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Pregled bibliografske jedinice broj: 1241662

Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach,


Habinovec, Iva; Mikulandra, Ivana; Pranjić, Paula; Kazazić, Saša; Čipčić Paljetak, Hana; Bertoša, Branimir; Barišić, Antun; Bukvić, Mirjana; Novak, Predrag
Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach, // Antibiotics, 11 (2022), 12; 1738, 15 doi:10.3390/antibiotics11121738 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 1241662 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach,

Autori
Habinovec, Iva ; Mikulandra, Ivana ; Pranjić, Paula ; Kazazić, Saša ; Čipčić Paljetak, Hana ; Bertoša, Branimir ; Barišić, Antun ; Bukvić, Mirjana ; Novak, Predrag

Izvornik
Antibiotics (2079-6382) 11 (2022), 12; 1738, 15

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

Ključne riječi
azithromycin conjugates ; macrozones ; diastereomers ; antibacterial activity ; HPLC-SPE/cryo NMR ; MS/MS ; molecular modeling

Sažetak
A well-known class of antibacterials, 14- and 15- membered macrolides are widely prescribed to treat upper and lower respiratory tract infections. Azithromycin is a 15-membered macrolide antibiotic possessing a broad spectrum of antibacterial potency and favorable pharmacokinetics. Bacterial resistance to marketed antibiotics is growing rapidly and represents one of the major global hazards to human health. Today, there is a high need for discovery of new anti-infective agents to combat resistance. Recently discovered conjugates of azithromycin and thiosemicarbazones, the macrozones, represent one such class that exhibits promising activities against resistant pathogens. In this paper, we employed an approach which combined LC-SPE/cryo NMR, MS/MS and molecular modeling for rapid separation, identification and characterization of bioactive macrozones and their diastereomers. Multitrapping of the chromatographic peaks on SPE cartridges enabled sufficient sample quantities for structure elucidation and biological testing. Furthermore, two-dimensional NOESY NMR data and molecular dynamics simulations revealed stereogenic centers with inversion of chirality. Differences in biological activities among diastereomers were detected. These results should be considered in the process of designing new macrolide compounds with bioactivity. We have shown that this methodology can be used for a fast screening and identification of the macrolide reaction components, including stereoisomers, which can serve as a source of new antibacterials

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekti:
HRZZ-IP-2018-01-8098 - Makrozoni, novi konjugati makrolidnih antibiotika: Dizajn, priprava i interakcije (Makrozoni/Macrozones) (Novak, Predrag, HRZZ - 2018-01) ( CroRIS)

Ustanove:
Medicinski fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Poveznice na cjeloviti tekst rada:

Pristup cjelovitom tekstu rada doi www.mdpi.com

Citiraj ovu publikaciju:

Habinovec, Iva; Mikulandra, Ivana; Pranjić, Paula; Kazazić, Saša; Čipčić Paljetak, Hana; Bertoša, Branimir; Barišić, Antun; Bukvić, Mirjana; Novak, Predrag
Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach, // Antibiotics, 11 (2022), 12; 1738, 15 doi:10.3390/antibiotics11121738 (međunarodna recenzija, članak, znanstveni)
Habinovec, I., Mikulandra, I., Pranjić, P., Kazazić, S., Čipčić Paljetak, H., Bertoša, B., Barišić, A., Bukvić, M. & Novak, P. (2022) Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach,. Antibiotics, 11 (12), 1738, 15 doi:10.3390/antibiotics11121738.
@article{article, author = {Habinovec, Iva and Mikulandra, Ivana and Pranji\'{c}, Paula and Kazazi\'{c}, Sa\v{s}a and \v{C}ip\v{c}i\'{c} Paljetak, Hana and Berto\v{s}a, Branimir and Bari\v{s}i\'{c}, Antun and Bukvi\'{c}, Mirjana and Novak, Predrag}, year = {2022}, pages = {15}, DOI = {10.3390/antibiotics11121738}, chapter = {1738}, keywords = {azithromycin conjugates, macrozones, diastereomers, antibacterial activity, HPLC-SPE/cryo NMR, MS/MS, molecular modeling}, journal = {Antibiotics}, doi = {10.3390/antibiotics11121738}, volume = {11}, number = {12}, issn = {2079-6382}, title = {Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach,}, keyword = {azithromycin conjugates, macrozones, diastereomers, antibacterial activity, HPLC-SPE/cryo NMR, MS/MS, molecular modeling}, chapternumber = {1738} }
@article{article, author = {Habinovec, Iva and Mikulandra, Ivana and Pranji\'{c}, Paula and Kazazi\'{c}, Sa\v{s}a and \v{C}ip\v{c}i\'{c} Paljetak, Hana and Berto\v{s}a, Branimir and Bari\v{s}i\'{c}, Antun and Bukvi\'{c}, Mirjana and Novak, Predrag}, year = {2022}, pages = {15}, DOI = {10.3390/antibiotics11121738}, chapter = {1738}, keywords = {azithromycin conjugates, macrozones, diastereomers, antibacterial activity, HPLC-SPE/cryo NMR, MS/MS, molecular modeling}, journal = {Antibiotics}, doi = {10.3390/antibiotics11121738}, volume = {11}, number = {12}, issn = {2079-6382}, title = {Screening of novel antimicrobial diastereomers of azithromycin-thiosemicarbazone conjugates: A combined LC-SPE/cryo NMR, LC-MS/MS and molecular modelling approach,}, keyword = {azithromycin conjugates, macrozones, diastereomers, antibacterial activity, HPLC-SPE/cryo NMR, MS/MS, molecular modeling}, chapternumber = {1738} }

Časopis indeksira:


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


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