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WO1996008270A9 - Procede permettant d'inhiber la transmission de maladies sexuellement transmissibles a l'aide d'antimicrobiens du type magainin ou de composes de squalamine - Google Patents

Procede permettant d'inhiber la transmission de maladies sexuellement transmissibles a l'aide d'antimicrobiens du type magainin ou de composes de squalamine

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Publication number
WO1996008270A9
WO1996008270A9 PCT/US1995/011675 US9511675W WO9608270A9 WO 1996008270 A9 WO1996008270 A9 WO 1996008270A9 US 9511675 W US9511675 W US 9511675W WO 9608270 A9 WO9608270 A9 WO 9608270A9
Authority
WO
WIPO (PCT)
Prior art keywords
sexually transmitted
magainin
transmitted disease
antimicrobials
squalamine
Prior art date
Application number
PCT/US1995/011675
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English (en)
Other versions
WO1996008270A2 (fr
WO1996008270A3 (fr
Filing date
Publication date
Application filed filed Critical
Priority to AU35125/95A priority Critical patent/AU3512595A/en
Publication of WO1996008270A2 publication Critical patent/WO1996008270A2/fr
Publication of WO1996008270A3 publication Critical patent/WO1996008270A3/fr
Publication of WO1996008270A9 publication Critical patent/WO1996008270A9/fr

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Definitions

  • This invention relates to a method for inhibiting sexually transmitted diseases. More particularly, sexually transmitted diseases can be inhibited in humans by
  • a magainin antimicrobial which is a polypeptide, or a squalamine compound, which is an aminosterol.
  • a sexually transmitted disease is one that is transmitted through sexual contact.
  • Sexually transmitted diseases (STDs) affect 12 million men and women in the United States each year. The highest risk of contracting STDs comes from having sexual intercourse, vaginal, anal or oral, with an infected person.
  • the most commonly known organisms that cause sexually transmitted diseases are Chlamydia , Gonorrhoea, Candida , Herpes Simplex Virus, and HIV.
  • the transmission of HIV is substantially increased in individuals with other STDs.
  • Antibiotics are not a viable solution because many strains of organisms have developed resistance to certain
  • the method comprises administering to a human one or more magainin antimicrobials in an amount sufficient to inhibit transmission of sexually transmitted disease. In another embodiment of the invention, the method comprises
  • the spread of sexually transmitted diseases is inhibited by administering to a human one or more magainin antimicrobials or
  • squalamine compounds in an amount sufficient to inhibit transmission of sexually transmitted diseases.
  • Magainin antimicrobials and squalamine compounds provide a safe, effective, female-controlled chemical barrier that can inhibit transmission of STDs.
  • Inhibit means at least to reduce the risk of transmission of STDs in the subject treated. It is possible that the amount of inhibition will result in complete prevention of STDs in the subjects treated up to 6 hours before or up to 6 hours after sexual contact, and preferably 1 hour or less before or 1 hour or less after sexual contact.
  • the host to which the magainin antimicrobials or squalamine compounds are administered is a male or female human subject in need of treatment for the inhibition of a sexually transmitted disease. Because of the importance of female-controlled barriers to transmission, the subject will generally be a human female patient in need of such treatment.
  • This invention is useful for inhibiting the spread of sexually transmitted diseases in general.
  • the invention is particularly effective for inhibiting the spread of
  • Immunodeficiency Virus Preferably, human subjects are treated according to the invention to inhibit the spread of Chlamydia trachoma tis , which is the most common sexually transmitted bacterial pathogen in the United
  • magainin antimicrobials or squalamine compounds employed in this invention are administered to the human subject in an effective amount to inhibit transmission of sexually transmitted disease. Effective amounts of these compounds can be administered by any one of several
  • these compounds are applied to the desired site by topical application or by subcutaneous injection. In a particularly preferred embodiment of the invention, these compounds are administered intravaginally to a female subject or applied to a condom.
  • the magainin is administered intravaginally to a female subject or applied to a condom.
  • antimicrobials and squalamine compounds can be applied or administered to a location proximate the area of sexual contact in order to obtain the beneficial effects of the invention.
  • magainin antimicrobials and squalamine compounds which are effective themselves, can be formulated and administered in the form of their pharmaceutically
  • Preferred pharmaceutically acceptable addition salts include salts of mineral acids, for example, hydrochloric acid, sulfuric acid, nitric acid, and the like; salts of monobasic
  • carboxylic acids for example, acetic acid, propionic acid, and the like; salts of dibasic carboxylic acids, for example, maleic acid, fumaric acid, and the like; and salts of tribasic carboxylic acids, such as carboxysuccinic acid, citric acid, and the like.
  • the magainin antimicrobials and squalamine compounds can be formulated into a form suitable for topical
  • the vehicle can be a solid, semi-solid, or liquid vehicle that is pharmaceutically acceptable or physiologically acceptable, and which enables the magainin antimicrobials and squalamine compounds to be conveyed to the locus of sexual contact at an appropriate dilution.
  • the nature of the vehicle will depend upon the method chosen for topical administration.
  • the vehicle can itself be inert or it can impart physiological or pharmaceutical benefits to the composition containing the other active ingredients.
  • the vehicle for topical application is a substance that acts as a diluent, dispersant, or solvent for the magainin antimicrobials, squalamine compounds, and other reagents in the composition so that the composition can be applied to and distributed substantially evenly over the site of sexual contact and at an appropriate concentration that inhibits the spread of sexually transmitted disease.
  • the vehicle is preferably one that aids in retention of the active ingredients upon the site of sexual contact.
  • Solutions or suspensions can also include the
  • a sterile diluent such as water for injection, saline solution, oils, polyethylene glycols, glycerine, propylene glycol, or synthetic solvents,
  • antibacterial agents such as benzyl alcohol or methyl parabens
  • antioxidants such as ascorbic acid or sodium bisulphite
  • buffers such as acetates, citrates, or
  • phosphates and agents for the adjustment of tonicity, such as sodium chloride or dextrose.
  • the vehicle for topical application can be based on water or at least one pharmaceutically acceptable vehicle other than water. It will be understood that non-aqueous pharmaceutically acceptable vehicles can also be combined with water to provide a composition suitable for topical application.
  • Vehicles that can be employed in practicing this invention include solids or liquids, such as
  • emollients emollients, solvents, humectins, thickeners, and powders.
  • magainin antimicrobials and squalamine compounds can be utilized in the methods of the present invention either alone or in combination with other known treatment agents.
  • these ingredients can be combined with other amino acids, vitamins, male or female sex hormones, antibacterial agents, anti-viral agents,
  • anti-inflammatory agents refrigerants, surfactants, perfumes, antioxidants, ultraviolet absorbers, and
  • the magainin antimicrobials and squalamine compounds employed in this invention can be either directly applied or sprayed onto the area of sexual contact or applied by percutaneous injection.
  • the dosage of these compounds employed in the method of this invention varies depending upon age, individual differences, symptoms, etc., but in the case of an adult, it is generally in a range of about 0.07 to about 7000 ⁇ g, and preferably in the range of about 1 to about 300 ⁇ g of the active ingredient per kg of body weight per day for topical administration.
  • Solutions that can be applied as coatings to condoms, sponges and other devices, suppositories, creams or gels generally should contain about .02% to 5% of the active ingredient, and preferably in the range of 0.2% - 3.0%.
  • the preferred vehicles for administration allow the direct application of the active ingredient to contact areas.
  • Effective quantities of the magainin antimicrobials and squalamine compounds can be administered orally, for example, with an inert diluent or with an edible carrier. They can be enclosed in gelatin capsules or compressed into tablets. For purposes of oral therapeutic administration, they can be incorporated with an excipient and used in the form of tablets, troches, capsules, elixirs, suspensions, syrups, wafers, chewing gums, and the like.
  • compositions and preparations should contain at least about 1% of active compound, but the amount can be varied depending upon the particular form and can conveniently be between 1% to about 50% of the weight of the unit.
  • the amount of active ingredient in such a composition is such that a suitable dosage will be obtained.
  • Preferred compositions and preparations according to the invention are prepared so that an oral dosage unit form contains between about 25 to about 400 mg of the magainin antimicrobial or the
  • the magainin antimicrobials and squalamine compounds can be incorporated into a solution or
  • compositions should contain at least about 0.1% of active compound, but can be varied between about 0.1% and about 10% of the weight thereof.
  • the amount of magainin antimicrobials and squalamine compounds in such compositions is such that a suitable dosage will be
  • compositions and preparations contain a parenteral dosage unit comprising between about 25 to about 400 mg of active ingredients.
  • the magainin antimicrobials and squalamine compounds can be administered to the human subject before, during, or after sexual contact. It is preferred that these active substances be administered before and after sexual contact and in multiple dosages as needed.
  • the active ingredients employed in the methods of this invention will now be described in greater detail.
  • magainin antimicrobials means a polypeptide having a molecular weight of about 3500 or less, which is water soluble at a concentration of greater than 5 mg per ml at neutral pH or in an aqueous solution of physiologic ionic strength, non-cytolytic to animal cells including red blood cells, amphiphilic, and which has a broad antibiotic spectrum at physiologic ionic strength and pH.
  • Magainin antimicrobials are reviewed in Bevins and Zasloff, 1990. The antimicrobial spectrum of magainin antimicrobials is described in U.S. Patent
  • the magainins exhibit antimicrobial activity against at least several of the following organisms: Eschericia coli , Acinetobacter caloaceticus, Shigella sonnei , Enterobacter somnes,
  • Eschericia coli Streptococcus pyogene ⁇ , Shigella flexneri , Ci trobacter freundii , Enterobacter aerogenes , Klebisiella pneumonia , Staphyloccus epidermidis, Streptococcus
  • magainin antimicrobials or magainins
  • Peptidomimetics are small organic molecules designed to mimic the function of the peptides.
  • polypeptides are not limited to the sequences shown but must have, at least in part or in whole, the amino acid sequence shown. All analogs and derivatives that are equivalent in structure and function to these magainins are encompassed within the scope of this invention.
  • a magainin antimicrobial exists in a random coiled conformation. Because of its overall cationic charge, the peptide binds electrostatically to membranes displaying accessible anionic phospholipid head groups. After binding to the membrane, magainin antimicrobials undergo a secondary structural transition into an amphipathic alpha helix (Guy and Ragunathan, 1988; Marion et al., 1988). The magainin antimicrobials appear to adopt an alpha-helical structure upon addition of 2.3 mol % of the organic solvent trifluoroethanol (Marion et al., 1988), and upon interaction with phosphatidylserine vesicles (Matsuzaki et al., 1989) and other micelles
  • Magainins and PGLa (a frog antimicrobial Eeptide, starting with Glycine, ending with Leucine, and in amide form) rapidly depolarize the bacterial cell membrane
  • antimicrobials form classical transmembrane channels as suggested for certain ionospheric peptides, such as gramicidin or alamethicin. Regardless of the precise design of this higher order structure, these peptides disrupt membrane permeability. It may be that magainin antimicrobials and their analogs simply form a continuous spectrum of "holes" or imperfections of sizes ranging from those of ions to small molecules rather than a discrete series of precisely organized ion-sized pores (Westerhoff et al., 1989a, b). Evidence for this mechanism include patch clamp analysis studies, which demonstrate for formation of channels in synthetic phospholipid bilayers (Cruciani et al., 1988), and disruption of membrane-linked free-energy transduction (Westerhoff et al., 1989).
  • magainin antimicrobials over other antimicrobial agents is, despite the magainins' activity on bacterial membranes, at antimicrobial
  • magainin efficacy has been demonstrated against antibiotic-resistant strains including, but not limited to, strains resistant to gentmicin, ciprofloxacin, cefotaxime, penicillin, oxacillin, methacillin, imipenem, piperacillin, carbenicillin, tobramycin, erythromycin, and mupirocin (Jacob, et al ., 1990) as set forth in Chart 1. This indicates a lack of cross-resistance between these drugs and magainin antimicrobials.
  • Some molecules are selective for gram-positive or gram-negative bacteria while others are active against both gram-positive and gram-negative
  • ⁇ M micromolar basis the variation in molecular weight (MW) among the compounds would not be a factor and MIC values for the compounds could be directly compared.
  • MW molecular weight
  • GIGKFLKKAKKFGKAFVKILKK-NH2-22 are 0.5 ⁇ g/ml and 4 ⁇ g/ml, respectively; however, the MICs on a micromolar basis are 1.1 ⁇ M and 1.3 ⁇ M.
  • potent analogs were designed based on a 7 amino acid repeat of 2 or 3 amino acids separated by 2 or 3 hydrophobic or neutral hydrophilic amino acids (i.e., BHHNBHH) where B is a basic amino acid, H is a hydrophobic amino acid and N is a neutral or basic hydrophilic amino acid).
  • BHHNBHH hydrophobic or neutral hydrophilic amino acids
  • H hydrophobic amino acid
  • N neutral or basic hydrophilic amino acid
  • magainin antimicrobial peptide analogs were designed based on the premise that the magainin activity is only dependent on the ability to form an amphipathic alpha-helix, and therefore it does not matter if the helix is right-handed, formed with all L-amino acids, or left-handed, formed with all D-amino acids, such as those disclosed in the following commonly assigned application: U.S.S.N. 07/908,455 to Maloy et al. for "Novel Peptide Compositions and Uses Therefore", which is specifically incorporated by reference.
  • An MSI-103 analog was prepared using all D-amino acids (MSI-30) and was shown to have antibacterial activity (Table 3) similar to the MSI-103 of Table 2.
  • a class of peptidomimetics (a molecule that mimics the biological activities of the parent peptide) was developed with the following structure:
  • magainin compounds exhibit potent microbial activity against many significant microbes as set forth in Table 5.
  • Table 6 contains the MIC data for the initial MIC and the MIC at the end of seven passages of the compound MSI-78 for two clinical strains of Staphylococcus aureus (one
  • magainin antimicrobials can be carried out by solid phase methodology (Merrifield, 1963) either on an ABI-431A peptide synthesizer using t-Boc (tert- butyloxycarbonyl) chemistry or on the Milligen 9050
  • the final deblocking step can be carried out with liquid hydrogen fluoride (HF). With Fmoc chemistry, t-butyl-based side chain protection can be used with appropriate resins for C-terminal acids or amide production.
  • the final deblocking step can be carried out with a mixture of TFA (trifluoroacetic acid) and appropriate scavengers.
  • the cleaved free peptides can be desalted on reverse phase high performance liquid chromatography (RP-HPLC) and purified to >95% purity by preparative RP-HPLC using gradient elution. As needed, the peptides can also be purified by weak cation exchange HPLC, using a salt (NaCl) gradient. The fractions containing >95% of the desired peptide peak on analytical HPLC and capillary zone
  • CZE electrophoresis
  • One or more magainin antimicrobials can be used to inhibit transmission of STDs.
  • One or more means a single magainin administered alone or a mixture comprising two or more magainins. Typically, an effective mixture contains 1 to 10 magainin antimicrobials.
  • Magainin antimicrobials can be used in conjunction with other agents.
  • another agent that can be employed in conjunction with a magainin antimicrobial is a spermicidal agent, such as Nonoxynol-9.
  • Spermicidal means an agent destructive to spermatozoa.
  • the magainin antimicrobials may also exhibit spermicidal activity.
  • Squalamine is another novel steroidal broad spectrum anti-infective agent, which has been the subject of analog synthesis and biological investigations.
  • Squalamine a novel aminosterol, is a host defense molecule isolated from the dog fish shark, Sgualus acanthias .
  • Squalamine has also been reported to be spermicidal at a dose of 0.123 mg/ml. (R. Blye, Personal Communication).
  • Squalamine antiviral tests yielded data showing a 70% plaque reduction in an HSV-1 absorption assay (Angelo Pinto, Personal Communication).
  • Squalamine inhibits the growth of gram-positive
  • Squalamine as used herein, also includes analogs of squalamine, such as those disclosed in the following commonly assigned application: U.S.S.N. 08/023,343 to Moriarety et al. entitled "Chemical Synthesis of
  • squalamine compounds can be employed in this invention. It will also be understood that magainin antimicrobials and squalamine compounds can be used in admixture.
  • Squalamine can be isolated from shark liver (sgualus acanthia ⁇ ) by a previous published procedure (Moore, et al ., 1993). A typical extraction of 40 kg of shark liver affords 300 mg of analytically pure squalamine after a sequence of C18 purification, ion exchange, salting-out, Folch extraction, and HPLC chromatography (C18). It has also been obtained by total synthesis (20 steps) in approximately 1% overall yield by Prof. Leah Frye at
  • C. trachomatis were carried out. Ten compounds were supplied for susceptibility testing of the type strain of C. trachoma tis serovar E. Serial twofold dilutions of each compound were prepared in water and added to an equal volume containing 10 4 inclusion-forming units of
  • concentrations ranged from 0.5 ⁇ g/ml to 256 ⁇ g/ml.
  • magainin antimicrobials The ability of a variety of magainin antimicrobials to inhibit plaque formation in Vero cells infected with HSV-1 or HSV-2 was tested. To date, the magainin antimicrobials tested have shown little or no toxicity at concentrations as high as 200 ⁇ g/ml as assessed visually and by neutral red dye inclusion 48 and 72 hours after addition of peptide. Following toxicity screenings, various nontoxic concentrations of magainin antimicrobials and virus were added together to monolayers of Vero cells and antiviral activity was determined by a plaque reduction assay (Pinto et al . , 1988).
  • MSI-843 and MSI-1331 also showed excellent antiviral activity.
  • MSI -843 inhibited plaque formation by 75-90% in Vero cells infected with virus and MSI-1331 completely inhibited HSV-1 and 2 at concentrations of 200 ⁇ g/ml.
  • amino acid sequences for these magainins are provided below.
  • this invention provides methods for inhibiting sexually
  • the methods are particularly useful for providing a
  • compositions employed in the methods of the invention comprise magainin antimicrobials and squalamine compounds. These ingredients can be administered proximate the locus of sexual contact where the pathogen responsible for the STD contacts the subject susceptible to infection. These active ingredients can inhibit STD by killing the pathogen responsible for the STD or by impeding the infection mechanism or replication cycle of the pathogen.
  • the methods of the invention are especially advantageous because they are easily and quickly implemented without special training.
  • Zasloff M. "Magainins, A Class of Antimicrobial Peptides From Xenopus Skin: Isolation, Characterization of Two Active Forms and Partial cDNA Sequence of a Precursor", Proc. Natl. Acad. Sci. USA, 84:5449-5453 (1987).

Abstract

Il est possible d'inhiber chez l'homme la transmission des maladies sexuellement transmissibles par un procédé consistant à administrer à un sujet un ou plusieurs antimicrobiens du type magainin et un ou plusieurs composés de squalamine en quantité suffisante pour assurer ladite inhibition.
PCT/US1995/011675 1994-09-13 1995-09-13 Procede permettant d'inhiber la transmission de maladies sexuellement transmissibles a l'aide d'antimicrobiens du type magainin ou de composes de squalamine WO1996008270A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU35125/95A AU3512595A (en) 1994-09-13 1995-09-13 Method for inhibiting sexually transmitted diseases using magaining antimicrobials or squalamine compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30547594A 1994-09-13 1994-09-13
US08/305,475 1994-09-13

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WO1996008270A2 WO1996008270A2 (fr) 1996-03-21
WO1996008270A3 WO1996008270A3 (fr) 1996-05-17
WO1996008270A9 true WO1996008270A9 (fr) 1996-06-27

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US7410959B1 (en) 2000-07-13 2008-08-12 Genaera Corporation Therapeutic uses for aminosterol compounds
AU2911197A (en) * 1996-05-24 1998-01-05 Imperial College Of Science, Technology And Medicine Polycationic sterol derivatives as transfection agents
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NL1008139C2 (nl) 1998-01-27 1999-07-28 Stichting Tech Wetenschapp Antimicrobiële peptiden.
US6767904B2 (en) 1998-03-06 2004-07-27 Bringham Young University Steroid derived antibiotics
NL1010692C2 (nl) * 1998-12-01 2000-06-06 Stichting Tech Wetenschapp Antivirale peptiden.
CN102145005A (zh) * 2006-02-01 2011-08-10 杨百翰大学 阳离子类固醇抗微生物剂组合物及其使用方法
WO2008048340A2 (fr) 2006-02-01 2008-04-24 Brigham Young University Compositions antibiotiques stéroïdiennes cationiques et procédés d'utilisation
WO2007089906A2 (fr) * 2006-02-01 2007-08-09 Brigham Young University Compositions antimicrobiennes stéroïdes cationiques et méthodes d'utilisation
JP2007314432A (ja) * 2006-05-23 2007-12-06 Japan Science & Technology Agency 新規抗菌性ペプチド及び該抗菌性ペプチドを有効成分とする無血清培地
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US8623416B2 (en) 2009-11-25 2014-01-07 Michael Zasloff Formulations comprising aminosterols
US10040817B2 (en) 2013-10-03 2018-08-07 Enterin Laboratories, Inc. Methods and compositions for stimulation of the intestinal enteroendocrine system for treating diseases or conditions related to the same
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WO2019234189A1 (fr) * 2018-06-06 2019-12-12 Centro Nacional De Investigaciones Cardiovasculares Carlos Iii (F.S.P.) Augmentation de l'immunité entraînée de cellules myéloïdes par inhibition de ship-1

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