A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold
Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer c...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Huber, Imre [verfasserIn] Zupkó, István [verfasserIn] Gyovai, András [verfasserIn] Horváth, Péter [verfasserIn] Kiss, Eszter [verfasserIn] Gulyás-Fekete, Gergely [verfasserIn] Schmidt, János [verfasserIn] Perjési, Pál [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2019 |
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| Übergeordnetes Werk: |
Enthalten in: Research on chemical intermediates - Dordrecht : Springer Netherlands, 1989, 45(2019), 9 vom: 24. Mai, Seite 4711-4735 |
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| Übergeordnetes Werk: |
volume:45 ; year:2019 ; number:9 ; day:24 ; month:05 ; pages:4711-4735 |
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| DOI / URN: |
10.1007/s11164-019-03859-4 |
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| Katalog-ID: |
SPR017295327 |
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| 245 | 1 | 2 | |a A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
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| 520 | |a Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. | ||
| 650 | 4 | |a Antiproliferative curcuminoids |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Cyclic curcuminoids |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a C |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a -curcuminoids |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a DNA binding of curcuminoids |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a MS fingerprint of curcuminoids |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Zupkó, István |e verfasserin |4 aut | |
| 700 | 1 | |a Gyovai, András |e verfasserin |4 aut | |
| 700 | 1 | |a Horváth, Péter |e verfasserin |4 aut | |
| 700 | 1 | |a Kiss, Eszter |e verfasserin |4 aut | |
| 700 | 1 | |a Gulyás-Fekete, Gergely |e verfasserin |4 aut | |
| 700 | 1 | |a Schmidt, János |e verfasserin |4 aut | |
| 700 | 1 | |a Perjési, Pál |e verfasserin |4 aut | |
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10.1007/s11164-019-03859-4 doi (DE-627)SPR017295327 (SPR)s11164-019-03859-4-e DE-627 ger DE-627 rakwb eng 540 ASE 35.13 bkl Huber, Imre verfasserin aut A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 Zupkó, István verfasserin aut Gyovai, András verfasserin aut Horváth, Péter verfasserin aut Kiss, Eszter verfasserin aut Gulyás-Fekete, Gergely verfasserin aut Schmidt, János verfasserin aut Perjési, Pál verfasserin aut Enthalten in Research on chemical intermediates Dordrecht : Springer Netherlands, 1989 45(2019), 9 vom: 24. Mai, Seite 4711-4735 (DE-627)328186511 (DE-600)2045085-0 1568-5675 nnns volume:45 year:2019 number:9 day:24 month:05 pages:4711-4735 https://dx.doi.org/10.1007/s11164-019-03859-4 kostenfrei 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_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_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_206 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_2056 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_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 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 35.13 ASE AR 45 2019 9 24 05 4711-4735 |
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10.1007/s11164-019-03859-4 doi (DE-627)SPR017295327 (SPR)s11164-019-03859-4-e DE-627 ger DE-627 rakwb eng 540 ASE 35.13 bkl Huber, Imre verfasserin aut A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 Zupkó, István verfasserin aut Gyovai, András verfasserin aut Horváth, Péter verfasserin aut Kiss, Eszter verfasserin aut Gulyás-Fekete, Gergely verfasserin aut Schmidt, János verfasserin aut Perjési, Pál verfasserin aut Enthalten in Research on chemical intermediates Dordrecht : Springer Netherlands, 1989 45(2019), 9 vom: 24. Mai, Seite 4711-4735 (DE-627)328186511 (DE-600)2045085-0 1568-5675 nnns volume:45 year:2019 number:9 day:24 month:05 pages:4711-4735 https://dx.doi.org/10.1007/s11164-019-03859-4 kostenfrei 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_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_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_206 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_2056 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_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 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 35.13 ASE AR 45 2019 9 24 05 4711-4735 |
| allfields_unstemmed |
10.1007/s11164-019-03859-4 doi (DE-627)SPR017295327 (SPR)s11164-019-03859-4-e DE-627 ger DE-627 rakwb eng 540 ASE 35.13 bkl Huber, Imre verfasserin aut A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 Zupkó, István verfasserin aut Gyovai, András verfasserin aut Horváth, Péter verfasserin aut Kiss, Eszter verfasserin aut Gulyás-Fekete, Gergely verfasserin aut Schmidt, János verfasserin aut Perjési, Pál verfasserin aut Enthalten in Research on chemical intermediates Dordrecht : Springer Netherlands, 1989 45(2019), 9 vom: 24. Mai, Seite 4711-4735 (DE-627)328186511 (DE-600)2045085-0 1568-5675 nnns volume:45 year:2019 number:9 day:24 month:05 pages:4711-4735 https://dx.doi.org/10.1007/s11164-019-03859-4 kostenfrei 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_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_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_206 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_2056 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_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 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 35.13 ASE AR 45 2019 9 24 05 4711-4735 |
| allfieldsGer |
10.1007/s11164-019-03859-4 doi (DE-627)SPR017295327 (SPR)s11164-019-03859-4-e DE-627 ger DE-627 rakwb eng 540 ASE 35.13 bkl Huber, Imre verfasserin aut A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 Zupkó, István verfasserin aut Gyovai, András verfasserin aut Horváth, Péter verfasserin aut Kiss, Eszter verfasserin aut Gulyás-Fekete, Gergely verfasserin aut Schmidt, János verfasserin aut Perjési, Pál verfasserin aut Enthalten in Research on chemical intermediates Dordrecht : Springer Netherlands, 1989 45(2019), 9 vom: 24. Mai, Seite 4711-4735 (DE-627)328186511 (DE-600)2045085-0 1568-5675 nnns volume:45 year:2019 number:9 day:24 month:05 pages:4711-4735 https://dx.doi.org/10.1007/s11164-019-03859-4 kostenfrei 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_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_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_206 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_2056 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_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 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 35.13 ASE AR 45 2019 9 24 05 4711-4735 |
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10.1007/s11164-019-03859-4 doi (DE-627)SPR017295327 (SPR)s11164-019-03859-4-e DE-627 ger DE-627 rakwb eng 540 ASE 35.13 bkl Huber, Imre verfasserin aut A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold 2019 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 Zupkó, István verfasserin aut Gyovai, András verfasserin aut Horváth, Péter verfasserin aut Kiss, Eszter verfasserin aut Gulyás-Fekete, Gergely verfasserin aut Schmidt, János verfasserin aut Perjési, Pál verfasserin aut Enthalten in Research on chemical intermediates Dordrecht : Springer Netherlands, 1989 45(2019), 9 vom: 24. Mai, Seite 4711-4735 (DE-627)328186511 (DE-600)2045085-0 1568-5675 nnns volume:45 year:2019 number:9 day:24 month:05 pages:4711-4735 https://dx.doi.org/10.1007/s11164-019-03859-4 kostenfrei 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_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_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_206 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_2056 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_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 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 35.13 ASE AR 45 2019 9 24 05 4711-4735 |
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Huber, Imre @@aut@@ Zupkó, István @@aut@@ Gyovai, András @@aut@@ Horváth, Péter @@aut@@ Kiss, Eszter @@aut@@ Gulyás-Fekete, Gergely @@aut@@ Schmidt, János @@aut@@ Perjési, Pál @@aut@@ |
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Huber, Imre ddc 540 bkl 35.13 misc Antiproliferative curcuminoids misc Cyclic curcuminoids misc C misc -curcuminoids misc DNA binding of curcuminoids misc MS fingerprint of curcuminoids A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
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540 ASE 35.13 bkl A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold Antiproliferative curcuminoids (dpeaa)DE-He213 Cyclic curcuminoids (dpeaa)DE-He213 C (dpeaa)DE-He213 -curcuminoids (dpeaa)DE-He213 DNA binding of curcuminoids (dpeaa)DE-He213 MS fingerprint of curcuminoids (dpeaa)DE-He213 |
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A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
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A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
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Huber, Imre Zupkó, István Gyovai, András Horváth, Péter Kiss, Eszter Gulyás-Fekete, Gergely Schmidt, János Perjési, Pál |
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novel cluster of $ c_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and dna binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
| title_auth |
A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
| abstract |
Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. |
| abstractGer |
Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. |
| abstract_unstemmed |
Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. A proposal is summarized based on mass spectrometric assessment for fingerprint analysis in biological research of such $ C_{5} $-curcuminoids. |
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A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">SPR017295327</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20230519181813.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">201006s2019 xx |||||o 00| ||eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1007/s11164-019-03859-4</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)SPR017295327</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(SPR)s11164-019-03859-4-e</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">540</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.13</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Huber, Imre</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="2"><subfield code="a">A novel cluster of $ C_{5} $-curcuminoids: design, synthesis, in vitro antiproliferative activity and DNA binding of bis(arylidene)-4-cyclanone derivatives based on 4-hydroxycyclohexanone scaffold</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2019</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract A new series (6) of $ C_{5} $-curcuminoid derivatives (2E,6E-2,6-dibenzylidene-4-hydroxycyclohexanones) is described here with their evaluation for in vitro antiproliferative activities. Evaluation of 31 compounds against human A2780 (ovarian), C33A (cervix) and MDA-MB-231 (breast) cancer cell lines was performed to obtain structure activity relation data. The best performer was (2E,6E)-2,6-bis(3′-nitrobenzylidene)-4-hydroxycyclohexanone (6h) with $ IC_{50} $ values of 0.68 μM (A2780), 0.69 μM (C33A) and 0.92 μM (MDA-MB-231) compared to cisplatin with 1.30 μM, 3.69 μM and 19.13 μM, respectively. According to calculated physicochemical properties some members in series 6, namely (2E,6E)-2,6-bis[(4′-pyridinyl)methylene]-4-hydroxycyclohexanone (6p) [$ IC_{50} $ = 0.76 μM (A2780), 2.69 μM (C33A), 1.28 μM (MDA-MB-231)] seem to have improved bioavailability compared to curcumin. Selected members of series 6 were involved in circular dichroism spectroscopic measurements in order to determine their interaction with natural DNA. Based on these data, we conclude that these derivatives do not bind to DNA in vitro. 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