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Ion-modified gallium protoporphyrin compound as well as preparation method and application thereof

An ion modification and compound technology, which is applied in the field of ion modified protoporphyrin gallium compounds and their preparation, can solve problems such as abuse and multidrug-resistant bacteria, and achieves the promotion of killing effect, overcoming bacterial resistance, high reactive oxygen species and the like. volume effect

Active Publication Date: 2020-10-30
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the long-term abuse of antibiotics, the emergence of multi-drug-resistant bacteria worldwide, and even the emergence of "super bacteria"

Method used

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  • Ion-modified gallium protoporphyrin compound as well as preparation method and application thereof
  • Ion-modified gallium protoporphyrin compound as well as preparation method and application thereof
  • Ion-modified gallium protoporphyrin compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Gallium (III) dimethyl-8,13-divinyl-3,7,12,17-tetramethyl-21H, 23H-porphyrin-2,18-bis[-N,N, Preparation of N-trimethyl-2-(propionyl ammonium)](CMP-Ga)

[0040] Synthetic route see figure 1 .

[0041] Weigh 100.0 mg of protoporphyrin into a reaction flask, add 200 mL of dichloromethane, stir to dissolve, cool down to -5°C, slowly add 22.6 mg of oxalyl chloride dropwise, stir for 1 hour, and rotate to evaporate the solvent and excess oxalyl chloride ;Add 200mL of dichloromethane again, stir to dissolve, cool down to -5°C, slowly add 15.7mg of N,N-dimethylethylenediamine dropwise, stir for 6h, rotary evaporate the solvent, add 400mL of deionized water, Stir for 6 hours, filter, rinse with deionized water, and vacuum-dry the filter cake at 60°C; Rinse with methane, and vacuum dry the filter cake at 40°C to obtain cation-modified protoporphyrin (CMP, see Figure 2-3 ); the cation-modified protoporphyrin was dissolved in 200mL of ultra-dry N,N-dimethylformamide...

Embodiment 2

[0042] Example 2: Gallium (III) dimethyl-8,13-divinyl-3,7,12,17-tetramethyl-21H, 23H-porphyrin-2,18-bis[-N-(carboxy Methyl)-N, N-dimethyl-2-(propionyl ammonium)], the preparation of internal salt (ZMP-Ga): the synthetic route sees Figure 5 .

[0043] Weigh 100mg of protoporphyrin into the reaction flask, add 200mL of tetrahydrofuran, stir to dissolve, cool down to 5°C, slowly add 45.1mg of oxalyl chloride dropwise, stir for 6h, rotary evaporate the solvent and excess oxalyl chloride; add 200mL again THF, stir to dissolve, cool down to 5°C, slowly add 23.5mL of N,N-dimethylethylenediamine dropwise, stir for 12h, rotary evaporate the solvent, add 400mL of deionized water, stir for 6h, filter, use Rinse with deionized water, dry the filter cake under vacuum at 60°C; dissolve the obtained filter cake with 200 mL of tetrahydrofuran, slowly add 37.0 mg of bromoacetic acid dropwise at room temperature, react at 60°C for 12 hours, filter, rinse with tetrahydrofuran, and dry the filt...

Embodiment 3

[0044] Example 3: Gallium(III) dimethyl-8,13-diethyl-3,7,12,17-tetramethyl-21H,23H-porphyrin-2,18-bis[-N-(sulfonic Propyl)-N, N-dimethyl-2-(butyryl ammonium)], the preparation of inner salt (SMP-Ga): see the synthetic route Figure 9 .

[0045] Weigh 100mg of Meso-protoporphyrin into a reaction flask, add 200mL of acetone, stir to dissolve, cool down to 0°C, slowly add 33.6mg of oxalyl chloride dropwise, stir for 3 hours, and rotate to evaporate the solvent and excess oxalyl chloride; Add 200mL of acetone, stir to dissolve, cool down to 0°C, slowly add 21.6mL of N, N-dimethylpropylenediamine dropwise, stir for 8h, rotate to evaporate the solvent, add 400mL of deionized water, stir for 6h, filter, Rinse with deionized water, vacuum-dry the filter cake at 60°C; dissolve the obtained filter cake with 200mL of acetone, slowly add 42.8mg of 3-bromo-1-propanesulfonic acid dropwise at room temperature, react at 40°C for 8h, filter, and rinse with acetone After washing, the filter c...

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Abstract

The invention belongs to the field of organic synthesis and medicines, and particularly relates to an ion-modified gallium protoporphyrin compound as well as a preparation method and application thereof. The ion-modified gallium protoporphyrin compound has a structure described in the specification, wherein m is 1, 2 or 3, n is 1, 2 or 3, R1 is ethyl or vinyl, R2 is H, COO<-> or SO<3->, and M-X isGa-Cl or Ga-NO3. After the protoporphyrin compound is complexed with gallium, the protoporphyrin compound not only has the photodynamic antibacterial property of a protoporphyrin photosensitizer, butalso is endowed with an antibacterial mechanism for blocking iron metabolism, so that the compound can resist bacteria synergistically in two ways, the minimum inhibitory concentration can be reduced, the antibacterial efficiency can be improved, the targeting property to bacteria can be enhanced, and the bacterial drug resistance can be overcome.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, and in particular relates to an ion-modified gallium protoporphyrin compound and its preparation method and application. Background technique [0002] Bacterial infection has become one of the important problems threatening human health. Since Fleming first discovered penicillin in 1928, antibiotics have made great contributions to the fight against pathogenic bacteria and saved countless lives. However, due to the long-term abuse of antibiotics, the emergence of multi-drug-resistant bacteria and even "super bacteria" have emerged worldwide. With the emergence of colistin-resistant bacteria, the "last line of defense" constructed by antibiotics is also in jeopardy. my country is a big consumer of antibiotics and one of the countries with the most serious bacterial resistance. The emergence of multidrug-resistant bacteria and the potential explosive trend have caused panic in count...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00A61K41/00A61P31/04
CPCC07F5/003A61K41/0071A61P31/04
Inventor 张雷朱迎男张浩
Owner TIANJIN UNIV
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