Synthesis method and application of gold (iii) metal complex with human serum albumin as carrier

A technology of human serum albumin and metal complexes, applied in the direction of gold organic compounds, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve tumor tissue accumulation, limit anti-tumor applications, and metal complexes issues such as lack of targeting

Inactive Publication Date: 2021-09-14
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metal complexes lack targeting and are difficult to accumulate in tumor tissues, which severely limits their application in anti-tumor

Method used

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  • Synthesis method and application of gold (iii) metal complex with human serum albumin as carrier
  • Synthesis method and application of gold (iii) metal complex with human serum albumin as carrier
  • Synthesis method and application of gold (iii) metal complex with human serum albumin as carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic method of C1 metal complex is:

[0029] 1) Dissolve 408mg (3mmol) of 5-methylsalicylaldehyde in 20ml of methanol. After dissolving, add 273mg (3mmol) of 3-thiosemicarbazide and mix well to obtain a mixed solution. Reflux the mixed solution at 65°C for 4h, filter, and The cake was washed 2-3 times with methanol to obtain ligand 1;

[0030] Yield: 0.62g, 98.8%, white solid; R f =0.314(Petroleum ether:EtOAc=2:1).m.p.123-125℃. 1 H NMR (400MHz, DMSO-d 6 )δ11.34(s,1H,OH),9.60(s,1H,NH),8.33(s,1H,NCH),8.10,7.90(2s,2H,NH 2 ),7.74(s,1H),7.01(dd,J=8.4,2.3Hz,1H),6.75(d,J=8.3Hz,1H),2.20(s,3H). 13 C NMR (100MHz, DMSO-d 6 )δ177.59, 154.25, 139.74, 131.70, 127.80, 126.67, 119.87, 115.89, 20.00.ESI + m / z: calcd for C 9 h 10 N 3 OS, 208 [M-H] - .

[0031] 2) After dissolving 20.1 mg (0.1 mmol) of Ligand 1 prepared in step 1) in 10 ml of methanol, add 39.7 mg (0.1 mmol) of Na[AuCl 4 ]·2H 2 O, stirred at room temperature for 12 hours, filtered to obtain a yellow-...

Embodiment 2

[0034] The synthetic method of C2 metal complex is:

[0035] 1) Dissolve 408mg (3mmol) of 5-methyl salicylaldehyde in 20ml of methanol. After dissolving, add 357mg (3mmol) of 4,4-dimethyl-thiosemicarbazide and mix well to obtain a mixed solution. Put the mixed solution at 65°C Reflux for 4 hours, filter, and wash the filter cake 2-3 times with methanol to obtain Ligand 2;

[0036] Yield: 0.59g, 82.98%, white solid; R f =0.414(Petroleum ether:EtOAc=2:1).m.p.128-130℃. 1 H NMR (400MHz, DMSO-d 6 )δ11.49(s,1H,OH),11.21(s,1H,NH),8.45(s,1H,NCH),7.16(d,J=2.1Hz,1H),7.07(dd,J=8.2, 2.2Hz, 1H), 6.79(d, J=8.3Hz, 1H), 3.29(s, 6H), 2.24(s, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ179.19, 154.91, 146.31, 131.33, 129.99, 127.46, 118.01, 116.32, 40.97, 19.87.C 11 h 14 N 3 OS 236[M-H] - .

[0037]2) After dissolving 23.7mg (0.1mmol) of ligand 2 prepared in step 1) in 10ml of methanol, add 39.7mg (0.1mmol) of Na[AuCl 4 ]·2H 2 O, stirred at room temperature for 12 hours, filtered to obtain a ...

Embodiment 3

[0040] The synthetic method of C3 metal complex is:

[0041] 1) 408mg (3mmol) 5-methyl salicylaldehyde was dissolved in 20ml methanol, after dissolving, 519mg (3mmol) 3-(4-methylpiperidine)-thiosemicarbazide was added and mixed uniformly to obtain a mixed solution, which was mixed in Reflux at 65°C for 4 hours, filter, and wash the filter cake with methanol 2-3 times to obtain Ligand 3;

[0042] Yield: 0.71g, 81.32%, white solid; R f =0.411 (Petroleum ether:EtOAc=2:1).m.p.134-136°C. 1 H NMR (400MHz, DMSO-d 6 )δ11.39(s,1H,OH),11.35(s,1H,NH),8.40(s,1H,NCH),7.17(d,J=1.8Hz,1H),7.06(dd,J=8.3, 2.0Hz, 1H), 6.78(d, J=8.3Hz, 1H), 4.69(d, J=13.1Hz, 2H), 3.12-3.06(m, 2H), 2.24(s, 3H), 1.73-1.65( m,3H),1.19-1.05(m,2H),0.92(d,J=6.1Hz,3H). 13 C NMR (100MHz, DMSO-d 6 )δ178.60, 154.86, 145.86, 131.32, 129.80, 127.46, 118.13, 116.29, 48.78, 33.58, 30.20, 21.33, 19.88.ESI + m / z: calcd for C 15 h 20 N 3 OS, 290 [M-H] - .

[0043] 2) After dissolving 29.1 mg (0.1 mmol) of ligand 3 pre...

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Abstract

The invention discloses a synthesis method and application of a gold (III) metal complex with human serum albumin as a carrier. The synthesis method of the gold (III) metal complex is: dissolving 5-methyl salicylaldehyde in methanol Finally, add thiosemicarbazide and mix evenly to obtain a mixed solution, reflux and filter the mixed solution, and wash the filter cake with methanol for 2-3 times to obtain the ligand; after the ligand is dissolved in methanol, add Na[AuCl 4 ]·2H 2 O, stirred at room temperature for 12 h, filtered to obtain a yellow-green solid, the yellow-green solid was washed 2-3 times with n-hexane, dried in vacuo, and then recrystallized with dichloromethane and n-hexane to obtain a black crystal that was a metal complex; The serum albumin solution and the metal complex solution were mixed and put into a sample tube to mix well, and after standing overnight at 4°C, the gold (III) metal complex with human serum albumin as the carrier was prepared. The metal complex targets the cancer tumor area, can effectively reduce the toxic and side effects of the metal complex, and improve the anti-tumor efficiency.

Description

technical field [0001] The invention relates to the technical field of antitumor drugs, in particular to a synthesis method and application of a gold (III) metal complex with human serum albumin as a carrier. Background technique [0002] The research on the antitumor biological activity of metal complexes began in the 1960s, initially due to the good antitumor activity of platinum complexes. This discovery has attracted people's attention to the antitumor research of metal complexes. In recent years, a large number of organometallic complexes have been synthesized, among which gold complexes have been found to have good antitumor activity, and compared with platinum complexes, their toxicity is relatively low. Thiosemicarbazone is a small molecule organic ligand with good anti-tumor activity. It has been studied as an anti-tumor compound for more than half a century. The main mechanism includes direct induction of DNA damage and inhibition of topoisomerase Ⅱ. However, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/64A61K31/555C07F1/12A61P35/00
Inventor 杨峰张琚政赵蕾梁宏
Owner GUANGXI NORMAL UNIV
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