Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands: antiproliferative effects, cellular uptake and DNA-interaction
Fluorescent 4-ethylthio-1,8-naphthalimides containing rhodium(I) N-heterocyclic carbene (NHC) and ruthenium (II) NHC fragments were synthesised and evaluated for their antiproliferative effects, cellular uptake and DNA-binding activity. Both types of organometallics triggered ligand dependent effici...
Gespeichert in:
| Hauptverfasser: | , , , , , , , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
25 June 2018
|
| In: |
European journal of medicinal chemistry
Year: 2018, Jahrgang: 156, Pages: 148-161 |
| ISSN: | 1768-3254 |
| DOI: | 10.1016/j.ejmech.2018.06.056 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1016/j.ejmech.2018.06.056 Verlag, lizenzpflichtig, Volltext: http://www.sciencedirect.com/science/article/pii/S0223523418305476 
|
| Verfasserangaben: | Wojciech Streciwilk, Alessio Terenzi, Xinlai Cheng, Laura Hager, Yasamin Dabiri, Pascal Prochnow, Julia Elisabeth Bandow, Stefan Wölfl, Bernhard K. Keppler, Ingo Ott |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1694971007 | ||
| 003 | DE-627 | ||
| 005 | 20230427070550.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 200420s2018 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.ejmech.2018.06.056 |2 doi | |
| 035 | |a (DE-627)1694971007 | ||
| 035 | |a (DE-599)KXP1694971007 | ||
| 035 | |a (OCoLC)1341315501 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 33 |2 sdnb | ||
| 100 | 1 | |a Streciwilk, Wojciech |d 1989- |e VerfasserIn |0 (DE-588)1198323787 |0 (DE-627)168070186X |4 aut | |
| 245 | 1 | 0 | |a Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands |b antiproliferative effects, cellular uptake and DNA-interaction |c Wojciech Streciwilk, Alessio Terenzi, Xinlai Cheng, Laura Hager, Yasamin Dabiri, Pascal Prochnow, Julia Elisabeth Bandow, Stefan Wölfl, Bernhard K. Keppler, Ingo Ott |
| 264 | 1 | |c 25 June 2018 | |
| 300 | |a 14 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 20.04.2020 | ||
| 520 | |a Fluorescent 4-ethylthio-1,8-naphthalimides containing rhodium(I) N-heterocyclic carbene (NHC) and ruthenium (II) NHC fragments were synthesised and evaluated for their antiproliferative effects, cellular uptake and DNA-binding activity. Both types of organometallics triggered ligand dependent efficient cytotoxic effects against tumor cells with the rhodium(I) NHC derivatives causing stronger effects than the ruthenium (II) NHC analogues. Antiproliferative effects could also be observed against several pathogenic Gram-positive bacterial strains, whereas the growth of Gram-negative bacteria was not substantially affected. Cellular uptake was confirmed by atomic absorption spectroscopy as well as by fluorescence microscopy indicating a general ligand dependent accumulation in the cells. An in-depth study on the interaction with DNA confirmed insertion of the naphthalimide moiety between the planar bases of B-DNA via an intercalation mechanism, as well as its stacking on top of the quartets of G-quadruplex structures. Furthermore, additional coordinative binding of the organometallic complexes to the model DNA base 9-ethylguanine could be detected. The studied compounds thus represent promising bioorganometallics featuring strong pharmacological effects in combination with excellent cellular imaging properties. | ||
| 650 | 4 | |a Bioorganometallics | |
| 650 | 4 | |a Carbene | |
| 650 | 4 | |a Naphthalimide | |
| 650 | 4 | |a Rhodium | |
| 650 | 4 | |a Ruthenium | |
| 700 | 1 | |a Terenzi, Alessio |e VerfasserIn |4 aut | |
| 700 | 1 | |a Cheng, Xinlai |d 1978- |e VerfasserIn |0 (DE-588)140211586 |0 (DE-627)616944179 |0 (DE-576)315074698 |4 aut | |
| 700 | 1 | |a Hager, Laura |e VerfasserIn |4 aut | |
| 700 | 1 | |a Dabiri, Yasamin |d 1988- |e VerfasserIn |0 (DE-588)1167446496 |0 (DE-627)1031115714 |0 (DE-576)511149182 |4 aut | |
| 700 | 1 | |a Prochnow, Pascal |e VerfasserIn |4 aut | |
| 700 | 1 | |a Bandow, Julia Elisabeth |e VerfasserIn |4 aut | |
| 700 | 1 | |a Wölfl, Stefan |d 1959- |e VerfasserIn |0 (DE-588)121047458 |0 (DE-627)081052618 |0 (DE-576)260692360 |4 aut | |
| 700 | 1 | |a Keppler, Bernhard K. |e VerfasserIn |4 aut | |
| 700 | 1 | |a Ott, Ingo |e VerfasserIn |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t European journal of medicinal chemistry |d Amsterdam [u.a.] : Elsevier Science, 1987 |g 156(2018), Seite 148-161 |h Online-Ressource |w (DE-627)320443213 |w (DE-600)2005170-0 |w (DE-576)25927125X |x 1768-3254 |7 nnas |a Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands antiproliferative effects, cellular uptake and DNA-interaction |
| 773 | 1 | 8 | |g volume:156 |g year:2018 |g pages:148-161 |g extent:14 |a Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands antiproliferative effects, cellular uptake and DNA-interaction |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.ejmech.2018.06.056 |x Verlag |x Resolving-System |z lizenzpflichtig |3 Volltext |
| 856 | 4 | 0 | |u http://www.sciencedirect.com/science/article/pii/S0223523418305476 |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20200420 | ||
| 993 | |a Article | ||
| 994 | |a 2018 | ||
| 998 | |g 121047458 |a Wölfl, Stefan |m 121047458:Wölfl, Stefan |d 160000 |d 160100 |e 160000PW121047458 |e 160100PW121047458 |k 0/160000/ |k 1/160000/160100/ |p 8 | ||
| 998 | |g 1167446496 |a Dabiri, Yasamin |m 1167446496:Dabiri, Yasamin |d 160000 |d 160100 |e 160000PD1167446496 |e 160100PD1167446496 |k 0/160000/ |k 1/160000/160100/ |p 5 | ||
| 998 | |g 140211586 |a Cheng, Xinlai |m 140211586:Cheng, Xinlai |d 160000 |d 160100 |e 160000PC140211586 |e 160100PC140211586 |k 0/160000/ |k 1/160000/160100/ |p 3 | ||
| 999 | |a KXP-PPN1694971007 |e 3627254325 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"name":{"displayForm":["Wojciech Streciwilk, Alessio Terenzi, Xinlai Cheng, Laura Hager, Yasamin Dabiri, Pascal Prochnow, Julia Elisabeth Bandow, Stefan Wölfl, Bernhard K. Keppler, Ingo Ott"]},"language":["eng"],"title":[{"title_sort":"Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands","title":"Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands","subtitle":"antiproliferative effects, cellular uptake and DNA-interaction"}],"note":["Gesehen am 20.04.2020"],"recId":"1694971007","relHost":[{"type":{"media":"Online-Ressource","bibl":"periodical"},"pubHistory":["Nachgewiesen 22.1987 -"],"part":{"extent":"14","volume":"156","pages":"148-161","year":"2018","text":"156(2018), Seite 148-161"},"physDesc":[{"extent":"Online-Ressource"}],"origin":[{"publisher":"Elsevier Science","dateIssuedKey":"1987","dateIssuedDisp":"1987-","publisherPlace":"Amsterdam [u.a.]"}],"note":["Gesehen am 22.11.04"],"id":{"issn":["1768-3254"],"eki":["320443213"],"zdb":["2005170-0"]},"recId":"320443213","disp":"Fluorescent organometallic rhodium(I) and ruthenium(II) metallodrugs with 4-ethylthio-1,8-naphthalimide ligands antiproliferative effects, cellular uptake and DNA-interactionEuropean journal of medicinal chemistry","language":["eng"],"title":[{"title":"European journal of medicinal chemistry","title_sort":"European journal of medicinal chemistry"}]}],"person":[{"given":"Wojciech","family":"Streciwilk","display":"Streciwilk, Wojciech","roleDisplay":"VerfasserIn","role":"aut"},{"roleDisplay":"VerfasserIn","role":"aut","family":"Terenzi","display":"Terenzi, Alessio","given":"Alessio"},{"display":"Cheng, Xinlai","family":"Cheng","roleDisplay":"VerfasserIn","role":"aut","given":"Xinlai"},{"given":"Laura","display":"Hager, Laura","family":"Hager","role":"aut","roleDisplay":"VerfasserIn"},{"given":"Yasamin","role":"aut","roleDisplay":"VerfasserIn","family":"Dabiri","display":"Dabiri, Yasamin"},{"role":"aut","roleDisplay":"VerfasserIn","family":"Prochnow","display":"Prochnow, Pascal","given":"Pascal"},{"given":"Julia Elisabeth","display":"Bandow, Julia Elisabeth","family":"Bandow","roleDisplay":"VerfasserIn","role":"aut"},{"roleDisplay":"VerfasserIn","role":"aut","family":"Wölfl","display":"Wölfl, Stefan","given":"Stefan"},{"roleDisplay":"VerfasserIn","role":"aut","family":"Keppler","display":"Keppler, Bernhard K.","given":"Bernhard K."},{"given":"Ingo","family":"Ott","display":"Ott, Ingo","roleDisplay":"VerfasserIn","role":"aut"}],"id":{"doi":["10.1016/j.ejmech.2018.06.056"],"eki":["1694971007"]},"physDesc":[{"extent":"14 S."}],"origin":[{"dateIssuedKey":"2018","dateIssuedDisp":"25 June 2018"}],"type":{"media":"Online-Ressource","bibl":"article-journal"}} | ||
| SRT | |a STRECIWILKFLUORESCEN2520 | ||