TY  - JOUR
AU  - Ilić-Stojanović, Snežana
AU  - Nikolić, Vesna D.
AU  - Nikolić, Ljubiša B.
AU  - Zdravković, Aleksandar S.
AU  - Kapor, Agneš
AU  - Popsavin, Mirjana
AU  - Petrović, Slobodan
PY  - 2015
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2891
AB  - The aim of this work was the preparation of the inclusion complex of naproxen with 2- hydroxypropyl-β-cyclodextrin (HP-β-CD) in order to improve the physical and chemical properties of naproxen. The molecular inclusion complexes of naproxen with HP-β-CD were prepared by using the co-precipitation method in the solid state with the molar ratio of 1:1. The structure of the obtained complex was characterized by using FTIR, 1H NMR, UV-Vis and XRD methods. The testing of naproxen photostability by the UV-Vis method indicated the degradation to aromatic ketone, 2-acetyl-6-methoxynaphthalene. FTIR analysis showed that the degradation has started 15 days after the exposure of naproxen to daylight while the inclusion complex of naproxen:2-hydroxypropyl-β-cyclodextrin was photostable for a period of 30 days.
AB  - Naproksen, (+)-(S)-2-(6-metoksinaftalen-2-il)propionska kiselina, je derivat 2-arilpropionske kiseline (profena) iz grupe nesteroidnih antiinflamatornih lekova koji u terapijskim dozama smanjuje biosintezu prostaglandina i snižava povišenu telesnu temperaturu. Ovaj slabo rastvoran i fotoosetljiv molekul se transformiše pod uticajem svetlosti dajući farmakološki neaktivne proizvode. Cilj ovog rada je priprema inkluzionog kompleksa naproksena sa 2-hidroksipropil-β-ciklodekstrinom (HP-β-CD) u cilju poboljšanja fizičko-hemijskih svojstava naproksena. Molekulski inkluzioni kompleks naproksena i HP-β-CD pripremljen je metodom koprecipitacije u čvrstom stanju u molskom odnosu 1:1. Za strukturnu karakterizaciju kompleksa, kompleksirajućeg agensa, odgovarajuće fizičke smeše i naproksena, korišćene su metode protonske nuklearne magnetne rezonance (1H-NMR), difrakcije rendgenskih zraka (XRD) i infracrvene spektrofotometrije sa Furijeovom transformacijom (FTIR). FTIR i UV-Vis metode korišćene su za analizu fotoosetljivih grupa naproksena u čistom i kompleksiranom obliku radi ispitivanja uticaja na fotostabilnost naproksena. Difraktogram inkluzionog kompleksa naproksen:2-hidroksipropil- β-ciklodekstrin ne sadrži pikove koji su karakteristični za difraktograme naproksena i HP-β-CD. Ovo ukazuje da je naproksen zaklonjen u šupljine domaćina prilikom molekularne inkapsulacije. Odsustvo karakterističnih pikova naproksena u FTIR spektru kompleksa ukazuje na formiranje supramolekularne strukture po tipu inkluzije. Hemijska pomeranja u 1H-NMR spektru nakon inkluzije naproksena u šupljine HP-β-CD, posebno H3, H6 i H9 protona i vodonika iz CH3 u HP-β-CD takođe ukazuju na formiranje molekulskog inkluzionog kompleksa. Ispitivanje fotostabilnosti naproksena, pomoću UV-Vis metode, ukazuje na degradaciju do aromatičnog ketona, 2-acetil-6-metoksinaftalena. FTIR analiza je pokazala da degradacija naproksena počinje nakon 15 dana izlaganja dnevnoj svetlosti i da je molekularnom inkapsulacijom on zaštićen od fotodegradacije za vremenski period od 30 dana.
PB  - Association of Chemical Engineers of Serbia
T2  - Hemijska industrija
T1  - The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin
T1  - Poboljšana fotostabilnost naproksena u inkluzionom kompleksu sa 2-hidroksipropil-β-ciklodekstrinom
EP  - 370
IS  - 4
SP  - 361
VL  - 69
DO  - 10.2298/HEMIND131128050I
ER  - 

@article{
author = "Ilić-Stojanović, Snežana and Nikolić, Vesna D. and Nikolić, Ljubiša B. and Zdravković, Aleksandar S. and Kapor, Agneš and Popsavin, Mirjana and Petrović, Slobodan",
year = "2015",
abstract = "The aim of this work was the preparation of the inclusion complex of naproxen with 2- hydroxypropyl-β-cyclodextrin (HP-β-CD) in order to improve the physical and chemical properties of naproxen. The molecular inclusion complexes of naproxen with HP-β-CD were prepared by using the co-precipitation method in the solid state with the molar ratio of 1:1. The structure of the obtained complex was characterized by using FTIR, 1H NMR, UV-Vis and XRD methods. The testing of naproxen photostability by the UV-Vis method indicated the degradation to aromatic ketone, 2-acetyl-6-methoxynaphthalene. FTIR analysis showed that the degradation has started 15 days after the exposure of naproxen to daylight while the inclusion complex of naproxen:2-hydroxypropyl-β-cyclodextrin was photostable for a period of 30 days., Naproksen, (+)-(S)-2-(6-metoksinaftalen-2-il)propionska kiselina, je derivat 2-arilpropionske kiseline (profena) iz grupe nesteroidnih antiinflamatornih lekova koji u terapijskim dozama smanjuje biosintezu prostaglandina i snižava povišenu telesnu temperaturu. Ovaj slabo rastvoran i fotoosetljiv molekul se transformiše pod uticajem svetlosti dajući farmakološki neaktivne proizvode. Cilj ovog rada je priprema inkluzionog kompleksa naproksena sa 2-hidroksipropil-β-ciklodekstrinom (HP-β-CD) u cilju poboljšanja fizičko-hemijskih svojstava naproksena. Molekulski inkluzioni kompleks naproksena i HP-β-CD pripremljen je metodom koprecipitacije u čvrstom stanju u molskom odnosu 1:1. Za strukturnu karakterizaciju kompleksa, kompleksirajućeg agensa, odgovarajuće fizičke smeše i naproksena, korišćene su metode protonske nuklearne magnetne rezonance (1H-NMR), difrakcije rendgenskih zraka (XRD) i infracrvene spektrofotometrije sa Furijeovom transformacijom (FTIR). FTIR i UV-Vis metode korišćene su za analizu fotoosetljivih grupa naproksena u čistom i kompleksiranom obliku radi ispitivanja uticaja na fotostabilnost naproksena. Difraktogram inkluzionog kompleksa naproksen:2-hidroksipropil- β-ciklodekstrin ne sadrži pikove koji su karakteristični za difraktograme naproksena i HP-β-CD. Ovo ukazuje da je naproksen zaklonjen u šupljine domaćina prilikom molekularne inkapsulacije. Odsustvo karakterističnih pikova naproksena u FTIR spektru kompleksa ukazuje na formiranje supramolekularne strukture po tipu inkluzije. Hemijska pomeranja u 1H-NMR spektru nakon inkluzije naproksena u šupljine HP-β-CD, posebno H3, H6 i H9 protona i vodonika iz CH3 u HP-β-CD takođe ukazuju na formiranje molekulskog inkluzionog kompleksa. Ispitivanje fotostabilnosti naproksena, pomoću UV-Vis metode, ukazuje na degradaciju do aromatičnog ketona, 2-acetil-6-metoksinaftalena. FTIR analiza je pokazala da degradacija naproksena počinje nakon 15 dana izlaganja dnevnoj svetlosti i da je molekularnom inkapsulacijom on zaštićen od fotodegradacije za vremenski period od 30 dana.",
publisher = "Association of Chemical Engineers of Serbia",
journal = "Hemijska industrija",
title = "The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin, Poboljšana fotostabilnost naproksena u inkluzionom kompleksu sa 2-hidroksipropil-β-ciklodekstrinom",
pages = "370-361",
number = "4",
volume = "69",
doi = "10.2298/HEMIND131128050I"
}

Ilić-Stojanović, S., Nikolić, V. D., Nikolić, L. B., Zdravković, A. S., Kapor, A., Popsavin, M.,& Petrović, S.. (2015). The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin. in Hemijska industrija
Association of Chemical Engineers of Serbia., 69(4), 361-370.
https://doi.org/10.2298/HEMIND131128050I

Ilić-Stojanović S, Nikolić VD, Nikolić LB, Zdravković AS, Kapor A, Popsavin M, Petrović S. The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin. in Hemijska industrija. 2015;69(4):361-370.
doi:10.2298/HEMIND131128050I .

Ilić-Stojanović, Snežana, Nikolić, Vesna D., Nikolić, Ljubiša B., Zdravković, Aleksandar S., Kapor, Agneš, Popsavin, Mirjana, Petrović, Slobodan, "The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin" in Hemijska industrija, 69, no. 4 (2015):361-370,
https://doi.org/10.2298/HEMIND131128050I . .

TY  - JOUR
AU  - Tacić, Ana
AU  - Savić, Ivan
AU  - Nikolić, Vesna
AU  - Savić, Ivana
AU  - Ilić-Stojanović, Snežana
AU  - Ilić, Dušica
AU  - Petrović, Slobodan
AU  - Popsavin, Mirjana
AU  - Kapor, Agneš
PY  - 2014
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2739
AB  - Sulfanilamide belongs to the group of drugs that have a bacteriostatic effect on different pathogenic microorganisms. This activity originates from the competitive antagonism with p-aminobenzoic acid, which is an integral part of folic acid. The safe use of sulfanilamide is limited due to poor solubility in the aqueous medium. Therefore, the aim of this paper is the synthesis of sulfanilamide, as well as preparing and structural characterization of its inclusion complexes with cyclodextrins. The crude sulfanilamide was obtained in the synthesis between acetanilide and chlorosulfonic acid according to the standard procedure. The synthesized sulfanilamide was recrystallized from water in order to obtain the satisfactory purity of the substance. Sufanilamide was complexed with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin by the co-precipitation method. A molecular encapsulation of sulfanilamide was confirmed by using FTIR, H-1-NMR, XRD and DSC methods. Phase-solubility techniques were used to assess the formation of the inclusion complex between sulfanilamide and cyclodextrins. The photostability of sulfanilamide and its inclusion complexes was estimated by UVB irradiation in a photochemical reactor by applying the UV-Vis method. Based on the UV-Vis analysis, sulfanilamide:2-hydroxypropyl-beta-cyclodextrin complex was presented as more photostable than sulfanilamide:beta-cyclodextrin complex and sulfanilamide. The obtained results enable the potential use of these inclusion complexes for the preparation of oral formulations due to the enhanced solubility of sulfanilamide.
PB  - Springer, Dordrecht
T2  - Journal of Inclusion Phenomena and Macrocyclic Chemistry
T1  - Inclusion complexes of sulfanilamide with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin
EP  - 124
IS  - 1-2
SP  - 113
VL  - 80
DO  - 10.1007/s10847-014-0410-x
ER  - 

@article{
author = "Tacić, Ana and Savić, Ivan and Nikolić, Vesna and Savić, Ivana and Ilić-Stojanović, Snežana and Ilić, Dušica and Petrović, Slobodan and Popsavin, Mirjana and Kapor, Agneš",
year = "2014",
abstract = "Sulfanilamide belongs to the group of drugs that have a bacteriostatic effect on different pathogenic microorganisms. This activity originates from the competitive antagonism with p-aminobenzoic acid, which is an integral part of folic acid. The safe use of sulfanilamide is limited due to poor solubility in the aqueous medium. Therefore, the aim of this paper is the synthesis of sulfanilamide, as well as preparing and structural characterization of its inclusion complexes with cyclodextrins. The crude sulfanilamide was obtained in the synthesis between acetanilide and chlorosulfonic acid according to the standard procedure. The synthesized sulfanilamide was recrystallized from water in order to obtain the satisfactory purity of the substance. Sufanilamide was complexed with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin by the co-precipitation method. A molecular encapsulation of sulfanilamide was confirmed by using FTIR, H-1-NMR, XRD and DSC methods. Phase-solubility techniques were used to assess the formation of the inclusion complex between sulfanilamide and cyclodextrins. The photostability of sulfanilamide and its inclusion complexes was estimated by UVB irradiation in a photochemical reactor by applying the UV-Vis method. Based on the UV-Vis analysis, sulfanilamide:2-hydroxypropyl-beta-cyclodextrin complex was presented as more photostable than sulfanilamide:beta-cyclodextrin complex and sulfanilamide. The obtained results enable the potential use of these inclusion complexes for the preparation of oral formulations due to the enhanced solubility of sulfanilamide.",
publisher = "Springer, Dordrecht",
journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",
title = "Inclusion complexes of sulfanilamide with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin",
pages = "124-113",
number = "1-2",
volume = "80",
doi = "10.1007/s10847-014-0410-x"
}

Tacić, A., Savić, I., Nikolić, V., Savić, I., Ilić-Stojanović, S., Ilić, D., Petrović, S., Popsavin, M.,& Kapor, A.. (2014). Inclusion complexes of sulfanilamide with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin. in Journal of Inclusion Phenomena and Macrocyclic Chemistry
Springer, Dordrecht., 80(1-2), 113-124.
https://doi.org/10.1007/s10847-014-0410-x

Tacić A, Savić I, Nikolić V, Savić I, Ilić-Stojanović S, Ilić D, Petrović S, Popsavin M, Kapor A. Inclusion complexes of sulfanilamide with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin. in Journal of Inclusion Phenomena and Macrocyclic Chemistry. 2014;80(1-2):113-124.
doi:10.1007/s10847-014-0410-x .

Tacić, Ana, Savić, Ivan, Nikolić, Vesna, Savić, Ivana, Ilić-Stojanović, Snežana, Ilić, Dušica, Petrović, Slobodan, Popsavin, Mirjana, Kapor, Agneš, "Inclusion complexes of sulfanilamide with beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin" in Journal of Inclusion Phenomena and Macrocyclic Chemistry, 80, no. 1-2 (2014):113-124,
https://doi.org/10.1007/s10847-014-0410-x . .