TY  - JOUR
AU  - Cerrone, Federico
AU  - Milovanović, Jelena
AU  - Nikodinović-Runić, Jasmina
AU  - Walsh, Meg
AU  - Kenny, Shane T.
AU  - Babu, Ramesh
AU  - O'Connor, Kevin 
PY  - 2019
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1199
AB  - A sodium alkyl disulfate mixture (SADM) synthesised from microbially produced 3-hydroxy fatty acids methyl esters (HFAMEs), showed 13-fold surface tension decrease when compared with the reference surfactant sodium dodecyl sulfate (SDS). Polyhydroxyalkanoates, accumulated by bacteria intracellularly when supplied with a mixture of fatty acids derived from hydrolysed rapeseed oil, were isolated, depolymerised and methylated to produce HFAMEs in very high yield (90%). A sequential chemical reduction and sulfation of the HFAMEs produced the sodium alkyl disulfates in high yields ( gt  65%). SADM performs also 1.3-times better than dodecyl (1,3) disulfate, in surface tension tests. SADM shows also the formation of a specific critical micelle concentration (CMC) at a concentration 21-fold lower than SDS. The wettability of the SADM mixture is similar to SDS but the foaming volume of SADM is 1.5-fold higher. The foam is also more stable with its volume decreasing 3 times slower over time compared to SDS at their respective CMC values. Established sulfation technologies in chemical manufacturing could use the 3-hydroxy fatty acids methyl esters moiety (3-HFAME) given its origin from rapeseed oil and the extra OH residue on 3-position in the molecule, which affords the opportunity to produce disulfate surfactants with a proven superior performance to monosulphated surfactants. Thus, not only addressing environmental issues by avoiding threats of deforestation and monocultivation associated with palm oil use but also achieve a higher performance with lower use of surfactants.
PB  - Elsevier, Amsterdam
T2  - Colloids and Surfaces B-Biointerfaces
T1  - Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters
VL  - 182
DO  - 10.1016/j.colsurfb.2019.06.062
ER  - 

@article{
author = "Cerrone, Federico and Milovanović, Jelena and Nikodinović-Runić, Jasmina and Walsh, Meg and Kenny, Shane T. and Babu, Ramesh and O'Connor, Kevin ",
year = "2019",
abstract = "A sodium alkyl disulfate mixture (SADM) synthesised from microbially produced 3-hydroxy fatty acids methyl esters (HFAMEs), showed 13-fold surface tension decrease when compared with the reference surfactant sodium dodecyl sulfate (SDS). Polyhydroxyalkanoates, accumulated by bacteria intracellularly when supplied with a mixture of fatty acids derived from hydrolysed rapeseed oil, were isolated, depolymerised and methylated to produce HFAMEs in very high yield (90%). A sequential chemical reduction and sulfation of the HFAMEs produced the sodium alkyl disulfates in high yields ( gt  65%). SADM performs also 1.3-times better than dodecyl (1,3) disulfate, in surface tension tests. SADM shows also the formation of a specific critical micelle concentration (CMC) at a concentration 21-fold lower than SDS. The wettability of the SADM mixture is similar to SDS but the foaming volume of SADM is 1.5-fold higher. The foam is also more stable with its volume decreasing 3 times slower over time compared to SDS at their respective CMC values. Established sulfation technologies in chemical manufacturing could use the 3-hydroxy fatty acids methyl esters moiety (3-HFAME) given its origin from rapeseed oil and the extra OH residue on 3-position in the molecule, which affords the opportunity to produce disulfate surfactants with a proven superior performance to monosulphated surfactants. Thus, not only addressing environmental issues by avoiding threats of deforestation and monocultivation associated with palm oil use but also achieve a higher performance with lower use of surfactants.",
publisher = "Elsevier, Amsterdam",
journal = "Colloids and Surfaces B-Biointerfaces",
title = "Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters",
volume = "182",
doi = "10.1016/j.colsurfb.2019.06.062"
}

Cerrone, F., Milovanović, J., Nikodinović-Runić, J., Walsh, M., Kenny, S. T., Babu, R.,& O'Connor, K.. (2019). Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters. in Colloids and Surfaces B-Biointerfaces
Elsevier, Amsterdam., 182.
https://doi.org/10.1016/j.colsurfb.2019.06.062

Cerrone F, Milovanović J, Nikodinović-Runić J, Walsh M, Kenny ST, Babu R, O'Connor K. Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters. in Colloids and Surfaces B-Biointerfaces. 2019;182.
doi:10.1016/j.colsurfb.2019.06.062 .

Cerrone, Federico, Milovanović, Jelena, Nikodinović-Runić, Jasmina, Walsh, Meg, Kenny, Shane T., Babu, Ramesh, O'Connor, Kevin , "Novel sodium alkyl-1,3-disulfates, anionic biosurfactants produced from microbial polyesters" in Colloids and Surfaces B-Biointerfaces, 182 (2019),
https://doi.org/10.1016/j.colsurfb.2019.06.062 . .

TY  - JOUR
AU  - Almahboub, Sarah A.
AU  - Narancić, Tanja
AU  - Devocelle, Marc
AU  - Kenny, Shane T.
AU  - Palmer-Brown, William
AU  - Murphy, Cormac
AU  - Nikodinović-Runić, Jasmina
AU  - O'Connor, Kevin 
PY  - 2018
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/1161
AB  - Terminal modification of peptides is frequently used to improve their hydrophobicity. While N-terminal modification with fatty acids (lipidation) has been reported previously, C-terminal lipidation is limited as it requires the use of linkers. Here we report the use of a biocatalyst for the production of an unnatural fatty amino acid, (S)-2-aminooctanoic acid (2-AOA) with enantiomeric excess  gt  98% ee and the subsequent use of 2-AOA to modify and improve the activity of an antimicrobial peptide. A transaminase originating from Chromobacterium violaceum was employed with a conversion efficiency 52-80% depending on the ratio of amino group donor to acceptor. 2-AOA is a fatty acid with amino functionality, which allowed direct C- and N-terminal conjugation respectively to an antimicrobial peptide (AMP) derived from lactoferricin B. The antibacterial activity of the modified peptides was improved by up to 16-fold. Furthermore, minimal inhibitory concentrations (MIC) of C-terminally modified peptide were always lower than N-terminally conjugated peptides. The C-terminally modified peptide exhibited MIC values of 25 mu g/ml for Escherichia coli, 50 mu g/ml for Bacillus subtilis, 100 mu g/ml for Salmonella typhimurium, 200 mu g/ml for Pseudomonas aeruginosa and 400 mu g/ml for Staphylococcus aureus. The C-terminally modified peptide was the only peptide tested that showed complete inhibition of growth of S. aureus.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Biosynthesis of 2-aminooctanoic acid and its use to terminally modify a lactoferricin B peptide derivative for improved antimicrobial activity
EP  - 799
IS  - 2
SP  - 789
VL  - 102
DO  - 10.1007/s00253-017-8655-0
ER  - 

@article{
author = "Almahboub, Sarah A. and Narancić, Tanja and Devocelle, Marc and Kenny, Shane T. and Palmer-Brown, William and Murphy, Cormac and Nikodinović-Runić, Jasmina and O'Connor, Kevin ",
year = "2018",
abstract = "Terminal modification of peptides is frequently used to improve their hydrophobicity. While N-terminal modification with fatty acids (lipidation) has been reported previously, C-terminal lipidation is limited as it requires the use of linkers. Here we report the use of a biocatalyst for the production of an unnatural fatty amino acid, (S)-2-aminooctanoic acid (2-AOA) with enantiomeric excess  gt  98% ee and the subsequent use of 2-AOA to modify and improve the activity of an antimicrobial peptide. A transaminase originating from Chromobacterium violaceum was employed with a conversion efficiency 52-80% depending on the ratio of amino group donor to acceptor. 2-AOA is a fatty acid with amino functionality, which allowed direct C- and N-terminal conjugation respectively to an antimicrobial peptide (AMP) derived from lactoferricin B. The antibacterial activity of the modified peptides was improved by up to 16-fold. Furthermore, minimal inhibitory concentrations (MIC) of C-terminally modified peptide were always lower than N-terminally conjugated peptides. The C-terminally modified peptide exhibited MIC values of 25 mu g/ml for Escherichia coli, 50 mu g/ml for Bacillus subtilis, 100 mu g/ml for Salmonella typhimurium, 200 mu g/ml for Pseudomonas aeruginosa and 400 mu g/ml for Staphylococcus aureus. The C-terminally modified peptide was the only peptide tested that showed complete inhibition of growth of S. aureus.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Biosynthesis of 2-aminooctanoic acid and its use to terminally modify a lactoferricin B peptide derivative for improved antimicrobial activity",
pages = "799-789",
number = "2",
volume = "102",
doi = "10.1007/s00253-017-8655-0"
}

Almahboub, S. A., Narancić, T., Devocelle, M., Kenny, S. T., Palmer-Brown, W., Murphy, C., Nikodinović-Runić, J.,& O'Connor, K.. (2018). Biosynthesis of 2-aminooctanoic acid and its use to terminally modify a lactoferricin B peptide derivative for improved antimicrobial activity. in Applied Microbiology and Biotechnology
Springer, New York., 102(2), 789-799.
https://doi.org/10.1007/s00253-017-8655-0

Almahboub SA, Narancić T, Devocelle M, Kenny ST, Palmer-Brown W, Murphy C, Nikodinović-Runić J, O'Connor K. Biosynthesis of 2-aminooctanoic acid and its use to terminally modify a lactoferricin B peptide derivative for improved antimicrobial activity. in Applied Microbiology and Biotechnology. 2018;102(2):789-799.
doi:10.1007/s00253-017-8655-0 .

Almahboub, Sarah A., Narancić, Tanja, Devocelle, Marc, Kenny, Shane T., Palmer-Brown, William, Murphy, Cormac, Nikodinović-Runić, Jasmina, O'Connor, Kevin , "Biosynthesis of 2-aminooctanoic acid and its use to terminally modify a lactoferricin B peptide derivative for improved antimicrobial activity" in Applied Microbiology and Biotechnology, 102, no. 2 (2018):789-799,
https://doi.org/10.1007/s00253-017-8655-0 . .

TY  - JOUR
AU  - Milovanović, Jelena
AU  - Škaro Bogojević, Sanja
AU  - Šenerović, Lidija
AU  - Vasiljević, Branka
AU  - Guzik, Maciej
AU  - Kenny, Shane T.
AU  - Maslak, Veselin
AU  - Nikodinović-Runić, Jasmina
AU  - O'Connor, Kevin 
PY  - 2016
UR  - https://imagine.imgge.bg.ac.rs/handle/123456789/974
AB  - A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds
EP  - 172
IS  - 1
SP  - 161
VL  - 100
DO  - 10.1007/s00253-015-6984-4
ER  - 

@article{
author = "Milovanović, Jelena and Škaro Bogojević, Sanja and Šenerović, Lidija and Vasiljević, Branka and Guzik, Maciej and Kenny, Shane T. and Maslak, Veselin and Nikodinović-Runić, Jasmina and O'Connor, Kevin ",
year = "2016",
abstract = "A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.8-7.0 mM and 0.1-6.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds",
pages = "172-161",
number = "1",
volume = "100",
doi = "10.1007/s00253-015-6984-4"
}

Milovanović, J., Škaro Bogojević, S., Šenerović, L., Vasiljević, B., Guzik, M., Kenny, S. T., Maslak, V., Nikodinović-Runić, J.,& O'Connor, K.. (2016). Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology
Springer, New York., 100(1), 161-172.
https://doi.org/10.1007/s00253-015-6984-4

Milovanović J, Škaro Bogojević S, Šenerović L, Vasiljević B, Guzik M, Kenny ST, Maslak V, Nikodinović-Runić J, O'Connor K. Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds. in Applied Microbiology and Biotechnology. 2016;100(1):161-172.
doi:10.1007/s00253-015-6984-4 .

Milovanović, Jelena, Škaro Bogojević, Sanja, Šenerović, Lidija, Vasiljević, Branka, Guzik, Maciej, Kenny, Shane T., Maslak, Veselin, Nikodinović-Runić, Jasmina, O'Connor, Kevin , "Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds" in Applied Microbiology and Biotechnology, 100, no. 1 (2016):161-172,
https://doi.org/10.1007/s00253-015-6984-4 . .