ANTIMICROBIAL EFFECT OF FERROCENYL DIARYL BUTENES AGAINST OLIVE PLANTLET DISEASES

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656 Ferrocenyl diaryl butenes against olive plantlets diseases Journal of Plant Pathology (2011), 93 (3), 651-657 Fig. 5. In vivo effect of P8 against the crown gall of olive plantlets. A : Non treated, B : Treated (250 µg ml –1 ). (not treated) and only 30% of the plants treated with 250 µg ml –1 of P8 developed the symptoms of crown gall (Fig. 5). We have previously shown that compounds P4, P5 and P6 are active against both hormone-dependent and hormone-independent breast cancer cell lines and have also antimicrobial activity (Vessières et al., 2005; Pigeon et al., 2009, 2011; El Arbi et al., 2011). Now evidence is provided that the same chemicals are also active in vitro against microorganisms pathogenic to young olive trees. The antimicrobial activity of P6 confirms the action of tamoxifen against Candida albicans (Dolan et al., 2009). Phenyl substitution by ferrocene, leading to compound P4, did not improve its efficacy, meanwhile the substitution of OH function by a dimethylaminopropoxy chain led to a more active compound P5. Another advantage of these ferrocenyl compounds such as P5 is their decreased cytotoxicity due to the low water-octanol partition coefficient (log P o/w ) (El Arbi et al., 2011), that restrains their persistence in the soil (Barceló et al., 1997). These features are compatible with agricultural applications and help preserving the environment. Since the action of P5 mimics that of Doxycycline, which is allowed in certain countries such as the USA (Kuldip et al., 2005), this compound could be a good alternative to antibiotics used in agriculture. In conclusion, the main objectives of our work were the synthesis and study of new products that could be useful in the chemical control of olive tree pathogens. P5 displayed a significant antimicrobial activity in vitro that could compete with antibiotics and performed better than copper sulphate. To facilitate field applications, P5 was converted into citrate salt (P8) which is hydrosoluble, maintained the antimicrobial activity, was not phytotoxic and was effective both in vivo and in vitro against the tested pathogens. Thus, ferrocenic derivatives of hydroxytamoxifen, especially P5, protect olive plantlets prior to their culture in the field and seem be promising potential pesticides for plant protection. REFERENCES Asatiani L.P., Lomtatidze Z.Sh., Kiladze S.Kh., Metskhvarishvili S.Sh., 1984. Synthesis and bactericidal activity of ferrocene-containing di- and tetrahydroxylic acetylenic alcohols. Pharmaceutical Chemistry Journal 18: 325-326. Barceló D., Hennion M.C., 1997. Trace Determination of Pesticides and their Degradation Products in Water. Elsevier Science B.V., Amsterdam, The Netherlands. Beer P.D., Bayly S.R., 2007. Organometallic receptors for charged and neutral guest species. Comprehensive Organometallic Chemistry III 12: 465-498. Biot C., Glorian G., Maciejewski L. A., Brocard J.S., Domarle O., Blampain G., Millet P., Georges A.J., Abessolo H., Dive D., Lebibi J., 1997. In vitro antimalarial activity of new organometallic analog ferrocene-chloroquine. Antimicrobial Agents and Chemotherapy 42: 540-544. Biot C., Delhaes L., Abessolo H., Domarle O., Maiejewski L.A., Mortuaire M., Delcourt P., Deloron P., Camus D., Dive D., Brocard J.S., 1999. Novel metallocenic compounds as antimalarial agents. Study of the position of ferrocene in chloroquine. Journal of Organometallic Chemistry 589: 59-65. Biot C., François N., Maciejewski L., Brocard J., Poulain D., 2000. Synthesis and antifungal activity of a ferrocene-fluconazole analogue. Bioorganic and Medicinal Chememistry Letters 10: 839-841. Buriez O., Labbé E., Pigeon P., Jaouen G., Amatore C., 2008. Electrochemical attachment of a conjugated amino-ferrocifen complex onto carbon and metal surfaces. Journal of Electroanalytical Chemistry 619: 169-175. Damljanović I., Vukićević M., Radulović N., Palić R., Ellmerer E., Ratković Z., Joksović M.D., Vukićević R.D., 2009. Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit. Bioorganic and Medicinal Chememistry Letters 19: 1093-1096. Di Gleria K., Hill H.A.O., McNeil C.J., Green M.J., 1986. Homogeneous ferrocene mediated amperometric biosensors. Analytical Chemistry 58: 1203-1205. Dolan K., Montgomery S., Buchheit B., Di Done L., Wellington M., Krysan D.J., 2009. Antifungal Activity of Tamox-
Journal of Plant Pathology (2011), 93 (3), 651-657 El Arbi et al. 657 ifen: In vitro and in vivo Activities and Mechanistic Characterization. Antimicrobial Agents and Chemotherapy 53: 3337-3346. Domarle O., Blaunpain G., Aguauiet H., Nzadiyabi T., Lebibi I., Brocard J., Maciejewski L., Riot C., Millet P., 1998. In vitro antimalarial activity and a new organometallic analog ferrocene-chloroquine. Antimicrobial Agents and Chemotherapy 42: 540-544. Dombrowski K.E., Baldwin W., Sheats J.E., 1986. Metallocenes in biochemistry, microbiology and medicine. Journal of Organometallic Chemistry 302: 281-306. Edwards E.I., Epton R., Marr G., 1979. The synthesis and reactions of homonuclear ferrocene acid anhydrides and their use in the preparation of ferrocenyl-penicillins and cephalosporins. Journal of Organometallic Chemistry 168: 259-263. El Arbi M., Pigeon P., Top S., Rhouma A., Aifa S., Rebai A., Vessières A., Plamont M. A., Jaouen G., 2011. Evaluation of bactericidal and fungicidal activity of ferrocenyl or phenyl derivatives in the diphenyl butene series. Journal of Organometallic Chemistry 696: 1038-1048. Ihara T., Maruo Y., Takenaka S., Takagi M., 1996. Ferroceneoligonucleotide conjugates for electrochemical probing of DNA. Nucleic Acid Research 24: 4273-4280. Jaouen G., Top S., Vessières A., Leclercq G., Quivy J., Jin L., Croisy A., 2000. The first organometallic antioestrogens and their antiproliferative effects. Comptes Rendus de l’Académie des Sciences - Series IIC - Chemistry 3: 89-93. Jaouen G., 2006. Bioorganometallics. Wiley-VCH, Weinheim, Germany. Kealy T.J., Pauson P.L., 1951. A new type of organo-iron compound. Nature 168: 1039. Kuldip K., Satish C.G., Yogesh C., Ashok K.S., 2005. Antibiotic use in agriculture and its impact on the terrestrial environment. Advances in Agronomy 87: 1-54. Manosroi J., Rueanto K., Boonpisuttinant K., Manosroi W., Biot C., Akazawa H., Akihisa T., Issarangporn W., Manosroi A., 2010. Novel ferrocenic steroidal drug derivatives and their bioactivities. Journal of Medicinal Chemistry 53: 3937-3943. Mues V., Niggemann J., Aktiengesellschaft B., 1977. Ferrocene derivative for supplying plants with iron. United States Patent US 4053296. Nakayama M., Ihara T., Nakano K., Maeda M., 2002. DNA sensors using a ferrocene-oligonucleotide conjugate. Talanta 56: 857-866. Neuse E.W., 2005. Macromolecular ferrocene compounds as cancer drug models. Journal of Inorganic and Organometallic Polymers and Materials 15: 3-32. Pandey P.C., Upadhyay S., Tiwari I., Singh G., Tripathi V.S., 2001. A novel ferrocene encapsulated palladium-linked ormosil-based electrocatalytic dopamine biosensor. Sensors and Actuators, B: Chemical 75: 48-55. Received November 19, 2010 Accepted July 30, 2011 Pigeon P., Top S., Zekri O., Hillard E.A., Vessières A., Plamont M-A., Buriez O., Labbé E., Huché M., Boutamine S., Amatore C., Jaouen G., 2009. The replacement of a phenol group by an aniline or acetanilide group enhances the cytotoxicity of 2-ferrocenyl-1,1-diphenyl-but-l-ene compounds against breast cancer cells. Journal of Organometallic Chemistry 694: 895-901. Pigeon P., Top S., Vessières A., Huché M., Görmen M., El Arbi M., Plamont M.-A., McGlinchey M.J., Jaouen G., 2011. A new series of ferrocifen derivatives, bearing two aminoalkyl chains, with strong antiproliferative effects on breast cancer cells. New Journal of Chemistry 35: 2212- 2218. Rugini E., 1984. In vitro propagation of some olive (Olea europaea L.) cultivars with different root ability, and medium development using analytical data from developing shoots and embryos. Scientia Horticultureae 24: 123-134. Tagg J.R., McGiven A.R., 1971. Assay system for bacteriocins. Applied Environmental Microbiology 21: 943. Top S., Tang J., Vessières A., Carrez D., Provot C., Jaouen G., 1996. Ferrocenyl hydroxytamoxifen: prototype for a new range of oestradiol receptor site-directed cytotoxics. Journal of the Chemical Society, Chemical Communications 8: 955-956. Top S., Vessières A., Leclercq G., Quivy J., Tang J., Vaissermann J., Huché M., Jaouen G., 2003. Synthesis, biochemical properties and molecular modelling studies of organometallic specific estrogen receptor modulators (SERMs), the ferrocifens and hydroxyferrocifens: evidence for an antiproliferative effect of hydroxyferrocifens on both hormone-dependent and hormone-independent breast cancer cell lines. Chemistry - A European Journal 9: 5223-5236. Top S., Vessières A., Jaouen G., Fish R.H., 2006. New synthetic pathways of cis- or trans-hydroxytamoxifen derivatives with in situ formed [Cp*Rh(solvent) 3 ] 2+ complexes: Kinetic and thermodynamic control, including a Novel, Intramolecular N-p rearrangement, and relative binding affinities of the h 6 complexes for the estrogen receptor. Organometallics 25: 3293-3296. Vessières A., Top S., Pigeon P., Hillard E.A., Boubeker L., Spera D., Jaouen G., 2005. Modification of the estrogenic properties of diphenols by the incorporation of ferrocene. Generation of antiproliferative effects in vitro. Journal of Medicinal Chemistry 48: 3937-3940. Zhong J., Yan H., Aihong H., Weifeng T., Ling S., Jianbing L., Jianxin F., 2006. Synthesis, characterization, and biological evaluation of novel ferrocene-triadimefon analogues. Journal of Organometallic Chemistry 691: 2340- 2345. Zucconi F., Forte M., Monac A., Beritodi M., 1981. Biological evaluation of compost maturity. Biocycle 22: 27-29.
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ANTIMICROBIAL EFFECT OF FERROCENYL DIARYL BUTENES AGAINST OLIVE PLANTLET DISEASES

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