Synthesis and antiproliferative activity of epoxy and bromo compounds derived from estrone

Milić, Dragana; Kop, Tatjana J.; Juranić, Zorica D.; Gašić, Miroslav J.; Šolaja, Bogdan A.

doi:10.1016/s0960-894x(01)00402-4

Cited by 12 publications

(14 citation statements)

References 12 publications

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“…[15][16][17][18] The TLC experiments were performed on 10 cm All experiments were performed at ambient temperature (22 ± 2 °C). All solvents used were of analytical grade purity.…”

Section: Methodsmentioning

confidence: 99%

“…[14] Recently, estrogen derived polyoxygenated steroids, were synthesized. [15][16][17][18] These compounds possess steroidal backbone which is large and conformationally restricted skeleton. The presence of different functional groups, which can be quite easily derivatized, made mentioned substances attractive building blocks for numerous applications.…”

Section: Introductionmentioning

confidence: 99%

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Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

Tosti

Šegan

Milić

et al. 2015

Journal of Liquid Chromatography & Related Technologies

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Unmodified silica gel in combination with two mobile phases, acetone -n-hexane andacetonitrile -dichloromethane, was used in order to evaluate the capability of normalphase (NP) chromatography on bare silica gel in estimation of lipophilicity of some polyoxygenated steroids. Soczewinski equation coefficients were employed as a measure of lipophilicity. The R M 0 values obtained in NP-systems were correlated with those derived by extrapolation from reversed-phase (RP) systems. In addition, retention data, i.e. lipophilicity parameters determined in NP systems were compared with logP values calculated by use of several commercial computer programs. The results showed that chromatographic parameters R M 0 , and m obtained in NP system consisted of silica gel as stationary phase and acetone -n-hexane as mobile phase, are acceptable as the measures of lipophilicity of polyoxygenated steroids. The mechanism of retention was discussed. Downloaded by [Massachusetts PRIM Board] at 16:21 05 April 2015 2

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“…[15][16][17][18] The TLC experiments were performed on 10 cm All experiments were performed at ambient temperature (22 ± 2 °C). All solvents used were of analytical grade purity.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

Tosti

Šegan

Milić

et al. 2015

Journal of Liquid Chromatography & Related Technologies

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“…Steroids were synthesized according to published procedures and their structures are presented in Supporting Information Table S1.…”

Section: Methodsmentioning

confidence: 99%

“…The A‐ring polyoxygenated steroids exhibit an antiproliferative activity on different cancer cell lines. Synthesis, structural characterization, and results of biological assay of the investigated steroids were previously reported . Earlier published articles inter alia showed that certain structural modifications of estrogens led to the change of their biological response, giving compounds with more pronounced antiproliferative activity .…”

Section: Introductionmentioning

confidence: 95%

Structure‐retention relationship study of polyoxygenated steroids

Tosti

Natić

Dabić

et al. 2012

J of Separation Science

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The chromatographic behavior of 31 newly synthesized polyoxygenated steroids was investigated by the means of reversed-phase planar chromatography. Retention data were correlated to molecular characteristics of the analytes with view to examine possible relationships by the means of multiple linear regression (MLR) and partial least square (PLS) regression. On the basis of comparison of the statistical parameters obtained for both MLR and PLS models, descriptors best describing the analyte behavior were selected. Statistically significant and physically meaningful structure-retention relationships were obtained. Calculated lipophilicity expressed as XlogP as well surface tension and Hansen hydrogen bonding was included in both MLR and PLS models.

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“…Contrary to the well known catechol metabolites of estrogens (Zhu and Conney, 1998), quinols possess no aromatic A-ring; thus, their (bio)chemistry should be substantially different from that of catechols. Although Ohe et al (2000) suggested quinol formation as a potential contributor to the carcinogenecity of estrogens, actual studies have shown no significant toxicity by estrogen-derived quinols (Solaja et al, 1996;Milic et al, 2001).…”

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confidence: 99%

Quinol-Based Metabolic Cycle for Estrogens in Rat Liver Microsomes

Prókai

Prókai-Tátrai

Perjési³

et al. 2003

Drug Metab Dispos

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This article is available online at http://dmd.aspetjournals.org ABSTRACT:According to a recently reported metabolic pathway, phenolic A-ring estrogens are metabolized in rat liver microsomes partially to the corresponding quinols by cytochrome P450 isoenzymes. We found that these quinols could, in turn, undergo reduction to regenerate the parent estrogens consumed during the metabolic process. Among the tested endogenous reducing agents, NADH and especially NADPH produced a significant extent of reductive conversion. Enzymes available in rat liver microsomes further catalyzed this reaction with 6.5 ؎ 1.5 nmol ⅐ min ؊1 ⅐ (mg of protein) ؊1 measured as the initial rate of estrone formation at 37°C, whereas the initial rate of second-order reaction for the reduction of E1-quinol by a 10-fold excess of NADPH in a microsome-free buffer solution and under identical incubation conditions was 0.62 ؎ 0.03 nmol ⅐ min ؊1 . The quinol route is, therefore, unique among estrogen-metabolizing pathways for its bioreversibility due to the facile regeneration of the phenolic A-ring estrogens consumed in the preceding oxidative process.

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Synthesis and antiproliferative activity of epoxy and bromo compounds derived from estrone

Cited by 12 publications

References 12 publications

Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

Estimation of Lipophilicity of Some Polyoxygenated Steroids by the Means of Normal-Phase Thin-Layer Chromatography

Structure‐retention relationship study of polyoxygenated steroids

Quinol-Based Metabolic Cycle for Estrogens in Rat Liver Microsomes

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