hrcak mascot   Srce   HID

Acta Pharmaceutica, Vol. 60 No. 3, 2010

Original scientific paper
https://doi.org/10.2478/v10007-010-0023-x

Utjecaj supstituenata na NMR značajke temeljnog bicikličkog prstenastog sustava fluorokinolonskih antibiotika, odnos između NMR kemijskih pomaka, molekulskih opisivača i parametara sličnosti s lijekovima

MILENA JADRIJEVIĆ-MLADAR TAKAČ ; Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia

Fulltext: english, pdf (166 KB) pages 237-254 downloads: 653* cite
APA 6th Edition
JADRIJEVIĆ-MLADAR TAKAČ, M. (2010). Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters. Acta Pharmaceutica, 60 (3), 237-254. https://doi.org/10.2478/v10007-010-0023-x
MLA 8th Edition
JADRIJEVIĆ-MLADAR TAKAČ, MILENA. "Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters." Acta Pharmaceutica, vol. 60, no. 3, 2010, pp. 237-254. https://doi.org/10.2478/v10007-010-0023-x. Accessed 25 Mar. 2019.
Chicago 17th Edition
JADRIJEVIĆ-MLADAR TAKAČ, MILENA. "Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters." Acta Pharmaceutica 60, no. 3 (2010): 237-254. https://doi.org/10.2478/v10007-010-0023-x
Harvard
JADRIJEVIĆ-MLADAR TAKAČ, M. (2010). 'Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters', Acta Pharmaceutica, 60(3), pp. 237-254. doi: https://doi.org/10.2478/v10007-010-0023-x
Vancouver
JADRIJEVIĆ-MLADAR TAKAČ M. Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters. Acta Pharm. [Internet]. 2010 [cited 2019 March 25];60(3):237-254. doi: https://doi.org/10.2478/v10007-010-0023-x
IEEE
M. JADRIJEVIĆ-MLADAR TAKAČ, "Effects of substituents on the NMR features of basic bicyclic ring system of fluoroquinolone antibiotics and the relationships between NMR chemical shifts, molecular descriptors and drug-likeness parameters", Acta Pharmaceutica, vol.60, no. 3, pp. 237-254, 2010. [Online]. doi: https://doi.org/10.2478/v10007-010-0023-x

Abstracts
U radu je opisano ispitivanje NMR spektroskopskih značajki trovafloksacin (TVA) mesilata, pefloksacin (PFX) mesilata i ciprofloksacin (CIP) hidroklorida u DMSO-d6 otopini s ciljem da se istraži utjecaj supstituenata i tip soli na NMR parametre bicikličkog fluorokinolonskog i fluoronaftiridonskog prstenastog sustava. Analizom jedno- i dvo-dimenzijskih, homo- i hetero-nuklearnih 1H- i 13C-NMR spektara potvrđena je struktura ispitivanih fluorokinolonskih soli.
1H- i 13C-NMR kemijski pomaci (, ppm) temeljnih prstenastih sustava korelirani su s izračunatim molekulskim opisivačima (relativnom molekulskom masom, Mr, topologijskom polarnom površinom, TPSA, lipofilnošću, miLogP i s volumenom, V) te s parametrima sličnosti s lijekovima poznate biološke aktivnosti, tj. s ligandom G protein-spregnutog receptora (GPCR ligand), ligandom ionskih kanala (ICL), inhibitorom kinaze (KI) i ligandom nuklearnog receptora (NRL) koji su izračunati za monoprotonske katione ispitivanih fluorokinolonskih soli (TVAH+, PFXH+ and CIPH+).
13C-NMR kemijski pomaci (/ppm) C4, C5 i C11 atoma i 1H-NMR kemijski pomaci (/ppm) protona u COOH, H5 i NHn+ ispitivanih fluorokinolonskih soli pokazali su se kao dobri parametri za istraživanje odnosa svojstvo-svojstvo i svojstvo-sličnost s lijekovima poznate biološke aktivnosti.
Tako je otkriven kolinearan odnos između 13C-NMR kemijskih pomaka (/ppm) C4, C5 i C11 atoma i izračunatih parametara za sličnost s kinaza inhibitorom (KI-ls) i ligandom nuklearnog receptora (NRL-ls) pored kolinearnosti s TPSA, miLogP, Mr i V (C4 /ppm s TPSA, R = 0,9964; C4 /ppm s miLogP, R = 0,9487; C4 /ppm s Mr, R = 0,9629; C4 /ppm s V, R = 0,8547; C4 /ppm s KI-ls, R = 0,9461 i C4 /ppm s NRL-ls, R = 0,9996; C5 s miLogP, R = 0,9994; C5 s KI-ls, R = 0,9990 i C5 s NRL-ls, R = 0,9510; C11 s TPSA, R = 0,9958; C11 /ppm s KI-ls, R = 0,9481 i C11 /ppm s NRL-ls, R = 0,9994).
1H-NMR kemijski pomaci (/ppm) protona COOH, H5 i NHn+ pokazali su kolinearanost odnosa s TPSA i miLogP, te s izračunatim parametrima za sličnost s kinaza inhibitorom (KI-ls), ligandom nuklearnog receptora (NRL-ls) i GPCR ligandom (GPCRl-ls) (/ppm H u COOH s TPSA, R = 0,9421; /ppm H u COOH s NRL-ls, R = 0,9216; H5 /ppm s miLogP, R = 0,9962; /ppm H5 s KI-ls, R = 0,9969; /ppm NHn+ s TPSA, R = 0,9875; /ppm NHn+ s NRL-ls, R = 0,9948; /ppm NHn+ s GPCR ligandom, R = 0,9873).
Rezultati istraživanja su pokazali razliku u eksperimentalnim i izračunatim parametrima za trovafloksacin mesilat u usporedbi s pefloksacin mesilatom i ciprofloksacin hidrokloridom, te je nađena značajna kolinearnost među ispitivanim parametrima ovih fluorokinolonskih antibiotika.

Keywords
fluorokionolonski antibiotici; trovafloksacin; pefloksacin; ciprofloksacin; 1H-NMR spektroskopija; 13C-NMR spektroskopija; molekulski opisivači; parametri sličnosti s lijekovima; QSAR

Hrčak ID: 53493

URI
https://hrcak.srce.hr/53493

[english]

Visits: 925 *