N -Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1
Transient receptor potential cation channel subfamily V member 1 (TRPV1)-targeted compounds were synthesized by modifying the structure of SB366791, a pharmaceutically representative TRPV1 antagonist. To avoid amide-iminol tautomerization, structurally supported -methylated amides ( , 3-alkoxy-subst...
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| creator | Kida, Tatsuya Takahashi, Nobuaki Mori, Masayuki X Sun, Jiacheng H Oota, Hideto Nishino, Kosuke Okauchi, Takashi Ochi, Yuta Kano, Daisuke Tateishi, Ukihide Watanabe, Yasuyoshi Cui, Yilong Mori, Yasuo Doi, Hisashi |
| description | Transient receptor potential cation channel subfamily V member 1 (TRPV1)-targeted compounds were synthesized by modifying the structure of SB366791, a pharmaceutically representative TRPV1 antagonist. To avoid amide-iminol tautomerization, structurally supported
-methylated amides (
, 3-alkoxy-substitued
-meythylamide derivatives of SB366791) were evaluated using a Ca
influx assay, in which cells expressed recombinant TRPV1 in the presence of 1.0 μM capsaicin. The antagonistic activities of
-(3-methoxyphenyl)-
-methyl-4-chlorocinnamamide (2) (RLC-TV1004) and
-{3-(3-fluoropropoxy)phenyl}-
-methyl-4-chlorocinnamamide (4) (RLC-TV1006) were found to be approximately three-fold higher (IC
: 1.3 μM and 1.1 μM, respectively) than that of SB366791 (IC
: 3.7 μM). These results will help reinvigorate the potential of SB366791 in medicinal chemistry applications. The 3-methoxy and 3-fluoroalkoxy substituents were used to obtain radioactive [
C]methoxy- or [
F]fluoroalkoxy-incorporated tracers for
positron emission tomography (PET). Using the
C- or
F-labeled derivatives, explorative PET imaging trials were performed in rats. |
| doi_str_mv | 10.1039/d2md00158f |
| format | Article |
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-methylated amides (
, 3-alkoxy-substitued
-meythylamide derivatives of SB366791) were evaluated using a Ca
influx assay, in which cells expressed recombinant TRPV1 in the presence of 1.0 μM capsaicin. The antagonistic activities of
-(3-methoxyphenyl)-
-methyl-4-chlorocinnamamide (2) (RLC-TV1004) and
-{3-(3-fluoropropoxy)phenyl}-
-methyl-4-chlorocinnamamide (4) (RLC-TV1006) were found to be approximately three-fold higher (IC
: 1.3 μM and 1.1 μM, respectively) than that of SB366791 (IC
: 3.7 μM). These results will help reinvigorate the potential of SB366791 in medicinal chemistry applications. The 3-methoxy and 3-fluoroalkoxy substituents were used to obtain radioactive [
C]methoxy- or [
F]fluoroalkoxy-incorporated tracers for
positron emission tomography (PET). Using the
C- or
F-labeled derivatives, explorative PET imaging trials were performed in rats.</description><identifier>ISSN: 2632-8682</identifier><identifier>ISSN: 2040-2503</identifier><identifier>EISSN: 2632-8682</identifier><identifier>EISSN: 2040-2511</identifier><identifier>DOI: 10.1039/d2md00158f</identifier><identifier>PMID: 36325399</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Amides ; Calcium influx ; Calcium ions ; Capsaicin ; Capsaicin receptors ; Chemistry ; Fluorine isotopes ; Ion channels ; Positron emission ; Positron emission tomography ; Radioactive tracers ; Transient receptor potential proteins</subject><ispartof>MedChemComm, 2022-10, Vol.13 (10), p.1197-1204</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2022</rights><rights>This journal is © The Royal Society of Chemistry 2022 RSC</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c406t-1f5d11fd9a7078efe30e712c8413483da5120e18394294220e874d4970d4bfd23</citedby><cites>FETCH-LOGICAL-c406t-1f5d11fd9a7078efe30e712c8413483da5120e18394294220e874d4970d4bfd23</cites><orcidid>0000-0001-9778-5841</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/PMC9579943/pdf/$$EPDF$$P50$$Gpubmedcentral$$H</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9579943/$$EHTML$$P50$$Gpubmedcentral$$H</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36325399$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kida, Tatsuya</creatorcontrib><creatorcontrib>Takahashi, Nobuaki</creatorcontrib><creatorcontrib>Mori, Masayuki X</creatorcontrib><creatorcontrib>Sun, Jiacheng H</creatorcontrib><creatorcontrib>Oota, Hideto</creatorcontrib><creatorcontrib>Nishino, Kosuke</creatorcontrib><creatorcontrib>Okauchi, Takashi</creatorcontrib><creatorcontrib>Ochi, Yuta</creatorcontrib><creatorcontrib>Kano, Daisuke</creatorcontrib><creatorcontrib>Tateishi, Ukihide</creatorcontrib><creatorcontrib>Watanabe, Yasuyoshi</creatorcontrib><creatorcontrib>Cui, Yilong</creatorcontrib><creatorcontrib>Mori, Yasuo</creatorcontrib><creatorcontrib>Doi, Hisashi</creatorcontrib><title>N -Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1</title><title>MedChemComm</title><addtitle>RSC Med Chem</addtitle><description>Transient receptor potential cation channel subfamily V member 1 (TRPV1)-targeted compounds were synthesized by modifying the structure of SB366791, a pharmaceutically representative TRPV1 antagonist. To avoid amide-iminol tautomerization, structurally supported
-methylated amides (
, 3-alkoxy-substitued
-meythylamide derivatives of SB366791) were evaluated using a Ca
influx assay, in which cells expressed recombinant TRPV1 in the presence of 1.0 μM capsaicin. The antagonistic activities of
-(3-methoxyphenyl)-
-methyl-4-chlorocinnamamide (2) (RLC-TV1004) and
-{3-(3-fluoropropoxy)phenyl}-
-methyl-4-chlorocinnamamide (4) (RLC-TV1006) were found to be approximately three-fold higher (IC
: 1.3 μM and 1.1 μM, respectively) than that of SB366791 (IC
: 3.7 μM). These results will help reinvigorate the potential of SB366791 in medicinal chemistry applications. The 3-methoxy and 3-fluoroalkoxy substituents were used to obtain radioactive [
C]methoxy- or [
F]fluoroalkoxy-incorporated tracers for
positron emission tomography (PET). Using the
C- or
F-labeled derivatives, explorative PET imaging trials were performed in rats.</description><subject>Amides</subject><subject>Calcium influx</subject><subject>Calcium ions</subject><subject>Capsaicin</subject><subject>Capsaicin receptors</subject><subject>Chemistry</subject><subject>Fluorine isotopes</subject><subject>Ion channels</subject><subject>Positron emission</subject><subject>Positron emission tomography</subject><subject>Radioactive tracers</subject><subject>Transient receptor potential proteins</subject><issn>2632-8682</issn><issn>2040-2503</issn><issn>2632-8682</issn><issn>2040-2511</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkV1rFDEUhoMotqy98QdIwBsRxuYkk8nEC0H7YYVWi67ehjTJ7KTMTGqS2bJe-dMbu7VUIZBDzsPLE16EngN5A4TJfUtHSwjwtnuEdmnDaNU2LX38YN5BeyldEkIoB2i4fIp2WNlxJuUu-v0ZV2cu95tBj966KuU4mzxHZ_G3D6xphARsXfRrnf3aJXztc497v-rx8uv5D8B6ynoVJp-yN1ibAvm8eYtzuNbR4vOjJY7a-pCjNi6m8o7XPs168L_cNuEZetLpIbm9u3uBvh8fLQ9OqtMvHz8dvD-tTE2aXEHHLUBnpRZEtK5zjDgB1LQ1sLplVnOgxEHLZE3LKXMraltLQWx90VnKFujdNvdqvhidNW4qToO6in7UcaOC9urfzeR7tQprJbmQsmYl4NVdQAw_Z5eyGn0ybhj05MKcFBUMBEgoNgv08j_0MsxxKt8rFOWSF62mUK-3lIkhpei6exkg6k-36pCeHd52e1zgFw_179G_TbIbyMmefA</recordid><startdate>20221019</startdate><enddate>20221019</enddate><creator>Kida, Tatsuya</creator><creator>Takahashi, Nobuaki</creator><creator>Mori, Masayuki X</creator><creator>Sun, Jiacheng H</creator><creator>Oota, Hideto</creator><creator>Nishino, Kosuke</creator><creator>Okauchi, Takashi</creator><creator>Ochi, Yuta</creator><creator>Kano, Daisuke</creator><creator>Tateishi, Ukihide</creator><creator>Watanabe, Yasuyoshi</creator><creator>Cui, Yilong</creator><creator>Mori, Yasuo</creator><creator>Doi, Hisashi</creator><general>Royal Society of Chemistry</general><general>RSC</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T5</scope><scope>7T7</scope><scope>7TO</scope><scope>7U7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9778-5841</orcidid></search><sort><creationdate>20221019</creationdate><title>N -Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1</title><author>Kida, Tatsuya ; Takahashi, Nobuaki ; Mori, Masayuki X ; Sun, Jiacheng H ; Oota, Hideto ; Nishino, Kosuke ; Okauchi, Takashi ; Ochi, Yuta ; Kano, Daisuke ; Tateishi, Ukihide ; Watanabe, Yasuyoshi ; Cui, Yilong ; Mori, Yasuo ; Doi, Hisashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-1f5d11fd9a7078efe30e712c8413483da5120e18394294220e874d4970d4bfd23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amides</topic><topic>Calcium influx</topic><topic>Calcium ions</topic><topic>Capsaicin</topic><topic>Capsaicin receptors</topic><topic>Chemistry</topic><topic>Fluorine isotopes</topic><topic>Ion channels</topic><topic>Positron emission</topic><topic>Positron emission tomography</topic><topic>Radioactive tracers</topic><topic>Transient receptor potential proteins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kida, Tatsuya</creatorcontrib><creatorcontrib>Takahashi, Nobuaki</creatorcontrib><creatorcontrib>Mori, Masayuki X</creatorcontrib><creatorcontrib>Sun, Jiacheng H</creatorcontrib><creatorcontrib>Oota, Hideto</creatorcontrib><creatorcontrib>Nishino, Kosuke</creatorcontrib><creatorcontrib>Okauchi, Takashi</creatorcontrib><creatorcontrib>Ochi, Yuta</creatorcontrib><creatorcontrib>Kano, Daisuke</creatorcontrib><creatorcontrib>Tateishi, Ukihide</creatorcontrib><creatorcontrib>Watanabe, Yasuyoshi</creatorcontrib><creatorcontrib>Cui, Yilong</creatorcontrib><creatorcontrib>Mori, Yasuo</creatorcontrib><creatorcontrib>Doi, Hisashi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Immunology Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>MedChemComm</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kida, Tatsuya</au><au>Takahashi, Nobuaki</au><au>Mori, Masayuki X</au><au>Sun, Jiacheng H</au><au>Oota, Hideto</au><au>Nishino, Kosuke</au><au>Okauchi, Takashi</au><au>Ochi, Yuta</au><au>Kano, Daisuke</au><au>Tateishi, Ukihide</au><au>Watanabe, Yasuyoshi</au><au>Cui, Yilong</au><au>Mori, Yasuo</au><au>Doi, Hisashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N -Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1</atitle><jtitle>MedChemComm</jtitle><addtitle>RSC Med Chem</addtitle><date>2022-10-19</date><risdate>2022</risdate><volume>13</volume><issue>10</issue><spage>1197</spage><epage>1204</epage><pages>1197-1204</pages><issn>2632-8682</issn><issn>2040-2503</issn><eissn>2632-8682</eissn><eissn>2040-2511</eissn><abstract>Transient receptor potential cation channel subfamily V member 1 (TRPV1)-targeted compounds were synthesized by modifying the structure of SB366791, a pharmaceutically representative TRPV1 antagonist. To avoid amide-iminol tautomerization, structurally supported
-methylated amides (
, 3-alkoxy-substitued
-meythylamide derivatives of SB366791) were evaluated using a Ca
influx assay, in which cells expressed recombinant TRPV1 in the presence of 1.0 μM capsaicin. The antagonistic activities of
-(3-methoxyphenyl)-
-methyl-4-chlorocinnamamide (2) (RLC-TV1004) and
-{3-(3-fluoropropoxy)phenyl}-
-methyl-4-chlorocinnamamide (4) (RLC-TV1006) were found to be approximately three-fold higher (IC
: 1.3 μM and 1.1 μM, respectively) than that of SB366791 (IC
: 3.7 μM). These results will help reinvigorate the potential of SB366791 in medicinal chemistry applications. The 3-methoxy and 3-fluoroalkoxy substituents were used to obtain radioactive [
C]methoxy- or [
F]fluoroalkoxy-incorporated tracers for
positron emission tomography (PET). Using the
C- or
F-labeled derivatives, explorative PET imaging trials were performed in rats.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36325399</pmid><doi>10.1039/d2md00158f</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-9778-5841</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | MedChemComm, 2022-10, Vol.13 (10), p.1197-1204 |
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| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9579943 |
| source | Royal Society Of Chemistry Journals 2008-; PubMed Central |
| subjects | Amides Calcium influx Calcium ions Capsaicin Capsaicin receptors Chemistry Fluorine isotopes Ion channels Positron emission Positron emission tomography Radioactive tracers Transient receptor potential proteins |
| title | N -Methylamide-structured SB366791 derivatives with high TRPV1 antagonistic activity: toward PET radiotracers to visualize TRPV1 |
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