Loading…
An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing
A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA ) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirorn...
Saved in:
| Published in: | Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (21), p.3833 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3 |
| container_end_page | |
| container_issue | 21 |
| container_start_page | 3833 |
| container_title | Molecules (Basel, Switzerland) |
| container_volume | 24 |
| creator | Diana, Rosita Panunzi, Barbara Tuzi, Angela Piotto, Stefano Concilio, Simona Caruso, Ugo |
| description | A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA
) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye. |
| doi_str_mv | 10.3390/molecules24213833 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_4d2b0bdd893245a29f52c8b720853e69</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_4d2b0bdd893245a29f52c8b720853e69</doaj_id><sourcerecordid>2548942734</sourcerecordid><originalsourceid>FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3</originalsourceid><addsrcrecordid>eNplkltrFDEUx4Motq5-AF9kwBdfRnOdSV6EZbG2ULDg5TXkcrI7S2ayJjPC-umNbi2tQuCE5H9-_M8FoZcEv2VM4XdjiuCWCIVySphk7BE6J5zilmGuHt-7n6FnpewxpoQT8RSdMdIJqmR3jr6tp2Y9HnZDPXFwzc0xD36Y0jG2u6PP5meaoLnJyUITUm42KaY8jDDnqjWTby7ikjIUB5OD5nDZfIapDNP2OXoSTCzw4jau0NeLD182l-31p49Xm_V164RQc8sh-AA9A6-U89RbIpQBAdYEjIULlleT3nWkCyB70veWWsCdCLL3vieBrdDVieuT2etDtWbyUScz6D8PKW-1yfPgImjuqcXWe6kY5cJQFQR10vYUS8GgU5X1_sQ6LHYEX0uas4kPoA9_pmGnt-mH7mTHeYWs0JtbQE7fFyizHofamRjNBGkpmjKsBO472Vfp63-k-7TkqbZKU8Gl4rRnvKrISeVyKiVDuDNDsP69Afq_Dag5r-5XcZfxd-TsF8yqsGs</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2548942734</pqid></control><display><type>article</type><title>An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing</title><source>Publicly Available Content Database</source><source>PubMed Central</source><creator>Diana, Rosita ; Panunzi, Barbara ; Tuzi, Angela ; Piotto, Stefano ; Concilio, Simona ; Caruso, Ugo</creator><creatorcontrib>Diana, Rosita ; Panunzi, Barbara ; Tuzi, Angela ; Piotto, Stefano ; Concilio, Simona ; Caruso, Ugo</creatorcontrib><description>A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA
) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules24213833</identifier><identifier>PMID: 31652986</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Ammonium ; Chromophores ; Colorimetry ; Ethanol ; Fluorescence ; Fluorescent Dyes - chemical synthesis ; Fluorescent Dyes - chemistry ; fluorophore/chromophore probe ; Hydrazones ; Hydrazones - chemical synthesis ; Hydrazones - chemistry ; Hydrogen-Ion Concentration ; Hydrophobicity ; Ligands ; Lipids ; Membranes ; molecular dynamic simulation ; Molecular dynamics ; Molecular Dynamics Simulation ; Molecular Structure ; ph sensor ; pH sensors ; Physiology ; Polarity ; Quantum dots ; Sensors ; Single crystals ; Solvents ; Spectral sensitivity ; Spectrometry, Fluorescence</subject><ispartof>Molecules (Basel, Switzerland), 2019-10, Vol.24 (21), p.3833</ispartof><rights>2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2019 by the authors. 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3</citedby><cites>FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3</cites><orcidid>0000-0002-0572-5436 ; 0000-0002-3102-1918 ; 0000-0002-1461-9301 ; 0000-0001-9253-0794</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2548942734/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2548942734?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31652986$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Diana, Rosita</creatorcontrib><creatorcontrib>Panunzi, Barbara</creatorcontrib><creatorcontrib>Tuzi, Angela</creatorcontrib><creatorcontrib>Piotto, Stefano</creatorcontrib><creatorcontrib>Concilio, Simona</creatorcontrib><creatorcontrib>Caruso, Ugo</creatorcontrib><title>An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA
) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye.</description><subject>Ammonium</subject><subject>Chromophores</subject><subject>Colorimetry</subject><subject>Ethanol</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemical synthesis</subject><subject>Fluorescent Dyes - chemistry</subject><subject>fluorophore/chromophore probe</subject><subject>Hydrazones</subject><subject>Hydrazones - chemical synthesis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Hydrophobicity</subject><subject>Ligands</subject><subject>Lipids</subject><subject>Membranes</subject><subject>molecular dynamic simulation</subject><subject>Molecular dynamics</subject><subject>Molecular Dynamics Simulation</subject><subject>Molecular Structure</subject><subject>ph sensor</subject><subject>pH sensors</subject><subject>Physiology</subject><subject>Polarity</subject><subject>Quantum dots</subject><subject>Sensors</subject><subject>Single crystals</subject><subject>Solvents</subject><subject>Spectral sensitivity</subject><subject>Spectrometry, Fluorescence</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplkltrFDEUx4Motq5-AF9kwBdfRnOdSV6EZbG2ULDg5TXkcrI7S2ayJjPC-umNbi2tQuCE5H9-_M8FoZcEv2VM4XdjiuCWCIVySphk7BE6J5zilmGuHt-7n6FnpewxpoQT8RSdMdIJqmR3jr6tp2Y9HnZDPXFwzc0xD36Y0jG2u6PP5meaoLnJyUITUm42KaY8jDDnqjWTby7ikjIUB5OD5nDZfIapDNP2OXoSTCzw4jau0NeLD182l-31p49Xm_V164RQc8sh-AA9A6-U89RbIpQBAdYEjIULlleT3nWkCyB70veWWsCdCLL3vieBrdDVieuT2etDtWbyUScz6D8PKW-1yfPgImjuqcXWe6kY5cJQFQR10vYUS8GgU5X1_sQ6LHYEX0uas4kPoA9_pmGnt-mH7mTHeYWs0JtbQE7fFyizHofamRjNBGkpmjKsBO472Vfp63-k-7TkqbZKU8Gl4rRnvKrISeVyKiVDuDNDsP69Afq_Dag5r-5XcZfxd-TsF8yqsGs</recordid><startdate>20191024</startdate><enddate>20191024</enddate><creator>Diana, Rosita</creator><creator>Panunzi, Barbara</creator><creator>Tuzi, Angela</creator><creator>Piotto, Stefano</creator><creator>Concilio, Simona</creator><creator>Caruso, Ugo</creator><general>MDPI AG</general><general>MDPI</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-0572-5436</orcidid><orcidid>https://orcid.org/0000-0002-3102-1918</orcidid><orcidid>https://orcid.org/0000-0002-1461-9301</orcidid><orcidid>https://orcid.org/0000-0001-9253-0794</orcidid></search><sort><creationdate>20191024</creationdate><title>An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing</title><author>Diana, Rosita ; Panunzi, Barbara ; Tuzi, Angela ; Piotto, Stefano ; Concilio, Simona ; Caruso, Ugo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Ammonium</topic><topic>Chromophores</topic><topic>Colorimetry</topic><topic>Ethanol</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemical synthesis</topic><topic>Fluorescent Dyes - chemistry</topic><topic>fluorophore/chromophore probe</topic><topic>Hydrazones</topic><topic>Hydrazones - chemical synthesis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Hydrophobicity</topic><topic>Ligands</topic><topic>Lipids</topic><topic>Membranes</topic><topic>molecular dynamic simulation</topic><topic>Molecular dynamics</topic><topic>Molecular Dynamics Simulation</topic><topic>Molecular Structure</topic><topic>ph sensor</topic><topic>pH sensors</topic><topic>Physiology</topic><topic>Polarity</topic><topic>Quantum dots</topic><topic>Sensors</topic><topic>Single crystals</topic><topic>Solvents</topic><topic>Spectral sensitivity</topic><topic>Spectrometry, Fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Diana, Rosita</creatorcontrib><creatorcontrib>Panunzi, Barbara</creatorcontrib><creatorcontrib>Tuzi, Angela</creatorcontrib><creatorcontrib>Piotto, Stefano</creatorcontrib><creatorcontrib>Concilio, Simona</creatorcontrib><creatorcontrib>Caruso, Ugo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health and Medical</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Diana, Rosita</au><au>Panunzi, Barbara</au><au>Tuzi, Angela</au><au>Piotto, Stefano</au><au>Concilio, Simona</au><au>Caruso, Ugo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2019-10-24</date><risdate>2019</risdate><volume>24</volume><issue>21</issue><spage>3833</spage><pages>3833-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA
) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>31652986</pmid><doi>10.3390/molecules24213833</doi><orcidid>https://orcid.org/0000-0002-0572-5436</orcidid><orcidid>https://orcid.org/0000-0002-3102-1918</orcidid><orcidid>https://orcid.org/0000-0002-1461-9301</orcidid><orcidid>https://orcid.org/0000-0001-9253-0794</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1420-3049 |
| ispartof | Molecules (Basel, Switzerland), 2019-10, Vol.24 (21), p.3833 |
| issn | 1420-3049 1420-3049 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_4d2b0bdd893245a29f52c8b720853e69 |
| source | Publicly Available Content Database; PubMed Central |
| subjects | Ammonium Chromophores Colorimetry Ethanol Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry fluorophore/chromophore probe Hydrazones Hydrazones - chemical synthesis Hydrazones - chemistry Hydrogen-Ion Concentration Hydrophobicity Ligands Lipids Membranes molecular dynamic simulation Molecular dynamics Molecular Dynamics Simulation Molecular Structure ph sensor pH sensors Physiology Polarity Quantum dots Sensors Single crystals Solvents Spectral sensitivity Spectrometry, Fluorescence |
| title | An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T20%3A26%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20Amphiphilic%20Pyridinoyl-hydrazone%20Probe%20for%20Colorimetric%20and%20Fluorescence%20pH%20Sensing&rft.jtitle=Molecules%20(Basel,%20Switzerland)&rft.au=Diana,%20Rosita&rft.date=2019-10-24&rft.volume=24&rft.issue=21&rft.spage=3833&rft.pages=3833-&rft.issn=1420-3049&rft.eissn=1420-3049&rft_id=info:doi/10.3390/molecules24213833&rft_dat=%3Cproquest_doaj_%3E2548942734%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c559t-4efdfe73ed99cd2db159ae5ebaf005cfb4986dc616fe87177b2be065f87dd71f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2548942734&rft_id=info:pmid/31652986&rfr_iscdi=true |