Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids
Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. Th...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Amić, Dragan [verfasserIn] Lučić, Bono [verfasserIn] Kovačević, Goran [verfasserIn] Trinajstić, Nenad [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2008 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Molecular diversity - Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995, 13(2008), 1 vom: 04. Nov., Seite 27-36 |
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| Übergeordnetes Werk: |
volume:13 ; year:2008 ; number:1 ; day:04 ; month:11 ; pages:27-36 |
| Links: |
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| DOI / URN: |
10.1007/s11030-008-9095-7 |
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SPR01582747X |
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| 245 | 1 | 0 | |a Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids |
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| 520 | |a Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. | ||
| 650 | 4 | |a Flavonoids |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Polyphenols |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Free radical scavenging |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a QSAR |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Activity cliff |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Bond dissociation enthalpy |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a PM3 |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Indicator variables |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Lučić, Bono |e verfasserin |4 aut | |
| 700 | 1 | |a Kovačević, Goran |e verfasserin |4 aut | |
| 700 | 1 | |a Trinajstić, Nenad |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Molecular diversity |d Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 |g 13(2008), 1 vom: 04. Nov., Seite 27-36 |w (DE-627)311010377 |w (DE-600)2003589-5 |x 1573-501X |7 nnns |
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10.1007/s11030-008-9095-7 doi (DE-627)SPR01582747X (SPR)s11030-008-9095-7-e DE-627 ger DE-627 rakwb eng 570 ASE 42.00 bkl Amić, Dragan verfasserin aut Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 Lučić, Bono verfasserin aut Kovačević, Goran verfasserin aut Trinajstić, Nenad verfasserin aut Enthalten in Molecular diversity Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 13(2008), 1 vom: 04. Nov., Seite 27-36 (DE-627)311010377 (DE-600)2003589-5 1573-501X nnns volume:13 year:2008 number:1 day:04 month:11 pages:27-36 https://dx.doi.org/10.1007/s11030-008-9095-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.00 ASE AR 13 2008 1 04 11 27-36 |
| spelling |
10.1007/s11030-008-9095-7 doi (DE-627)SPR01582747X (SPR)s11030-008-9095-7-e DE-627 ger DE-627 rakwb eng 570 ASE 42.00 bkl Amić, Dragan verfasserin aut Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 Lučić, Bono verfasserin aut Kovačević, Goran verfasserin aut Trinajstić, Nenad verfasserin aut Enthalten in Molecular diversity Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 13(2008), 1 vom: 04. Nov., Seite 27-36 (DE-627)311010377 (DE-600)2003589-5 1573-501X nnns volume:13 year:2008 number:1 day:04 month:11 pages:27-36 https://dx.doi.org/10.1007/s11030-008-9095-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.00 ASE AR 13 2008 1 04 11 27-36 |
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10.1007/s11030-008-9095-7 doi (DE-627)SPR01582747X (SPR)s11030-008-9095-7-e DE-627 ger DE-627 rakwb eng 570 ASE 42.00 bkl Amić, Dragan verfasserin aut Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 Lučić, Bono verfasserin aut Kovačević, Goran verfasserin aut Trinajstić, Nenad verfasserin aut Enthalten in Molecular diversity Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 13(2008), 1 vom: 04. Nov., Seite 27-36 (DE-627)311010377 (DE-600)2003589-5 1573-501X nnns volume:13 year:2008 number:1 day:04 month:11 pages:27-36 https://dx.doi.org/10.1007/s11030-008-9095-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.00 ASE AR 13 2008 1 04 11 27-36 |
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10.1007/s11030-008-9095-7 doi (DE-627)SPR01582747X (SPR)s11030-008-9095-7-e DE-627 ger DE-627 rakwb eng 570 ASE 42.00 bkl Amić, Dragan verfasserin aut Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 Lučić, Bono verfasserin aut Kovačević, Goran verfasserin aut Trinajstić, Nenad verfasserin aut Enthalten in Molecular diversity Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 13(2008), 1 vom: 04. Nov., Seite 27-36 (DE-627)311010377 (DE-600)2003589-5 1573-501X nnns volume:13 year:2008 number:1 day:04 month:11 pages:27-36 https://dx.doi.org/10.1007/s11030-008-9095-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.00 ASE AR 13 2008 1 04 11 27-36 |
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10.1007/s11030-008-9095-7 doi (DE-627)SPR01582747X (SPR)s11030-008-9095-7-e DE-627 ger DE-627 rakwb eng 570 ASE 42.00 bkl Amić, Dragan verfasserin aut Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids 2008 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 Lučić, Bono verfasserin aut Kovačević, Goran verfasserin aut Trinajstić, Nenad verfasserin aut Enthalten in Molecular diversity Dordrecht [u.a.] : Springer Science + Business Media B.V., 1995 13(2008), 1 vom: 04. Nov., Seite 27-36 (DE-627)311010377 (DE-600)2003589-5 1573-501X nnns volume:13 year:2008 number:1 day:04 month:11 pages:27-36 https://dx.doi.org/10.1007/s11030-008-9095-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.00 ASE AR 13 2008 1 04 11 27-36 |
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Enthalten in Molecular diversity 13(2008), 1 vom: 04. Nov., Seite 27-36 volume:13 year:2008 number:1 day:04 month:11 pages:27-36 |
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Flavonoids Polyphenols Free radical scavenging QSAR Activity cliff Bond dissociation enthalpy PM3 Indicator variables |
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Molecular diversity |
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Amić, Dragan @@aut@@ Lučić, Bono @@aut@@ Kovačević, Goran @@aut@@ Trinajstić, Nenad @@aut@@ |
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The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. 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Amić, Dragan |
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Amić, Dragan ddc 570 bkl 42.00 misc Flavonoids misc Polyphenols misc Free radical scavenging misc QSAR misc Activity cliff misc Bond dissociation enthalpy misc PM3 misc Indicator variables Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids |
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570 ASE 42.00 bkl Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids Flavonoids (dpeaa)DE-He213 Polyphenols (dpeaa)DE-He213 Free radical scavenging (dpeaa)DE-He213 QSAR (dpeaa)DE-He213 Activity cliff (dpeaa)DE-He213 Bond dissociation enthalpy (dpeaa)DE-He213 PM3 (dpeaa)DE-He213 Indicator variables (dpeaa)DE-He213 |
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ddc 570 bkl 42.00 misc Flavonoids misc Polyphenols misc Free radical scavenging misc QSAR misc Activity cliff misc Bond dissociation enthalpy misc PM3 misc Indicator variables |
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Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids |
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bond dissociation enthalpies calculated by the pm3 method confirm activity cliffs in radical scavenging of flavonoids |
| title_auth |
Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids |
| abstract |
Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. |
| abstractGer |
Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. |
| abstract_unstemmed |
Abstract Radical scavenging potency of flavonoids is associated with activity cliffs, i.e., small chemical modifications on flavonoid core can have a significant effect on activity. The presence or absence of the 3′,4′-diOH and/or 3-OH group may serve as an activity switch for radical scavenging. The physicochemical background of such an indicator variable, defined previously (Amić et al. (2003) Croat Chem Acta 76:55–61), is confirmed by computation of bond dissociation enthalpies and selecting the minimal of all values relating to flavonoid OH groups. Bond dissociation enthalpies for hydrogen abstraction from OH groups for 29 flavonoids were calculated by the PM3 method. Minimal bond dissociation enthalpy values were obtained for OH groups attached to C-3, C-3′ and C-4′ positions, and they correspond to the previously introduced indicator variable. Taking into account some driving forces of the radical scavenging mechanism, it is possible to relate structural characteristics of flavonoids to their radical scavenging potency as well as to develop reliable structure-activity models. |
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1 |
| title_short |
Bond dissociation enthalpies calculated by the PM3 method confirm activity cliffs in radical scavenging of flavonoids |
| url |
https://dx.doi.org/10.1007/s11030-008-9095-7 |
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| author2 |
Lučić, Bono Kovačević, Goran Trinajstić, Nenad |
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Lučić, Bono Kovačević, Goran Trinajstić, Nenad |
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| doi_str |
10.1007/s11030-008-9095-7 |
| up_date |
2024-07-03T18:50:07.262Z |
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| score |
7.4006186 |