CN107753947B - Imidazole ionic liquid photosensitizer and preparation method and application thereof - Google Patents
Imidazole ionic liquid photosensitizer and preparation method and application thereof Download PDFInfo
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- CN107753947B CN107753947B CN201711107237.XA CN201711107237A CN107753947B CN 107753947 B CN107753947 B CN 107753947B CN 201711107237 A CN201711107237 A CN 201711107237A CN 107753947 B CN107753947 B CN 107753947B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
Abstract
The invention discloses an imidazole ionic liquid photosensitizer and a preparation method and application thereof. Belongs to the technical field of photodynamic antibacterial. The imidazole ionic liquid photosensitizer is prepared by the reaction of imidazole cation and photosensitizer anion. The invention utilizes carboxyl in the photosensitizer and imidazole ring with alkyl to form anion and cation to prepare the ionic liquid photosensitizer, effectively solves the defect of poor solubility of the photosensitizer in physiological environment, and utilizes the specific anion and cation pair structure of the ionic liquid photosensitizer to improve the water solubility and membrane permeability of the photosensitizer and enhance the antibacterial effect of the photosensitizer.
Description
Technical Field
The invention belongs to the technical field of photodynamic antibacterial, and particularly relates to an imidazole ionic liquid photosensitizer as well as a preparation method and application thereof.
Background
Abuse of antibiotics has caused bacterial resistance and the number of deaths from wound infections has increased. Although new antibiotics are continuously developed and applied to clinic, the research and development speed of the new antibiotics is far behind the variation speed of pathogenic bacteria, and the emergence of 'super bacteria' with drug resistance to various antibiotics makes the research and development of novel antibacterial drugs and antibacterial methods which are not easy to generate drug resistance and have strong bactericidal effect on the existing drug-resistant bacteria urgent. Among the most promising approaches, the photodynamic antibacterial therapy (PACT) shows a very good therapeutic effect on infections caused by bacteria, fungi and viruses, in particular on drug-resistant bacterial infections.
The photosensitizer is a crucial determinant factor in photodynamic antibiosis, and the second-generation photosensitizer such as porphyrin, porphin and the like has the characteristics of single component, high singlet state and triplet state oxygen yield, low dark toxicity, long action wavelength, large action depth and the like, and has good application prospect.
However, these photosensitizers have poor solubility and are very easy to agglomerate under physiological conditions, and the photodynamic curative effect of the photosensitizers is reduced. And because the bacterial wall composition structures of gram-negative bacteria and positive bacteria are different, some photosensitizers are only effective on gram-positive bacteria or gram-negative bacteria, and efficient photosensitizers effective on both gram-negative bacteria and gram-positive bacteria are rare. Therefore, the design and preparation of photosensitive drugs effective on gram-negative bacteria, gram-positive bacteria and super bacteria can greatly expand the application of photodynamic antibiosis.
Disclosure of Invention
The invention aims to provide an imidazole ionic liquid photosensitizer and a preparation method and application thereof.
The invention is realized by the following technical scheme:
the invention discloses an imidazole ionic liquid photosensitizer which is prepared by the reaction of imidazole cations and photosensitizer anions; wherein: the molar ratio of the imidazole cation to the photosensitizer anion is (3-6): 1.
Preferably, the imidazolium cation is with C10～C18Alkyl substituted imidazoles; the photosensitizer anion is a photosensitizer with carboxyl.
Further preferably, C is adjusted according to the number of carboxyl groups in the anion of the photosensitizer10～C18The dosage of the alkyl imidazole is 1-2 times of the mole number of carboxyl carried by the anion of the photosensitizer.
Preferably, the photosensitizer having a carboxyl group is a porphyrin-based photosensitizer having a carboxyl group or a porphine-based photosensitizer having a carboxyl group.
Further preferably, the porphyrin-based photosensitizer with carboxyl is hematoporphyrin or hematoporphyrin monomethyl ether; the porphin photosensitizer with carboxyl is chlorin or porphin sodium.
The invention also discloses a preparation method of the imidazole ionic liquid photosensitizer, which comprises the following steps:
1) reacting an alkyl compound and imidazole at a molar ratio of 1:1 at 45-65 ℃ for 48-96 h, purifying a reaction product, dissolving the reaction product in absolute ethyl alcohol, adding strong base under an ice bath condition, and reacting at 0-10 ℃ for 6-12 h;
2) adding a photosensitizer with carboxyl into the product prepared in the step 1), reacting at room temperature for 8-24 h, removing a reaction solvent, and separating and purifying the obtained reactant to prepare the imidazole ionic liquid photosensitizer;
wherein the molar ratio of the product prepared in the step 1) to the photosensitizer with carboxyl is (3-6) to 1.
Preferably, the alkyl compound is halogenated C10-C18The alkyl and imidazole are vinyl imidazole.
The invention also discloses application of the imidazole ionic liquid photosensitizer in preparation of a photodynamic antibacterial photosensitizer.
Preferably, the photodynamic antibacterial photosensitizer is a photodynamic antibacterial photosensitizer for resisting gram-negative bacteria, gram-positive bacteria and super bacteria.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention discloses an imidazole ionic liquid photosensitizer, which is characterized in that a corresponding ionic liquid is designed according to the molecular structure of a photosensitizer with carboxyl; secondly, in order to improve the antibacterial performance of the photosensitizer on gram-negative bacteria, alkyl which has strong destructibility on the bacterial wall is introduced on an imidazole ring, and the photosensitizer which is made into ionic liquid by double actions of negative ions and positive ions has broad-spectrum antibacterial effect on gram-negative bacteria such as escherichia coli (e.coli), gram-positive bacteria staphylococcus aureus (s.aureus) and methicillin-resistant staphylococcus aureus (MRSA). The invention utilizes carboxyl in the photosensitizer and imidazole ring with alkyl to form anion and cation to prepare the ionic liquid photosensitizer, effectively solves the defect of poor solubility of the photosensitizer in physiological environment, and utilizes the specific anion and cation pair structure of the ionic liquid photosensitizer to improve the water solubility and membrane permeability of the photosensitizer and enhance the antibacterial and antitumor effects of the photosensitizer. The experimental verification results are as follows:
1. water solubility: can increase the solubility of the water-insoluble chlorin to 16.8 g/L;
2. membrane permeability: the cell-entering rate of E.coli in gram-negative bacteria is increased from 13.0% to more than 90%, the cell-entering rate of S.aureus in gram-positive bacteria is increased from about 40% to 100%, and the cell-entering rate of MRSA is increased from 90% to 100%;
3. the antibacterial effect is as follows: greatly reduces half Inhibitory Concentration (IC) of photosensitizer with carboxyl to E.coli in gram-negative bacteria50Value), IC50Decrease from 0.5mM to 0.0075mM, IC of S.aureus in gram-positive bacteria50IC of MRSA decreased from 0.09mM to 0.0068mM50The concentration is reduced from 0.065mM to 0.0032 mM.
Drawings
FIG. 1 is a reaction flow chart of the present invention for preparing an ionic liquid type photosensitizer (Ce 6-IL);
FIG. 2 is a nuclear magnetic spectrum of Ce6 and Ce 6-IL;
fig. 3 is TEM characterization of e.colis structural changes at MBC concentration for Ce6 and Ce 6-IL; coli + Ce 6; coli + Ce6+ illumination; c is E.coli + Ce 6-IL; d is E.coli + Ce6-IL + illumination; coli;
FIG. 4 is a TEM characterization of the S.aureus structural changes at MBC concentration for Ce6 and Ce 6-IL; in the figure, a is s.aureus + Ce 6; b is S.aureus + Ce6+ illumination; c is S.aureus + Ce 6-IL; d is S.aureus + Ce6-IL + illumination; e is s.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
The invention discloses an ionic liquid type photosensitizer, which comprises imidazole cations and photosensitizer anions; the ionic liquid type photosensitizer is an imidazole ionic liquid type photosensitizer and has good water solubility and permeability.
The anion of the photosensitizer is photosensitizer with carboxyl.
The imidazole cation is provided with C10～C18The alkyl substituted imidazole can improve the destructive capacity of the ionic liquid photosensitizer on the bacterial wall of gram-negative bacteria and enhance the antibacterial capacity of photodynamic antibacterial on the gram-negative bacteria.
Referring to fig. 1, a reaction flow chart for preparing the ionic liquid photosensitizer (Ce6-IL) according to the present invention, the specific preparation method is as follows:
preparation of a polypeptide having a structure of C10～C18Dissolving the alkyl imidazole chloride ionic liquid in an anhydrous solvent, adding strong base in an ice bath, adding a photosensitizer with carboxyl after complete low-temperature reaction, adding the photosensitizer with carboxyl, reacting at room temperature for 8-24 h, removing the solvent by rotary evaporation, adding an extracting agent, centrifuging to remove the unreacted photosensitizer, collecting supernatant, and drying in vacuum at 45-70 ℃ after rotary evaporation.
1. Preparation of ionic liquid type photosensitizer
Dissolving 0.1g of 1-vinyl-3-dodecyl imidazole chloride (IL) in absolute ethyl alcohol, adding 0.02g of potassium hydroxide under the ice bath condition, reacting at 0 ℃ for 6h, adding 0.048g of chlorin, reacting at room temperature for 12h, and performing rotary evaporation to remove the absolute ethyl alcohol. Adding methanol: and (3) rapidly stirring acetonitrile 9:1(v/v), separating out unreacted chlorin, centrifuging at 3000rpm/min for 5min, removing the unreacted chlorin, collecting supernatant, performing rotary evaporation, and performing vacuum drying at 45-70 ℃.
The nuclear magnetic spectrum of the prepared ionic liquid photosensitizer is shown in figure 2.
2. Preparation and preparation of strains required for experiments
A standard quality control strain Escherichia coli (ATCC 25922); methicillin-resistant staphylococcus aureus (clinically isolated by the cijing hospital) strains; staphylococcus aureus (ATCC 29213)
Conventional bacterial culture methods:
① the frozen tube containing the strain is taken out from the liquid nitrogen tank, put into water bath at 37 deg.C quickly, shaken to melt, then inoculated into LB liquid medium, and shake-cultured at 37 deg.C for 24 h.
② streaking the above cultured strains on solid culture medium, placing in a constant temperature incubator, culturing to grow new colonies, selecting newly activated single colony from solid culture medium plate, inoculating in LB liquid culture medium, and shake culturing at 37 deg.C for 12 hr until late logarithmic growth stage is available.
3. Imidazole ionic liquid photosensitizer antibacterial experiment
Example 1
Taking the bacterial liquid in the logarithmic growth phase, centrifuging, washing with PBS solution, and suspending to pH5.0 LB liquid culture medium to make the bacterial concentration reach 106CFU/mL。
① the above-mentioned bacterial liquid is added into 12 6-well culture plates, each well contains 2mL of dihydroporphin (Ce6) with 0.005, 0.001, 0.05, 0.1, 0.5mM in No. 1 6-well plate, the E.coli control group and the 0.005, 0.001, 0.05, 0.1, 0.5mM Ce6 light irradiation group in No. 2 6-well plate, the E.coli control group and the 0.005, 0.001, 0.05, 0.1, 0.5mM ionic liquid photosensitizer (Ce6-IL) group in No. 3-6-well plate, the E.coli control group and the 0.005, 0.001, 0.05, 0.1, 0.5mM Ce 4-IL 6-IL 5 light irradiation group in No. 4-well plate, the S.aureus control group and the 0.005, 0.001, 0.05, 0.1, 0.5mM MRS 5-IL 5-well plate, the S.001, 0.05, 0.5mM MRAUREE.5 mM MRSE control group and the 0.05, 0.5mM MRS 6-IL 5mM control group in No. 6-well plate, the 0.5mM MR5-well plate, the 0.5mM control group, 0.5-0.5 mM MRAURE control group, the 0.001, 0.5-0.5 mM MR5-0.5 mM MR5-0.5-IL 5-well plate, the light irradiation group, the control group, 0.05, 0.5-0.5 mM MRAURE control group, 0.5-0.05, 0.5-0..
② adding different photosensitizers for 30min, irradiating with 660nm red light for 15min, and culturing for 6 h.
③ colonies were counted from the samples by plating and the experiment was repeated three times.
④ analysis of the antibacterial effects of Ce6 and Ce6-IL in pH5.0 medium and calculation of IC50And Minimum Bactericidal Concentration (MBC), results are shown in table 1.
⑤ at pH5.0, 2mL 10 was added to each 6-well plate6CFU/mLE. colis, S.aureus and MRSA, and Ce6 and Ce6-IL with the same molar number are added respectively for culturing for 10min, and the cell entry rate of Ce6 and Ce6-IL under the condition of pH5.0 is calculated by using a flow cytometer, and the results are shown in Table 2.
Example 2
Taking the bacterial liquid in the logarithmic growth phase, centrifuging, washing with PBS solution, and suspending to pH 6.0LB liquid culture medium to make the bacterial concentration reach 106CFU/mL。
The following procedures were carried out in the same manner as in example 1 except that the pH of the medium was 6.0. IC of Ce6 and Ce6-IL in culture medium under pH 6.0 condition50And Minimum Bactericidal Concentration (MBC) results are shown in table 1.
Example 3
Taking the bacterial liquid in the logarithmic growth phase, centrifuging, washing with PBS solution, and suspending to pH 7.0LB liquid culture medium to make the bacterial concentration reach 106CFU/mL。
The following procedures were carried out in the same manner as in example 1 except that the pH of the medium was 7.0. IC of Ce6 and Ce6-IL in culture medium at pH 7.050And Minimum Bactericidal Concentration (MBC) results are shown in table 1.
The results of the same molar numbers of Ce6 and Ce6-IL at pH 7.0 in the culture medium are shown in Table 2.
Example 4
Taking the bacterial liquid in the logarithmic growth phase, centrifuging, washing with PBS solution, and suspending to pH 8.0LB liquid culture medium to make the bacterial concentration reach 106CFU/mL。
The following stepsThe same procedure as in example 1 was repeated, except that the pH of the medium was 8.0. IC of Ce6 and Ce6-IL in culture medium under pH 8.0 condition50And Minimum Bactericidal Concentration (MBC) results are shown in table 1.
The results of the same molar numbers of Ce6 and Ce6-IL at pH 8.0 in the culture medium are shown in Table 2.
Example 5
Taking the bacterial liquid in the logarithmic growth phase, centrifuging, washing with PBS solution, and suspending to pH 9.0LB liquid culture medium to make the bacterial concentration reach 106CFU/mL。
The following procedures were carried out in the same manner as in example 1 except that the pH of the medium was 9.0. IC of Ce6 and Ce6-IL in culture medium under pH 9.0 condition50And Minimum Bactericidal Concentration (MBC) results are shown in table 1.
The results of the same molar numbers of Ce6 and Ce6-IL at pH 9.0 in the culture medium are shown in Table 2.
TABLE 1 half Inhibitory Concentrations (IC) of Ce6 and Ce6-IL on E.coli, S.aureus and MRSA50) And Minimum Bactericidal Concentration (MBC)
TABLE 2 cell-entry rates of Ce6 and Ce6-IL at different pH conditions in E.coli, S.aureus and MRSA
As can be seen from Table 1, after Ce6 was prepared into Ce6-IL, the IC of Ce6-IL was compared with E.coli, S.aureus and MRSA50The values are all reduced by about 100 times, and the MBC is also reduced by about 10 times.
As can be seen from table 2, compared with Ce6, the cell entry rate of Ce6-IL to e.coli is increased from 13.0% to over 90%, the cell entry rate of s.aureus is increased from about 40% to 100%, the cell entry rate of MRSA is increased from 90% to 100%, and the ability of photosensitizer to enter into bacteria is greatly improved.
4. Effect of Ce6-IL on bacterial Structure and integrity
The surrounding environment of the initial stage of human wound infection is weakly acidic, gram-negative bacteria and gram-positive bacteria are treated by bacteria cultured under the condition of pH 6.8-7.0 through MBC concentration, TEM is adopted to characterize the bacterial wall and integrity of the bacteria, and the results are shown in FIGS. 3 and 4.
It can be obviously seen from fig. 3e.coli that e.coli has a complete bacterial wall and membrane structure, a in Ce6 diagram or b in Ce6 plus light diagram has less damage to e.coli structure, Ce6 has poor bacteriostatic effect on gram-negative bacteria. Ce6-IL can cause swelling deformation of e.coli by destroying the structure of the bacterial wall (c in the figure), and after light irradiation, the bacterial membrane of e.coli generates a large number of pores, and the integrity of the bacteria is destroyed. It can also be seen from FIG. 4 that Ce6-IL has a greater disruption of the integrity of S.aureus relative to Ce6 (a and b in the figure) (c and d in the figure).
Claims (8)
1. An imidazole ionic liquid photosensitizer is characterized in that the photosensitizer is prepared by the reaction of imidazole cations and photosensitizer anions; wherein: the molar ratio of imidazole cations to photosensitizer anions is (3-6) to 1;
the imidazolium cation is provided with C10～C18Alkyl substituted imidazoles; the photosensitizer anion is a photosensitizer with carboxyl.
2. The imidazole-based ionic liquid photosensitizer according to claim 1, wherein C is adjusted according to the number of carboxyl groups in the anion of the photosensitizer10～C18The dosage of the alkyl imidazole is 1-2 times of the mole number of carboxyl carried by the anion of the photosensitizer.
3. The imidazole-based ionic liquid photosensitizer according to claim 1, wherein the photosensitizer having a carboxyl group is a porphyrin-based photosensitizer having a carboxyl group or a porphine-based photosensitizer having a carboxyl group.
4. The imidazole-based ionic liquid photosensitizer according to claim 3, wherein the porphyrin-based photosensitizer having a carboxyl group is hematoporphyrin or hematoporphyrin monomethyl ether; the porphin photosensitizer with carboxyl is chlorin or porphin sodium.
5. A preparation method of an imidazole ionic liquid photosensitizer is characterized by comprising the following steps:
1) reacting an alkyl compound and imidazole at a molar ratio of 1:1 at 45-55 ℃ for 48-96 h, purifying a reaction product, dissolving the reaction product in absolute ethyl alcohol, adding strong base under an ice bath condition, and reacting at 0-10 ℃ for 6-12 h;
2) adding a photosensitizer with carboxyl into the product prepared in the step 1), reacting at room temperature for 8-24 h, removing a reaction solvent, and separating and purifying the obtained reactant to prepare the imidazole ionic liquid photosensitizer;
wherein the molar ratio of the product prepared in the step 1) to the photosensitizer with carboxyl is (3-6) to 1; the alkyl compound is halogenated C10～C18An alkane.
6. The method for preparing the imidazole-based ionic liquid photosensitizer according to claim 5, wherein the imidazole is vinylimidazole.
7. The application of the imidazole ionic liquid photosensitizer as claimed in any one of claims 1 to 4 in preparation of photodynamic antibacterial photosensitizer.
8. The use according to claim 7, wherein the photodynamic antibacterial photosensitiser is a photodynamic antibacterial photosensitiser against gram negative bacteria, gram positive bacteria and superbacteria.
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| CN1425657A (en) * | 2002-12-30 | 2003-06-25 | 中国科学院兰州化学物理研究所 | Olefine epoxidation method in ionic liquid |
| WO2009026313A1 (en) * | 2007-08-20 | 2009-02-26 | Colorado Seminary, Which Owns And Operates The University Of Denver | Photoinduced signal amplification through externally sensitized photofragmentation in masked photosensitizers and photoamplified fluorescence turn-off system |
| WO2009076530A1 (en) * | 2007-12-11 | 2009-06-18 | The Regents Of The University Of Colorado | Heteroaryl salts and methods for producing and using the same |
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