Methyl Viologens of Bis-(4'-Pyridylethynyl)Arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology.
DNA/RNA binding
cell imaging
methyl viologen
singlet oxygen
two-photon absorption
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 Jul 2022
15 Jul 2022
Historique:
received:
09
03
2022
pubmed:
4
5
2022
medline:
19
7
2022
entrez:
3
5
2022
Statut:
ppublish
Résumé
A series of bis-(4'-pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis-N-methylpyridinium compounds were investigated as a class of π-extended methyl viologens. Their structures were determined by single crystal X-ray diffraction, and their photophysical and electrochemical properties (cyclic voltammetry), as well as their interactions with DNA/RNA were investigated. The dications showed bathochromic shifts in emission compared to the neutral compounds. The neutral compounds showed very small Stokes shifts, which are a little larger for the dications. All of the compounds showed very short fluorescence lifetimes (<4 ns). The neutral compound with an anthracene core has a quantum yield of almost unity. With stronger acceptors, the analogous bis-N-methylpyridinium compound showed a larger two-photon absorption cross-section than its neutral precursor. All of the dicationic compounds interact with DNA/RNA; while the compounds with benzene and tetrafluorobenzene cores bind in the grooves, the one with an anthracene core intercalates as a consequence of its large, condensed aromatic linker moiety, and it aggregates within the polynucleotide when in excess over DNA/RNA. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents.
Identifiants
pubmed: 35502627
doi: 10.1002/chem.202200753
pmc: PMC9400870
doi:
Substances chimiques
Anthracenes
0
RNA
63231-63-0
DNA
9007-49-2
Benzene
J64922108F
Paraquat
PLG39H7695
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200753Subventions
Organisme : Alexander von Humboldt-Stiftung
Organisme : Julius-Maximilians-Universität Würzburg
Organisme : Croatian Science Foundation
ID : IP-2018-01-5475
Organisme : Grand Équipement National De Calcul Intensif
ID : 2021-080649
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
Bioconjug Chem. 2007 Nov-Dec;18(6):1972-80
pubmed: 17896811
Methods Enzymol. 2000;319:37-49
pubmed: 10907497
Chemistry. 2015 Jun 1;21(23):8569-77
pubmed: 25919359
Inorg Chem. 2017 Dec 18;56(24):14926-14935
pubmed: 29200269
Angew Chem Int Ed Engl. 2011 Aug 16;50(34):7948-52
pubmed: 21732507
J Mol Biol. 1974 Jun 25;86(2):469-89
pubmed: 4416620
Org Biomol Chem. 2003 Jan 7;1(1):100-3
pubmed: 12929395
Chem Commun (Camb). 2010 Nov 28;46(44):8362-4
pubmed: 20922231
Chem Asian J. 2019 Jun 14;14(12):2086-2090
pubmed: 30968564
J Org Chem. 2000 Jan 28;65(2):593-5
pubmed: 10813978
Biophys J. 2019 Jun 4;116(11):2062-2072
pubmed: 31084902
Br J Surg. 2021 Sep 27;108(9):1056-1063
pubmed: 33761533
Org Lett. 2010 Apr 16;12(8):1888-91
pubmed: 20337447
Anal Chem. 2019 Aug 6;91(15):9407-9412
pubmed: 31272151
Chem Rev. 2012 Mar 14;112(3):1710-50
pubmed: 22040166
J Org Chem. 2017 Sep 1;82(17):9258-9262
pubmed: 28759234
Chemistry. 2017 May 2;23(25):6029-6033
pubmed: 28074501
Chem Sci. 2019 Apr 23;10(20):5405-5422
pubmed: 31217943
J Am Chem Soc. 2020 Feb 5;142(5):2601-2608
pubmed: 31939661
Inorg Chem. 2018 Jul 2;57(13):7975-7981
pubmed: 29911863
Photochem Photobiol. 2022 Jan;98(1):193-201
pubmed: 34719028
J Am Chem Soc. 2005 Nov 30;127(47):16559-66
pubmed: 16305245
Chemistry. 2019 Jun 7;25(32):7679-7688
pubmed: 30900778
Chem Rev. 2019 Feb 13;119(3):2043-2086
pubmed: 30721030
J Mol Graph. 1996 Feb;14(1):33-8, 27-8
pubmed: 8744570
Methods Enzymol. 2001;340:68-98
pubmed: 11494876
Biochemistry. 1985 Sep 24;24(20):5503-10
pubmed: 4074711
Angew Chem Int Ed Engl. 2018 Jan 2;57(1):231-235
pubmed: 29181865
Acc Chem Res. 2003 Sep;36(9):668-75
pubmed: 12974650
J Am Chem Soc. 2017 May 10;139(18):6282-6285
pubmed: 28407710
J Phys Chem B. 2020 Feb 13;124(6):1049-1064
pubmed: 31941271
Chemistry. 2015 Jan 26;21(5):2090-106
pubmed: 25450858
Opt Express. 2008 Mar 17;16(6):4029-47
pubmed: 18542501
Chem Commun (Camb). 2001 Nov 7;(21):2256-7
pubmed: 12240138
Chemistry. 2022 Jul 15;28(40):e202200753
pubmed: 35502627
ACS Appl Mater Interfaces. 2019 Jul 24;11(29):25750-25757
pubmed: 31245990
J Appl Crystallogr. 2011 Dec 1;44(Pt 6):1281-1284
pubmed: 22477785
Chem Commun (Camb). 2017 Sep 21;53(76):10596-10599
pubmed: 28900650
Dalton Trans. 2014 Sep 21;43(35):13159-68
pubmed: 25032996
Nucleic Acids Res. 2016 May 19;44(9):3971-88
pubmed: 27085806
Cold Spring Harb Protoc. 2018 Jun 1;2018(6):
pubmed: 29858336
Chem Sci. 2018 May 21;9(26):5709-5715
pubmed: 30079179
Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3606-10
pubmed: 26845734
Chemphyschem. 2005 May;6(5):893-6
pubmed: 15884072
Chemistry. 2019 Oct 11;25(57):13164-13175
pubmed: 31322301
Angew Chem Int Ed Engl. 2002 Oct 4;41(19):3648-50, 3518
pubmed: 12370918
J Chem Phys. 2010 Apr 21;132(15):154104
pubmed: 20423165
Chemistry. 2010 Mar 8;16(10):3036-56
pubmed: 20119980
Methods Enzymol. 2000;319:3-20
pubmed: 10907494
J Am Chem Soc. 2012 Feb 1;134(4):1958-61
pubmed: 22242714
Science. 1998 Sep 11;281(5383):1653-6
pubmed: 9733507
Biochemistry. 1991 Jun 11;30(23):5631-43
pubmed: 1904272
J Comput Chem. 2011 May;32(7):1456-65
pubmed: 21370243
J Org Chem. 2016 Jul 1;81(13):5474-86
pubmed: 27284956
J Am Chem Soc. 2017 Dec 20;139(50):18170-18173
pubmed: 29185739
J Am Chem Soc. 2004 Nov 3;126(43):14036-42
pubmed: 15506767
Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8
pubmed: 25537383
J Am Chem Soc. 1991 Jun;113(13):5131-5133
pubmed: 27715028
Angew Chem Int Ed Engl. 2007;46(1-2):245-9
pubmed: 17136789
Chemistry. 2020 May 12;26(27):6017-6028
pubmed: 32104942
J Org Chem. 2020 Mar 20;85(6):4256-4266
pubmed: 32129624
Chem Sci. 2019 Jun 24;10(32):7516-7534
pubmed: 31588303
Angew Chem Int Ed Engl. 2021 Feb 23;60(9):4833-4840
pubmed: 33231909
J Gen Physiol. 1933 Jul 20;16(6):859-73
pubmed: 19872744
Chemistry. 2014 Mar 24;20(13):3652-66
pubmed: 24615869
Angew Chem Int Ed Engl. 2001 Mar 16;40(6):1104-1106
pubmed: 11268089
Bioorg Med Chem. 2019 Jun 1;27(11):2253-2260
pubmed: 30982658
Chem Rev. 2005 Sep;105(9):3371-87
pubmed: 16159156
J Am Chem Soc. 2005 Jul 6;127(26):9386-7
pubmed: 15984863
Chemistry. 2005 Jul 4;11(14):4191-8
pubmed: 15861373
Angew Chem Int Ed Engl. 2015 Jan 7;54(2):430-5
pubmed: 25476702
J Am Chem Soc. 2015 Mar 11;137(9):3366-71
pubmed: 25730100
Chemistry. 2021 Sep 24;27(54):13591-13604
pubmed: 34263955
Nat Commun. 2018 Sep 28;9(1):3977
pubmed: 30266899
Chem Sci. 2018 Dec 11;10(7):1994-2000
pubmed: 30881628
Chemistry. 2016 Oct 4;22(41):14701-6
pubmed: 27627995
Beilstein J Org Chem. 2018 Jan 8;14:84-105
pubmed: 29441133
Biochemistry. 1978 Nov 14;17(23):4845-54
pubmed: 718859
Chemistry. 2021 Mar 17;27(16):5142-5159
pubmed: 33411942
Phys Chem Chem Phys. 2018 Jan 24;20(4):2851-2864
pubmed: 29327004
Nat Nanotechnol. 2015 Jun;10(6):547-53
pubmed: 25984834
Phys Chem Chem Phys. 2020 May 13;22(18):9974-9981
pubmed: 32356545
J Mater Chem B. 2015 Jan 14;3(2):184-190
pubmed: 32261938
Chem Sci. 2020 Jan 21;11(9):2494-2503
pubmed: 34084415
Chemistry. 2017 Dec 1;23(67):16924-16940
pubmed: 28815887
Nucleic Acids Res. 2001 Sep 1;29(17):3611-20
pubmed: 11522831
Nucleic Acids Res. 2002 Nov 15;30(22):4918-25
pubmed: 12433995
Bioorg Med Chem Lett. 2008 May 1;18(9):2977-81
pubmed: 18395444
Proc Natl Acad Sci U S A. 1986 Aug;83(15):5355-9
pubmed: 16593731
Nature. 2015 Nov 5;527(7576):78-81
pubmed: 26503039
Int J Mol Sci. 2021 May 06;22(9):
pubmed: 34066402
Chem Commun (Camb). 2017 May 30;53(43):5886-5889
pubmed: 28509921
Org Biomol Chem. 2011 Jan 7;9(1):198-209
pubmed: 21076779
Biochemistry. 1982 Aug 17;21(17):3933-40
pubmed: 7126524
IUCrJ. 2016 Oct 18;3(Pt 6):430-439
pubmed: 27840682
Adv Energy Mater. 2016 Feb;6(4):1501489
pubmed: 27134618
Annu Rev Physiol. 2017 Feb 10;79:93-117
pubmed: 27860833
Inorg Chem. 2005 Jul 11;44(14):5047-59
pubmed: 15998033
J Am Chem Soc. 2017 Jun 28;139(25):8467-8473
pubmed: 28481091
Chemistry. 2021 Feb 5;27(8):2837-2853
pubmed: 33231335
J Med Chem. 2013 Dec 27;56(24):10171-82
pubmed: 24299550
Phys Rev Lett. 1996 Oct 28;77(18):3865-3868
pubmed: 10062328
Chem Asian J. 2018 Jan 4;13(1):55-65
pubmed: 29120080
J Microsc. 2006 Dec;224(Pt 3):213-32
pubmed: 17210054
Org Lett. 2012 Jan 20;14(2):506-9
pubmed: 22220836
Chem Sci. 2016 Mar 1;7(3):1862-1866
pubmed: 29899908
Chem Soc Rev. 2013 Jun 21;42(12):5323-51
pubmed: 23450221
Materials (Basel). 2010 Dec 02;3(12):5130-5142
pubmed: 28883373
Biochemistry. 1981 Mar 31;20(7):1887-92
pubmed: 7225364
Chem Commun (Camb). 2017 Apr 4;53(28):3978-3981
pubmed: 28332658
Chem Rev. 2016 Sep 14;116(17):9994-10034
pubmed: 27128098
Chem Rev. 2005 Aug;105(8):2999-3093
pubmed: 16092826
Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22
pubmed: 18156677
J Am Chem Soc. 2015 Sep 9;137(35):11376-82
pubmed: 26284535
Nat Protoc. 2007;2(12):3166-72
pubmed: 18079716
Cancers (Basel). 2011;3(2):2516-39
pubmed: 23914299
Chem Soc Rev. 2010 Aug;39(8):3181-209
pubmed: 20571680
Chem Commun (Camb). 2015 Apr 30;51(34):7352-5
pubmed: 25820787
Angew Chem Int Ed Engl. 2010 Mar 22;49(13):2349-53
pubmed: 20209540
Chemistry. 2000 Jul 14;6(14):2618-32
pubmed: 10961407
Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12971-12975
pubmed: 30070421