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Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data

Procena stepena vezivanja inhibitora angiotenzin-konvertujućeg enzima za proteine plazme primenom hromatografski dobijenih parametara hidrofobnosti

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2015
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Authors
Trbojević-Stanković, Jasna
Aleksić, Mirjana
Odović, Jadranka
Article (Published version)
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Abstract
Introduction Angiotensin-converting enzyme (ACE) inhibitors represent a significant group of drugs primarily used in the treatment of hypertension and congestive heart failure. Objective Selected ACE inhibitors (enalapril, quinapril, fosinopril, lisinopril, cilazapril) were studied in order to establish a fast and easy estimation method of their plasma protein binding degree based on their lipophilicity data. Methods Chromatographic hydrophobicity data (parameter C0) were obtained on cellulose layers under conditions of normal-phase thin-layer chromatography (NPTLC), using different binary solvent systems. The ACE inhibitors lipophilicity descriptors (logP) values were calculated using the software package Virtual Computational Chemistry Laboratory. The ACE inhibitors plasma protein binding data were collected from relevant literature. Results ACE inhibitors protein binding data varied from negligible (lisinopril) to 99% (fosinopril). The calculated lipophilicity descriptors, logPKOWWI...N values ranged from -0.94 (lisinopril) to 6.61 (fosinopril). Good correlations were established between plasma protein binding values and calculated logPKOWWIN values (R2=0.8026) as well as chromatographic hydrophobicity data, C0 parameters (R2=0.7662). Even though good correlation coefficients (R2) were obtained in both relations, unacceptable probability value with p>0.05 was found in relation between protein binding data and calculated logPKOWWIN values. Subsequently, taking into consideration the request for probability value lower than 0.05, a better relationship was observed between protein binding data and chromatographically obtained hydrophobicity parameters C0 values. Conclusion Cellulose layers are easily available and cost effective sorbent to assess hydrophobicity. Experimentally obtained data on ACE inhibitors hydrophobicity and plasma protein binding estimation are important parameters in evaluating bioavailability of these drugs.

Uvod Inhibitori angiotenzin-konvertujućeg enzima (ACE) su velika grupa lekova izuzetno značajna u lečenju hipertenzije. Cilj rada Analizirani su izabrani ASE-inhibitori (enalapril, kvinapril, fozinopril, lizinopril, cilazapril) radi postavljanja novog pristupa pogodnog za brzu i jednostavnu procenu vezivanja za proteine plazme na osnovu njihovih parametara lipofilnosti. Metode rada Hromatografski parametri hidrofobnosti (vrednosti C0) dobijeni su u uslovima normalnofazne hromatografije (NPTLC) na tankom sloju celuloze, uz korišćenje dvokomponentnih mobilnih faza. Vrednosti parametara lipofilnosti ACE-inhibitora (logP) izračunate su pomoću softverskog paketa Virtual Computational Chemistry Laboratory. Podaci o procentu vezivanja ACE-inhibitora za proteine plazme preuzeti su iz odgovarajuće literature. Rezultati Procenat vezivanja za proteine plazme ispitivanih ASE-inhibitora bio je u opsegu od 0% (lizinopril) do 99% (fozinopril), dok su vrednosti izračunatih parametara lipofilnosti (vre...dnosti logP KOWWIN) bile od -0,94 (lizinopril) do 6,61 (fozinopril). Dobijene su zadovoljavajuće korelacije između vrednosti vezivanja ASE- inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti (koeficijent korelacije R2 bio je 0,8026), kao i hromatografski dobijenih parametara hidrofobnosti, C0 (R2=0,7662). Iako su zadovoljavajući koeficijenti korelacije dobijeni u obe relacije, neprihvatljive vrednosti verovatnoće (p>0,05) dobijene su za zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti. Stoga se, uzimajući u obzir zahtev da vrednosti verovatnoće budu niže od 0,05, boljom može smatrati zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i hromatografski dobijenih parametara hidrofobnosti. Zaključak Primena hidrofobnih parametara ASE-inhibitora eksperimentalno dobijenih u uslovima normalnofazne hromatografije na tankom sloju celuloze za procenu stepena njihovog vezivanja za proteine plazme značajna je za razvoj i ispitivanje lekova ove grupe i procenu njihove bioraspoloživosti.

Keywords:
angiotensin-converting enzyme inhibitors / plasma protein binding / hydrophobicity / inhibitori angiotenzin-konvertujućeg enzima(ASE-inhibitori) / vezivanje za proteine plazme / lipofilnost
Source:
Srpski arhiv za celokupno lekarstvo, 2015, 143, 1-2, 50-55
Publisher:
  • Srpsko lekarsko društvo, Beograd
Funding / projects:
  • Structure-properties relationships of natural and synthetic molecules and their metal complexes (RS-172017)
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.2298/SARH1502050T

ISSN: 0370-8179

WoS: 000350928900008

Scopus: 2-s2.0-84924410634
[ Google Scholar ]
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2485
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Trbojević-Stanković, Jasna
AU  - Aleksić, Mirjana
AU  - Odović, Jadranka
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2485
AB  - Introduction Angiotensin-converting enzyme (ACE) inhibitors represent a significant group of drugs primarily used in the treatment of hypertension and congestive heart failure. Objective Selected ACE inhibitors (enalapril, quinapril, fosinopril, lisinopril, cilazapril) were studied in order to establish a fast and easy estimation method of their plasma protein binding degree based on their lipophilicity data. Methods Chromatographic hydrophobicity data (parameter C0) were obtained on cellulose layers under conditions of normal-phase thin-layer chromatography (NPTLC), using different binary solvent systems. The ACE inhibitors lipophilicity descriptors (logP) values were calculated using the software package Virtual Computational Chemistry Laboratory. The ACE inhibitors plasma protein binding data were collected from relevant literature. Results ACE inhibitors protein binding data varied from negligible (lisinopril) to 99% (fosinopril). The calculated lipophilicity descriptors, logPKOWWIN values ranged from -0.94 (lisinopril) to 6.61 (fosinopril). Good correlations were established between plasma protein binding values and calculated logPKOWWIN values (R2=0.8026) as well as chromatographic hydrophobicity data, C0 parameters (R2=0.7662). Even though good correlation coefficients (R2) were obtained in both relations, unacceptable probability value with p>0.05 was found in relation between protein binding data and calculated logPKOWWIN values. Subsequently, taking into consideration the request for probability value lower than 0.05, a better relationship was observed between protein binding data and chromatographically obtained hydrophobicity parameters C0 values. Conclusion Cellulose layers are easily available and cost effective sorbent to assess hydrophobicity. Experimentally obtained data on ACE inhibitors hydrophobicity and plasma protein binding estimation are important parameters in evaluating bioavailability of these drugs.
AB  - Uvod Inhibitori angiotenzin-konvertujućeg enzima (ACE) su velika grupa lekova izuzetno značajna u lečenju hipertenzije. Cilj rada Analizirani su izabrani ASE-inhibitori (enalapril, kvinapril, fozinopril, lizinopril, cilazapril) radi postavljanja novog pristupa pogodnog za brzu i jednostavnu procenu vezivanja za proteine plazme na osnovu njihovih parametara lipofilnosti. Metode rada Hromatografski parametri hidrofobnosti (vrednosti C0) dobijeni su u uslovima normalnofazne hromatografije (NPTLC) na tankom sloju celuloze, uz korišćenje dvokomponentnih mobilnih faza. Vrednosti parametara lipofilnosti ACE-inhibitora (logP) izračunate su pomoću softverskog paketa Virtual Computational Chemistry Laboratory. Podaci o procentu vezivanja ACE-inhibitora za proteine plazme preuzeti su iz odgovarajuće literature. Rezultati Procenat vezivanja za proteine plazme ispitivanih ASE-inhibitora bio je u opsegu od 0% (lizinopril) do 99% (fozinopril), dok su vrednosti izračunatih parametara lipofilnosti (vrednosti logP KOWWIN) bile od -0,94 (lizinopril) do 6,61 (fozinopril). Dobijene su zadovoljavajuće korelacije između vrednosti vezivanja ASE- inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti (koeficijent korelacije R2 bio je 0,8026), kao i hromatografski dobijenih parametara hidrofobnosti, C0 (R2=0,7662). Iako su zadovoljavajući koeficijenti korelacije dobijeni u obe relacije, neprihvatljive vrednosti verovatnoće (p>0,05) dobijene su za zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti. Stoga se, uzimajući u obzir zahtev da vrednosti verovatnoće budu niže od 0,05, boljom može smatrati zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i hromatografski dobijenih parametara hidrofobnosti. Zaključak Primena hidrofobnih parametara ASE-inhibitora eksperimentalno dobijenih u uslovima normalnofazne hromatografije na tankom sloju celuloze za procenu stepena njihovog vezivanja za proteine plazme značajna je za razvoj i ispitivanje lekova ove grupe i procenu njihove bioraspoloživosti.
PB  - Srpsko lekarsko društvo, Beograd
T2  - Srpski arhiv za celokupno lekarstvo
T1  - Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data
T1  - Procena stepena vezivanja inhibitora angiotenzin-konvertujućeg enzima za proteine plazme primenom hromatografski dobijenih parametara hidrofobnosti
VL  - 143
IS  - 1-2
SP  - 50
EP  - 55
DO  - 10.2298/SARH1502050T
ER  - 
@article{
author = "Trbojević-Stanković, Jasna and Aleksić, Mirjana and Odović, Jadranka",
year = "2015",
abstract = "Introduction Angiotensin-converting enzyme (ACE) inhibitors represent a significant group of drugs primarily used in the treatment of hypertension and congestive heart failure. Objective Selected ACE inhibitors (enalapril, quinapril, fosinopril, lisinopril, cilazapril) were studied in order to establish a fast and easy estimation method of their plasma protein binding degree based on their lipophilicity data. Methods Chromatographic hydrophobicity data (parameter C0) were obtained on cellulose layers under conditions of normal-phase thin-layer chromatography (NPTLC), using different binary solvent systems. The ACE inhibitors lipophilicity descriptors (logP) values were calculated using the software package Virtual Computational Chemistry Laboratory. The ACE inhibitors plasma protein binding data were collected from relevant literature. Results ACE inhibitors protein binding data varied from negligible (lisinopril) to 99% (fosinopril). The calculated lipophilicity descriptors, logPKOWWIN values ranged from -0.94 (lisinopril) to 6.61 (fosinopril). Good correlations were established between plasma protein binding values and calculated logPKOWWIN values (R2=0.8026) as well as chromatographic hydrophobicity data, C0 parameters (R2=0.7662). Even though good correlation coefficients (R2) were obtained in both relations, unacceptable probability value with p>0.05 was found in relation between protein binding data and calculated logPKOWWIN values. Subsequently, taking into consideration the request for probability value lower than 0.05, a better relationship was observed between protein binding data and chromatographically obtained hydrophobicity parameters C0 values. Conclusion Cellulose layers are easily available and cost effective sorbent to assess hydrophobicity. Experimentally obtained data on ACE inhibitors hydrophobicity and plasma protein binding estimation are important parameters in evaluating bioavailability of these drugs., Uvod Inhibitori angiotenzin-konvertujućeg enzima (ACE) su velika grupa lekova izuzetno značajna u lečenju hipertenzije. Cilj rada Analizirani su izabrani ASE-inhibitori (enalapril, kvinapril, fozinopril, lizinopril, cilazapril) radi postavljanja novog pristupa pogodnog za brzu i jednostavnu procenu vezivanja za proteine plazme na osnovu njihovih parametara lipofilnosti. Metode rada Hromatografski parametri hidrofobnosti (vrednosti C0) dobijeni su u uslovima normalnofazne hromatografije (NPTLC) na tankom sloju celuloze, uz korišćenje dvokomponentnih mobilnih faza. Vrednosti parametara lipofilnosti ACE-inhibitora (logP) izračunate su pomoću softverskog paketa Virtual Computational Chemistry Laboratory. Podaci o procentu vezivanja ACE-inhibitora za proteine plazme preuzeti su iz odgovarajuće literature. Rezultati Procenat vezivanja za proteine plazme ispitivanih ASE-inhibitora bio je u opsegu od 0% (lizinopril) do 99% (fozinopril), dok su vrednosti izračunatih parametara lipofilnosti (vrednosti logP KOWWIN) bile od -0,94 (lizinopril) do 6,61 (fozinopril). Dobijene su zadovoljavajuće korelacije između vrednosti vezivanja ASE- inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti (koeficijent korelacije R2 bio je 0,8026), kao i hromatografski dobijenih parametara hidrofobnosti, C0 (R2=0,7662). Iako su zadovoljavajući koeficijenti korelacije dobijeni u obe relacije, neprihvatljive vrednosti verovatnoće (p>0,05) dobijene su za zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i izračunatih logP KOWWIN vrednosti. Stoga se, uzimajući u obzir zahtev da vrednosti verovatnoće budu niže od 0,05, boljom može smatrati zavisnost između vrednosti vezivanja ASE-inhibitora za proteine plazme i hromatografski dobijenih parametara hidrofobnosti. Zaključak Primena hidrofobnih parametara ASE-inhibitora eksperimentalno dobijenih u uslovima normalnofazne hromatografije na tankom sloju celuloze za procenu stepena njihovog vezivanja za proteine plazme značajna je za razvoj i ispitivanje lekova ove grupe i procenu njihove bioraspoloživosti.",
publisher = "Srpsko lekarsko društvo, Beograd",
journal = "Srpski arhiv za celokupno lekarstvo",
title = "Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data, Procena stepena vezivanja inhibitora angiotenzin-konvertujućeg enzima za proteine plazme primenom hromatografski dobijenih parametara hidrofobnosti",
volume = "143",
number = "1-2",
pages = "50-55",
doi = "10.2298/SARH1502050T"
}
Trbojević-Stanković, J., Aleksić, M.,& Odović, J.. (2015). Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data. in Srpski arhiv za celokupno lekarstvo
Srpsko lekarsko društvo, Beograd., 143(1-2), 50-55.
https://doi.org/10.2298/SARH1502050T
Trbojević-Stanković J, Aleksić M, Odović J. Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data. in Srpski arhiv za celokupno lekarstvo. 2015;143(1-2):50-55.
doi:10.2298/SARH1502050T .
Trbojević-Stanković, Jasna, Aleksić, Mirjana, Odović, Jadranka, "Estimation of angiotensin-converting enzyme inhibitors protein binding degree using chromatographic hydrophobicity data" in Srpski arhiv za celokupno lekarstvo, 143, no. 1-2 (2015):50-55,
https://doi.org/10.2298/SARH1502050T . .

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