A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent
In the present study, fluorogenic coumarin-based probes ( 1-3 ) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of 2b and 3 in different solvents were studied, and a considera...
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| Veröffentlicht in: | RSC advances 2023-03, Vol.13 (15), p.9811-9823 |
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| creator | Hosseinjani-Pirdehi, Hamide Amigh, Soode Mohajeri, Afshan Nazeri, Elahe Taheri, Amir Majidzadeh-A, Keivan Mohammadpour, Zahra Esmaeili, Rezvan |
| description | In the present study, fluorogenic coumarin-based probes (
1-3
) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of
2b
and
3
in different solvents were studied, and a considerable solvatochromic effect was observed. The sensitivity of chemosensors
2b
and
3
toward various cations and anions was investigated. It was revealed that compound
3
had a distinct selectivity toward Sn
2+
, possibly
via
a chelation enhanced quenching mechanism. The fluorescence signal was quenched over the concentration range of 6.6-120 μM, with an LOD value of 3.89 μM. The cytotoxicity evaluation of
3
against breast cancer cell lines demonstrated that the chemosensor was nontoxic and could be used successfully in cellular imaging. The probe responded to tin ions not only
via
fluorescence quenching, but also through colorimetric signal change. The change in optical properties was observed in ambient conditions and inside living cells.
A fluorogenic and colorimetric coumarin-based probe was synthesized and used for sensing Sn
2+
inside and ouside of living cells. |
| doi_str_mv | 10.1039/d2ra07884h |
| format | Article |
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1-3
) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of
2b
and
3
in different solvents were studied, and a considerable solvatochromic effect was observed. The sensitivity of chemosensors
2b
and
3
toward various cations and anions was investigated. It was revealed that compound
3
had a distinct selectivity toward Sn
2+
, possibly
via
a chelation enhanced quenching mechanism. The fluorescence signal was quenched over the concentration range of 6.6-120 μM, with an LOD value of 3.89 μM. The cytotoxicity evaluation of
3
against breast cancer cell lines demonstrated that the chemosensor was nontoxic and could be used successfully in cellular imaging. The probe responded to tin ions not only
via
fluorescence quenching, but also through colorimetric signal change. The change in optical properties was observed in ambient conditions and inside living cells.
A fluorogenic and colorimetric coumarin-based probe was synthesized and used for sensing Sn
2+
inside and ouside of living cells.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d2ra07884h</identifier><identifier>PMID: 36994144</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chelation ; Chemical sensors ; Chemistry ; Chemoreceptors ; Coumarin ; Emission analysis ; Fluorescence ; Optical properties ; Quenching ; Tin ; Toxicity</subject><ispartof>RSC advances, 2023-03, Vol.13 (15), p.9811-9823</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-76916533e978a004a4df12f4dc99f81ae16b63ba9788aa90c500f0d52e26d4c03</citedby><cites>FETCH-LOGICAL-c429t-76916533e978a004a4df12f4dc99f81ae16b63ba9788aa90c500f0d52e26d4c03</cites><orcidid>0000-0001-9308-0158 ; 0000-0002-1857-6687 ; 0000-0002-7384-7187</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10041825/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10041825/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36994144$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hosseinjani-Pirdehi, Hamide</creatorcontrib><creatorcontrib>Amigh, Soode</creatorcontrib><creatorcontrib>Mohajeri, Afshan</creatorcontrib><creatorcontrib>Nazeri, Elahe</creatorcontrib><creatorcontrib>Taheri, Amir</creatorcontrib><creatorcontrib>Majidzadeh-A, Keivan</creatorcontrib><creatorcontrib>Mohammadpour, Zahra</creatorcontrib><creatorcontrib>Esmaeili, Rezvan</creatorcontrib><title>A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>In the present study, fluorogenic coumarin-based probes (
1-3
) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of
2b
and
3
in different solvents were studied, and a considerable solvatochromic effect was observed. The sensitivity of chemosensors
2b
and
3
toward various cations and anions was investigated. It was revealed that compound
3
had a distinct selectivity toward Sn
2+
, possibly
via
a chelation enhanced quenching mechanism. The fluorescence signal was quenched over the concentration range of 6.6-120 μM, with an LOD value of 3.89 μM. The cytotoxicity evaluation of
3
against breast cancer cell lines demonstrated that the chemosensor was nontoxic and could be used successfully in cellular imaging. The probe responded to tin ions not only
via
fluorescence quenching, but also through colorimetric signal change. The change in optical properties was observed in ambient conditions and inside living cells.
A fluorogenic and colorimetric coumarin-based probe was synthesized and used for sensing Sn
2+
inside and ouside of living cells.</description><subject>Chelation</subject><subject>Chemical sensors</subject><subject>Chemistry</subject><subject>Chemoreceptors</subject><subject>Coumarin</subject><subject>Emission analysis</subject><subject>Fluorescence</subject><subject>Optical properties</subject><subject>Quenching</subject><subject>Tin</subject><subject>Toxicity</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdks1LAzEQxYMoWtSLdyXgRYTVJJtNNycpfkNB8OMcpkm2XdlNatIV_O_NWq3VXBLe_HjzhglCB5ScUZLLc8MCkGFZ8tkGGjDCRcaIkJtr7x20H-MrSUcUlAm6jXZyISWnnA-QHmHtuxZC7bIJRGtw1XQ-2KitW2A9s62P1kUfMEQM-Mnh2plaw6JXnEnSH942TddAwHUL09pNMUyTvIe2Kmii3f--d9HLzfXz5V02fri9vxyNM82ZXGRDIako8tzKYQmEcOCmoqziRktZlRQsFRORTyCVSwBJdEFIRUzBLBOGa5Lvooul77ybtNb0iQI0ah5SmvChPNTqb8XVMzX174qmbrRkRXI4-XYI_q2zcaHaOvZDgbO-i4oNJZOkyAlP6PE_9NV3waX5eqqQjMqiNzxdUjr4GIOtVmkoUf3-1BV7HH3t7y7BR-v5V-jPthJwuARC1Kvq7wfIPwGHRp_y</recordid><startdate>20230327</startdate><enddate>20230327</enddate><creator>Hosseinjani-Pirdehi, Hamide</creator><creator>Amigh, Soode</creator><creator>Mohajeri, Afshan</creator><creator>Nazeri, Elahe</creator><creator>Taheri, Amir</creator><creator>Majidzadeh-A, Keivan</creator><creator>Mohammadpour, Zahra</creator><creator>Esmaeili, Rezvan</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9308-0158</orcidid><orcidid>https://orcid.org/0000-0002-1857-6687</orcidid><orcidid>https://orcid.org/0000-0002-7384-7187</orcidid></search><sort><creationdate>20230327</creationdate><title>A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent</title><author>Hosseinjani-Pirdehi, Hamide ; Amigh, Soode ; Mohajeri, Afshan ; Nazeri, Elahe ; Taheri, Amir ; Majidzadeh-A, Keivan ; Mohammadpour, Zahra ; Esmaeili, Rezvan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-76916533e978a004a4df12f4dc99f81ae16b63ba9788aa90c500f0d52e26d4c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Chelation</topic><topic>Chemical sensors</topic><topic>Chemistry</topic><topic>Chemoreceptors</topic><topic>Coumarin</topic><topic>Emission analysis</topic><topic>Fluorescence</topic><topic>Optical properties</topic><topic>Quenching</topic><topic>Tin</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hosseinjani-Pirdehi, Hamide</creatorcontrib><creatorcontrib>Amigh, Soode</creatorcontrib><creatorcontrib>Mohajeri, Afshan</creatorcontrib><creatorcontrib>Nazeri, Elahe</creatorcontrib><creatorcontrib>Taheri, Amir</creatorcontrib><creatorcontrib>Majidzadeh-A, Keivan</creatorcontrib><creatorcontrib>Mohammadpour, Zahra</creatorcontrib><creatorcontrib>Esmaeili, Rezvan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hosseinjani-Pirdehi, Hamide</au><au>Amigh, Soode</au><au>Mohajeri, Afshan</au><au>Nazeri, Elahe</au><au>Taheri, Amir</au><au>Majidzadeh-A, Keivan</au><au>Mohammadpour, Zahra</au><au>Esmaeili, Rezvan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2023-03-27</date><risdate>2023</risdate><volume>13</volume><issue>15</issue><spage>9811</spage><epage>9823</epage><pages>9811-9823</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>In the present study, fluorogenic coumarin-based probes (
1-3
) through condensation of 4-hydroxy coumarin with malondialdehyde bis(diethyl acetal)/triethyl orthoformate were prepared. The absorption and fluorescence emission properties of
2b
and
3
in different solvents were studied, and a considerable solvatochromic effect was observed. The sensitivity of chemosensors
2b
and
3
toward various cations and anions was investigated. It was revealed that compound
3
had a distinct selectivity toward Sn
2+
, possibly
via
a chelation enhanced quenching mechanism. The fluorescence signal was quenched over the concentration range of 6.6-120 μM, with an LOD value of 3.89 μM. The cytotoxicity evaluation of
3
against breast cancer cell lines demonstrated that the chemosensor was nontoxic and could be used successfully in cellular imaging. The probe responded to tin ions not only
via
fluorescence quenching, but also through colorimetric signal change. The change in optical properties was observed in ambient conditions and inside living cells.
A fluorogenic and colorimetric coumarin-based probe was synthesized and used for sensing Sn
2+
inside and ouside of living cells.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36994144</pmid><doi>10.1039/d2ra07884h</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-9308-0158</orcidid><orcidid>https://orcid.org/0000-0002-1857-6687</orcidid><orcidid>https://orcid.org/0000-0002-7384-7187</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Chelation Chemical sensors Chemistry Chemoreceptors Coumarin Emission analysis Fluorescence Optical properties Quenching Tin Toxicity |
| title | A coumarin-based fluorescent chemosensor as a Sn indicator and a fluorescent cellular imaging agent |
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