TY  - JOUR
AU  - Trbojević-Ivić, Jovana
AU  - Dimitrijević, Aleksandra
AU  - Milosavić, Nenad
AU  - Bezbradica, Dejan
AU  - Drakulić, Branko
AU  - Gavrović-Jankulović, Marija
AU  - Pavlović, Marija
AU  - Rogniaux, Helene
AU  - Veličković, Dušan
PY  - 2016
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3442
AB  - Hydroxyapatite (HAP), a calcium-phosphate bioactive ceramic, is actively employed in medical and separation sciences. Although different classes of biomacromolecules interact with this material, interactions with proteins are the most important, since they directly affect the biocompatibility of the carrier and it's industrial application. In the presented work, we thoroughly investigate and elucidate the interaction mechanism between Candida rugosa lipase (CRL) upon it's immobilization on HAP, since this immobilized enzyme showed advanced catalytic properties in previous studies. Applying elution and protein modification strategies we concluded that Ca-chelation of HAP's C-site and CRL's -COOH groups is the most probable interacting mechanism. A proteomics approach revealed that this chelation is conserved throughout all CRL isoforms, while results of molecular modelling led us to propose the involvement of a specific region of the protein surface and side chains in interactions with HAP.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Assessment of the interacting mechanism between Candida rugosa lipases and hydroxyapatite and identification of the hydroxyapatite-binding sequence through proteomics and molecular modelling
EP  - 34824
IS  - 41
SP  - 34818
VL  - 6
DO  - 10.1039/c6ra07521e
ER  - 

@article{
author = "Trbojević-Ivić, Jovana and Dimitrijević, Aleksandra and Milosavić, Nenad and Bezbradica, Dejan and Drakulić, Branko and Gavrović-Jankulović, Marija and Pavlović, Marija and Rogniaux, Helene and Veličković, Dušan",
year = "2016",
abstract = "Hydroxyapatite (HAP), a calcium-phosphate bioactive ceramic, is actively employed in medical and separation sciences. Although different classes of biomacromolecules interact with this material, interactions with proteins are the most important, since they directly affect the biocompatibility of the carrier and it's industrial application. In the presented work, we thoroughly investigate and elucidate the interaction mechanism between Candida rugosa lipase (CRL) upon it's immobilization on HAP, since this immobilized enzyme showed advanced catalytic properties in previous studies. Applying elution and protein modification strategies we concluded that Ca-chelation of HAP's C-site and CRL's -COOH groups is the most probable interacting mechanism. A proteomics approach revealed that this chelation is conserved throughout all CRL isoforms, while results of molecular modelling led us to propose the involvement of a specific region of the protein surface and side chains in interactions with HAP.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Assessment of the interacting mechanism between Candida rugosa lipases and hydroxyapatite and identification of the hydroxyapatite-binding sequence through proteomics and molecular modelling",
pages = "34824-34818",
number = "41",
volume = "6",
doi = "10.1039/c6ra07521e"
}

Trbojević-Ivić, J., Dimitrijević, A., Milosavić, N., Bezbradica, D., Drakulić, B., Gavrović-Jankulović, M., Pavlović, M., Rogniaux, H.,& Veličković, D.. (2016). Assessment of the interacting mechanism between Candida rugosa lipases and hydroxyapatite and identification of the hydroxyapatite-binding sequence through proteomics and molecular modelling. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(41), 34818-34824.
https://doi.org/10.1039/c6ra07521e

Trbojević-Ivić J, Dimitrijević A, Milosavić N, Bezbradica D, Drakulić B, Gavrović-Jankulović M, Pavlović M, Rogniaux H, Veličković D. Assessment of the interacting mechanism between Candida rugosa lipases and hydroxyapatite and identification of the hydroxyapatite-binding sequence through proteomics and molecular modelling. in RSC Advances. 2016;6(41):34818-34824.
doi:10.1039/c6ra07521e .

Trbojević-Ivić, Jovana, Dimitrijević, Aleksandra, Milosavić, Nenad, Bezbradica, Dejan, Drakulić, Branko, Gavrović-Jankulović, Marija, Pavlović, Marija, Rogniaux, Helene, Veličković, Dušan, "Assessment of the interacting mechanism between Candida rugosa lipases and hydroxyapatite and identification of the hydroxyapatite-binding sequence through proteomics and molecular modelling" in RSC Advances, 6, no. 41 (2016):34818-34824,
https://doi.org/10.1039/c6ra07521e . .

TY  - JOUR
AU  - Marković, Jelena M.
AU  - Trišović, Nemanja
AU  - Mutavdžić, Dragosav
AU  - Radotić, Ksenija
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Marinković, Aleksandar
PY  - 2015
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3026
AB  - Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
EP  - 446
SP  - 435
VL  - 135
DO  - 10.1016/j.saa.2014.07.023
ER  - 

@article{
author = "Marković, Jelena M. and Trišović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranić, Ivan and Drakulić, Branko and Marinković, Aleksandar",
year = "2015",
abstract = "Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study",
pages = "446-435",
volume = "135",
doi = "10.1016/j.saa.2014.07.023"
}

Marković, J. M., Trišović, N., Mutavdžić, D., Radotić, K., Juranić, I., Drakulić, B.,& Marinković, A.. (2015). Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Pergamon-Elsevier Science Ltd, Oxford., 135, 435-446.
https://doi.org/10.1016/j.saa.2014.07.023

Marković JM, Trišović N, Mutavdžić D, Radotić K, Juranić I, Drakulić B, Marinković A. Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2015;135:435-446.
doi:10.1016/j.saa.2014.07.023 .

Marković, Jelena M., Trišović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranić, Ivan, Drakulić, Branko, Marinković, Aleksandar, "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 135 (2015):435-446,
https://doi.org/10.1016/j.saa.2014.07.023 . .

TY  - JOUR
AU  - Drakulić, Branko
AU  - Marinković, Aleksandar
AU  - Juranić, Ivan
PY  - 2012
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2222
AB  - Rate constants for the esterification of eleven 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane in ethanol at 30 degrees C were determined, and correlated with substituent constants using classical Hammett and related methods. Statistically valid results for the para-substituted compounds were obtained by the Swain-Lupton approach. The compounds studied had significant conformational mobility due to seven rotatable bonds in their backbone. Going beyond the classical Hammett approach, we established a relatively fast procedure to find the optimal conformations that can be used in linear free-energy relationships, combining molecular dynamics with semiempirical calculations, and calculations using a higher level of theory (DFT and MP2). Fair correlations were observed with frontier orbitals, allowing inclusion of ortho-substituted derivatives and clarifying artifact-like data, as perceived by the Hammett-type approach.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane
EP  - 556
IS  - 5
SP  - 553
VL  - 53
DO  - 10.1016/j.tetlet.2011.11.097
ER  - 

@article{
author = "Drakulić, Branko and Marinković, Aleksandar and Juranić, Ivan",
year = "2012",
abstract = "Rate constants for the esterification of eleven 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane in ethanol at 30 degrees C were determined, and correlated with substituent constants using classical Hammett and related methods. Statistically valid results for the para-substituted compounds were obtained by the Swain-Lupton approach. The compounds studied had significant conformational mobility due to seven rotatable bonds in their backbone. Going beyond the classical Hammett approach, we established a relatively fast procedure to find the optimal conformations that can be used in linear free-energy relationships, combining molecular dynamics with semiempirical calculations, and calculations using a higher level of theory (DFT and MP2). Fair correlations were observed with frontier orbitals, allowing inclusion of ortho-substituted derivatives and clarifying artifact-like data, as perceived by the Hammett-type approach.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane",
pages = "556-553",
number = "5",
volume = "53",
doi = "10.1016/j.tetlet.2011.11.097"
}

Drakulić, B., Marinković, A.,& Juranić, I.. (2012). On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 53(5), 553-556.
https://doi.org/10.1016/j.tetlet.2011.11.097

Drakulić B, Marinković A, Juranić I. On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane. in Tetrahedron Letters. 2012;53(5):553-556.
doi:10.1016/j.tetlet.2011.11.097 .

Drakulić, Branko, Marinković, Aleksandar, Juranić, Ivan, "On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane" in Tetrahedron Letters, 53, no. 5 (2012):553-556,
https://doi.org/10.1016/j.tetlet.2011.11.097 . .

TY  - JOUR
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Petrović, Slobodan
AU  - Mijin, Dušan
AU  - Stanković, Miroslav
PY  - 2006
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1001
AB  - Acute toxicity in vivo toward rats, of nineteen N-alkyl and N-cycloalkyl fluorocetamides [F-CH2-C(O)-NH-R] was correlated with their structure-dependent properties. Used descriptors are: molecular weights (M-w) and heat of formation (Delta H-f) of compounds; molar refractivity (CMR), lipophilicity (Clog P), Broto lipol values, virtual log P, molecular lipophilic potential (MLP), Van der Waals surfaces (VdW SAS) and hydropathicity surface (ILM) of whole molecules; Taft steric parameters (E-s); E-s values with Hancock corrections (E-s(CH)) and Verloop sterimol (B-5) and (L) parameters of alkyl and cycloalkyl residues; superdelocalizabilities and electron densities on the [NH-C(O)-CH2-F] fragment. Strong quantitative structure-activity relationships were assessed. Obtained correlation suggested that lipophilicity, shape and bulkiness of the alkyl and cycloalkyl substituents, particular nearest vicinity of the amide nitrogen, as well charges on the amide moiety are the main factors that influence on the acute toxicity of studied compounds toward rats. Mechanism of toxic action was proposed.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Chemosphere
T1  - A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats
EP  - 649
IS  - 4
SP  - 641
VL  - 62
DO  - 10.1016/j.chemosphere.2005.05.005
ER  - 

@article{
author = "Juranić, Ivan and Drakulić, Branko and Petrović, Slobodan and Mijin, Dušan and Stanković, Miroslav",
year = "2006",
abstract = "Acute toxicity in vivo toward rats, of nineteen N-alkyl and N-cycloalkyl fluorocetamides [F-CH2-C(O)-NH-R] was correlated with their structure-dependent properties. Used descriptors are: molecular weights (M-w) and heat of formation (Delta H-f) of compounds; molar refractivity (CMR), lipophilicity (Clog P), Broto lipol values, virtual log P, molecular lipophilic potential (MLP), Van der Waals surfaces (VdW SAS) and hydropathicity surface (ILM) of whole molecules; Taft steric parameters (E-s); E-s values with Hancock corrections (E-s(CH)) and Verloop sterimol (B-5) and (L) parameters of alkyl and cycloalkyl residues; superdelocalizabilities and electron densities on the [NH-C(O)-CH2-F] fragment. Strong quantitative structure-activity relationships were assessed. Obtained correlation suggested that lipophilicity, shape and bulkiness of the alkyl and cycloalkyl substituents, particular nearest vicinity of the amide nitrogen, as well charges on the amide moiety are the main factors that influence on the acute toxicity of studied compounds toward rats. Mechanism of toxic action was proposed.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Chemosphere",
title = "A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats",
pages = "649-641",
number = "4",
volume = "62",
doi = "10.1016/j.chemosphere.2005.05.005"
}

Juranić, I., Drakulić, B., Petrović, S., Mijin, D.,& Stanković, M.. (2006). A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats. in Chemosphere
Pergamon-Elsevier Science Ltd, Oxford., 62(4), 641-649.
https://doi.org/10.1016/j.chemosphere.2005.05.005

Juranić I, Drakulić B, Petrović S, Mijin D, Stanković M. A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats. in Chemosphere. 2006;62(4):641-649.
doi:10.1016/j.chemosphere.2005.05.005 .

Juranić, Ivan, Drakulić, Branko, Petrović, Slobodan, Mijin, Dušan, Stanković, Miroslav, "A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats" in Chemosphere, 62, no. 4 (2006):641-649,
https://doi.org/10.1016/j.chemosphere.2005.05.005 . .

TY  - JOUR
AU  - Stevović, LS
AU  - Drakulić, Branko
AU  - Juranić, Ivan
AU  - Drmanić, Saša
AU  - Jovanović, Bratislav Ž.
PY  - 1999
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/264
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Reactivity of beta-aroylacrylic acids with diazodiphenylmethane (vol 63, pg 359, 1998)
EP  - 495
IS  - 7-8
SP  - 495
VL  - 64
UR  - https://hdl.handle.net/21.15107/rcub_technorep_264
ER  - 

@article{
author = "Stevović, LS and Drakulić, Branko and Juranić, Ivan and Drmanić, Saša and Jovanović, Bratislav Ž.",
year = "1999",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane (vol 63, pg 359, 1998)",
pages = "495-495",
number = "7-8",
volume = "64",
url = "https://hdl.handle.net/21.15107/rcub_technorep_264"
}

Stevović, L., Drakulić, B., Juranić, I., Drmanić, S.,& Jovanović, B. Ž.. (1999). Reactivity of beta-aroylacrylic acids with diazodiphenylmethane (vol 63, pg 359, 1998). in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 64(7-8), 495-495.
https://hdl.handle.net/21.15107/rcub_technorep_264

Stevović L, Drakulić B, Juranić I, Drmanić S, Jovanović BŽ. Reactivity of beta-aroylacrylic acids with diazodiphenylmethane (vol 63, pg 359, 1998). in Journal of the Serbian Chemical Society. 1999;64(7-8):495-495.
https://hdl.handle.net/21.15107/rcub_technorep_264 .

Stevović, LS, Drakulić, Branko, Juranić, Ivan, Drmanić, Saša, Jovanović, Bratislav Ž., "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane (vol 63, pg 359, 1998)" in Journal of the Serbian Chemical Society, 64, no. 7-8 (1999):495-495,
https://hdl.handle.net/21.15107/rcub_technorep_264 .

TY  - JOUR
AU  - Stevović, Ljubomir S.
AU  - Drakulić, Branko
AU  - Juranić, Ivan
AU  - Drmanić, Saša
AU  - Jovanović, Bratislav Ž.
PY  - 1998
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/157
AB  - The rate constants for 10 trans-substituted beta-aroylacrylic acids in their reaction with diazodiphenylmethane (DDM) were determined in ethanol at 30 degrees C. The intention was to study the transmission of electronic effects of substituents on the phenyl nuclei to the carboxylic group reaction center, through the -C(=O)-CH=CH-group. The obtained rate constants were analyzed with the classical Hammett equation and the extended Hammett and Taft equation. It was possible, using Taft's relationship, to effect the separation of the overall polar effect into inductive and resonance components. The pattern of transmission through the observed conjugated system has been discussed. Conformational variations caused by variable substituents in an aromatic ring were calculated using the MNDO-AM I semiempirical method. The inclusion of a calculated conformational effect considerably improves the regression.
PB  - Serbian Chemical Society, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Reactivity of beta-aroylacrylic acids with diazodiphenylmethane
EP  - 365
IS  - 5
SP  - 359
VL  - 63
UR  - https://hdl.handle.net/21.15107/rcub_technorep_157
ER  - 

@article{
author = "Stevović, Ljubomir S. and Drakulić, Branko and Juranić, Ivan and Drmanić, Saša and Jovanović, Bratislav Ž.",
year = "1998",
abstract = "The rate constants for 10 trans-substituted beta-aroylacrylic acids in their reaction with diazodiphenylmethane (DDM) were determined in ethanol at 30 degrees C. The intention was to study the transmission of electronic effects of substituents on the phenyl nuclei to the carboxylic group reaction center, through the -C(=O)-CH=CH-group. The obtained rate constants were analyzed with the classical Hammett equation and the extended Hammett and Taft equation. It was possible, using Taft's relationship, to effect the separation of the overall polar effect into inductive and resonance components. The pattern of transmission through the observed conjugated system has been discussed. Conformational variations caused by variable substituents in an aromatic ring were calculated using the MNDO-AM I semiempirical method. The inclusion of a calculated conformational effect considerably improves the regression.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane",
pages = "365-359",
number = "5",
volume = "63",
url = "https://hdl.handle.net/21.15107/rcub_technorep_157"
}

Stevović, L. S., Drakulić, B., Juranić, I., Drmanić, S.,& Jovanović, B. Ž.. (1998). Reactivity of beta-aroylacrylic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 63(5), 359-365.
https://hdl.handle.net/21.15107/rcub_technorep_157

Stevović LS, Drakulić B, Juranić I, Drmanić S, Jovanović BŽ. Reactivity of beta-aroylacrylic acids with diazodiphenylmethane. in Journal of the Serbian Chemical Society. 1998;63(5):359-365.
https://hdl.handle.net/21.15107/rcub_technorep_157 .

Stevović, Ljubomir S., Drakulić, Branko, Juranić, Ivan, Drmanić, Saša, Jovanović, Bratislav Ž., "Reactivity of beta-aroylacrylic acids with diazodiphenylmethane" in Journal of the Serbian Chemical Society, 63, no. 5 (1998):359-365,
https://hdl.handle.net/21.15107/rcub_technorep_157 .