TY - JOUR AU - Hegedüs, Zsófia AU - Wéber, Edit AU - Kriston-Pál, Éva AU - Makra, Ildikó AU - Czibula, Ágnes AU - Monostori, Éva AU - Martinek, Tamás TI - Foldameric α/β-Peptide Analogs of the β-Sheet-Forming Antiangiogenic Anginex: Structure and Bioactivity JF - JOURNAL OF THE AMERICAN CHEMICAL SOCIETY J2 - J AM CHEM SOC VL - 135 PY - 2013 IS - 44 SP - 16578 EP - 16584 PG - 7 SN - 0002-7863 DO - 10.1021/ja408054f UR - https://m2.mtmt.hu/api/publication/2459240 ID - 2459240 AB - The principles of beta-sheet folding and design for alpha-peptidic sequences are well established, while those for sheet mimetics containing homologated amino acid building blocks are still under investigation. To reveal the structure-function relations of beta-amino-acid-containing foldamers, we followed a top-down approach to study a series of alpha/beta-peptidic analogs of anginex, a beta-sheet-forming antiangiogenic peptide. Eight anginex analogs were developed by systematic alpha --> beta(3) substitutions and analyzed by using NMR and CD spectroscopy. The foldamers retained the beta-sheet tendency, though with a decreased folding propensity. beta-Sheet formation could be induced by a micellar environment, similarly to that of the parent peptide. The destructuring effect was higher when the alpha --> beta(3) exchange was located in the beta-sheet core. Analysis of the beta-sheet stability versus substitution pattern and the local conformational bias of the bulky beta(3)V and beta(3)I residues revealed that a mismatch between the H-bonding preferences of the alpha- and beta-residues played a minor role in the structure-breaking effect. Temperature-dependent CD and NMR measurements showed that the hydrophobic stabilization was scaled-down for the alpha/beta-peptides. Analysis of the biological activity of the foldamer peptides showed that four anginex derivatives dose-dependently inhibited the proliferation of a mouse endothelial cell line. The alpha --> beta(3) substitution strategy applied in this work can be a useful approach to the construction of bioactive beta-sheet mimetics with a reduced aggregation tendency and improved pharmacokinetic properties. LA - English DB - MTMT ER - TY - JOUR AU - Sipos, László AU - Ilisz, István AU - Nonn, Melinda AU - Fülöp, Ferenc AU - Pataj, Zoltán AU - Armstrong, D W AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on macrocyclic glycopeptide-based chiral stationary phases JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1232 PY - 2012 SP - 142 EP - 151 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2011.11.027 UR - https://m2.mtmt.hu/api/publication/1819649 ID - 1819649 N1 - Megjegyzés-24876107 Megjegyzés-22306621 WC: Biochemical Research Methods; Chemistry, Analytical ISSN:0021-9673 LA - English DB - MTMT ER - TY - JOUR AU - Sipos, László AU - Ilisz, István AU - Aranyi, Anita AU - Gecse, Zsanett AU - Nonn, Melinda AU - Fülöp, Ferenc AU - Ho, Hyun Myung AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phases JF - CHIRALITY: THE PHARMACOLOGICAL BIOLOGICAL AND CHEMICAL CONSEQUENCES OF MOLECULAR ASYMMETRY J2 - CHIRALITY VL - 24 PY - 2012 IS - 10 SP - 817 EP - 824 PG - 8 SN - 0899-0042 DO - 10.1002/chir.22077 UR - https://m2.mtmt.hu/api/publication/1949178 ID - 1949178 N1 - Funding Agency and Grant Number: Hungarian National Science Foundation [K 67563] Funding text: Contract grant sponsor: Hungarian National Science Foundation; Contract grant number: K 67563. ISSN:0899-0042 AB - The enantiomers of four unusual isoxazoline-fused 2-aminocyclopentanecarboxylic acids were directly separated on chiral stationary phases containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The nature of the alcoholic modifier (MeOH, EtOH, IPA) exerted a great effect on the retention, whereas the selectivity and resolution did not change substantially. Two types of dependence of retention on alcohol content were detected: k1 increased continuously with increasing alcohol content or a U-shaped retention curve was observed. A comparison of the chromatographic data obtained with HCOOH, AcOH, TFA, HClO4, H2SO4, or H3PO4 as acidic modifier at a constant concentration demonstrated that in most cases, larger k values were obtained on the application of AcOH or HCOOH, and an increase of the acid content resulted in a decrease of retention. Some mechanistic aspects of the chiral recognition process are discussed with respect to the structures of the analytes and selector. The sequence of elution of the enantiomers was determined in all cases. Chirality 24:817-824, 2012. (c) 2012 Wiley Periodicals, Inc. LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Pataj, Zoltán AU - Berkecz, Róbert AU - Misicka, A AU - Tymecka, D AU - Fülöp, Ferenc AU - Choi, HJ AU - Hyun, MH AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of β2-amino acids using a long-tethered (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1217 PY - 2010 IS - 7 SP - 1075 EP - 1082 PG - 8 SN - 0021-9673 DO - 10.1016/j.chroma.2009.07.003 UR - https://m2.mtmt.hu/api/publication/1321220 ID - 1321220 N1 - Funding Agency and Grant Number: OTKA [K 67563]; LIE [LSHC-CT-2006-037733]; Korea Science and Engineering Foundation [R15-2006-022-03001-0]; Bolyai Janos Postdoctoral Research Scholarship Funding text: This work was supported by OTKA grant K 67563, by LIE grant LSHC-CT-2006-037733 and by the Korea Science and Engineering Foundation (NCRC program: R15-2006-022-03001-0). I.I. wishes to express his thanks for a Bolyai Janos Postdoctoral Research Scholarship to support his work. AB - Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural [beta]2-amino acids on a new chiral stationary phase, using the 11-methylene-unit spacer of aminoundecylsilica gel for the bonding of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as selector. The nature and concentration of the acidic and organic modifiers, the pH, the mobile phase composition, and the structures of the analytes substantially influenced the retention and resolution. Separations were carried out at constant mobile phase compositions in the temperature range 7-40 °C and the changes in enthalpy, [Delta]([Delta]H°), entropy, [Delta]([Delta]S°), and free energy, [Delta]([Delta]G°) were calculated. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers. LA - English DB - MTMT ER - TY - JOUR AU - Berkecz, Róbert AU - Ilisz, István AU - Benedek, G AU - Fülöp, Ferenc AU - Armstrong, DW AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of 2-aminomono- and dihydroxycyclopentanecarboxylic and 2-aminodihydroxycyclohexanecarboxylic acids on macrocyclic glycopeptide-based phases JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1216 PY - 2009 IS - 6 SP - 927 EP - 932 PG - 6 SN - 0021-9673 DO - 10.1016/j.chroma.2008.12.011 UR - https://m2.mtmt.hu/api/publication/1189444 ID - 1189444 N1 - Hungarian National Science Foundation [OTKA K 67563]; NationalInstitutes of Health [R01 GM53825-12]; Bolyai Janos Postdoctoral Research Scholarship AB - The direct separation of the enantiomers of four 2-aminomono- or dihydroxycyclopentanecarboxylic acids and four 2-aminodihydroxycyclohexanecarboxylic acids was performed on chiral stationary phases containing macrocyclic glycopeptide antibiotics such as teicoplanin (Astec Chirobiotic T and T2), teicoplanin aglycone (Chirobiotic TAG) or ristocetin A (Chirobiotic R) as chiral selectors. The effects of the nature of organic modifiers, the pH, the mobile phase composition and the structures of the analytes oil the separation were investigated. Chirobiotic TAG, and in some cases Chirobiotic T, proved to be the Most useful of these columns. The elution sequence was determined in most cases. (C) 2008 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Berkecz, Róbert AU - Ilisz, István AU - Misicka, A AU - Tymecka, D AU - Fülöp, Ferenc AU - Choi, HJ AU - Hyun, MH AU - Péter, Antal TI - HPLC enantioseparation of beta(2)-homoamino acids using crown ether-based chiral stationary phase JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 32 PY - 2009 IS - 7 SP - 981 EP - 987 PG - 7 SN - 1615-9306 DO - 10.1002/jssc.200800561 UR - https://m2.mtmt.hu/api/publication/1230499 ID - 1230499 N1 - WoS:hiba:000265123100010 2019-12-06 00:22 első szerző nem egyezik AB - RP high-performance liquid chromatographic methods were developed for the enantioseparation of eleven unusual beta(2)-homoamino acids. The underivatized analytes were separated on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The effects of organic (alcoholic) and acidic modifiers, the mobile phase composition and temperature on the separation were investigated. The structures of the substituents in the alpha-position of the analytes substantially influenced the retention and resolution. The elution sequence was determined in some cases: the S enantiomers eluted before the R enantiomers. LA - English DB - MTMT ER - TY - JOUR AU - Berkecz, Róbert AU - Ilisz, István AU - Fülöp, Ferenc AU - Pataj, Zoltán AU - Hyun, MH AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of beta-3-homo-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1189 PY - 2008 IS - 1-2 SP - 285 EP - 291 PG - 7 SN - 0021-9673 DO - 10.1016/j.chroma.2007.09.054 UR - https://m2.mtmt.hu/api/publication/1122999 ID - 1122999 N1 - 31st International Symposium on High Performance Liquid Phase Separations and Related Techniques Location: Ghent, BELGIUM Date: JUN 17-21, 2007. AB - High-performance liquid chromatographic methods were developed for the separation of the enantiomers of thirteen unusual beta-3-homo-amino acids and three of its ethyl esters on a chiral stationary phase containing (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as chiral selector. The effects of the mobile phase composition and the acidic modifiers on the separation were investigated. The structures of the substiments in beta-position substantially influenced the retention and enantioseparation. The influence of ionic strength. on the enantioseparation was established experimentally. The elution sequence was determined in all cases. (c) 2007 Elsevier B.V. All rights reserved. LA - English DB - MTMT ER - TY - JOUR AU - Keresztes, Attila AU - Szűcs, Mária AU - Borics, Attila AU - E Kövér, Katalin AU - Forró, Enikő AU - Fülöp, Ferenc AU - Tömböly, Csaba AU - Péter, Antal AU - Pahi, A AU - Fábián, Gabriella AU - Muranyi, M AU - Tóth, Géza TI - New endomorphin analogues containing alicyclic beta-amino acids: Influence on bioactive conformation and pharmacological profile JF - JOURNAL OF MEDICINAL CHEMISTRY J2 - J MED CHEM VL - 51 PY - 2008 IS - 14 SP - 4270 EP - 4279 PG - 10 SN - 0022-2623 DO - 10.1021/jm800223t UR - https://m2.mtmt.hu/api/publication/1127901 ID - 1127901 N1 - Institute of Biochemistry, Biological Research Center, Hungarian Academy of Sciences, P.O. Box 521, H-6701 Szeged, Hungary Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary Department of Chemistry, University of Debrecen, P.O. Box 21, H-4010 Debrecen, Hungary Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary Cited By :46 Export Date: 4 June 2023 CODEN: JMCMA Correspondence Address: Tóth, G.; Institute of Biochemistry, P.O. Box 521, H-6701 Szeged, Hungary; email: geza@brc.hu Chemicals/CAS: endomorphin 1, 189388-22-5; endomorphin 2, 141801-26-5; enkephalin[2 dextro alanine 4 methylphenylalanine 5 glycine], 78123-71-4; guanosine 5' o (3 thiotriphosphate), 37589-80-3; proline, 147-85-3, 7005-20-1; sulfur 35, 15117-53-0; Amino Acids; Opioid Peptides; Receptors, Opioid AB - Endomorphins were subjected to a number of structural modifications in a search for their bioactive conformations. The alicyclic beta-amino acids cis-(1S,2R)ACPC/ACHC, cis-(IR,2S)ACPC/ACHC, trans(IS,2S)ACPC/ACHC, and trans-(1R,2R)ACPC/ACHC were introduced into endomorphins to examine the conformational effects on the bioactivity. Use of a combination of receptor binding techniques, H-1 NMR, and molecular modeling allowed the conclusion that Pro(2) substitution by these residues causes changes in structure, proteolytic stability, and pharmacological activity. It seems that the size of the alicyclic beta-amino acids does not have marked influence on the receptor binding affinities and/or selectivities. Among the new analogues, the cis-(1S,2R)ACPC(2) and cis-(1S,2R)ACHC(2)-containing derivatives displayed the highest binding potencies and efficacies in receptor binding and ligand-stimulated [S-35]GTP gamma S functional experiments. Molecular dynamic simulations and H-1 NMR studies of the cis-ACPC/ACHC-containing analogues revealed that many conformations are accessible, though it is most likely that these peptides bind to the mu-opioid receptor in a compact, folded structure rather than extended. LA - English DB - MTMT ER - TY - JOUR AU - Lukaszuk, A AU - Demaegdt, H AU - Szemenyei, Erzsébet AU - Tóth, Géza AU - Tymecka, D AU - Misicka, A AU - Karoyan, P AU - Vanderheyden, P AU - Vauquelin, G AU - Tourwe, D TI - Beta-homo-amino acid scan of angiotensin IV JF - JOURNAL OF MEDICINAL CHEMISTRY J2 - J MED CHEM VL - 51 PY - 2008 IS - 7 SP - 2291 EP - 2296 PG - 6 SN - 0022-2623 DO - 10.1021/jm701490g UR - https://m2.mtmt.hu/api/publication/1916846 ID - 1916846 AB - Angiotensin IV, a metabolite of angiotensin II, inhibits the enzyme insulin regulated aminopeptidase or IRAP and also, although with lower potency, aminopeptidase-N (AP-N). When both beta(2)-homo amino acid- and beta(3)-homo amino acid substitutions were used, allowed the identification of H-(R) beta(2)hVal-Tyr-Ile-His-Pro-beta(3) hPhe-OH as a potent and stable Ang IV analog with high selectivity for IRAP versus AP-N and the AT1 receptor. LA - English DB - MTMT ER - TY - JOUR AU - Berkecz, Róbert AU - Sztojkov-Ivanov, Anita AU - Ilisz, István AU - Forró, Enikő AU - Fülöp, Ferenc AU - Hyun, MH AU - Péter, Antal TI - High-performance liquid chromatographic enantioseparation of beta-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1125 PY - 2006 IS - 1 SP - 138 EP - 143 PG - 6 SN - 0021-9673 DO - 10.1016/j.chroma.2006.06.064 UR - https://m2.mtmt.hu/api/publication/1078949 ID - 1078949 LA - English DB - MTMT ER - TY - JOUR AU - Ilisz, István AU - Berkecz, Róbert AU - Péter, Antal TI - HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic-based chiral stationary phases: A review JF - JOURNAL OF SEPARATION SCIENCE J2 - J SEP SCI VL - 29 PY - 2006 IS - 10 SP - 1305 EP - 1321 PG - 17 SN - 1615-9306 DO - 10.1002/jssc.200600046 UR - https://m2.mtmt.hu/api/publication/1323957 ID - 1323957 LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal AU - Arki, A AU - Vekes, E AU - Tourwe, D AU - Lázár, László AU - Fülöp, Ferenc AU - Armstrong, D W TI - Direct and indirect high-performance liquid chromatographic enantioseparation of beta-amino acids JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1031 PY - 2004 SP - 171 EP - 178 PG - 8 SN - 0021-9673 DO - 10.1016/j.chroma.2003.08.070 UR - https://m2.mtmt.hu/api/publication/1013257 ID - 1013257 N1 - Funding Agency and Grant Number: NIGMS NIH HHSUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USANIH National Institute of General Medical Sciences (NIGMS) [R01 GM53825-08] LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal AU - Torok, R AU - Wright, K AU - Wakselman, M AU - Mazaleyrat, JP TI - Liquid chromatographic enantioseparation of spin-labelled beta-amino acids JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 1021 PY - 2003 IS - 1-2 SP - 1 EP - 10 PG - 10 SN - 0021-9673 DO - 10.1016/j.chroma.2003.09.015 UR - https://m2.mtmt.hu/api/publication/1322892 ID - 1322892 N1 - WoS:hiba:000187662500001 2019-03-02 02:14 cikkazonosító nem egyezik LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal TI - Direct high-performance liquid chromatographic enantioseparation of apolar beta-amino acids on a quinine-derived chiral anion-exchanger stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 955 PY - 2002 IS - 1 SP - 141 EP - 150 PG - 10 SN - 0021-9673 DO - 10.1016/S0021-9673(02)00192-9 UR - https://m2.mtmt.hu/api/publication/1322901 ID - 1322901 N1 - WoS:hiba:000175433800014 2019-03-02 02:14 cikkazonosító nem egyezik LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal AU - Vekes, E AU - Armstrong, DW TI - Effects of temperature on retention of chiral compounds on a ristocetin A chiral stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 958 PY - 2002 IS - 1-2 SP - 89 EP - 107 PG - 19 SN - 0021-9673 DO - 10.1016/S0021-9673(02)00390-4 UR - https://m2.mtmt.hu/api/publication/1322900 ID - 1322900 N1 - WoS:hiba:000176487000010 2019-03-02 02:14 cikkazonosító nem egyezik LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal AU - Lázár, László AU - Fülöp, Ferenc AU - Armstrong, D W TI - High-performance liquid chromatographic enantioseparation of beta-amino acids JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 926 PY - 2001 IS - 2 SP - 229 EP - 238 PG - 10 SN - 0021-9673 DO - 10.1016/S0021-9673(01)01078-0 UR - https://m2.mtmt.hu/api/publication/1013893 ID - 1013893 N1 - Funding Agency and Grant Number: NIGMS NIH HHSUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USANIH National Institute of General Medical Sciences (NIGMS) [R01 GM53825-05] AB - Direct and indirect high-performance liquid chromatographic methods were developed for the enantioseparation of beta -amino acids (beta -substituted- beta -alanines). Direct separation involved the application of chiral columns: Crownpak CR(+), Chirobiotic T and Chirobiotic R. Indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl isothiocyanate or N-alpha-(2,4-dinitro-5-fluorophenyl)-L-alanineamide (Marfey's reagent), with subsequent separation on an achiral column. The chromatographic conditions were varied to achieve optimum separation. LA - English DB - MTMT ER - TY - JOUR AU - Péter, Antal AU - Torok, G AU - Armstrong, DW AU - Tóth, Géza AU - Tourwe, D TI - Effect of temperature on retention of enantiomers of beta-methyl amino acids on a teicoplanin chiral stationary phase JF - JOURNAL OF CHROMATOGRAPHY A J2 - J CHROMATOGR A VL - 828 PY - 1998 IS - 1-2 SP - 177 EP - 190 PG - 14 SN - 0021-9673 DO - 10.1016/S0021-9673(98)00835-8 UR - https://m2.mtmt.hu/api/publication/1322919 ID - 1322919 LA - English DB - MTMT ER -