Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds

Link to this page

info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//

Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (en)
Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (sr)
Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (sr_RS)
Authors

Publications

Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents

Kovačević, Strahinja; Karadžić Banjac, Milica; Milošević, Nataša; Ćurčić, Jelena; Marjanović, Dunja; Todorović, Nemanja; Krmar, Jovana; Podunavac-Kuzmanović, Sanja; Banjac, Nebojša; Ušćumlić, Gordana

(Elsevier B.V., 2020)

TY  - JOUR
AU  - Kovačević, Strahinja
AU  - Karadžić Banjac, Milica
AU  - Milošević, Nataša
AU  - Ćurčić, Jelena
AU  - Marjanović, Dunja
AU  - Todorović, Nemanja
AU  - Krmar, Jovana
AU  - Podunavac-Kuzmanović, Sanja
AU  - Banjac, Nebojša
AU  - Ušćumlić, Gordana
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3645
AB  - Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in or- der to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromato- graphic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccinimide derivatives was conducted. The chemometric analysis of their physico-chemical properties was carried out by us- ing unsupervised (hierarchical cluster analysis and principal component analysis) and supervised pattern recognition methods (linear discriminant analysis), while the correlations between the in silico molecular features and chromatographic lipophilicity were examined applying linear and non-linear Quantitative Structure–Retention Relationship (QSRR) approaches. The main aim of the conducted research was to determine similarities and dissimilarities among the studied 1-arylsuccinimides, to point out the molec- ular features which have significant influence on their lipophilicity, as well as to establish high-quality QSRR models which can be used in prediction of chromatographic lipophilicity of structurally similar 1-arylsuccinimides. This study is a continuation of analysis and determination of the physico-chemical properties of 1-arylsuccinimides which could be important guidelines in further in vitro and eventually in vivo studies of their biological potential.
PB  - Elsevier B.V.
T2  - Journal of Chromatography A
T1  - Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents
VL  - 1628
DO  - 10.1016/j.chroma.2020.461439
ER  - 
@article{
author = "Kovačević, Strahinja and Karadžić Banjac, Milica and Milošević, Nataša and Ćurčić, Jelena and Marjanović, Dunja and Todorović, Nemanja and Krmar, Jovana and Podunavac-Kuzmanović, Sanja and Banjac, Nebojša and Ušćumlić, Gordana",
year = "2020",
abstract = "Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in or- der to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromato- graphic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccinimide derivatives was conducted. The chemometric analysis of their physico-chemical properties was carried out by us- ing unsupervised (hierarchical cluster analysis and principal component analysis) and supervised pattern recognition methods (linear discriminant analysis), while the correlations between the in silico molecular features and chromatographic lipophilicity were examined applying linear and non-linear Quantitative Structure–Retention Relationship (QSRR) approaches. The main aim of the conducted research was to determine similarities and dissimilarities among the studied 1-arylsuccinimides, to point out the molec- ular features which have significant influence on their lipophilicity, as well as to establish high-quality QSRR models which can be used in prediction of chromatographic lipophilicity of structurally similar 1-arylsuccinimides. This study is a continuation of analysis and determination of the physico-chemical properties of 1-arylsuccinimides which could be important guidelines in further in vitro and eventually in vivo studies of their biological potential.",
publisher = "Elsevier B.V.",
journal = "Journal of Chromatography A",
title = "Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents",
volume = "1628",
doi = "10.1016/j.chroma.2020.461439"
}
Kovačević, S., Karadžić Banjac, M., Milošević, N., Ćurčić, J., Marjanović, D., Todorović, N., Krmar, J., Podunavac-Kuzmanović, S., Banjac, N.,& Ušćumlić, G.. (2020). Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents. in Journal of Chromatography A
Elsevier B.V.., 1628.
https://doi.org/10.1016/j.chroma.2020.461439
Kovačević S, Karadžić Banjac M, Milošević N, Ćurčić J, Marjanović D, Todorović N, Krmar J, Podunavac-Kuzmanović S, Banjac N, Ušćumlić G. Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents. in Journal of Chromatography A. 2020;1628.
doi:10.1016/j.chroma.2020.461439 .
Kovačević, Strahinja, Karadžić Banjac, Milica, Milošević, Nataša, Ćurčić, Jelena, Marjanović, Dunja, Todorović, Nemanja, Krmar, Jovana, Podunavac-Kuzmanović, Sanja, Banjac, Nebojša, Ušćumlić, Gordana, "Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents" in Journal of Chromatography A, 1628 (2020),
https://doi.org/10.1016/j.chroma.2020.461439 . .
11
5
13

Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode

Vajdle, O; Guzsvány, V; Škorić, D; Csanádi, J; Petković, Miloš; Avramov-Ivić, M; Kónya, Z; Petrović, Slobodan D.; Bobrowski, A

(Elsevier Ltd, 2017)

TY  - JOUR
AU  - Vajdle, O
AU  - Guzsvány, V
AU  - Škorić, D
AU  - Csanádi, J
AU  - Petković, Miloš
AU  - Avramov-Ivić, M
AU  - Kónya, Z
AU  - Petrović, Slobodan D.
AU  - Bobrowski, A
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2970
AB  - The renewable silver-amalgam film electrode (Hg(Ag)FE) was applied for voltammetric characterization and determination of semi-synthetic macrolide antibiotics azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) in the Britton-Robinson buffer as supporting electrolyte ranging the pH from 4.0 to 11.9. All three macrolides showed reduction signals in fairly negative potential range. During direct cathodic square wave voltammetric (SWV) investigations conducted over the potential range from −0.75 V to −2.00 V vs SCE, either one or two reduction peaks were obtained in the potential range from −1.5 to −1.9 V. The shapes and intensities of the signals depend on the applied pH values in wider pH ranges. For analytical purposes concerning the development of direct cathodic SWV and adsorptive stripping SWV (SW-AdSV) methods the neutral and slightly alkaline media were suitable as pH 7.2, pH 7.4 and pH 7.0 for AZI, CLA and ROX, respectively. Based on the cyclic voltammograms recorded at these pH values, adsorption-controlled electrode kinetics process can be proposed for all three macrolides. Furthermore, the water suppressed 1H NMR measurements in the pH range between 6.0 and 10.5 indicated that the macrolide molecules at the optimal analytical conditions are predominantly in protonated form via their tertiary amino groups which supported in all three cases their adsorption on the appropriately polarized Hg(Ag)FE electrode. The optimized direct cathodic SWV methods showed good linearity in concentration ranges 4.81–23.3 μg mL−1, 1.96–28.6 μg mL−1 and 1.48–25.9 μg mL−1 for AZI, CLA and ROX, respectively. The development of the SW-AdSV methods resulted in the linear responses at lower concentration ranges as 1.0–2.46 μg mL−1, 0.05–0.99 μg mL−1 and 0.10–0.99 μg mL−1, for AZI, CLA and ROX, respectively. The relative standard deviation for all developed methods was not higher than 1.0% except the SWV method for AZI with 4.7%. In the case of all three investigated macrolide antibiotics the protonated form of the tertiary amino group(s) at appropriate accumulation potential and time favored the adsorption of the ionic form of the target molecules offering the opportunity for the development of SW-AdSV methods for their trace level analysis on Hg(Ag)FE. Optimized SW-AdSV method was applied for determination of ROX in pharmaceutical preparation Runac®.
PB  - Elsevier Ltd
T2  - Electrochimica Acta
T1  - Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode
VL  - 229
SP  - 334
EP  - 344
DO  - 10.1016/j.electacta.2017.01.146
ER  - 
@article{
author = "Vajdle, O and Guzsvány, V and Škorić, D and Csanádi, J and Petković, Miloš and Avramov-Ivić, M and Kónya, Z and Petrović, Slobodan D. and Bobrowski, A",
year = "2017",
abstract = "The renewable silver-amalgam film electrode (Hg(Ag)FE) was applied for voltammetric characterization and determination of semi-synthetic macrolide antibiotics azithromycin (AZI), clarithromycin (CLA) and roxithromycin (ROX) in the Britton-Robinson buffer as supporting electrolyte ranging the pH from 4.0 to 11.9. All three macrolides showed reduction signals in fairly negative potential range. During direct cathodic square wave voltammetric (SWV) investigations conducted over the potential range from −0.75 V to −2.00 V vs SCE, either one or two reduction peaks were obtained in the potential range from −1.5 to −1.9 V. The shapes and intensities of the signals depend on the applied pH values in wider pH ranges. For analytical purposes concerning the development of direct cathodic SWV and adsorptive stripping SWV (SW-AdSV) methods the neutral and slightly alkaline media were suitable as pH 7.2, pH 7.4 and pH 7.0 for AZI, CLA and ROX, respectively. Based on the cyclic voltammograms recorded at these pH values, adsorption-controlled electrode kinetics process can be proposed for all three macrolides. Furthermore, the water suppressed 1H NMR measurements in the pH range between 6.0 and 10.5 indicated that the macrolide molecules at the optimal analytical conditions are predominantly in protonated form via their tertiary amino groups which supported in all three cases their adsorption on the appropriately polarized Hg(Ag)FE electrode. The optimized direct cathodic SWV methods showed good linearity in concentration ranges 4.81–23.3 μg mL−1, 1.96–28.6 μg mL−1 and 1.48–25.9 μg mL−1 for AZI, CLA and ROX, respectively. The development of the SW-AdSV methods resulted in the linear responses at lower concentration ranges as 1.0–2.46 μg mL−1, 0.05–0.99 μg mL−1 and 0.10–0.99 μg mL−1, for AZI, CLA and ROX, respectively. The relative standard deviation for all developed methods was not higher than 1.0% except the SWV method for AZI with 4.7%. In the case of all three investigated macrolide antibiotics the protonated form of the tertiary amino group(s) at appropriate accumulation potential and time favored the adsorption of the ionic form of the target molecules offering the opportunity for the development of SW-AdSV methods for their trace level analysis on Hg(Ag)FE. Optimized SW-AdSV method was applied for determination of ROX in pharmaceutical preparation Runac®.",
publisher = "Elsevier Ltd",
journal = "Electrochimica Acta",
title = "Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode",
volume = "229",
pages = "334-344",
doi = "10.1016/j.electacta.2017.01.146"
}
Vajdle, O., Guzsvány, V., Škorić, D., Csanádi, J., Petković, M., Avramov-Ivić, M., Kónya, Z., Petrović, S. D.,& Bobrowski, A.. (2017). Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode. in Electrochimica Acta
Elsevier Ltd., 229, 334-344.
https://doi.org/10.1016/j.electacta.2017.01.146
Vajdle O, Guzsvány V, Škorić D, Csanádi J, Petković M, Avramov-Ivić M, Kónya Z, Petrović SD, Bobrowski A. Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode. in Electrochimica Acta. 2017;229:334-344.
doi:10.1016/j.electacta.2017.01.146 .
Vajdle, O, Guzsvány, V, Škorić, D, Csanádi, J, Petković, Miloš, Avramov-Ivić, M, Kónya, Z, Petrović, Slobodan D., Bobrowski, A, "Voltammetric behavior and determination of the macrolide antibiotics azithromycin, clarithromycin and roxithromycin at a renewable silver – amalgam film electrode" in Electrochimica Acta, 229 (2017):334-344,
https://doi.org/10.1016/j.electacta.2017.01.146 . .
31
24
32

Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents

Trisović, Nemanja; Timić, Tamara; Divljaković, Jovana; Rogan, Jelena; Poleti, Dejan; Savić, Miroslav; Uscumlić, Gordana

(Springer Wien, Wien, 2012)

TY  - JOUR
AU  - Trisović, Nemanja
AU  - Timić, Tamara
AU  - Divljaković, Jovana
AU  - Rogan, Jelena
AU  - Poleti, Dejan
AU  - Savić, Miroslav
AU  - Uscumlić, Gordana
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1649
AB  - Considering the importance of hydantoin derivatives in treatment of status epilepticus, four 5-phenylhydantoins, whose lipophilicities were estimated to be similar to that of phenytoin, were synthesized. Evaluation of their anticonvulsant activities was performed on rats by subcutaneous pentylenetetrazol seizure test and intravenous pentylenetetrazol threshold test, and spontaneous locomotor activity test was used to assess possible sedative effects. X-ray analysis of three compounds suggested that certain analogies might be drawn between interactions in crystal packing and biological interactions responsible for their anticonvulsant activity. It was found that 5-ethyl-5-phenyl-3-propylhydantoin exhibits the most favorable pharmacological properties among the synthesized compounds, i.e., anticonvulsant activity comparable to phenytoin with lower liability for induction of sedation in rats.
PB  - Springer Wien, Wien
T2  - Monatshefte für Chemie Chemical Monthly
T1  - Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents
VL  - 143
IS  - 10
SP  - 1451
EP  - 1457
DO  - 10.1007/s00706-012-0791-8
ER  - 
@article{
author = "Trisović, Nemanja and Timić, Tamara and Divljaković, Jovana and Rogan, Jelena and Poleti, Dejan and Savić, Miroslav and Uscumlić, Gordana",
year = "2012",
abstract = "Considering the importance of hydantoin derivatives in treatment of status epilepticus, four 5-phenylhydantoins, whose lipophilicities were estimated to be similar to that of phenytoin, were synthesized. Evaluation of their anticonvulsant activities was performed on rats by subcutaneous pentylenetetrazol seizure test and intravenous pentylenetetrazol threshold test, and spontaneous locomotor activity test was used to assess possible sedative effects. X-ray analysis of three compounds suggested that certain analogies might be drawn between interactions in crystal packing and biological interactions responsible for their anticonvulsant activity. It was found that 5-ethyl-5-phenyl-3-propylhydantoin exhibits the most favorable pharmacological properties among the synthesized compounds, i.e., anticonvulsant activity comparable to phenytoin with lower liability for induction of sedation in rats.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte für Chemie Chemical Monthly",
title = "Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents",
volume = "143",
number = "10",
pages = "1451-1457",
doi = "10.1007/s00706-012-0791-8"
}
Trisović, N., Timić, T., Divljaković, J., Rogan, J., Poleti, D., Savić, M.,& Uscumlić, G.. (2012). Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents. in Monatshefte für Chemie Chemical Monthly
Springer Wien, Wien., 143(10), 1451-1457.
https://doi.org/10.1007/s00706-012-0791-8
Trisović N, Timić T, Divljaković J, Rogan J, Poleti D, Savić M, Uscumlić G. Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents. in Monatshefte für Chemie Chemical Monthly. 2012;143(10):1451-1457.
doi:10.1007/s00706-012-0791-8 .
Trisović, Nemanja, Timić, Tamara, Divljaković, Jovana, Rogan, Jelena, Poleti, Dejan, Savić, Miroslav, Uscumlić, Gordana, "Synthesis, structural and biological characterization of 5-phenylhydantoin derivatives as potential anticonvulsant agents" in Monatshefte für Chemie Chemical Monthly, 143, no. 10 (2012):1451-1457,
https://doi.org/10.1007/s00706-012-0791-8 . .
7
9
9