CN102180883B - Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof - Google Patents
Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof Download PDFInfo
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Abstract
The invention discloses substituted porphyrin gold (III) compounds with anticancer activity and a preparation method thereof, belonging to the technical field of medicament preparation. The preparation method comprises the following steps of: coordinating substituted tetraphenylporphyrin and gold to generate a substituted tetraphenyl porphyrin gold (III) compound; and introducing a targeting group onto a porphyrin ring to enhance the targeting selectivity of porphyrin gold, lower the toxicity of the porphyrin gold, further improve the performance of the porphyrin gold (III) compound and preserve or enhance the anticancer activity of the porphyrin gold (III) compound. As proved by in-vitro detection data of an S180 cell, the compound synthesized with the method has a remarkable suppressing function, the highest suppression ratio up to 92.863 percent higher than that of tetraphenyl porphyrin gold (III) serving as a lead compound and a weak suppressing function on normal cells. The preparation method is scientific and reasonable; and the prepared substituted porphyrin gold (III) compounds have high anticancer activity, a small toxic or side effect and a simple, convenient, and practical preparation process, and is suitable for industrial mass production.
Description
Technical field
The invention discloses replacement porphyrin gold (III) compounds with antitumour activity and preparation method thereof, belong to field of medicine preparing technology.
Background technology
Cancer is the high common disease of present lethality rate, and its clinical treatment means are mainly operation, radiotherapy and chemotherapy.In antineoplastic chemotherapy medicine, the clinically widespread use of some noble metal coordination compounds, for example cis-platinum.But the same with most of chemotherapeutics, the target selectivity of cis-platinum is relatively poor, also injures the normal cell of body in kill cancer cell, shows larger toxicity.
Au (III) and Pt (II) are d
8Electronic configuration, the four-coordination compound of Au (III) and the two dimensional structure of cis-platinum are similar, therefore infer that Au (III) class title complex may have and the similar antitumour activity of cis-platinum.Existing studies show that, tetraphenylporphyrin gold vitro culture to the various human cancerous cell line (such as cancer cell of oral cavity KB-3-1 ， Palace neck cancer cells HeLa, leukemia HL-60, nasopharyngeal carcinoma cell SUNE1, liver cancer cell HepG2 etc.) all have higher restraining effect [Marcon, G.; Carotti, S.; Corronnello, W.et al.J.Med.Chem.2002,45,1672-1677; Messori, L.; Abbate, F.et al.J.Med.Chem.2000,43,35-41; Guo, Z.; Sadler, P.J.Angew.Chem.Int.Ed.1999,38,1512; Che, C.M.; Sun, R.W.Y.; Yu, W.Y.et al.Chem.Commun.2003,1718-1719; Wang, Y; He, Q.Y; Sun, R.W.Y.et al.Eur.J.Pharmacol.2007,554 (2-3), 113-122; Wang, Y.; He, Q.Y.; Che, C.M.et al.Proteomics.2006,6 (1), 131-142; Wang, Y; He, Q.Y.; Sun, R.W.Y.et al.Cancer Res.2005,65 (24), 11553-11564.], and antitumour activity is better than cis-platinum.Yet the tetraphenylporphyrin gold is also relatively poor to the target selectivity of cancer cells, and toxicity is larger, thereby the distance between its experimental study and the clinical application is also very large.Therefore, carry out chemically modified, make this metalloid coordination compound have desirable antitumour activity and lower toxic side effect, then become the technological difficulties that the synthetic field of medicine is captured.
Summary of the invention
The objective of the invention is for the deficiencies in the prior art, replacement porphyrin gold (III) compounds with antitumour activity and preparation method thereof is provided.
First purpose of the present invention is achieved through the following technical solutions, and has replacement porphyrin gold (III) compounds of antitumour activity, and its general formula is:
R ' is H or CO in the formula
2CH
3R " is OCH
3Or CO
2CH
3Or NO
2X is C or N.
Described R ' is H; R " is CO
2CH
3Or OCH
3X is C or N.
Described R ' is H; R " is CO
2CH
3X is C.
Second purpose of the present invention is achieved through the following technical solutions, preparation method with replacement porphyrin gold (III) compounds of antitumour activity, it is characterized in that, described compound is to replace porphyrin as part, in the acetic acid solution system, with the potassium chloraurate reaction, then carry out ion-exchange by lithium chloride and obtain; Described replacement porphyrin is 5-(4-p-methoxyphenyl)-10,15,20-Triphenylporphyrin or 5,10,15,20-four (4-methoxycarbonyl) phenyl porphyrin or 5-(4-methoxycarbonyl) phenyl-10,15,20-Triphenylporphyrin compound or 5-(4-nitro) phenyl-10,15,20-Triphenylporphyrin compound or 5-(4-pyridyl)-10,15,20-Triphenylporphyrin compound.
The synthetic reaction equation that replaces porphyrin:
Reagent and reaction conditions, productive rate in the formula: propionic acid, backflow 2-4h.Products collection efficiency is 6.5-25%.
Replacement porphyrin gold (III) compounds preparation feedback equation with antitumour activity:
Reagent in the formula: (1) KAuCl
4, NaOAc, HOAc; (2) LiCl.Products collection efficiency is 40.2-95.5%.
Described preparation method may further comprise the steps:
(1) be 1 with mol ratio: the glacial acetic acid that the replacement porphyrin of 2.8-3.2: 10-14, potassium chloraurate, sodium acetate and corresponding every mmole replace porphyrin 300-610ml adds in the reaction vessel successively, at reaction vessel internal reflux 3-4h, TLC monitors to reacting completely;
(2) steam the acetic acid that removes in step (1) reaction solution through rotatory evaporator and obtain the purple solid, the purple solid is dissolved in the methylene dichloride that corresponding every mmole replaces porphyrin 150-300ml, and with the distilled water wash of corresponding every mmole replacement porphyrin 600-1220ml 3-5 time;
(3) methylene dichloride in the solution behind distilled water wash in the step (2) is replaced mutually the anhydrous sodium sulfate drying of porphyrin 3.2-4kg with corresponding every mmole, filter, remove methylene dichloride through the rotatory evaporator vacuum rotary steam;
(4) will remove the solution of methylene dichloride take methylene chloride/methanol as eluent through the rotatory evaporator vacuum rotary steam in the step (3), neutral alumina or silica gel column chromatography, the the second colour band product that forms is removed eluent methylene dichloride, methyl alcohol fully, use acetone afterwards until dissolved product removes by filter insolubles;
(5) filtrate in the step (4) being added concentration is the lithium chloride solution that 0.1-0.3g/mL, corresponding every mmole replace porphyrin 100-200ml, slowly revolve steaming, treat that the purple solid occurs, obtain to have replacement porphyrin gold (III) compounds of antitumour activity after filtering.
The present invention generates replacement tetraphenylporphyrin gold (III) compound by replacing tetraphenylporphyrin and golden coordination, introduces target group CO at porphyrin ring
2CH
3, OCH
3, NO
2, increased the target selectivity of replacement tetraphenylporphyrin gold (III) compound, in the hope of keeping or strengthen the antitumour activity of porphyrin gold (III) compound.The compound that adopts the present invention to synthesize shows to have obvious restraining effect through external detection data to the S180 cell, the highest inhibiting rate reaches 92.386%, the highest inhibiting rate that is higher than lead compound tetraphenylporphyrin gold (III) 79.375%, and little to Normocellular restraining effect.The present invention is scientific and reasonable, and replacement porphyrin gold (III) compounds antitumour activity of preparation is good, and toxic side effect is little, and preparation technology is simple and feasible, is fit to industrialized production.
Description of drawings
Fig. 1 is that the present invention is on the figure that affects of normal mouse spleen lymphocyte.
Embodiment
Further specify in conjunction with the embodiments the present invention:
The following example is used for explanation the present invention.Plant and instrument used in following each embodiment before use should be dry, and reaction will be carried out under anhydrous condition, the logical atmosphere of reflux condensing tube upper end dress drying tube.
In the round-bottomed flask of 250mL, add 200mL propionic acid, phenyl aldehyde (60mmol) and aubepine (20mmol), reflux.After 5.53mL (80mmol) newly steamed pyrroles and 10mL propionic acid and mix, in 30min, slowly be added drop-wise in the propionic acid solution.Then continue reaction 1h, be cooled to room temperature, separate out solid, filter, solid is used respectively methyl alcohol, hot wash, drying.The acquisition yield is 8.8% 5-(4-p-methoxyphenyl)-10,15,20-Triphenylporphyrin (L1).
Add 5-(4-p-methoxyphenyl)-10 in the 50mL flask, 15,20-Triphenylporphyrin (L1) (0.025mmol), potassium chloraurate (0.07-0.08mmol), sodium acetate (0.25-0.35mmol) and 7.5-15.25mL glacial acetic acid, conventional heating backflow 3-4h.The TLC monitoring is to reacting completely.Steaming obtains the purple solid except acetic acid in the rotatory evaporator.The purple solid is dissolved in the 3.75-7.5mL methylene dichloride, and with 15-30.5mL distilled water wash 3-5 time.Methylene dichloride 80-100g anhydrous sodium sulfate drying filters.Revolve in the rotatory evaporator to steam and remove methylene dichloride.Take methylene chloride/methanol as eluent, neutral alumina or silicagel column adopt conventional chromatography and drip washing, further refined product.The first colour band is unreacted raw material, and saffron the second colour band is the product of wanting.Saffron the second colour band product is placed rotatory evaporator, remove fully behind eluent methylene dichloride, the methyl alcohol with minimum acetone solution product, remove by filter insolubles, filtrate adds the aqueous solution (concentration is 1g-3gLiCl/10mL distilled water) of 2.5-5mL lithium chloride.Slowly revolve steaming, namely have the purple solid to occur, filter, obtaining yield is the chlorination 5-(4-p-methoxyphenyl)-10,15 of 94.2-95.5%, 20-Triphenylporphyrin gold compound (G1).mp?156-158℃；
1HNMR(600MHz，CDCl
3)，δ(ppm)：4.13(s，3H)，7.40(d，J＝8.4Hz，2H)，7.86-7.92(m，9H)，8.16(d，J＝8.4Hz，2H)，8.24(d，J＝8.4Hz，6H)，9.28(d，J＝7.2Hz，6H)，9.34(d，J＝5.4Hz，2H)；IR(KBr)：υ2922(s)，2856(w)，1737(w)，1612(w)，1453(w)，1368(w)，1251(w)，1176(w)，1081(w)，1027(w)，806(w)，756(w)，705(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?408，520；MS：839.9(M+1-Cl-，100％)。
In the round-bottomed flask of 250mL, add 200mL propionic acid and 4-methoxycarbonyl phenyl aldehyde (80mmol), be heated to backflow.After 5.53mL (80mmol) newly steamed pyrroles and 10mL propionic acid and mix, in 30min, slowly be added drop-wise in the propionic acid solution.Then continue reaction 1h, be cooled to room temperature, separate out solid, filter, solid is used respectively methyl alcohol, hot wash, drying.Obtain yield and be 22.0% 5,10,15,20-four (4-methoxycarbonyl) phenyl porphyrin (L2): mp＞250 ℃;
1H NMR (600MHz, CDCl
3), δ (ppm) :-2.79 (s, 2H, inner-NH), 4.11 (s, 12H ,-COOCH3), 8.29 (d, J=7.8Hz, 8H, Ph-CH), 8.44 (d, J=7.8Hz, 8H, Ph-CH), 8.81 (s, 8H, Por-CH); IR (KBr): υ 3425 (m), 2919 (w), 1724 (s), 1607 (w), 1435 (w), 1383 (w), 1277 (m), 1108 (m), 965 (w), 803 (w), 762 (w) cm
-1UV-Vis (CH
2Cl
2)/nm 417,515,549,588, and 645.
Use the method for embodiment 1, with 5,10,15,20-four (4-methoxycarbonyl) phenyl porphyrin (L2) replaces 5-(4-is to the oxygen aminomethyl phenyl)-10,15,20-Triphenylporphyrin (L1) participates in reaction, and obtaining yield is the chlorination 5,10 of 64.5-66.9%, 15,20-four (4-methoxycarbonyl) phenyl porphyrin gold (G2).mp＞250℃；
1HNMR(600MHz，CDCl
3)，δ(ppm)：4.13(s，12H，-COOCH
3)，8.36(d，J＝7.8Hz，8H，Ph-CH)，8.52(d，J＝7.8Hz，8H，Ph-CH)，9.18(s，8H，Por-CH)；IR(KBr)：υ3433(m)，2923(m)，2856(w)，1717(s)，1609(w)，1436(w)，1278(s)，1185(w)，1107(m)，1024(m)，808(w)，762(w)，708(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?408，519；MS：1041.8(M+1-Cl-，100％)。
Embodiment 3 chlorination 5-(4-methoxycarbonyl) phenyl-10,15,20-Triphenylporphyrin gold (G3) compound and preparation method.
Use the method for embodiment 1, replace aubepine (20mmol) to participate in reaction with 4-methoxycarbonyl phenyl aldehyde (20mmol), the acquisition yield is 9.0% 5-(4-methoxycarbonyl) phenyl-10,15,20-Triphenylporphyrin compound (L3).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：-2.79(s，2H，inner-NH)，4.11(s，3H，-COOCH
3)，7.74-7.79(m，9H，Ph-CH)，8.21(d，J＝6.6Hz，6H，Ph-CH)，8.31(d，J＝7.8Hz，2H，Ph-CH)，8.44(d，J＝7.8Hz，2H，Ph-CH)，8.79(d，J＝4.2Hz，2H，Por-CH)，8.85(s，6H，Por-CH)；IR(KBr)：υ3442(s)，3319(w)，2924(w)，2853(w)，1812(m)，1722(s)，1604(w)，1472(w)，1437(w)，1394(w)，1353(w)，1279(s)，1182(w)，1106(w)，800(m)，739(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?416，513，548，589，646。
Use the method for embodiment 1, with 5-(4-methoxycarbonyl) phenyl-10,15,20-Triphenylporphyrin compound (L3) replaces 5-(4-p-methoxyphenyl)-10,15,20-Triphenylporphyrin (L1) participates in reaction, and obtaining yield is chlorination 5-(4-methoxycarbonyl) phenyl-10 of 81.5-83%, 15,20-Triphenylporphyrin gold (G3).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：4.13(s，3H，-COOCH
3)，7.82-7.88(m，9H，Ph-CH)，8.30(s，6H，Ph-CH)，8..42(d，J＝8.4Hz，2H，Ph-CH)，8.51(d，J＝7.2Hz，2H，Ph-CH)，9.19(s，2H，Por-CH)，9.26-9.27(m，6H，Por-CH)；IR(KBr)：υ＝3414(w)，2921(s)，2852(m)，1737(w)，1601(w)，1498(w)，1460(w)，1357(w)，1242(m)，1176(w)，1079(w)，1026(m)，802(w)，756(w)，702(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?410，521；MS：868.1(M+1-Cl-，100％)。
The method of use embodiment 1 replaces aubepine (20mmol) to participate in reaction with 4-nitrobenzaldehyde (20mmol), and the acquisition yield is 8.5% 5-(4-nitro) phenyl-10,15,20-Triphenylporphyrin compound (L4).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：-2.79(s，2H，inner-NH)，7.75-7.81(m，9H，Ph-CH)，8.21(d，J＝7.2Hz，6H，Ph-CH)，8.40(d，J＝8.4Hz，2H，Ph-CH)，8.64(d，J＝8.4Hz，2H，Ph-CH)，8.74(d，J＝4.2Hz，2H，Por-CH)，8.86-8.90(m，6H，Por-CH)；IR(KBr)：υ3446(s)，2918(w)，2850(w)，1596(w)，1517(w)，1472(w)，1392(w)，1345(m)，1073(w)，840(w)，798(m)，706(m)cm
-1；UV-Vis(CH
2Cl
2)/nm?418，514，549，588，645。
Use the method for embodiment 1, with 5-(4-nitro) phenyl-10,15,20-Triphenylporphyrin compound (L4) replaces 5-(4-p-methoxyphenyl)-10,15,20-Triphenylporphyrin (L1) participates in reaction, and obtaining yield is chlorination 5-(4-nitro) phenyl-10 of 40.2-42.6%, 15,20-Triphenylporphyrin gold (G4).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：7.78-7.82(m，9H，Ph-CH)，8.18(s，6H，Ph-CH)，8.47(s，2H，Ph-CH)，8.65(s，2H，Ph-CH)，9.06(s，2H，Ph-CH)，9.18(d，J＝8.4Hz，6H，Por-CH)；IR(KBr)：υ3438(s)，2922(m)，2856(w)，1733(w)，1629(w)，1517(w)，1452(w)，1346(w)，1086(w)，1028(w)，803(w)，756(w)，703(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?408，520；MS：855.1(M+1-Cl-，100％)。
Embodiment 5 chlorination 5-(4-pyridyl)-10,15,20-Triphenylporphyrin gold (G5) compound and preparation method.
The method of use embodiment 1 replaces aubepine (20mmol) to participate in reaction with 4-pyridylaldehyde (20mmol), and the acquisition yield is 6.5% 5-(4-pyridyl)-10,15,20-Triphenylporphyrin compound (L5).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：-2.82(s，2H，inner-NH)，7.75-7.80(m，9H，Ph-CH)，8.17(d，J＝5.4Hz，2H，Ph-CH)，8.21(d，J＝6.6Hz，6H，Ph-CH)，8.79(d，J＝4.2Hz，2H，Ph-CH)，8.86-8.90(m，6H，Por-CH)，9.03(s，2H，Por-CH)；IR(KBr)：υ3446(s)，1634(w)，1590(w)，1473(w)，1396(w)，1351(w)，1070(w)，970(w)，798(m)，710(m)，657(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?416，513，548，586，644。
Use the method for embodiment 1, with 5-(4-pyridyl)-10,15,20-Triphenylporphyrin compound (L5) replaces 5-(4-p-methoxyphenyl)-10,15,20-Triphenylporphyrin (L1) participates in reaction, and obtaining yield is the chlorination 5-(4-pyridyl)-10 of 81.5-82.2%, 15,20-Triphenylporphyrin gold (G5).mp＞250℃；
1H?NMR(CDCl
3，600MHz)，δ(ppm)：7.84-7.91(m，9H，Ph-CH)，8.25(d，J＝7.8Hz，8H，Ph-CH)，9.14(d，J＝4.2Hz，2H，Ph-CH)，9.18(d，J＝5.4Hz，2H，Por-CH)，9.26(s，4H，Por-CH)，9.29(s，2H，Por-CH)；IR(KBr)：υ3437(s)，2925(m)，2859(w)，1629(w)，1447(w)，1368(w)，1083(w)，1031(w)，804(w)，759(w)，706(w)cm
-1；UV-Vis(CH
2Cl
2)/nm?407，519；MS：811.2(M+1-Cl-，100％)。
Its high-efficiency low-toxicity characteristic sees following explanation for details:
1. the inhibiting rate to tumour cell is high, and half-inhibition concentration is little
Get the S180 cell (Chinese Academy of Sciences's Shanghai cell research provides) that external continuous passage is in logarithmic phase, adjust cell count to 1 * 10 with RPMI1640 (the Gbico company product) nutrient solution that contains 10% newborn calf serum behind the centrifuge washing
5/ mL.Get this cell suspension 100 μ L, add 96 well culture plates, the every hole of dosing group adds the testing sample 100 μ L of different concns, the blank group adds RPMI-1640 100 μ L, positive controls adds the cis-platinum solution 100 μ L of different concns, and each concentration is established 3 multiple holes, and culture plate is placed 5%CO
2, 37 ℃ of saturated humidities incubator in cultivate 48h.4h sucking-off 100 μ L supernatants from each hole discard before cultivating end, add MTT10 μ L (final concentration 5mg/mL, MTT is sigma company product), after continuing to cultivate 4h, add 100 μ L acidifying Virahol termination reactions, vibration 10min, with the OD value of microplate reader in each hole of mensuration, 570nm place, the height of OD value is directly proportional with viable count.By formula " inhibiting rate=(1-medicine hole OD value/control wells OD value) * 100% " calculates the external inhibiting rate to S180 cell proliferation of test-compound, and calculation of half inhibitory concentration IC
50The results are shown in Table 1.
The restraining effect of table 1 pair S180 cells in vitro propagation
Table 1 result shows, replaces porphyrin gold (III) compounds G1, G3 and G5 the S180 cell is had obvious restraining effect, wherein the IC of G1 and G3
50All less than lead compound (G0), G3 is 92.386% to the highest inhibiting rate of tumour cell, is higher than the highest inhibiting rate 79.375% of lead compound, and G2, G4 to the restraining effect of S180 cell relatively a little less than.
2. the toxicity to normal mouse spleen lymphocyte is little
Prepare according to a conventional method ICR mouse spleen lymphocyte suspension, regulating cell concn is 1 * 10
7/ mL.Get this cell suspension 100 μ L, add 96 well culture plates, the every hole of dosing group adds the testing sample 100 μ L of different concns, the blank group adds 1640 (Gbico company product) nutrient solution, 100 μ L, positive controls adds the cis-platinum solution 100 μ L of different concns, each concentration is established 3 multiple holes, places the incubator of 5%CO2,37 ℃ of saturated humidities to cultivate 48h culture plate.4h sucking-off 100 μ L supernatants from each hole discard before cultivating end, add MTT10 μ L (final concentration 5mg/mL, MTT is sigma company product), after continuing to cultivate 4h, add 100 μ L acidifying Virahol termination reactions, vibration 10min is with the OD value of microplate reader in each hole of mensuration, 570nm place, the height of OD value becomes positive correlation with the quantity of viable cell, and Normocellular toxicity is become negative correlation.The result as shown in Figure 1.
Fig. 1 result shows: test-compound all has certain toxicity to normal mouse spleen lymphocyte, wherein lead compound G0 toxicity is larger, secondly be cis-platinum, the toxicity of compound G1 and G3 is less, measure in conjunction with antitumour activity, new synthetic targeting compounds selectivity is good, toxicity is low, probably becomes anticancer potential drug to show these two.
Claims (3)
1. have replacement porphyrin gold (III) compounds of antitumour activity, its structural formula is:
R ' is H in the formula; R " is CO
2CH
3X is C.
2. have the preparation method of replacement porphyrin gold (III) compounds of antitumour activity, it is characterized in that, described compound with the potassium chloraurate reaction, then carries out ion-exchange by lithium chloride and obtains in the acetic acid solution system to replace porphyrin as part; Described replacement porphyrin is the 5-(4-methoxycarbonyl) phenyl-10,15,20-Triphenylporphyrin compound.
3. the preparation method of replacement porphyrin gold (III) compounds with antitumour activity according to claim 2 is characterized in that described preparation method may further comprise the steps:
(1) be that the replacement porphyrin, potassium chloraurate, sodium acetate of 1:2.8-3.2:10-14 and glacial acetic acid that corresponding every mmole replaces porphyrin 300-610 ml add in the reaction vessel successively with mol ratio, at reaction vessel internal reflux 3-4 h, TLC monitors to reacting completely;
(2) steam the acetic acid that removes in step (1) reaction solution through rotatory evaporator and obtain the purple solid, the purple solid is dissolved in the methylene dichloride that corresponding every mmole replaces porphyrin 150-300 ml, and with the distilled water wash of corresponding every mmole replacement porphyrin 600-1220 ml 3-5 time;
(3) methylene dichloride in the solution behind distilled water wash in the step (2) is replaced mutually the anhydrous sodium sulfate drying of porphyrin 3.2-4 kg with corresponding every mmole, filter, remove methylene dichloride through the rotatory evaporator vacuum rotary steam;
(4) will remove the solution of methylene dichloride take methylene chloride/methanol as eluent through the rotatory evaporator vacuum rotary steam in the step (3), neutral alumina or silica gel column chromatography, the the second colour band product that forms is removed eluent methylene dichloride, methyl alcohol fully, use acetone afterwards until dissolved product removes by filter insolubles;
(5) filtrate in the step (4) being added concentration is the lithium chloride solution that 0.1-0.3 g/mL, corresponding every mmole replace porphyrin 100-200 ml, slowly revolve steaming, treat that the purple solid occurs, obtain to have replacement porphyrin gold (III) compounds of antitumour activity after filtering.
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| US11135310B2 (en) * | 2015-12-08 | 2021-10-05 | The University Of Hong Kong | Gold porphyrin-PEG conjugates and methods of use |
| WO2020012934A1 (en) | 2018-07-09 | 2020-01-16 | 花王株式会社 | Inorganic coated sand |
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| TWI338692B (en) * | 2002-09-16 | 2011-03-11 | Univ Hong Kong | Pharmaceutical compositions for induction of apoptosis of cancer cells and inhibition of reverse transcriptase of human immunodeficiency virus-1 |
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2011
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Non-Patent Citations (4)
| Title |
|---|
| In Vitro Inhibition of Human Immunodeficiency Virus Type-1 (HIV-1) Reverse Transcriptase by Gold(iii)Porphyrins;Raymond Wai-Yin Sun等;《ChemBioChem》;20041231(第5期);全文 * |
| Raymond Wai-Yin Sun.Stable Anticancer GoldACHTUNGTRENUNG(III)–Porphyrin Complexes:Effects of Porphyrin Structure.《Chem. Eur. J.》.2010,(第16期),3097 – 3113. |
| Raymond Wai-Yin Sun等.In Vitro Inhibition of Human Immunodeficiency Virus Type-1 (HIV-1) Reverse Transcriptase by Gold(iii)Porphyrins.《ChemBioChem》.2004,(第5期),1293-1298. |
| Stable Anticancer GoldACHTUNGTRENUNG(III)–Porphyrin Complexes:Effects of Porphyrin Structure;Raymond Wai-Yin Sun;《Chem. Eur. J.》;20101231(第16期);3099页化合物5a，3010-3112页图1-11，表1-7 * |
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