WO2002014464A2 - Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections - Google Patents
Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections Download PDFInfo
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- WO2002014464A2 WO2002014464A2 PCT/FI2001/000726 FI0100726W WO0214464A2 WO 2002014464 A2 WO2002014464 A2 WO 2002014464A2 FI 0100726 W FI0100726 W FI 0100726W WO 0214464 A2 WO0214464 A2 WO 0214464A2
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- 150000001875 compounds Chemical class 0.000 claims abstract description 103
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- 239000000284 extract Substances 0.000 claims description 35
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- Plant-derived and synthetic phenolic compounds and plant extracts effective in the treatment and prevention of chlamydial infections
- the invention relates to effective plant-derived phenolic compounds and to the corresponding synthetic compounds and their derivatives and plant extracts as well as compositions containing them, useful in the treatment and prevention of chlamydial infections and the use of the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives and plant extracts and compositions containing them in the treatment and prevention of chlamydial infections.
- the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives and plant extracts can be used in the preparation of pharmaceutical preparations, food additive compositions and functional food stuffs beneficial for health.
- Chlamydiae are small Gram-negative bacteria. Due to their unique intracellular reproduction cycle they have been classified as a separate order Chlamydiales, including genus Chlamydia. The genus Chlamydia was already initially divided into two species, C. trachomatis and C. psittaci. The division was based on biochemical properties:
- C. trachomatis was considered a homogeneous group and "C. psittaci” a very heterogeneous group.
- C. psittaci a very heterogeneous group.
- C. psittaci a very heterogeneous group.
- C. trachomatis a d C. pneumoniae are different in respect of their surface structure.
- the main component of the surface structure of C. trachomatis is the major outer membrane protein (MOMP) that varies at four different sites and gives the basis on the division of C.
- MOMP major outer membrane protein
- C. pneumoniae uses a heparin receptor which is not used by genital chlamydiae with the exception of LGV.
- C. pneumoniae is transmitted via respiratory tract and may spread inside monocytes into the circulatory system, whereas C. trachomatis is transmitted principally in sexual contacts.
- the treatment is different: C. trachomatis is usually treated with a single dose, whereas for C. pneumoniae, even three-week antibiotic courses are recommended.
- COPD chronic obstructive pulmonary disease
- C. trachomatis has extragenomic plasmids not found in human C. pneumoniae strains. The genomes of both species have been sequenced and the number of genes is considerably higher (about 200) in C. pneumoniae than in C. trachomatis. In a recent reclassification of chlamydiae, it has already been transferred to a to- tally different genus, Chlamydophila. Thus, there is good reason to believe that all that is known from C. trachomatis cannot be applied to C. pneumoniae.
- C. pneumoniae and C. trachomatis which cause common important diseases.
- C. psittaci is very widespread in the animal kingdom but can only occasionally also cause infections in man.
- C. pecorum is known causing infections in ruminants.
- the classification of new genera and species in order Chlamydiales is in progress.
- C. pneumoniae is the most common chlamydiae of the centuries and almost eve- rybody gets infected with it 2 to 3 times during the life time. C. pneumoniae can easily invade lung tissue and multiply in macrophages and endothelium of blood vessels. The clinical picture of respiratory infections caused by C. pneumoniae varies largely from the usually mild upper respiratory tract infections in children to serious pneumonias of adults. 5-10% of all pneumonias are caused by C. pneu- moniae. C. pneumoniae is spread as an airway infection from people to people.
- Chlamydial infections are of incidious and latent nature and their chronic late complications are obviously most significant of all.
- Epidemiological studies indicate an important association between chronic C. pneumoniae infections and atherosclerosis: many studies have also revealed a connection between chlamydial infections and the incidence of acute myocardial infarction (AMI). Further, the chronic C. pneumoniae infection apparently plays a role in the outbreak of asthma as well as of chronic obstructive pulmonary disease.
- Arteriosclerosis is a chronic inflammation state and C. pneumonia particles can be demonstrated in foam cells and smooth muscle cells in over half ofthe atherosclerotic plaques.
- C. pneumonia particles can be demonstrated in foam cells and smooth muscle cells in over half ofthe atherosclerotic plaques.
- LPS chlamydial lipopolysaccharide
- C. pneumo- niae have been discovered to play a role in cerebral infarcts and transient cerebral ischemic attacks.
- Antibiotic treatment has been observed to reduce the risk of heart attacks and it has also been possible to influence the common inflammation marker CRP and serum fibrinogen levels with antibiotic treatment.
- CRP common inflammation marker
- serum fibrinogen levels with antibiotic treatment.
- the morbidity of heart diseases began to sink when the use of antibiot- ics, very effective against chlamydiae, became common in the treatment of other infections.
- C. trachomatis is the most important cause of the genital infections of women. Additionally a part of the bacterial culture negative urinary tract infections of women in fertile age are caused by C. trachomatis. C. trachomatis is a common cause of the chronic endometriosis, and PID is the most common complication of C. trachomatis infections in women. A C. trachomatis infection can be almost symptomless, and even extrauterine pregnancy as well as infertility are known as complications of the obstructive scar formation caused by the incidious silent in- fection.
- C. trachomatis pneumonia As a complication. C. trachomatis also causes genital infections in men.
- Chlamydiae are sensitive to tetracyclines and erythromycin; rifampicin and some new fluorokinolones are effective too.
- C. trachomatis is also, in contrast to e.g. C. pneumoniae, sensitive to sulpha drugs.
- chlamydial infections are often recurring and there is also a risk that they become chronic.
- Chlamydiae multiply only inside the cell, and hence the new macrolide antibiotics and azalides concentrating efficiently into the cells are nowadays alter- natives to tetracycline and erythromycin as a primary drug.
- the treatment possibly has to be continued for a long time and for example in Reiter's disease caused by chlamydiae, a three month's treatment is recommended.
- patent EP O 377 722 a method for the evaluation of he risk of a cardiac infarct, a method of diagnosing a heart and blood vessel disease as well as the use of drugs effective against chlamydiae are described.
- tetracyclines, erythromycin, rifampicillin and fluorokinolones are described as suitable drugs for the treatment or prevention of a chronic heart disease caused by chlamydiae.
- WO 98/50074 describes, especially for the treatment of an infection caused by C. pneumoniae, a combination of anti-chlamydiae agents wherein the active ingredients are each effective at a certain stage ofthe life cycle of chlamydia.
- patent US 5 830 874 a method for diagnosing of arterial chlamydial granuloma caused by C. pneumoniae, as well as therapeutical compositions for the treatment of arterial chlamydial granulomatosis are described.
- suitable therapeutically acting compounds tetracyclines, erythromycins, clarithromycins, azitromycin and kinolones etc. effective against chlamydiae are mentioned.
- Patent JP 10 139 686 describes for the treatment of atherosclerosis caused by C. pneumoniae the use of 2-(3,4-dimetoxycinnamoyl)-aminobenzoic acid as a thera- Chamberically active compound at a daily dosage of 100-1000 mg.
- Shikimates or compounds formed from shikimic acid via a biosynthetic pathway, compounds formed via the acetate-malonate biosynthetic pathway and compounds formed via combinations of both pathways belong to the group of plant-derived phenolic compounds.
- Simple aromates, phenols, coumarins, lignans, lignms as well as fiavonoids and their derivatives belong to said compounds.
- Simple aromates mainly include phenylpropane derivatives and phenylmethane derivatives.
- fiavonoids which are structurally phenolic compounds, form a widespread plant pigment group. Fiavonoids occur everywhere in the plant kingdom, in bryophytes, in the stonecrop family and in other lower plants.
- Fiavonoids occur in nature mainly in the glycosidic form, but they can also be free phenols and sulphates in the so-called aglycon form or as bound to polysaccha- rides and proteins. In most cases the fiavonoids are of their chemical structure polyphenolic compounds. Over 8000 fiavonoids have been identified from plants and they have a myriad of functions. They, due to their bitter taste, protect plants against noxious insects and, due to their antibiotic properties, protect plants against viruses and bacteria. According to the current opinion fiavonoids are not nutritionally important compounds, but they seem to have beneficial effects on the health.
- fiavonoids The daily intake of fiavonoids from the nutrition varies, for example according to a Dutch research, between 0-30 mg.
- fiavonoids have been noticed to show a modest protecting effect against the morbidity of heart and blood vessel diseases, but the differences in the intake of fiavonoids on the other hand were rather small, the total amounts being about 2-6 mg/day.
- an inverse relation between from nutrition acquirable flavonols and flavanols and death cases caused by the heart and blood vessel diseases has been noticed.
- An inverse relation between the intake of flavonols and flavones and the risk of cardiac infarct has also been noticed.
- the fiavonoids are further known to have an effect on inflammation and immune responses as well as on many other functions of the cell. Some fiavonoids and many other phenolic natural compounds can prevent or enhance the calcium intake to the cell which is also demonstrated in Table 1 presented later.
- the calcium channel blocking drugs have an important role in the treatment of heart and blood vessel diseases, such as chest pain caused by cardiac anoxia, of myocardial infarct, atherosclerosis and hypertension. These drugs act on the cal- cium channels by preventing the influx of calcium to the cell and thus enlarge the coronary artery as well as lower the peripheral resistance of blood vessels wherein the cardiac load is diminished. Large scale use of calcium blockers has lead e.g. to the development of screening programs in order to find the calcium channel blocking effect of compounds isolated from nature. As the screening medium in the studies e.g.
- the present invention relates to effective plant-derived phenolic compounds and to the corresponding synthetic compounds and their derivatives and plant extracts and compositions containing them, useful in the treatment and prevention of chlamydial infections, as well as to the use of the plant-derived phenolic com- pounds and the corresponding synthetic compounds and their derivatives and plant extracts and of compositions containing them, in the treatment and prevention of chlamydial infections.
- the plant-derived phenolic compounds are phenolic compounds formed from shikimic acid via a biosynthetic pathway, phenolic compounds formed via the acetate- malonate pathway and phenolic compounds formed as a result of combinations of both pathways.
- These compounds such as simple aromates, phenols, coumarins, lignans, lignins and fiavonoids are obtained from products of the vegetable king- dom such as fruits and vegetables, especially citrus fruits, vegetables, berries, onions, tea, red wines etc.
- the plant-derived phenolic compounds, the corresponding synthetic compounds and their derivatives and extracts and fractions and partial fractions containing them may be used as such or as mixtures of them, optionally in combination with sulphur compounds contained in garlic, such as alliicine or derivatives of alliicine.
- Preferred plant-derived natural phenolic compounds are fiavonoids as well as phenylmethane and phenylpropane derivatives, phenolic acids, triterpenes, cou- niarins and cathecins, and extracts and partial fractions containing them, as well as fractions containing simple phenols, fiavonoids, their derivatives, polyphenols, diterpene phenols and diterpene kinones, as well as fractions from which the tannin and diterpene fractions have been removed.
- Preferred are also the corresponding synthetic compounds and derivatives thereof and pharmaceutically ac- ceptable salts, esters and derivatives ofthe above cited compounds.
- Preferred compounds and extracts thereof are the ones with the anti-chlamydial effect (inhition of formation of inclusions) of equal or more than 30% and particularly preferable are the ones with the anti-chlamydial effect of equal or more than 90%, as defined in the examples.
- groups of preferred compounds and extracts - Flavones, such as apigenin, luteolin, flavone
- Flavonols such as quercetin, rhamnetin, morin
- Flavonones such as naringin
- Phenyhnethane-derived compounds such as methyl gallate, propyl gallate, octyl gallate, dodecyl gallate, isopropyl gallate
- Natural plant extracts such as extracts o ⁇ Mentha longifolia, Mentha arvensis, Galeopsis speciosa, Salvia ojficinalis, Thymus vulgaris, Rumex acetocella, Rosa rugosa, Veronica longifolia, Symphytum asperum, Artemisia vulgaris,
- the plant-derived phenolic compounds, extracts and partial fractions containing them can conveniently be obtained from natural plants or parts of them by using any conventional technique for extracting and isolating substances. Braces, roots or leaves are suitably hydrodistilled and macerated or only hydrodistilled in order to obtain the desired extract, which may further be purified using any conventional purification technique known to a man skilled in the art.
- the corresponding synthetic compounds or their derivatives are usually commercially available substances or they may be manufactured using any known synthetic methods.
- Vitexin-2 -0-rhamnoside " OH H OH H GluRha OH H - 14.6 0.3 587.5 n.d.
- M w The molecular weight of the compounds (g/moles)
- Glu Glucose
- OGlu Oglucose
- ORha Orhamnose
- ORut Orutinose
- OGluRha Oglucoserhamnose
- ORhaGlu Orhamnoseglucose n.d.: not determined
- the anti-chlamydial effect of the plant-derived phenolic compounds quercetin, morin, rhamnetin and octyl gallate on C. pneumoniae and C. trachomatis was studied in examples 1-4. All of these compounds inhibited the growth of the C. pneumoniae in a concentration of 0.5-50 ⁇ g and quercetin, morin and rhamnetin were shown particularly effective on C. trachomatis when pretreated host cells were used.
- Preferable compounds for the treatment and prevention of a C. pneumoniae infection thus are for example phenolic compounds quercetin, morin, rhamnetin and octyl gallate isolated from natural materials, and for the treatment and prevention of a C. trachomatis infection in turn quercetin, morin and rham- netin and extracts and partial fractions containing them.
- Preferred compounds and extracts and fractions are the ones with the anti- chlamydial effect (inhition of formation of inclusions) of equal or more than 30% and particularly preferable are the ones with the anti-chlamydial effect of equal or more than 90%, as defined in the examples.
- a compound according to the present invention typically effective against chlamydia, is additionally an antioxidant and has an effect on the Ca 2+ intake in the cell.
- Octyl gallate is also a compound commonly used as a food additive.
- active ingredients the plant-derived phenolic compounds, the corresponding synthetic compounds and their derivatives and plant extracts, fractions and mixtures of them may be dosed so that the daily supply counted as an aglycon is from 25 ⁇ g to 3000 mg.
- the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives and plant extracts and fractions and mixtures of them may, according to the present invention, be prepared as pharmaceutical preparations in the form of capsules, tablets, ointments, liquid preparations or in other corresponding forms known to one skilled in the art.
- the preparations contain the active ingredient so that the daily supply is from 25 ⁇ g to 3000 mg counted as an aglycon, as unit doses preferably of from 25 ⁇ g to 500 mg.
- the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives and plant extracts and fractions and mixtures of them may also be added as such to food stuffs or they can be prepared as compositions suitable for food stuffs, such as herbal preparations, spices, granules or the like, which can be used as such, as added to the daily nourishment or functional food stuffs beneficial to health also called pro-health products, such as ready-prepared foods, porridges, salad dressings, drinks, milk-based products, edible fats, frozen products, freeze-dried food stuffs, speciality food stuffs, potato ships, dipping sauces etc. in connection with the production.
- the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives can exist in the compositions according to the present invention either in an aglycon form or in a glycosidic form.
- the plant-derived phenolic compounds and the corresponding synthetic compounds and their derivatives and plant extracts and fractions and mixtures of them according to the present invention are safe as compounds.
- the compositions and preparations according to the invention can be used both as a course of treatment of an acute chlamydial infection or by dosing the composition or preparation con- tinuously and regularly with the daily nourishment in order to prevent a chlamydial infection.
- compositions and preparations according to the invention can also be used for the treatment and prevention of an acute C. trachomatis infection as well as for the prevention of the late complications, such as infertility, exfrauterine pregnancy and cervical cancer, and also for the treatment and prevention of other chlamydiae related infections and complications.
- the host cells were incubated for 1 day with the compound to be studied before infection.
- the test procedure was continued by the way described in the determination method.
- DMSO 0 0 The host cells were incubated for 1 day with the compound to be studied before infection. To 24-well plates containing host cells the compound to be studied in lml of maintenance medium was added in the same concentration as in the test procedure itself. The intention of this was to study the possible effect of the compound on the host cells themselves, which effect could be a factor inhibiting the infection. The test procedure was continued by the way described in the determination method.
- the host cells were incubated for 1 day with the compound to be studied before infection.
- the test procedure was continued by the way described in the determination method. Results/Concentration 0.5 ⁇ M:
- the host cells were incubated for 1 day with the compound to be studied before infection.
- the test procedure was continued by the way described in the determination method.
- the host cells were incubated for 1 day with the compound to be studied before infection.
- the test procedure was continued by the way described in the determination method.
- the host cells were incubated for 1 day with the compound to be studied before infection.
- the test procedure was continued by the way described in the determi- nation method.
- HL-CD HL cells with a DMSO addition
- the concentration used was 50 ⁇ M.
- HL cells Passage cultures of HL cells are made with intervals of 3 days.
- the host cells are inoculated on the day preceding the infection.
- the cells are rinsed with PBS 1 x 10 mis and harvested by trypsinisation (1:10, 1.5-2.0 ml/bottle; ca. 5 min in a laminar flow cabinet or 2 min in CO 2 at +37°C).
- the cell suspension is diluted to a level of ca. 350000 cells/ml of nutrition medium (RN). Cultivation at +37°C, CO 2 (5.0 %) and the RN medium changed 1-2 times a week.
- the HL cells can be freezed in liquid nitrogen [1 ml 7.5% FCS (RN) + 1 ml DMSO].
- the cells are suspended well and kept in an ultrasonic bed for 2 minutes altogether [20 seconds of sonication (Amplitude is 24-25) and 10 seconds of cooling x 6].
- the cells are broken and the chlamydiae remain undamaged.
- the suspension is centrifuged for 10 minutes at 1600 rpm (550 x g), wherein the chlamydiaes are in the supernatant (the HL cells remnants are discarded).
- the supernatant is aspirated away and 5 ml of PBS is added, suspended and sonicated for 1 minute (10 seconds of sonication - 5 seconds of cooling x 6).
- the chlamydiae can be stored frozen at -70°C.
- the cultivated HL cells are infected with C. pneumoniae EB's.
- the EB's which have invaded the cell are changed into the metabolically active reticulate body (RB) which are dividing by binary fission in the endosome vacuole or inclusion.
- RB metabolically active reticulate body
- the C. pneumoniae RB's are condensing back into EB's, after which the inclusions are broken, the host cells are broken and the EB's are liberated.
- the intention is to verify the inclusions before the breaking up ofthe host cells.
- HL cells As the host cell of C. pneumoniae in in vitro conditions HL cells are used. As the host cells of C. trachomatis in in vitro conditions McCoy cells often are used.
- the host cells are inoculated on a 24-well plate: the cells are harvested by trypsinisation, they are suspended in ca. 5 ml ofthe nu- trition liquid and counted in a Burker's chamber. Each well are seeded using a concentration of 250000 - 400000 cells/well for cultivation. Before the addition of the cells to the well is if necessary round cover glass (diameter 13 mm) put for staining. Nutrition liquid is added so that the volume is 1 ml/well. On the following day the cells are infected with the desired bacterium. Solution to be used in the infection and containing chlamydiae particles is mixed throughout. The old nutrition liquid is aspirated away.
- the inoculum which has been stored at -70°C is diluted to an IFU concentration of ca. 10 3 so that the volume of the solution is at least 200 ⁇ l/well on a 24-well plate.
- the cells are infected by centrifuging at 1600 rpm (550 x g)/l hr.
- the nutrition medium is aspirated away and changed to a maintenance medium containing cyclo- hexamide and also containing the studied compound (DMSO concentration 0.2%), 1 ml/well.
- the cells are incubated in a 5% CO 2 atmosphere at +35°C.
- the cells infected with C. pneumoniae are incubated for 3 days.
- the nutrition medium which is above the cover glass left for stairiing, is aspirated away.
- the infected cells are fixed on the cover glass with methanol for 10 min.
- the cover glass is removed from the well and transferred onto a suitable fluores- cein-conjugated monoclonal antibody on Parafilm in a moist chamber with the cell-containing side down.
- the cover glass is incubated for 30 min at +37°C and washed twice with PBS and once with water. Finally it is dried.
- the cover glass is put with the cell-containing side down on an object glass containing a fixative (e.g. Mounting medium).
- a fixative e.g. Mounting medium
- RN - FCS nutrition medium 100 ml of RPMI 1640 (Sigma), to which 3.5% L- glutamine and 10 mg streptomycin have been added (final concentration 20 ⁇ g/ml), 7.5 ml FCS.
- the ready solutions are stored at +8°C.
- PBS Dulbecco's Phosphate buffered saline, Gibco
- pH 7.4 SPG Saccharose 0.2M (37.5 g), KH 2 PO 4 3.8 mM (0.26 g), Na 2 HPO 4 x 2H 2 O 6.7 mM (0.61 g), glutamic acid (C 5 H 9 NO ) 5 mM (0.36 g) as mixed to 500 ml of milli-Q water. Is after sterilisation stored at -20°C.
- FCS Foetal Calf Serum (Gibco, Scotland) is inactivated at 56°C, 30 min, filtered and stored at -70°C.
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Abstract
Description
Claims
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
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MXPA03001435A MXPA03001435A (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections. |
NZ524128A NZ524128A (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
EEP200300064A EE200300064A (en) | 2000-08-17 | 2001-08-16 | Pharmaceutical composition for the treatment and / or prevention of C. pneumoniae infections, organic composition and their use |
AU8220101A AU8220101A (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
HU0300732A HUP0300732A3 (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
AU2001282201A AU2001282201B2 (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
US10/344,451 US20040058983A1 (en) | 2000-08-18 | 2001-08-16 | Plan-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
EP01960802A EP1309333B1 (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
CA002419716A CA2419716A1 (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
AT01960802T ATE441424T1 (en) | 2000-08-17 | 2001-08-16 | HERBAL AND SYNTHETIC PHENOLIC COMPOUNDS AND PLANT EXTRACTS EFFECTIVE FOR THE TREATMENT AND PREVENTION OF CHLAMYDIA INFECTIONS |
DE60139783T DE60139783D1 (en) | 2000-08-17 | 2001-08-16 | GENE AND PLANT EXTRACTS, EFFECTIVE FOR THE TREATMENT AND PREVENTION OF CHLAMYDIENE INFECTIONS |
JP2002519592A JP2004506656A (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts effective in the treatment and prevention of Chlamydia infection |
BR0113463-9A BR0113463A (en) | 2000-08-17 | 2001-08-16 | Pharmaceutical composition for the treatment and / or prevention of chlamydial infections, health composition and their use |
KR1020037002334A KR100851357B1 (en) | 2000-08-17 | 2001-08-16 | Plant-Derived and Synthetic Phenolic Compounds and Plant Extracts, Effective in the Treatment and Prevention of Chlamydial Infections |
PL362405A PL204232B1 (en) | 2000-08-18 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
NO20030728A NO20030728L (en) | 2000-08-17 | 2003-02-14 | Plant-derived and synthetic phenolic compounds and plant extracts that are effective in the treatment and prevention of chlamydia infections |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US22573500P | 2000-08-17 | 2000-08-17 | |
US60/225,735 | 2000-08-17 | ||
FI20001832A FI113942B (en) | 2000-08-18 | 2000-08-18 | Use of Vegetable Phenolic Compounds in the Manufacture of Pharmaceutical Preparation Useful in the Treatment and Prevention of Chlamydia Infection, Nutritional Benefits or Composition for Addition to Such Foods |
FI20001832 | 2000-08-18 |
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WO2002014464A2 true WO2002014464A2 (en) | 2002-02-21 |
WO2002014464A3 WO2002014464A3 (en) | 2002-05-10 |
WO2002014464B1 WO2002014464B1 (en) | 2002-11-21 |
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PCT/FI2001/000726 WO2002014464A2 (en) | 2000-08-17 | 2001-08-16 | Plant-derived and synthetic phenolic compounds and plant extracts, effective in the treatment and prevention of chlamydial infections |
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EP (1) | EP1309333B1 (en) |
JP (1) | JP2004506656A (en) |
KR (1) | KR100851357B1 (en) |
CN (1) | CN100500141C (en) |
AR (1) | AR034141A1 (en) |
AT (1) | ATE441424T1 (en) |
AU (2) | AU8220101A (en) |
BR (1) | BR0113463A (en) |
CA (1) | CA2419716A1 (en) |
CZ (1) | CZ2003449A3 (en) |
DE (1) | DE60139783D1 (en) |
EE (1) | EE200300064A (en) |
ES (1) | ES2330306T3 (en) |
HU (1) | HUP0300732A3 (en) |
MX (1) | MXPA03001435A (en) |
NO (1) | NO20030728L (en) |
NZ (1) | NZ524128A (en) |
PT (1) | PT1309333E (en) |
SG (1) | SG90259A1 (en) |
TW (1) | TWI282275B (en) |
WO (1) | WO2002014464A2 (en) |
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JP2005047896A (en) * | 2003-07-15 | 2005-02-24 | Hayashibara Takeshi | Anti-chlamydial composition |
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WO2009003832A2 (en) * | 2007-07-05 | 2009-01-08 | Unilever N.V. | Composition comprising polyphenol |
WO2009003838A2 (en) * | 2007-07-05 | 2009-01-08 | Unilever N.V. | Composition comprising polyphenol |
WO2011161655A1 (en) * | 2010-06-25 | 2011-12-29 | Horphag Research (Ip) Pre Ltd | Composition for improving sexual wellness |
EP3085688A1 (en) * | 2015-04-21 | 2016-10-26 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Adamantane or pinene derivatives for use in the treatment of chlamydiales infections |
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US8455541B2 (en) | 2005-05-30 | 2013-06-04 | Korea Research Institute Of Bioscience And Biotechnology | Pharmaceutical composition comprising an extract of pseudolysimachion longifolium and the catalpol derivatives isolated therefrom having antiinflammatory, antiallergic and antiasthmatic activity |
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- 2001-08-14 TW TW090119889A patent/TWI282275B/en active
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- 2001-08-16 DE DE60139783T patent/DE60139783D1/en not_active Expired - Lifetime
- 2001-08-16 EP EP01960802A patent/EP1309333B1/en not_active Expired - Lifetime
- 2001-08-16 CN CNB018153968A patent/CN100500141C/en not_active Expired - Fee Related
- 2001-08-16 PT PT01960802T patent/PT1309333E/en unknown
- 2001-08-16 AU AU2001282201A patent/AU2001282201B2/en not_active Ceased
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---|---|---|---|---|
JP2005047896A (en) * | 2003-07-15 | 2005-02-24 | Hayashibara Takeshi | Anti-chlamydial composition |
FR2890311A1 (en) * | 2005-09-07 | 2007-03-09 | Oreal | Use of plant extract of genus Rosa with composition as an agent for preventing or reducing adhesion of micro-organisms on skin surface and/or mucous membranes |
WO2009003832A2 (en) * | 2007-07-05 | 2009-01-08 | Unilever N.V. | Composition comprising polyphenol |
WO2009003838A2 (en) * | 2007-07-05 | 2009-01-08 | Unilever N.V. | Composition comprising polyphenol |
WO2009003832A3 (en) * | 2007-07-05 | 2009-03-19 | Unilever Nv | Composition comprising polyphenol |
WO2009003838A3 (en) * | 2007-07-05 | 2009-03-19 | Unilever Nv | Composition comprising polyphenol |
WO2011161655A1 (en) * | 2010-06-25 | 2011-12-29 | Horphag Research (Ip) Pre Ltd | Composition for improving sexual wellness |
US9028890B2 (en) | 2010-06-25 | 2015-05-12 | Horphag Research (Ip) Pre Ltd. | Composition for improving sexual wellness |
EP3085688A1 (en) * | 2015-04-21 | 2016-10-26 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Adamantane or pinene derivatives for use in the treatment of chlamydiales infections |
US10039727B2 (en) | 2015-04-21 | 2018-08-07 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Adamantane or pinene derivatives for use in the treatment of chlamydiales infections |
Also Published As
Publication number | Publication date |
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ATE441424T1 (en) | 2009-09-15 |
AU8220101A (en) | 2002-02-25 |
CA2419716A1 (en) | 2002-02-21 |
EP1309333B1 (en) | 2009-09-02 |
KR100851357B1 (en) | 2008-08-08 |
NO20030728L (en) | 2003-04-14 |
SG90259A1 (en) | 2002-07-23 |
WO2002014464B1 (en) | 2002-11-21 |
CN1454093A (en) | 2003-11-05 |
WO2002014464A3 (en) | 2002-05-10 |
JP2004506656A (en) | 2004-03-04 |
EE200300064A (en) | 2004-12-15 |
ES2330306T3 (en) | 2009-12-09 |
MXPA03001435A (en) | 2004-12-13 |
PT1309333E (en) | 2009-09-29 |
HUP0300732A2 (en) | 2003-09-29 |
HUP0300732A3 (en) | 2005-09-28 |
EP1309333A2 (en) | 2003-05-14 |
NZ524128A (en) | 2006-01-27 |
AR034141A1 (en) | 2004-02-04 |
NO20030728D0 (en) | 2003-02-14 |
CZ2003449A3 (en) | 2003-06-18 |
AU2001282201B2 (en) | 2006-05-11 |
KR20030051623A (en) | 2003-06-25 |
CN100500141C (en) | 2009-06-17 |
TWI282275B (en) | 2007-06-11 |
DE60139783D1 (en) | 2009-10-15 |
BR0113463A (en) | 2003-07-15 |
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