hypocrellin derivative, preparation method therefor, and uses thereof |
| US11154548B2 (en) | 2015-10-21 | 2021-10-26 | Technical Institute of Physics and Chemistry of the Chinese Academy of Sciences | Monosubstituted or polysubstituted amphiphilic hypocrellin derivative, and preparation method and application thereof |
| CN107935964A (en) * | 2016-10-13 | 2018-04-20 | 中国科学院理化技术研究所 | A kind of polysubstituted near-infrared hypocrellin derivant and its preparation method and application |
| CN107935943A (en) * | 2016-10-13 | 2018-04-20 | 中国科学院理化技术研究所 | Amphiphilic hypocrellin derivant of ester water and its preparation method and application |
| CN111825624A (en) * | 2016-10-13 | 2020-10-27 | 中国科学院理化技术研究所 | Ester-water amphiphilic hypocrellin derivative and preparation method and application thereof |
| CN109456210A (en) * | 2017-09-06 | 2019-03-12 | 中国科学院理化技术研究所 | A kind of hypocrellin peri-position and the 2- derivatives and its preparation method and application that amino replaces simultaneously |
| WO2019047846A1 (en) * | 2017-09-06 | 2019-03-14 | 中国科学院理化技术研究所 | Derivatives of hypocrellin with peri-position and 2-position simultaneously substituted by amino groups |
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