Synthesis, DNA/RNA-interaction and biological activity of benzo[
Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and m...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Tumir, Lidija-Marija [verfasserIn] Zonjić, Iva [verfasserIn] Žuna, Kristina [verfasserIn] Brkanac, Sandra Radić [verfasserIn] Jukić, Marijana [verfasserIn] Huđek, Ana [verfasserIn] Durgo, Ksenija [verfasserIn] Crnolatac, Ivo [verfasserIn] Glavaš-Obrovac, Ljubica [verfasserIn] Cardullo, Nunzio [verfasserIn] Pulvirenti, Luana [verfasserIn] Muccilli, Vera [verfasserIn] Tringali, Corrado [verfasserIn] Stojković, Marijana Radić [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2020 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Bioorganic chemistry - San Diego, Calif. : Elsevier, 1971, 104 |
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| Übergeordnetes Werk: |
volume:104 |
| DOI / URN: |
10.1016/j.bioorg.2020.104190 |
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| Katalog-ID: |
ELV004995619 |
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| 520 | |a Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. | ||
| 650 | 4 | |a DNA/RNA recognition | |
| 650 | 4 | |a Benzo[ | |
| 650 | 4 | |a G-quadruplex interaction | |
| 650 | 4 | |a HSA interaction | |
| 650 | 4 | |a Antiproliferative effect | |
| 700 | 1 | |a Zonjić, Iva |e verfasserin |4 aut | |
| 700 | 1 | |a Žuna, Kristina |e verfasserin |4 aut | |
| 700 | 1 | |a Brkanac, Sandra Radić |e verfasserin |4 aut | |
| 700 | 1 | |a Jukić, Marijana |e verfasserin |4 aut | |
| 700 | 1 | |a Huđek, Ana |e verfasserin |4 aut | |
| 700 | 1 | |a Durgo, Ksenija |e verfasserin |4 aut | |
| 700 | 1 | |a Crnolatac, Ivo |e verfasserin |4 aut | |
| 700 | 1 | |a Glavaš-Obrovac, Ljubica |e verfasserin |4 aut | |
| 700 | 1 | |a Cardullo, Nunzio |e verfasserin |4 aut | |
| 700 | 1 | |a Pulvirenti, Luana |e verfasserin |4 aut | |
| 700 | 1 | |a Muccilli, Vera |e verfasserin |4 aut | |
| 700 | 1 | |a Tringali, Corrado |e verfasserin |4 aut | |
| 700 | 1 | |a Stojković, Marijana Radić |e verfasserin |4 aut | |
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10.1016/j.bioorg.2020.104190 doi (DE-627)ELV004995619 (ELSEVIER)S0045-2068(20)31487-5 DE-627 ger DE-627 rda eng 540 DE-600 35.50 bkl 35.70 bkl Tumir, Lidija-Marija verfasserin aut Synthesis, DNA/RNA-interaction and biological activity of benzo[ 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect Zonjić, Iva verfasserin aut Žuna, Kristina verfasserin aut Brkanac, Sandra Radić verfasserin aut Jukić, Marijana verfasserin aut Huđek, Ana verfasserin aut Durgo, Ksenija verfasserin aut Crnolatac, Ivo verfasserin aut Glavaš-Obrovac, Ljubica verfasserin aut Cardullo, Nunzio verfasserin aut Pulvirenti, Luana verfasserin aut Muccilli, Vera verfasserin aut Tringali, Corrado verfasserin aut Stojković, Marijana Radić verfasserin aut Enthalten in Bioorganic chemistry San Diego, Calif. : Elsevier, 1971 104 Online-Ressource (DE-627)254631681 (DE-600)1462232-4 (DE-576)104193603 1090-2120 nnns volume:104 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 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_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.50 Organische Chemie: Allgemeines 35.70 Biochemie: Allgemeines AR 104 |
| spelling |
10.1016/j.bioorg.2020.104190 doi (DE-627)ELV004995619 (ELSEVIER)S0045-2068(20)31487-5 DE-627 ger DE-627 rda eng 540 DE-600 35.50 bkl 35.70 bkl Tumir, Lidija-Marija verfasserin aut Synthesis, DNA/RNA-interaction and biological activity of benzo[ 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect Zonjić, Iva verfasserin aut Žuna, Kristina verfasserin aut Brkanac, Sandra Radić verfasserin aut Jukić, Marijana verfasserin aut Huđek, Ana verfasserin aut Durgo, Ksenija verfasserin aut Crnolatac, Ivo verfasserin aut Glavaš-Obrovac, Ljubica verfasserin aut Cardullo, Nunzio verfasserin aut Pulvirenti, Luana verfasserin aut Muccilli, Vera verfasserin aut Tringali, Corrado verfasserin aut Stojković, Marijana Radić verfasserin aut Enthalten in Bioorganic chemistry San Diego, Calif. : Elsevier, 1971 104 Online-Ressource (DE-627)254631681 (DE-600)1462232-4 (DE-576)104193603 1090-2120 nnns volume:104 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 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_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.50 Organische Chemie: Allgemeines 35.70 Biochemie: Allgemeines AR 104 |
| allfields_unstemmed |
10.1016/j.bioorg.2020.104190 doi (DE-627)ELV004995619 (ELSEVIER)S0045-2068(20)31487-5 DE-627 ger DE-627 rda eng 540 DE-600 35.50 bkl 35.70 bkl Tumir, Lidija-Marija verfasserin aut Synthesis, DNA/RNA-interaction and biological activity of benzo[ 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect Zonjić, Iva verfasserin aut Žuna, Kristina verfasserin aut Brkanac, Sandra Radić verfasserin aut Jukić, Marijana verfasserin aut Huđek, Ana verfasserin aut Durgo, Ksenija verfasserin aut Crnolatac, Ivo verfasserin aut Glavaš-Obrovac, Ljubica verfasserin aut Cardullo, Nunzio verfasserin aut Pulvirenti, Luana verfasserin aut Muccilli, Vera verfasserin aut Tringali, Corrado verfasserin aut Stojković, Marijana Radić verfasserin aut Enthalten in Bioorganic chemistry San Diego, Calif. : Elsevier, 1971 104 Online-Ressource (DE-627)254631681 (DE-600)1462232-4 (DE-576)104193603 1090-2120 nnns volume:104 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 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_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.50 Organische Chemie: Allgemeines 35.70 Biochemie: Allgemeines AR 104 |
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10.1016/j.bioorg.2020.104190 doi (DE-627)ELV004995619 (ELSEVIER)S0045-2068(20)31487-5 DE-627 ger DE-627 rda eng 540 DE-600 35.50 bkl 35.70 bkl Tumir, Lidija-Marija verfasserin aut Synthesis, DNA/RNA-interaction and biological activity of benzo[ 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect Zonjić, Iva verfasserin aut Žuna, Kristina verfasserin aut Brkanac, Sandra Radić verfasserin aut Jukić, Marijana verfasserin aut Huđek, Ana verfasserin aut Durgo, Ksenija verfasserin aut Crnolatac, Ivo verfasserin aut Glavaš-Obrovac, Ljubica verfasserin aut Cardullo, Nunzio verfasserin aut Pulvirenti, Luana verfasserin aut Muccilli, Vera verfasserin aut Tringali, Corrado verfasserin aut Stojković, Marijana Radić verfasserin aut Enthalten in Bioorganic chemistry San Diego, Calif. : Elsevier, 1971 104 Online-Ressource (DE-627)254631681 (DE-600)1462232-4 (DE-576)104193603 1090-2120 nnns volume:104 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 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_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.50 Organische Chemie: Allgemeines 35.70 Biochemie: Allgemeines AR 104 |
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10.1016/j.bioorg.2020.104190 doi (DE-627)ELV004995619 (ELSEVIER)S0045-2068(20)31487-5 DE-627 ger DE-627 rda eng 540 DE-600 35.50 bkl 35.70 bkl Tumir, Lidija-Marija verfasserin aut Synthesis, DNA/RNA-interaction and biological activity of benzo[ 2020 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect Zonjić, Iva verfasserin aut Žuna, Kristina verfasserin aut Brkanac, Sandra Radić verfasserin aut Jukić, Marijana verfasserin aut Huđek, Ana verfasserin aut Durgo, Ksenija verfasserin aut Crnolatac, Ivo verfasserin aut Glavaš-Obrovac, Ljubica verfasserin aut Cardullo, Nunzio verfasserin aut Pulvirenti, Luana verfasserin aut Muccilli, Vera verfasserin aut Tringali, Corrado verfasserin aut Stojković, Marijana Radić verfasserin aut Enthalten in Bioorganic chemistry San Diego, Calif. : Elsevier, 1971 104 Online-Ressource (DE-627)254631681 (DE-600)1462232-4 (DE-576)104193603 1090-2120 nnns volume:104 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 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_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.50 Organische Chemie: Allgemeines 35.70 Biochemie: Allgemeines AR 104 |
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Enthalten in Bioorganic chemistry 104 volume:104 |
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DNA/RNA recognition Benzo[ G-quadruplex interaction HSA interaction Antiproliferative effect |
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Bioorganic chemistry |
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Tumir, Lidija-Marija @@aut@@ Zonjić, Iva @@aut@@ Žuna, Kristina @@aut@@ Brkanac, Sandra Radić @@aut@@ Jukić, Marijana @@aut@@ Huđek, Ana @@aut@@ Durgo, Ksenija @@aut@@ Crnolatac, Ivo @@aut@@ Glavaš-Obrovac, Ljubica @@aut@@ Cardullo, Nunzio @@aut@@ Pulvirenti, Luana @@aut@@ Muccilli, Vera @@aut@@ Tringali, Corrado @@aut@@ Stojković, Marijana Radić @@aut@@ |
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2020-01-01T00:00:00Z |
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Tumir, Lidija-Marija Zonjić, Iva Žuna, Kristina Brkanac, Sandra Radić Jukić, Marijana Huđek, Ana Durgo, Ksenija Crnolatac, Ivo Glavaš-Obrovac, Ljubica Cardullo, Nunzio Pulvirenti, Luana Muccilli, Vera Tringali, Corrado Stojković, Marijana Radić |
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synthesis, dna/rna-interaction and biological activity of benzo[ |
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Synthesis, DNA/RNA-interaction and biological activity of benzo[ |
| abstract |
Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. |
| abstractGer |
Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. |
| abstract_unstemmed |
Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity. |
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Synthesis, DNA/RNA-interaction and biological activity of benzo[ |
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Zonjić, Iva Žuna, Kristina Brkanac, Sandra Radić Jukić, Marijana Huđek, Ana Durgo, Ksenija Crnolatac, Ivo Glavaš-Obrovac, Ljubica Cardullo, Nunzio Pulvirenti, Luana Muccilli, Vera Tringali, Corrado Stojković, Marijana Radić |
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| score |
7.3993196 |