Cargando…

Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor

Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil,...

Descripción completa

Detalles Bibliográficos
Autores principales: Idzik, Krzysztof Ryszard, Cywinski, Piotr J., Cranfield, Charles G., Mohr, Gerhard J., Beckert, Rainer
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120969/
https://www.ncbi.nlm.nih.gov/pubmed/21222147
http://dx.doi.org/10.1007/s10895-010-0798-7
_version_ 1782206779546927104
author Idzik, Krzysztof Ryszard
Cywinski, Piotr J.
Cranfield, Charles G.
Mohr, Gerhard J.
Beckert, Rainer
author_facet Idzik, Krzysztof Ryszard
Cywinski, Piotr J.
Cranfield, Charles G.
Mohr, Gerhard J.
Beckert, Rainer
author_sort Idzik, Krzysztof Ryszard
collection PubMed
description Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson–Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern–Volmer equation and represented by Stern–Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs.
format Online
Article
Text
id pubmed-3120969
institution National Center for Biotechnology Information
language English
publishDate 2011
publisher Springer US
record_format MEDLINE/PubMed
spelling pubmed-31209692011-07-14 Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor Idzik, Krzysztof Ryszard Cywinski, Piotr J. Cranfield, Charles G. Mohr, Gerhard J. Beckert, Rainer J Fluoresc Original Paper Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson–Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern–Volmer equation and represented by Stern–Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs. Springer US 2011-01-11 2011 /pmc/articles/PMC3120969/ /pubmed/21222147 http://dx.doi.org/10.1007/s10895-010-0798-7 Text en © The Author(s) 2011 https://creativecommons.org/licenses/by-nc/4.0/ This article is distributed under the terms of the Creative Commons Attribution Noncommercial License which permits any noncommercial use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.
spellingShingle Original Paper
Idzik, Krzysztof Ryszard
Cywinski, Piotr J.
Cranfield, Charles G.
Mohr, Gerhard J.
Beckert, Rainer
Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title_full Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title_fullStr Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title_full_unstemmed Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title_short Molecular Recognition of the Antiretroviral Drug Abacavir: Towards the Development of a Novel Carbazole-Based Fluorosensor
title_sort molecular recognition of the antiretroviral drug abacavir: towards the development of a novel carbazole-based fluorosensor
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120969/
https://www.ncbi.nlm.nih.gov/pubmed/21222147
http://dx.doi.org/10.1007/s10895-010-0798-7
work_keys_str_mv AT idzikkrzysztofryszard molecularrecognitionoftheantiretroviraldrugabacavirtowardsthedevelopmentofanovelcarbazolebasedfluorosensor
AT cywinskipiotrj molecularrecognitionoftheantiretroviraldrugabacavirtowardsthedevelopmentofanovelcarbazolebasedfluorosensor
AT cranfieldcharlesg molecularrecognitionoftheantiretroviraldrugabacavirtowardsthedevelopmentofanovelcarbazolebasedfluorosensor
AT mohrgerhardj molecularrecognitionoftheantiretroviraldrugabacavirtowardsthedevelopmentofanovelcarbazolebasedfluorosensor
AT beckertrainer molecularrecognitionoftheantiretroviraldrugabacavirtowardsthedevelopmentofanovelcarbazolebasedfluorosensor