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Pregled bibliografske jedinice broj: 786591

Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules


Skočibušić, Mirjana; Odžak, Renata; Štefanić, Zoran; Križić, Ivana; Krišto, Lucija; Jović, Ozren; Hrenar, Tomica; Primožič, Ines; Jurašin, Darija
Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules // Colloids and surfaces. B, Biointerfaces, 140 (2016), 548-559 doi:10.1016/j.colsurfb.2015.11.023 (međunarodna recenzija, članak, znanstveni)


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Naslov
Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules

Autori
Skočibušić, Mirjana ; Odžak, Renata ; Štefanić, Zoran ; Križić, Ivana ; Krišto, Lucija ; Jović, Ozren ; Hrenar, Tomica ; Primožič, Ines ; Jurašin, Darija

Izvornik
Colloids and surfaces. B, Biointerfaces (0927-7765) 140 (2016); 548-559

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
cationic surfactants; quinuclidinium oximes; biologically active compounds; structure-property relationship; crystal structure; antimicrobial efficacy

Sažetak
Motivated by diverse biological and pharmacological activity of quinuclidine and oxime compounds we have synthesized and characterized novel class of surfactants, 3-hydroxyimino quinuclidinium bromides with different alkyl chains lengths (CnQNOH ; n = 12, 14 and 16). The incorporation of nonconventional hydroxyimino quinuclidinium headgroup and variation in alkyl chain length affects hydrophilic-hydrophobic balance of surfactant molecule and thereby physicochemical properties important for its application. Therefore, newly synthesized surfactants were characterized by the combination of different experimental techniques: X-ray analysis, potentiometry, electrical conductivity, surface tension and dynamic light scattering measurements, as well as antimicrobial susceptibility tests. Comprehensive investigation of CnQNOH surfactants enabled insight into structure-property relationship, i.e. way in which the arrangement of surfactant molecules in the crystal phase correlates with their solution behavior and biologically activity. The synthesized CnQNOH surfactants exhibited high adsorption efficiency and relatively low critical micelle concentrations. In addition, all investigated compounds showed very potent and promising activity against Gram-positive and clinically relevant Gram-negative bacterial strains compared to conventional antimicrobial agents: tetracycline and gentamicin. The overall results indicate that bicyclic headgroup with oxime moiety, which affects both hydrophilicity and hydrophobicity of CnQNOH molecule in addition to enabling hydrogen bonding, has dominant effect on crystal packing and physicochemical properties. The unique structural features of cationic surfactants with hydroxyimino quinuclidine headgroup along with diverse biological activity have made them promising structures in novel drug discovery. Obtained fundamental understanding how combination of different functionalities in a single surfactant molecule affects its physicochemical properties represents a good starting point for further biological research.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija



POVEZANOST RADA


Projekti:
098-0982915-2949 - Površinski aktivne tvari, procesi u otopinama i na međupovršinama (Dutour Sikirić, Maja, MZOS ) ( CroRIS)
HRZZ-IP-2013-11-5055 - Bioinspirirani materijali - mehanizmi nastajanja i interakcija (Bio-Mat-Form) (Kralj, Damir, HRZZ - 2013-11) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Split

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com dx.doi.org

Citiraj ovu publikaciju:

Skočibušić, Mirjana; Odžak, Renata; Štefanić, Zoran; Križić, Ivana; Krišto, Lucija; Jović, Ozren; Hrenar, Tomica; Primožič, Ines; Jurašin, Darija
Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules // Colloids and surfaces. B, Biointerfaces, 140 (2016), 548-559 doi:10.1016/j.colsurfb.2015.11.023 (međunarodna recenzija, članak, znanstveni)
Skočibušić, M., Odžak, R., Štefanić, Z., Križić, I., Krišto, L., Jović, O., Hrenar, T., Primožič, I. & Jurašin, D. (2016) Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules. Colloids and surfaces. B, Biointerfaces, 140, 548-559 doi:10.1016/j.colsurfb.2015.11.023.
@article{article, author = {Sko\v{c}ibu\v{s}i\'{c}, Mirjana and Od\v{z}ak, Renata and \v{S}tefani\'{c}, Zoran and Kri\v{z}i\'{c}, Ivana and Kri\v{s}to, Lucija and Jovi\'{c}, Ozren and Hrenar, Tomica and Primo\v{z}i\v{c}, Ines and Jura\v{s}in, Darija}, year = {2016}, pages = {548-559}, DOI = {10.1016/j.colsurfb.2015.11.023}, keywords = {cationic surfactants, quinuclidinium oximes, biologically active compounds, structure-property relationship, crystal structure, antimicrobial efficacy}, journal = {Colloids and surfaces. B, Biointerfaces}, doi = {10.1016/j.colsurfb.2015.11.023}, volume = {140}, issn = {0927-7765}, title = {Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules}, keyword = {cationic surfactants, quinuclidinium oximes, biologically active compounds, structure-property relationship, crystal structure, antimicrobial efficacy} }
@article{article, author = {Sko\v{c}ibu\v{s}i\'{c}, Mirjana and Od\v{z}ak, Renata and \v{S}tefani\'{c}, Zoran and Kri\v{z}i\'{c}, Ivana and Kri\v{s}to, Lucija and Jovi\'{c}, Ozren and Hrenar, Tomica and Primo\v{z}i\v{c}, Ines and Jura\v{s}in, Darija}, year = {2016}, pages = {548-559}, DOI = {10.1016/j.colsurfb.2015.11.023}, keywords = {cationic surfactants, quinuclidinium oximes, biologically active compounds, structure-property relationship, crystal structure, antimicrobial efficacy}, journal = {Colloids and surfaces. B, Biointerfaces}, doi = {10.1016/j.colsurfb.2015.11.023}, volume = {140}, issn = {0927-7765}, title = {Structure-Property Relationship of Quinuclidinium Surfactants – Towards Multifunctional Biologically Active Molecules}, keyword = {cationic surfactants, quinuclidinium oximes, biologically active compounds, structure-property relationship, crystal structure, antimicrobial efficacy} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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