Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazol...
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Autor*in:	Eduardo Soriano [verfasserIn] Cory Holder [verfasserIn] Andrew Levitz [verfasserIn] Maged Henary [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2015

Schlagwörter:	cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 21(2015), 1, p 23
Übergeordnetes Werk:	volume:21 ; year:2015 ; number:1, p 23

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules21010023

Katalog-ID:	DOAJ01012814X

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520			\|a Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
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spelling	10.3390/molecules21010023 doi (DE-627)DOAJ01012814X (DE-599)DOAJ8a60bdc96256407eaa8808b5a7eec060 DE-627 ger DE-627 rakwb eng QD241-441 Eduardo Soriano verfasserin aut Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form. cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves Organic chemistry Cory Holder verfasserin aut Andrew Levitz verfasserin aut Maged Henary verfasserin aut In Molecules MDPI AG, 2003 21(2015), 1, p 23 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:21 year:2015 number:1, p 23 https://doi.org/10.3390/molecules21010023 kostenfrei https://doaj.org/article/8a60bdc96256407eaa8808b5a7eec060 kostenfrei http://www.mdpi.com/1420-3049/21/1/23 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 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_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 21 2015 1, p 23
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allfieldsGer	10.3390/molecules21010023 doi (DE-627)DOAJ01012814X (DE-599)DOAJ8a60bdc96256407eaa8808b5a7eec060 DE-627 ger DE-627 rakwb eng QD241-441 Eduardo Soriano verfasserin aut Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form. cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves Organic chemistry Cory Holder verfasserin aut Andrew Levitz verfasserin aut Maged Henary verfasserin aut In Molecules MDPI AG, 2003 21(2015), 1, p 23 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:21 year:2015 number:1, p 23 https://doi.org/10.3390/molecules21010023 kostenfrei https://doaj.org/article/8a60bdc96256407eaa8808b5a7eec060 kostenfrei http://www.mdpi.com/1420-3049/21/1/23 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 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_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 21 2015 1, p 23
allfieldsSound	10.3390/molecules21010023 doi (DE-627)DOAJ01012814X (DE-599)DOAJ8a60bdc96256407eaa8808b5a7eec060 DE-627 ger DE-627 rakwb eng QD241-441 Eduardo Soriano verfasserin aut Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form. cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves Organic chemistry Cory Holder verfasserin aut Andrew Levitz verfasserin aut Maged Henary verfasserin aut In Molecules MDPI AG, 2003 21(2015), 1, p 23 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:21 year:2015 number:1, p 23 https://doi.org/10.3390/molecules21010023 kostenfrei https://doaj.org/article/8a60bdc96256407eaa8808b5a7eec060 kostenfrei http://www.mdpi.com/1420-3049/21/1/23 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 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_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 21 2015 1, p 23
language	English
source	In Molecules 21(2015), 1, p 23 volume:21 year:2015 number:1, p 23
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institution	findex.gbv.de
topic_facet	cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves Organic chemistry
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authorswithroles_txt_mv	Eduardo Soriano @@aut@@ Cory Holder @@aut@@ Andrew Levitz @@aut@@ Maged Henary @@aut@@
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callnumber-first	Q - Science
author	Eduardo Soriano
spellingShingle	Eduardo Soriano misc QD241-441 misc cyanine dye misc unsymmetrical misc synthesis misc optical properties misc DFT calculations misc DNA grooves misc Organic chemistry Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties
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topic_title	QD241-441 Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties cyanine dye unsymmetrical synthesis optical properties DFT calculations DNA grooves
topic	misc QD241-441 misc cyanine dye misc unsymmetrical misc synthesis misc optical properties misc DFT calculations misc DNA grooves misc Organic chemistry
topic_unstemmed	misc QD241-441 misc cyanine dye misc unsymmetrical misc synthesis misc optical properties misc DFT calculations misc DNA grooves misc Organic chemistry
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title	Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties
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title_sort	benz[c,d]indolium-containing monomethine cyanine dyes: synthesis and photophysical properties
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title_auth	Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties
abstract	Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
abstractGer	Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
abstract_unstemmed	Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
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title_short	Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties
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