Photosensitizing agents for antimicrobial photodynamic therapy

FIELD: medicine, in particular photosensitizing agents for antimicrobial photodynamic therapy.

SUBSTANCE: invention relates to new photosensitizing agents for antimicrobial photodynamic therapy namely cationic phthalocyanines of general formula MPc(CH2X)nCln, wherein Pc is phthalocyanine rest C32H16N8; M is Zn, AlY; n = 6-8; X is Y is Cl, OH, OSO3H. Claimed agents is characterized by wide range of antimicrobial activity. Single complex action of nontoxic in darkness micromolar (up to 2.0 muM) concentration thereof and low dose of red irradiation make it possible to produce high inactivation levels (up to 97-99 %) both gram-negative bacteria and yeast fungi of genus Candida.

EFFECT: improved agents for treatment of various severe complications of inflammation diseases.

3 dwg, 13 ex, 2 tbl

 

The present invention relates to pharmaceutical chemistry, and more specifically to products for antimicrobial photodynamic therapy (PDT) of pathogenic microorganisms. Antimicrobial PDT is selective oxidative destruction of pathogenic microorganisms in the combined effect of the dye photosensitizer (PS) and optical radiation corresponding to the spectral composition [Wainwright, M. (1998) Photodynamic antimicrobial chemotherapy (PACT). J. Antimicrob. Chemother., 42, 13-28]. Objects of antimicrobial photodynamic therapy are viruses, bacteria, fungi and protozoan organisms. However, the practical application at the present time have only dyes (mainly phenothiazines) with antiviral activity that are used in the sterilization of drugs in blood plasma [2. Ben-Hur E. and Horowitz, B. (1995) Advances in photochemical approaches for blood sterilization. Photochem. PhotobioL, 62, 383-388].

Due to the growth of acquired resistance to bacterial and fungal pathogens to chemotherapy (antibiotics, antimycotics) great importance is the development of FS with antibacterial and antifungal activity, and antimicrobial PDT is considered as an alternative way of dealing with pathogens of humans and animals. The selectivity of the method is due to local irradiation of infected areas and larger (20-200 times depending on the species di is) sensitivity to photodynamic effects of microorganisms compared with animal cells [Zeina B, Greenman J, Corry D, Purcell W.M. (2002) Cytotoxic effects of antimicrobial photodynamic therapy on keratinocytes in vitro. Br. J. DermatoL, 146, 568-573].

Among microbial pathogens are more resistant to photodynamic effects are gram-negative bacteria [Z. Malik, J. Hanania, Nitzan Y. (1990) Bactericidal effects of photoactivated porphyrins - an alternative approach to antimicrobial drugs. J. Photochem. Photobiol. B: Biol. V.5, 281-293]that is due to the low permeability of their outer membrane dye. The mechanism of transmembrane transport FS is facilitated migration, an important initial step is the binding of the dye cell. The negative charge of the outer surface of viable bacterial cells determines the active linking to them and, accordingly, expressed antibacterial activity of cationic dyes, for example dyes methylene blue and toluidine blue from class fenotiazinas [Millson C.E., Wilson M., MacRobert AJ, Bown S.G. (1996) Ex vivo treatment of gastric Helicobacter infection by photodynamic therapy. J. Photochem. Photobiol. B: Biol., 32, 59-66]. Photosensitization of fungi have been studied mainly in vitro systems for the yeast fungi. Based on the screening of dyes with different physico-chemical characteristics of the set that have the most activity of water-soluble anionic FS asymmetric location of charged groups - chlorines (RF patent No. 2230107, C 12 N 1/14 2004) or cationic dyes phenothiazines (Wilsn M. and Mia N. (1993) Sensitisation of Candida albicans to killing by low-power laser light. J. Oral Patrol. Med., 22, 354-357).

Know the use of a photosensitizer photosense based on sulfonated phthalocyanine hydroxylamine for the treatment of infected wounds and trophic ulcers with antibiotic-resistant microflora (Stranadko E.P., Tolstykh M.P., Riabov, M.V., Krivikhin DV (2003) Photodynamic therapy of persistent purulent wounds and trophic ulcers of lower extremeties. DC World Congress of the International Photodynamic Association. Abstracts. Miyazaki, 28). However, the anionic nature of this FS is the reason for its lack of effectiveness against gram-negative bacteria.

The objective of the invention is the finding of photosensitizers, which would be more effective in the process of antimicrobial PDT than photosense. To solve this problem it is proposed to use as antimicrobial photosensitizers for PDT cationic quaternion chlorotoluene phthalocyanine following General formula:

MPc(CH2X)nCln,

where Pc=phthalocyanine residue C32H16N8,

M=Zn, AlY,

n=6÷8,

Y=Cl, OH, OSO3H, for example:

AlPcChol8- octakis(β-hydroxyethylaminomethyl)phthalocyanine chloramine octaploid;

ZnPcChol8- octakis(β-hydroxyethylaminomethyl)phthalocyanine zinc octaploid;

ZnPcPym8- octakis(pyridiniomethyl)phthalocyanine zinc is octaploid;

AlPcPym8- octakis(pyridiniomethyl)phthalocyanine chloramine octaploid;

AlPcChol6- hexacis(β-hydroxyethylaminomethyl)phthalocyanine chloramine the hexachloride;

AlPcPym6- hexacis(pyridiniomethyl)phthalocyanine chloramine the hexachloride.

The invention is illustrated by the following examples.

Example 1

To 2.5 g (2.58 mmol) octakis(chloromethyl)phthalocyanine zinc (found, %: Cl 29.05; calculated % Cl 29.36), obtained as described in patent No. 844338, 1953, add 5 ml of dimethylformamide and 5 ml of N,N-dimethylaminoethanol. The mixture is stirred for 2 h at 100°C, the precipitation is filtered off, washed with acetone and dried, yielding 3.4 g (78.3%) octakis(N-(2-hydroxyethyl)-N,N-dimethylaminomethyl)phthalocyanine zinc octaploid (ZnPcChol8). The electronic absorption spectrum, λmaxnm (H2O): 679-680. Found, %: C, 51.41; H, 6.84; N, 13.07; Cl 15.88. Calculated for C72H112AlCl8N16O8Zn, %: C, 51.50; H, 6.72; N, 13.35; Cl 16.89.

Example 2

Similarly, from chlorocinnamate phthalocyanine chloramine (found, %: Cl 32.50; calculated for ClAlPc(CH2Cl)8, %: Cl 33.14) receive N-(2-hydroxyethyl)-N,N-dimethylaminomethylene phthalocyanine chloramine with the degree of substitution approximately equal to eight (AlPcChol8). The electronic absorption spectrum, λmaxnm (H2O): 682-684.

the example 3

Heated at boiling mixture of 0.150 mg octakis(chloromethyl)phthalocyanine zinc and 2 ml of pyridine for 1 h, the mixture is then filtered, washed with acetone and dried, yielding 0.228 g (87.6%) octakis(pyridiniomethyl)phthalocyanine zinc octaploid (ZnPcPym8). The electronic absorption spectrum, λmaxnm (H2O): 679-680.

Example 4

Similarly, from octakis(chloromethyl)phthalocyanine chloramine get octakis(pyridiniomethyl)phthalocyanine chloramine octaploid (AlPcPym8). The electronic absorption spectrum, λmaxnm (H2O): 680. Found, %: C, 59.09; H, 4.36; N, 13.49; Cl 18.41. Calculated for C80H64AlCl9N16, %: C, 60.22; H, 4.04; N, 14.04; Cl 19.99.

Example 5

Similarly, from chlorocinnamate aluminum phthalocyanine with a degree of substitution approximately equal to six (found, %: Cl 23.27; calculated for HO3SOAlPc(CH2Cl)8, %: Cl 22.93), get hexacis(pyridiniomethyl)phthalocyanine hydrosulfate the hexachloride (AlPcPym6). The electronic absorption spectrum, λmaxnm (H2O): 680-682.

Example 6

Similarly, from chlorocinnamate aluminum phthalocyanine with a degree of substitution approximately equal to six (found, %: Cl 23.27; calculated for (ClCH2)6-PcAlOSO3H, %: Cl 22.93), get hexacis(N-(2-hydroxyethyl)-N,N-dimethylaminomethyl)phthalocyanine hydrosulfate the hexachloride (AlPcChol6). The electron is first absorption spectrum, λmaxnm (H2O): 680-682.

Photobacterium activity of photosensitizers was determined using bacterial bioluminescent test. On the basis of known (Strahov MG, Zarubina A.P., Rumball AV, Danilov V.S., Stranadko E.F. Genetically engineered luminous bacteria as a new tool for evaluation of antimicrobial efficacy of photosensitizers. In: Laser and information technologies in medicine of the XXI century. 2001. S-268) correlation between photosensibilisation damping bioluminescence cultures of bacteria genetically engineered strain of Escherichia coli pXen7 and reduction in their number of colony forming units (CFU) is a measure of the intensity of bioluminescence is a rapid method of determining the degree of photoinactivation of bacterial cultures. The use of bacterial bioluminescent test on the basis of genetically engineered strains of gram-negative bacteria allows the selection of FS with a broad spectrum of antimicrobial action, because gram-negative bacteria possess the greatest among pathogenic microorganisms resistant to photosensitivity. The use of bacterial bioluminescence also allows you to choose non-toxic in the absence of exposure concentrations filesystem.

The determination of the activity of FS using bacterial bioluminescence what about the test is performed as follows. To negidrirovannogo distilled water sample (1 ml) of the bacteria E.coli pXen7, the reagent test systems "Ecolum" (Danilov V.S., Hansen V.M. Bacterial biosensors with bioluminescent output.//Sensory systems. 1998. Vol.12. N 1. P.56-68), add a solution FS (5 ál). While inactivated (30 min) of the samples at room temperature in the absence of light periodically measure the intensity of bioluminescence using a luminometer "Biotox-6" (Moscow) to determine the possible toxicity of the drug. Carry out the irradiation of the samples, for example, using a source of cold white light acomp with a red filter KS-11. Measure the intensity of bioluminescence irradiated samples for determination of phototoxicity.

The fungicidal activity of photosensitizers was determined using culture of yeast fungi of the genus Candida (C. guilliermondii yeast).

In a medium containing a culture of yeast fungi add FCS, incubated for 15 minutes, then irradiated, for example, using a source of cold white light acomp with a red filter KS-11.

The evaluation of the results of inactivation is carried out by the determination of colony forming ability (survival) yeast fungi subjected to FS and radiation, compared with the control untreated cultures or processed only Psili only radiation.

The results of this research allow us to conclude that a single combined effect of non-toxic in the dark micromolar (up to 2.0 µm) concentrations FS ZnPcChol8, ZnPcPym8, AlPcChol8or AlPcPym8and low doses of radiation red range allows to achieve high (up to 97-99%) levels of inactivation of crops like gram-negative bacteria, and Candida., i.e. offer FS have a broad spectrum of antimicrobial action. FS AlPcChol6and AlPcPym6can be used as fotoangelo.

Example 7

To negidrirovannogo for 20 minutes at 4°C chilled distilled water for 20 minutes in distilled water at 20-22°C biosensor "Ecolum" (concentration of 108cells/ml) add ZnPcChol8at a concentration of 0.5-2.0 μm, incubated 15 minutes in the absence of light and is irradiated 1-5 minutes using source acomp with a red filter KS-11. The repetition of three experiments. At one time combined with the influence of FS ZnPcChol8and light red band is observed damping of bioluminescence to 99%. The results of the experiments are presented in figure 1.

Example 8

Similarly, when you use ZnPcPym8instead ZnPcChol8there is also a damping of bioluminescence to 99%. The experimental results presented at the Phi is .2.

Example 9

Similarly studied AlPcPym8, AlPcChol8, AlPcChol8and AlPcPym6at a concentration of 1.0 μm and irradiated for 2.5 minutes. Received the following number of Photobacterium activity FCS: AlPcPym8>AlPcChol8>AlPcChol6>AlPcPym6(table 1).

Table 1

The effectiveness of FS (1 ám) - induced suppression of bioluminescence of E. coli pXen7
The photosensitizerThe quenching of bioluminescence after 2.5 minutes of exposure, O.E.
AlPcChol81.70±0.15
AlPcChol61.53±0.14
AlPcPym82.29±0.23
AlPcPym61.29±0.11

Example 10

In a three-day, suspended in physiological solution pure cultures of C. guilliermondii yeast BWA-656 at a concentration of 106fungal cells in a milliliter add ZnPcCholg or ZnPcPym8at a concentration of 0.5 μm, incubated 30 minutes in the dark and irradiated 10-20 seconds using source acomp with a red filter KS-11. The repetition of three experiments. In a single combined effects of FS and light red range up to 99.5-99.7% of fungal cells in culture C. guilliermondii yeast has lost the ability to reproduce. The experimental results depict what aulani figure 3.

Example 11

Similarly, use AlPcPym8, AlPcChol8, AlPcChol6and AlPcPym6at a concentration of 1 μm. Received the following number of photofunctional activity:

AlPcPym8>AlPcChol8>AlPcChol6>AlPcPym6(table 2).

Table 2

The efficiency of photosensitizers (1 ám) - induced inactivation of yeast fungi Candida guilliermondii yeast.
PhotoThe efficiency of inactivation, O.E.
Sensitizersafter 10 seconds of irradiationafter 20 sec exposure
AlPcChol89.1±0.820.0±1.7
AlPcChol61.3±0.13.1±0.3
AlPcPym814.3±1.329.5±2.5
AlPcPym61.2±0.12.5±0.2

Conducted PDT severe septic complications of inflammatory diseases of ENT-organs with the use of cationic phthalocyanines ZnPcPym8and ZnPcChol8. Under our observation were patients with severe septic complications of chronic tonsillitis, acute and chronic suppurative otitis media, acute and chronic inflammation of the paranasal sinuses and is also injuries the facial area, the head and neck. Including: purulent peritonsillitis and parapharyngeal, phlegmon submandibular region, the lateral surface of the neck and floor of mouth, front and rear mediastinitis, odontogenic, autogenie and winogene subperiosteal abscesses, festering hematoma infected and gunshot wounds of the face, head, neck.

Photodynamic therapy was started immediately after surgical opening of purulent foci and carrying out emergency and resuscitation. As a light source is used, the radiation of the semiconductor laser therapeutic instrument "Mustang" with a wavelength of 0.67 μm, with a capacity of 24 mW.

therapy consisted in the fact that the cavity is surgically opened the abscess was laid gauze impregnated wipes FS, the time from 10 min to 24 h and Then were irradiated purulent wounds with exposure time of 7 minutes the Procedure was performed daily until complete cleansing wounds from pus and wound detritus, from 5 to 10 treatments on the course of treatment depending on the severity and prevalence of purulent process. At the end of the course of PDT and the disappearance of signs of wound infection last usualis again delayed seams.

Our observations showed that complete purification of the festering wounds from the products of decomposition and microbial life, accompanying with the give the appearance of healthy granulation and mild inflammation, occurred, usually in 5-7 days with a daily application of PDT, while in normal conditions and the use of standard antibiotics and local treatment of these periods averaged 2 to 3 weeks, and sometimes more (according to archival records). It is also important to the cosmetic aspect is the absence of severe cicatricial deformities with large soft tissue defects of the face, head, neck.

PDT severe septic complications of inflammatory diseases of ENT-organs using the proposed cationic FS significantly optimizes the treatment of this disease and has broad prospects. It allows to significantly reduce the number of used expensive anti-inflammatory and antibacterial drugs, including antibiotics, to which modern microbial flora insensitive and application which causes the violation of local and General immunity of the body. In addition, significantly reduced the hospitalization for inpatient treatment due to the speed of inflammation and rehabilitation.

Example 12

Patient A., 25 years old, was admitted to the ENT clinic RSMU, Moscow (GCB) 12.06.04 in an emergency with a diagnosis of right-sided peritonsillar abscess, parapharyngeal, submandibular cellulitis area of the law.

13.06.04 - the patient was accessorieswelcome right with revision parapharyngeal space on the right and the opening of the submandibular cellulitis area right outside access. The patient's condition is severe, the body temperature 39.0, chills. There is a festering wound in the throat right on the remote place of the tonsils, which connects to a skin wound in the right submandibular region through an infected pharyngotomy diameter of about 2 cm Copious purulent discharge in the mouth and in the right submandibular region.

14.06.04 - patient began a course of PDT with ZnPcChol8the exposure of PS in the wound in the throat and submandibular region to the right is 10 minutes. The light source of semiconductor laser "Mustang" with a wavelength of 0.67 μm, the exposure time of 7 minutes. Treatments were performed daily. Since the second procedure impregnated FS tampons left in the wound during the day (before the next procedure).

15.06.04 - the condition of the patient is moderate, the wound is cleaned, detachable moderate purulent serous, pharyngotomy narrowed, the temperature of the reaction is present in 37.8.

16.06.04 - the patient's condition is satisfactory, temperature 36.8, pharyngotomy is completely closed, the wound in the submandibular region clear, serous discharge, connection with the throat there. Cancelled parenteral administration of antibiotics. PDT was carried out for 6 the ducks.

19.06.04 - wound in the throat epithelisation, the wound in the submandibular area clean and covered in a healthy pink granulation, no detachable. The patient's General condition is satisfactory, the temperature of 36.4, blood parameters stabilize. On the same day, the wound in the right submandibular region layers stitched tightly, separate silk sutures. Sutures were removed on day 7, the patient dehospitalization with recovery 27.06.04.

This observation took 6 treatments of photodynamic therapy for complete relief of purulent process in the mouth and on the side of the neck.

Example 13

Patient K., 82 years old, was admitted to the Department of oral and maxillofacial surgery GCB 1.07.04 in an emergency with a diagnosis of carbuncle left cheek, abscess of the upper eyelid of the left eye, diabetes mellitus type 1 (insulin dependent). At admission the patient's condition moderate body temperature 39.2, chills, blood sugar - 14 mg/L.

1.07.04 - made surgical opening phlegmon of the upper eyelid of the right eye and carbuncle of the left cheek cruciate incision started traditional antibacterial, anti-inflammatory therapy and correction of blood sugar.

2.07.04 - the condition of the patient is essentially unchanged, the body temperature of 38.2 separated from wounds copious, purulent, with a putrid odor. Started a course of PDT with FS ZnPcPym8and the semiconductor, Nikodym laser "Mustang" with a wavelength of 0.67 μm. On the surface of purulent wounds were overlapped impregnated FS gauze napkins with exposure time of 10 minutes and was performed laser irradiation for 7 minutes.

5.07.04 (4th procedure PDT) - the patient's condition is satisfactory, temperature 36.8, blood sugar - 8 mm/l of Wounds in the area of the upper eyelid of the left eye in the region of the left cheek was completely cleansed of purulent debris, covered with bleeding granulations, edema and infiltration in the area of RAS is not defined. Cancelled antibiotic therapy. 6.07.04 - wounds in the area of the upper eyelid of the left eye and left cheek layers tightly sutured with silk sutures. Sutures were removed on day 7. The patient was discharged with recovery 13.07.04.

This observation took 4 treatments of PDT for complete relief of purulent process, complicated by diabetes mellitus type 1.

Thus, the proposed FS have a broad spectrum of antimicrobial action: single combined effect of non-toxic in the dark their micromolar (up to 2.0 µm) concentrations and low doses of radiation red range allows to achieve high (up to 97-99%) levels of inactivation of crops like gram-negative bacteria, and Candida.

PDT severe septic complications of inflammatory diseases of ENT-organs using the proposed cationic FS significantly optimizes the treatment of this patol the GII and has broad prospects.

Cationic phthalocyanines of General formula

Mrs(CH2X)nCln,

where PC=phthalocyanine residue C32H16N8,

M=Zn, AlY,

n=6÷8,

Y=Cl, HE, OSO3N

as the antimicrobial photosensitizers for photodynamic therapy.



 

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SUBSTANCE: invention relates to quaternary phthalocyanines of general formula MPc(CH2X)nCln, wherein Pc is phthalocyanine rest C32H16N8; M is Zn, AlY; n = 6-8; X is Y is Cl, OH, OSO3H, useful as photosensitizing agents in photodynamic therapy having high photoinduced activity in vivo and in vitro.

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< / BR>
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SUBSTANCE: invention relates to quaternary phthalocyanines of general formula MPc(CH2X)nCln, wherein Pc is phthalocyanine rest C32H16N8; M is Zn, AlY; n = 6-8; X is Y is Cl, OH, OSO3H, useful as photosensitizing agents in photodynamic therapy having high photoinduced activity in vivo and in vitro.

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5 cl, 2 ex, 1 dwg

FIELD: organic chemistry, medicine, oncology.

SUBSTANCE: invention relates to photosensitizing agents used in photodynamic therapy of neoplasm and some other diseases. Invention describes tetraazachlorines of the general formula: wherein R1R2 mean -C6H4; R3 = R4 = R5 mean -CH3; M means HH (H2TBTAC); R1R2 means 1,2-C10H6; R3 = R4 = R5 mean -CH3; M means Zn(Zn-1,2-TNTAC); R1 = R2 mean -C6H5; R3 = R4 = R5 mean -CH3; M means HH (H2TACPh6); R1 = R3 mean hydrogen atom (H); R2 =R4 mean -C6H5; R5R5 mean -CH2N(CH3)CH2; M means HH (H2PyrTACPh4); R1R2 mean 4-C(CH3)3C6H3; R3 = R4 mean hydrogen atom (H); R5R5 mean -CH2N(CH3)CH2; M means HH (H2TBtTACPyrN-Me) used as photosensitizing agents in the near IR-region of spectrum for carrying out the photodynamic therapy. These photosensitizing agents possess the intensive absorption in spectral region 710-750 nm and can be used in treatment of deep tumor tissues by the photodynamic therapy method.

EFFECT: valuable medicinal properties of compounds.

1 cl, 4 ex

FIELD: luminescent materials.

SUBSTANCE: invention provides novel electroluminescent material comprised of injecting layer, metal chelate complex-based active luminescent layer, hole-transition layer and hole-injecting layer. Luminescent substance is selected from oxyquinolate metallocomplexes of zinc 8-hydroxy-2-methoxyquinolate and zinc 8-hydroxy-2-methylquinolate. Electroluminescent material shows emission in green spectrum region.

EFFECT: increased heat resistance and widened choice of stable green-emitting materials.

2 cl, 3 ex

FIELD: chemistry of organometallic compounds, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing the chelate compound bis-(1-vinylimidazole)zinc diacetate (I) representing the medicinal preparation of acizol that is the effective antidote and antioxidant. Method for preparing the compound (I) is carried out in the absence of organic solvents at temperature 20-35°C in the mole ratio 1-vinylimidazole : zinc diacetate in the range from 10:1 to 3:1. Method provides exclusion fire hazard and explosion hazard solvent from the technological process and enhancement of the yield of highly pure acizol satisfied for Pharmacopoeia requirements.

EFFECT: improved method for preparing.

2 cl, 4 ex

The invention relates to petrochemistry, specifically to the production dialkyldithiocarbamate accelerators of vulcanization of rubbers
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