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Insect Repellents Based on Para-Menthane-3,8-Diol

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Insect Repellents Based on Para-Menthane-3,8-Diol Insect Repellents Based on para-Menthane-3,8-diol DISSERTATION ZUR ERLANGUNG DES DOKTORGRADES DER NATURWISSENSCHAFTEN (DR.RER. NAT.) DER FAKULTÄT FÜR CHEMIE UND PHARMAZIE DER UNIVERSITÄT REGENSBURG vorgelegt von Jeremy Drapeau aus Sèvres, Frankreich 2017 Promotionsgesuch eingereicht am: 14.11.2017 Die Arbeit wurde angeleitet von: Prof. Dr. Werner Kunz Thesis committee Chair: Prof. Dr. Henri Brunner Examiners: Prof. Dr. Werner Kunz Prof. Dr. Rainer Müller Prof. Dr. Jörg Heilmann To my parents, thank you ever so much for your generous support and patience Abstract 1.Abstract Vector-borne diseases transmitted by mosquitoes are a major cause of morbidity and mortality in the world by transmitting infections such as malaria, dengue, yellow fever, West Nile fever or chikungunya, to more than 700 million people each year. Without existing vaccines for each disease, skin repellents are one of the most effective defenses against mosquitoes for an individual protection. N,N-diethyl-m-methylbenzamide (DEET) is an efficient and commonly used active since decades. New molecules have appeared on the market and proved their repellent action mostly comparable to DEET in regards to different vectors, and para-Menthane-3,8-diol (PMD) is one of them. In this study, PMD was first synthesized in a new green process and confirmed its high repellent activity against Aedes aegypti mosquitoes (dengue, yellow fever, chikungunya, zika vector). The work then consisted to develop formulation systems (surfactantless or classical microemulsions, O/W lotions), which are able to extend the lasting protection of PMD based repellents. As an example, a leave-on lotion was designed with ingredients meeting eco-friendly standards and showed a repellent activity statistically comparable to the reference product on the market, Autan® Protection Plus, with more than 7 hours of protection. Additionally, a large study on the complexation of PMD with cyclodextrins (CD) was considered in order to increase its solubility in water and provide a controlled release over time. PMD:HP-β-CD was confirmed by spectroscopic analysis nevertheless, mosquito repellent tests with Aedes aegypti did not show any efficient protection. In a second study, a new ester derived from PMD, so called PMD-Succinate (PMD-S) was investigated and synthesized under sustainable routes. Physical, chemical and cytotoxicity properties are reported and showed as main interests: 1/ a high water solubility whereas the other actives are insoluble, 2/ a surface activity comparable to common hydrotropes in order to solubilize other repellent actives in aqueous mediums I Abstract and thus reach longer protection times 3/ a very good tolerance in regards to skin irritations and allergic reactions. These functions highlight the interest for the new PMD- Succinate active in order to make simple, long-lasting, environmentally friendly and harmless formulations to protect the populations against mosquitoes. In a third part, a study of 19 Corsican (French island) essential oils was carried out in order to determine their protection activity against mosquitoes. Laurus nobilis was found to provide the highest repellent action and the preferred hedonic dimension and acceptance by the volunteers. In a near future, this essential oil could be integrated into new repellent formulations based on PMD-S as a booster effect and as a pleasant olfactive signature. II Contents 2.Contents General ................................................................................................................. 7 Dengue and Chikungunya cases ........................................................................... 9 Lifecycle ............................................................................................................. 10 Host ..................................................................................................................... 11 General ............................................................................................................... 12 Repellents ........................................................................................................... 14 Overview of PMD .............................................................................................. 15 Isolation of PMD ................................................................................................ 17 Synthesis of PMD ............................................................................................... 18 I STUDIES OF PARA-MENTHANE-3,8-DIOL FROM A NEW SYNTHESIS PROCESS TO ITS INTEGRATION INTO DIFFERENT FORMULATION SYSTEMS 1 Contents Synthesis and Analysis ....................................................................................... 29 Mosquito repellent studies .................................................................................. 31 Transformation of Eucalyptus citriodora oil and synthesis of para-Menthane- 3,8-diol isomers ............................................................................................................ 33 Mosquito repellent study .................................................................................... 36 Thermogravimetric analysis ............................................................................... 38 Formulation and characterization ....................................................................... 44 Preparation of microemulsions ........................................................................... 45 Mosquito repellent studies .................................................................................. 45 Statistical analysis .............................................................................................. 47 Dose effect of PMD in isopropanol on a bio-assay ............................................ 47 Solubility of PMD in a hydro- alcoholic system: “surfactantless microemulsion” 48 Addition of a surfactant in the “regular microemulsion”: Cremophor® RH40 .. 51 Incorporation of a co-surfactant in the microemulsion: 2-ethyl-1,3-hexanediol 52 Addition of a second surfactant in the system: Texapon® N70 .......................... 53 Incorporation of a co-solvent in the microemulsion: Ethyl (S)-(-) lactate ......... 55 Formulation and characterization ....................................................................... 61 Microbiological tests: Challenge tests ................................................................ 63 Mosquito repellent study .................................................................................... 64 Statistical analysis .............................................................................................. 66 General properties .............................................................................................. 66 Microbiological tests .......................................................................................... 69 2 Contents Mosquito bioassay .............................................................................................. 71 Chemicals and Analysis ..................................................................................... 79 Mosquitoes bioassay ........................................................................................... 81 Characterization of the inclusion complex PMD:CD in aqueous solutions: example with β-CD ...................................................................................................... 83 Preparation and characterization of solid inclusion complex of PMD:CD ........ 87 Evolution of PMD:CD complexation as a function of time ............................... 89 Influence of PMD/CD ratio on the complexation .............................................. 91 Influence of the addition of Ethanol on PMD:CDs complexation ..................... 93 Role of CDs’ concentration on complexation .................................................... 94 Solubility of PMD:γ-CD and PMD:HP-β-CD inclusion complexes .................. 96 Mosquito Repellent Studies ................................................................................ 96 II DEVELOPMENT OF A NEW REPELLENT ACTIVE DERIVED FROM PARA- MENTHANE-3,8-DIOL Chemical ........................................................................................................... 103 Analytical equipment ........................................................................................ 103 Synthesis of PMD-S ......................................................................................... 104 Mosquito repellent studies ................................................................................ 105 Statistical analysis ............................................................................................ 106 Synthesis ........................................................................................................... 106 Study of repellent properties ............................................................................ 110 3 Contents Chemical ........................................................................................................... 115 Analytical equipment ........................................................................................ 115 Synthesis of PMD-S ......................................................................................... 117 Material ............................................................................................................. 131 Cell viability assay ..........................................................................................
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