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Reverzno-faznom tečnom hromatografijom pod visokim pritiskom primenom dva sistemarastvarača ispitano je ponašanje i hromatografska lipofilnost prirodnih stiril laktona 7-(+)-goniofufurona, 7-epi-(+)-goniofufurona, krasalaktona B i C i dvadeset njihovihnovosintetizovanih derivata i analoga. U ranijim ispitivanjima pokazalo se da ova jedinjenjaimaju veliki biološki potencijal jer pokazuju zapaženu citotoksičnost prema više humanihtumorskih ćelijskih linija. Hromatografsko ponašanje jedinjenja uglavnom je u skladu sanjihovom strukturom. Ustanovljene su linearne veze između hromatografskih retencionihkonstanti i većine in silico parametara lipofilnosti. Primenom hemometrijske QSRR analizeutvrđeni su veoma dobri multi linearni regresioni prediktivni modeli kvantitativne zavisnostiizmeđu eksperimentalno dobijene hromatografske retencione konstante, koja definišeretenciju jedinjenja u čistoj vodi i in silico molekulskih deskriptora odnosno strukturejedinjenja. Lipofilnost jedinjenja ima najveći uticaj na njihove farmakokinetičke, tj. ADME(apsorpcija, distribucija, metabolizam, eliminacija) osobine. Definisani su i statističkipotvrđeni najbolji multi linearni regresioni modeli zavisnosti farmakokinetičkih parametarastiril laktona i od drugih molekulskih deskriptora. In vitro citotoksična aktivnost jedinjenjaevaluirana je prema četiri nove humane maligne ćelijske linije: kancer prostate (PC3), kancer debelog creva (HT-29), melanom (Hs294T), adenokancer pluća (A549). Najaktivnijenovosintetizovano jedinjenje je triciklični 4-fluorocinamatni analog, koji ispoljavananomolarnu aktivnost (IC50 2,1 nM) prema ćelijama melanoma i aktivniji je preko 2250 puta od komercijalnog antitumorskog agensa doksorubicina (DOX). SAR analizom utvrđena je zavisnost između strukture i biološke aktivnosti jedinjenja. Molekulskim dokingom ispitana je veza stiril laktona i ciljanog proteina značajnog za kancer prostate. Jedinjenja sa visokom inhibitornom aktivnošću prema ćelijama kancera prostate imaju visok doking skor i mogu graditi koordinativno-kovalentnu vezu sa Fe2+jonom prisutnim u aktivnom centru enzima. 3D-QSAR analizom, koja je izvedena metodama komparativnih polja CoMFA i CoMSIA, formiran je značajan prediktivni model između hemijske strukture i biološke aktivnosti stiril laktona., The behavior and the chromatographic lipophilicity natural styryl lactone 7-(+)-goniofufurone, 7-epi-(+)-goniofufurone, crassalactones B and C and twenty of their newlysynthesized derivatives and analogs were examined using reverse-phase high performance liquid chromatography in the two solvent systems. In previous studies it has been shown that these compounds have great biological potential toward several human tumor cell lines. Chromatographic behavior of the compounds is generally in accordance with their structure. The relationships between the chromatographic retention constants and the majority of their in silico lipophilicity parameters are linear. The application of chemometric QSRR analysis determined very good multiple linear regression predictive models of quantitative correlation between experimentally obtained chromatographic retention constant, which determines the retention of the compound in pure water and in silico molecular descriptors, i.e. the structure of the compound. The lipophilicity of the compounds has a major influence on their pharmacokinetics, i.e. ADME (absorption, distribution, metabolism, elimination) properties. The best multi-linear regression models depending on the pharmacokinetic parameters of styryl lactone and other molecular descriptors have been defined and statistically validated. In vitro cytotoxic activity of the compounds was evaluated according to four novel human malignant cell lines: prostate cancer (PC3), colon cancer (HT-29), melanoma (Hs294T), lung adenocarcinom (A549). The most active compound was tricyclic 4-fluorocinnamic analog, which exhibits a nanomolar activity (IC50 2,1 nM) toward melanoma cells. This compound is over 2250 times more active than commercial antitumor agent doxorubicin (DOX). SAR analysis has revealed a correlation between the structure and the biological activity of the compounds. Using the molecular docking the relationship of the styryl lactone and the target protein important for prostate cancer was examined. The compounds with high inhibitory activity against prostate cancer cells have a high docking score and are capable to form a coordinative-covalent bond with a Fe2+ ion present in the active centre of the enzyme. 3DQSAR analysis, which was performed by methods of comparative CoMFA and CoMSIA fields, has formed a good predictive model between chemical structure and biological activity of the styryl lactone.