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Photophysical and spectroscopic features of 3,4-dihydro-β-carbolines: a combined experimental and theoretical approach
3,4-Dihydro-β-carbolines (DHβCs) are a set of endogenously synthesized alkaloids spread over a great variety of living species ( e.g. , plants, animals and microorganisms), playing a broad spectrum of biological, biochemical and/or pharmacological roles, in a structure-dependent manner. Addressing u...
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Published in: | Physical chemistry chemical physics : PCCP 2020-09, Vol.22 (36), p.291-2913 |
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creator | Villarruel, Fernando D Denofrio, M. Paula Erra-Balsells, Rosa Wolcan, Ezequiel Cabrerizo, Franco M |
description | 3,4-Dihydro-β-carbolines (DHβCs) are a set of endogenously synthesized alkaloids spread over a great variety of living species (
e.g.
, plants, animals and microorganisms), playing a broad spectrum of biological, biochemical and/or pharmacological roles, in a structure-dependent manner. Addressing unresolved fundamental aspects related to the photophysical properties of DHβCs might help to gain further insights into the molecular basis of the mechanisms of the biological processes where these alkaloids are involved. In this work, the UV-visible spectroscopic features of DHβCs are revisited and they are further analyzed by calculations at the Density Functional Theory (DFT) level. In addition, steady-state and time-resolved fluorescence spectroscopy, as well as quantitative singlet oxygen production analysis is reported. Data obtained herein are discussed in the framework of the potential biological role of these alkaloids.
The spectroscopic and photophysical properties of 3,4-dihydro-β-carboline alkaloids in aqueous were revisited. Absorbing and emitting species present in aqueous solution in the entire pH range were reassigned by DFT calculations. |
doi_str_mv | 10.1039/d0cp03363d |
format | article |
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e.g.
, plants, animals and microorganisms), playing a broad spectrum of biological, biochemical and/or pharmacological roles, in a structure-dependent manner. Addressing unresolved fundamental aspects related to the photophysical properties of DHβCs might help to gain further insights into the molecular basis of the mechanisms of the biological processes where these alkaloids are involved. In this work, the UV-visible spectroscopic features of DHβCs are revisited and they are further analyzed by calculations at the Density Functional Theory (DFT) level. In addition, steady-state and time-resolved fluorescence spectroscopy, as well as quantitative singlet oxygen production analysis is reported. Data obtained herein are discussed in the framework of the potential biological role of these alkaloids.
The spectroscopic and photophysical properties of 3,4-dihydro-β-carboline alkaloids in aqueous were revisited. Absorbing and emitting species present in aqueous solution in the entire pH range were reassigned by DFT calculations.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/d0cp03363d</identifier><identifier>PMID: 32915175</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkaloids ; Biological activity ; Carbolines - chemistry ; Carbolines - radiation effects ; Density Functional Theory ; Fluorescence ; Light ; Microorganisms ; Models, Chemical ; Molecular Structure ; Oxygen production ; Singlet oxygen ; Singlet Oxygen - chemistry ; Spectrophotometry, Ultraviolet</subject><ispartof>Physical chemistry chemical physics : PCCP, 2020-09, Vol.22 (36), p.291-2913</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c399t-bc91f51ed81bb9cdd54001754f9b022e178058e30d9a3fa3e430ff6cba11e16c3</citedby><cites>FETCH-LOGICAL-c399t-bc91f51ed81bb9cdd54001754f9b022e178058e30d9a3fa3e430ff6cba11e16c3</cites><orcidid>0000-0001-9584-4369</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32915175$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Villarruel, Fernando D</creatorcontrib><creatorcontrib>Denofrio, M. Paula</creatorcontrib><creatorcontrib>Erra-Balsells, Rosa</creatorcontrib><creatorcontrib>Wolcan, Ezequiel</creatorcontrib><creatorcontrib>Cabrerizo, Franco M</creatorcontrib><title>Photophysical and spectroscopic features of 3,4-dihydro-β-carbolines: a combined experimental and theoretical approach</title><title>Physical chemistry chemical physics : PCCP</title><addtitle>Phys Chem Chem Phys</addtitle><description>3,4-Dihydro-β-carbolines (DHβCs) are a set of endogenously synthesized alkaloids spread over a great variety of living species (
e.g.
, plants, animals and microorganisms), playing a broad spectrum of biological, biochemical and/or pharmacological roles, in a structure-dependent manner. Addressing unresolved fundamental aspects related to the photophysical properties of DHβCs might help to gain further insights into the molecular basis of the mechanisms of the biological processes where these alkaloids are involved. In this work, the UV-visible spectroscopic features of DHβCs are revisited and they are further analyzed by calculations at the Density Functional Theory (DFT) level. In addition, steady-state and time-resolved fluorescence spectroscopy, as well as quantitative singlet oxygen production analysis is reported. Data obtained herein are discussed in the framework of the potential biological role of these alkaloids.
The spectroscopic and photophysical properties of 3,4-dihydro-β-carboline alkaloids in aqueous were revisited. Absorbing and emitting species present in aqueous solution in the entire pH range were reassigned by DFT calculations.</description><subject>Alkaloids</subject><subject>Biological activity</subject><subject>Carbolines - chemistry</subject><subject>Carbolines - radiation effects</subject><subject>Density Functional Theory</subject><subject>Fluorescence</subject><subject>Light</subject><subject>Microorganisms</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Oxygen production</subject><subject>Singlet oxygen</subject><subject>Singlet Oxygen - chemistry</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kb9OwzAYxC0EoqWwsIOC2BABO3bSmA21_JMq0QHmyLE_K6na2tiJoK_Fg_BMuKSUjckn-ac73X0IHRN8RTDl1wpLiynNqNpBfcIyGnOcs92tHmY9dOD9DGNMUkL3UY8mPKhh2kfv08o0xlYrX0sxj8RSRd6CbJzx0thaRhpE0zrwkdERvWSxqquVcib--oylcKWZ10vwN5GIpFmUQasIPiy4egHLZmPYVGAcNF2Atc4IWR2iPS3mHo427wC93t-9jB7jyfPD0-h2EkvKeROXkhOdElA5KUsulUpZKDFMmeYlThIgwxynOVCsuKBaUGAUa53JUhACJJN0gM473xD71oJviplp3TJEFgljLF8vlQfqoqNk6O0d6MKGBsKtCoKL9cbFGI-mPxuPA3y6sWzLBagt-jtqAM46wHm5_f07UmGVDszJfwz9BjdajoA</recordid><startdate>20200923</startdate><enddate>20200923</enddate><creator>Villarruel, Fernando D</creator><creator>Denofrio, M. Paula</creator><creator>Erra-Balsells, Rosa</creator><creator>Wolcan, Ezequiel</creator><creator>Cabrerizo, Franco M</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9584-4369</orcidid></search><sort><creationdate>20200923</creationdate><title>Photophysical and spectroscopic features of 3,4-dihydro-β-carbolines: a combined experimental and theoretical approach</title><author>Villarruel, Fernando D ; Denofrio, M. Paula ; Erra-Balsells, Rosa ; Wolcan, Ezequiel ; Cabrerizo, Franco M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c399t-bc91f51ed81bb9cdd54001754f9b022e178058e30d9a3fa3e430ff6cba11e16c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkaloids</topic><topic>Biological activity</topic><topic>Carbolines - chemistry</topic><topic>Carbolines - radiation effects</topic><topic>Density Functional Theory</topic><topic>Fluorescence</topic><topic>Light</topic><topic>Microorganisms</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Oxygen production</topic><topic>Singlet oxygen</topic><topic>Singlet Oxygen - chemistry</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Villarruel, Fernando D</creatorcontrib><creatorcontrib>Denofrio, M. Paula</creatorcontrib><creatorcontrib>Erra-Balsells, Rosa</creatorcontrib><creatorcontrib>Wolcan, Ezequiel</creatorcontrib><creatorcontrib>Cabrerizo, Franco M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Villarruel, Fernando D</au><au>Denofrio, M. Paula</au><au>Erra-Balsells, Rosa</au><au>Wolcan, Ezequiel</au><au>Cabrerizo, Franco M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photophysical and spectroscopic features of 3,4-dihydro-β-carbolines: a combined experimental and theoretical approach</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><addtitle>Phys Chem Chem Phys</addtitle><date>2020-09-23</date><risdate>2020</risdate><volume>22</volume><issue>36</issue><spage>291</spage><epage>2913</epage><pages>291-2913</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>3,4-Dihydro-β-carbolines (DHβCs) are a set of endogenously synthesized alkaloids spread over a great variety of living species (
e.g.
, plants, animals and microorganisms), playing a broad spectrum of biological, biochemical and/or pharmacological roles, in a structure-dependent manner. Addressing unresolved fundamental aspects related to the photophysical properties of DHβCs might help to gain further insights into the molecular basis of the mechanisms of the biological processes where these alkaloids are involved. In this work, the UV-visible spectroscopic features of DHβCs are revisited and they are further analyzed by calculations at the Density Functional Theory (DFT) level. In addition, steady-state and time-resolved fluorescence spectroscopy, as well as quantitative singlet oxygen production analysis is reported. Data obtained herein are discussed in the framework of the potential biological role of these alkaloids.
The spectroscopic and photophysical properties of 3,4-dihydro-β-carboline alkaloids in aqueous were revisited. Absorbing and emitting species present in aqueous solution in the entire pH range were reassigned by DFT calculations.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32915175</pmid><doi>10.1039/d0cp03363d</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-9584-4369</orcidid><oa>free_for_read</oa></addata></record> |
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source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
subjects | Alkaloids Biological activity Carbolines - chemistry Carbolines - radiation effects Density Functional Theory Fluorescence Light Microorganisms Models, Chemical Molecular Structure Oxygen production Singlet oxygen Singlet Oxygen - chemistry Spectrophotometry, Ultraviolet |
title | Photophysical and spectroscopic features of 3,4-dihydro-β-carbolines: a combined experimental and theoretical approach |
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