4‑(Pyrazolyl)benzenesulfonamide Ureas as Carbonic Anhydrases Inhibitors and Hypoxia-Mediated Chemo-Sensitizing Agents in Colorectal Cancer Cells
Hypoxia in tumors contributes to chemotherapy resistance, worsened by acidosis driven by carbonic anhydrases (hCA IX and XII). Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas (SH7a–t) were develo...
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| Veröffentlicht in: | Journal of medicinal chemistry 2024-11, Vol.67 (22), p.20438-20454 |
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| creator | Eldehna, Wagdy M. Fares, Mohamed Bonardi, Alessandro Avgenikos, Moscos Baselious, Fady Schmidt, Matthias Al-Warhi, Tarfah Abdel-Aziz, Hatem A. Rennert, Robert Peat, Thomas S. Supuran, Claudiu T. Wessjohann, Ludger A. Ibrahim, Hany S. |
| description | Hypoxia in tumors contributes to chemotherapy resistance, worsened by acidosis driven by carbonic anhydrases (hCA IX and XII). Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas (SH7a–t) were developed and evaluated for their inhibitory activity against hCA IX and XII. They showed promising results (hCA IX: K I = 15.9–67.6 nM, hCA XII: K I = 16.7–65.7 nM). Particularly, SH7s demonstrated outstanding activity (K Is = 15.9 nM for hCA IX and 55.2 nM for hCA XII) and minimal off-target kinase inhibition over a panel of 258 kinases. In NCI anticancer screening, SH7s exhibited broad-spectrum activity with an effective growth inhibition full panel GI50 (MG-MID) value of 3.5 μM and a subpanel GI50 (MG-MID) range of 2.4–6.3 μM. Furthermore, SH7s enhanced the efficacy of Taxol and 5-fluorouracil in cotreatment regimens under hypoxic conditions in HCT-116 colorectal cancer cells, indicating its potential as a promising anticancer agent. |
| doi_str_mv | 10.1021/acs.jmedchem.4c01894 |
| format | Article |
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Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas (SH7a–t) were developed and evaluated for their inhibitory activity against hCA IX and XII. They showed promising results (hCA IX: K I = 15.9–67.6 nM, hCA XII: K I = 16.7–65.7 nM). Particularly, SH7s demonstrated outstanding activity (K Is = 15.9 nM for hCA IX and 55.2 nM for hCA XII) and minimal off-target kinase inhibition over a panel of 258 kinases. In NCI anticancer screening, SH7s exhibited broad-spectrum activity with an effective growth inhibition full panel GI50 (MG-MID) value of 3.5 μM and a subpanel GI50 (MG-MID) range of 2.4–6.3 μM. Furthermore, SH7s enhanced the efficacy of Taxol and 5-fluorouracil in cotreatment regimens under hypoxic conditions in HCT-116 colorectal cancer cells, indicating its potential as a promising anticancer agent.</description><identifier>ISSN: 0022-2623</identifier><identifier>ISSN: 1520-4804</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/acs.jmedchem.4c01894</identifier><identifier>PMID: 39550697</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antigens, Neoplasm ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Benzenesulfonamides ; Carbonic Anhydrase Inhibitors - chemical synthesis ; Carbonic Anhydrase Inhibitors - chemistry ; Carbonic Anhydrase Inhibitors - pharmacology ; Carbonic Anhydrase IX - antagonists & inhibitors ; Carbonic Anhydrase IX - metabolism ; Carbonic Anhydrases - metabolism ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Colorectal Neoplasms - drug therapy ; Colorectal Neoplasms - pathology ; Drug Screening Assays, Antitumor ; Humans ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Structure-Activity Relationship ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry ; Sulfonamides - pharmacology ; Urea - analogs & derivatives ; Urea - chemistry ; Urea - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2024-11, Vol.67 (22), p.20438-20454</ispartof><rights>2024 The Authors. Published by American Chemical Society</rights><rights>2024 The Authors. Published by American Chemical Society 2024 The Authors</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a329t-d07313ca5f611bdb0b4d8e364328e6f7973a0641d020570624b97c4ae264001c3</cites><orcidid>0000-0002-6488-0831 ; 0000-0001-6996-4017 ; 0000-0003-4262-0323 ; 0000-0002-1048-4059 ; 0000-0003-0589-3955 ; 0000-0003-2060-8235</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.4c01894$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jmedchem.4c01894$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39550697$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Eldehna, Wagdy M.</creatorcontrib><creatorcontrib>Fares, Mohamed</creatorcontrib><creatorcontrib>Bonardi, Alessandro</creatorcontrib><creatorcontrib>Avgenikos, Moscos</creatorcontrib><creatorcontrib>Baselious, Fady</creatorcontrib><creatorcontrib>Schmidt, Matthias</creatorcontrib><creatorcontrib>Al-Warhi, Tarfah</creatorcontrib><creatorcontrib>Abdel-Aziz, Hatem A.</creatorcontrib><creatorcontrib>Rennert, Robert</creatorcontrib><creatorcontrib>Peat, Thomas S.</creatorcontrib><creatorcontrib>Supuran, Claudiu T.</creatorcontrib><creatorcontrib>Wessjohann, Ludger A.</creatorcontrib><creatorcontrib>Ibrahim, Hany S.</creatorcontrib><title>4‑(Pyrazolyl)benzenesulfonamide Ureas as Carbonic Anhydrases Inhibitors and Hypoxia-Mediated Chemo-Sensitizing Agents in Colorectal Cancer Cells</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Hypoxia in tumors contributes to chemotherapy resistance, worsened by acidosis driven by carbonic anhydrases (hCA IX and XII). Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas (SH7a–t) were developed and evaluated for their inhibitory activity against hCA IX and XII. They showed promising results (hCA IX: K I = 15.9–67.6 nM, hCA XII: K I = 16.7–65.7 nM). Particularly, SH7s demonstrated outstanding activity (K Is = 15.9 nM for hCA IX and 55.2 nM for hCA XII) and minimal off-target kinase inhibition over a panel of 258 kinases. In NCI anticancer screening, SH7s exhibited broad-spectrum activity with an effective growth inhibition full panel GI50 (MG-MID) value of 3.5 μM and a subpanel GI50 (MG-MID) range of 2.4–6.3 μM. Furthermore, SH7s enhanced the efficacy of Taxol and 5-fluorouracil in cotreatment regimens under hypoxic conditions in HCT-116 colorectal cancer cells, indicating its potential as a promising anticancer agent.</description><subject>Antigens, Neoplasm</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Benzenesulfonamides</subject><subject>Carbonic Anhydrase Inhibitors - chemical synthesis</subject><subject>Carbonic Anhydrase Inhibitors - chemistry</subject><subject>Carbonic Anhydrase Inhibitors - pharmacology</subject><subject>Carbonic Anhydrase IX - antagonists & inhibitors</subject><subject>Carbonic Anhydrase IX - metabolism</subject><subject>Carbonic Anhydrases - metabolism</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Colorectal Neoplasms - drug therapy</subject><subject>Colorectal Neoplasms - pathology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfonamides - pharmacology</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemistry</subject><subject>Urea - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UU1v1DAUtBCILoV_gJCP5ZDl-SPJ5oRWEbSVikCCni3Hedl1ldiLnSCyJ_5C-Yn8Elx2W8EFydI7eGbevBlCXjJYMuDsjTZxeTNga7Y4LKUBtqrkI7JgOYdMrkA-JgsAzjNecHFCnsV4AwCCcfGUnIgqz6GoygX5KX_9uD37NAe99_3cv27Q7dFhnPrOOz3YFul1QB1perUOjXfW0LXbzm3QESO9dFvb2NGHhHAtvZh3_rvV2QdsrR6xpXVy57PP6KId7d66DV1v0I2RWkdr3_uAZtR9knYGA62x7-Nz8qTTfcQXx3lKrt-_-1JfZFcfzy_r9VWmBa_GrIVSMGF03hWMNW0DjWxXKAop-AqLrqxKoaGQrAUOeQkFl01VGqmRFxKAGXFK3h50d1Nzl2OyFXSvdsEOOszKa6v-_XF2qzb-m2KsYELmMimcHRWC_zphHNVgo0k3aId-iiqlXXFWVeUqQeUBaoKPMWD3sIeBuutTpT7VfZ_q2Geivfrb4wPpvsAEgAPgD91PwaXI_q_5GyU3s5I</recordid><startdate>20241128</startdate><enddate>20241128</enddate><creator>Eldehna, Wagdy M.</creator><creator>Fares, Mohamed</creator><creator>Bonardi, Alessandro</creator><creator>Avgenikos, Moscos</creator><creator>Baselious, Fady</creator><creator>Schmidt, Matthias</creator><creator>Al-Warhi, Tarfah</creator><creator>Abdel-Aziz, Hatem A.</creator><creator>Rennert, Robert</creator><creator>Peat, Thomas S.</creator><creator>Supuran, Claudiu T.</creator><creator>Wessjohann, Ludger A.</creator><creator>Ibrahim, Hany S.</creator><general>American Chemical Society</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>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6488-0831</orcidid><orcidid>https://orcid.org/0000-0001-6996-4017</orcidid><orcidid>https://orcid.org/0000-0003-4262-0323</orcidid><orcidid>https://orcid.org/0000-0002-1048-4059</orcidid><orcidid>https://orcid.org/0000-0003-0589-3955</orcidid><orcidid>https://orcid.org/0000-0003-2060-8235</orcidid></search><sort><creationdate>20241128</creationdate><title>4‑(Pyrazolyl)benzenesulfonamide Ureas as Carbonic Anhydrases Inhibitors and Hypoxia-Mediated Chemo-Sensitizing Agents in Colorectal Cancer Cells</title><author>Eldehna, Wagdy M. ; Fares, Mohamed ; Bonardi, Alessandro ; Avgenikos, Moscos ; Baselious, Fady ; Schmidt, Matthias ; Al-Warhi, Tarfah ; Abdel-Aziz, Hatem A. ; Rennert, Robert ; Peat, Thomas S. ; Supuran, Claudiu T. ; Wessjohann, Ludger A. ; Ibrahim, Hany S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a329t-d07313ca5f611bdb0b4d8e364328e6f7973a0641d020570624b97c4ae264001c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Antigens, Neoplasm</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Benzenesulfonamides</topic><topic>Carbonic Anhydrase Inhibitors - chemical synthesis</topic><topic>Carbonic Anhydrase Inhibitors - chemistry</topic><topic>Carbonic Anhydrase Inhibitors - pharmacology</topic><topic>Carbonic Anhydrase IX - antagonists & inhibitors</topic><topic>Carbonic Anhydrase IX - metabolism</topic><topic>Carbonic Anhydrases - metabolism</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Colorectal Neoplasms - drug therapy</topic><topic>Colorectal Neoplasms - pathology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfonamides - pharmacology</topic><topic>Urea - analogs & derivatives</topic><topic>Urea - chemistry</topic><topic>Urea - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eldehna, Wagdy M.</creatorcontrib><creatorcontrib>Fares, Mohamed</creatorcontrib><creatorcontrib>Bonardi, Alessandro</creatorcontrib><creatorcontrib>Avgenikos, Moscos</creatorcontrib><creatorcontrib>Baselious, Fady</creatorcontrib><creatorcontrib>Schmidt, Matthias</creatorcontrib><creatorcontrib>Al-Warhi, Tarfah</creatorcontrib><creatorcontrib>Abdel-Aziz, Hatem A.</creatorcontrib><creatorcontrib>Rennert, Robert</creatorcontrib><creatorcontrib>Peat, Thomas S.</creatorcontrib><creatorcontrib>Supuran, Claudiu T.</creatorcontrib><creatorcontrib>Wessjohann, Ludger A.</creatorcontrib><creatorcontrib>Ibrahim, Hany S.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eldehna, Wagdy M.</au><au>Fares, Mohamed</au><au>Bonardi, Alessandro</au><au>Avgenikos, Moscos</au><au>Baselious, Fady</au><au>Schmidt, Matthias</au><au>Al-Warhi, Tarfah</au><au>Abdel-Aziz, Hatem A.</au><au>Rennert, Robert</au><au>Peat, Thomas S.</au><au>Supuran, Claudiu T.</au><au>Wessjohann, Ludger A.</au><au>Ibrahim, Hany S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>4‑(Pyrazolyl)benzenesulfonamide Ureas as Carbonic Anhydrases Inhibitors and Hypoxia-Mediated Chemo-Sensitizing Agents in Colorectal Cancer Cells</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2024-11-28</date><risdate>2024</risdate><volume>67</volume><issue>22</issue><spage>20438</spage><epage>20454</epage><pages>20438-20454</pages><issn>0022-2623</issn><issn>1520-4804</issn><eissn>1520-4804</eissn><abstract>Hypoxia in tumors contributes to chemotherapy resistance, worsened by acidosis driven by carbonic anhydrases (hCA IX and XII). Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas (SH7a–t) were developed and evaluated for their inhibitory activity against hCA IX and XII. They showed promising results (hCA IX: K I = 15.9–67.6 nM, hCA XII: K I = 16.7–65.7 nM). Particularly, SH7s demonstrated outstanding activity (K Is = 15.9 nM for hCA IX and 55.2 nM for hCA XII) and minimal off-target kinase inhibition over a panel of 258 kinases. In NCI anticancer screening, SH7s exhibited broad-spectrum activity with an effective growth inhibition full panel GI50 (MG-MID) value of 3.5 μM and a subpanel GI50 (MG-MID) range of 2.4–6.3 μM. Furthermore, SH7s enhanced the efficacy of Taxol and 5-fluorouracil in cotreatment regimens under hypoxic conditions in HCT-116 colorectal cancer cells, indicating its potential as a promising anticancer agent.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>39550697</pmid><doi>10.1021/acs.jmedchem.4c01894</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0002-6488-0831</orcidid><orcidid>https://orcid.org/0000-0001-6996-4017</orcidid><orcidid>https://orcid.org/0000-0003-4262-0323</orcidid><orcidid>https://orcid.org/0000-0002-1048-4059</orcidid><orcidid>https://orcid.org/0000-0003-0589-3955</orcidid><orcidid>https://orcid.org/0000-0003-2060-8235</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Antigens, Neoplasm Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Benzenesulfonamides Carbonic Anhydrase Inhibitors - chemical synthesis Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrase Inhibitors - pharmacology Carbonic Anhydrase IX - antagonists & inhibitors Carbonic Anhydrase IX - metabolism Carbonic Anhydrases - metabolism Cell Line, Tumor Cell Proliferation - drug effects Colorectal Neoplasms - drug therapy Colorectal Neoplasms - pathology Drug Screening Assays, Antitumor Humans Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Structure-Activity Relationship Sulfonamides - chemical synthesis Sulfonamides - chemistry Sulfonamides - pharmacology Urea - analogs & derivatives Urea - chemistry Urea - pharmacology |
| title | 4‑(Pyrazolyl)benzenesulfonamide Ureas as Carbonic Anhydrases Inhibitors and Hypoxia-Mediated Chemo-Sensitizing Agents in Colorectal Cancer Cells |
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