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Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent
A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophili...
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| Published in: | Journal of medicinal chemistry 2017-04, Vol.60 (7), p.2993-3001 |
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| Main Authors: | , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c307t-3d98c89bb7a256d18b1cd94f5923d850080f556bdb2156da6b1c1ab55fa7329f3 |
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| cites | cdi_FETCH-LOGICAL-c307t-3d98c89bb7a256d18b1cd94f5923d850080f556bdb2156da6b1c1ab55fa7329f3 |
| container_end_page | 3001 |
| container_issue | 7 |
| container_start_page | 2993 |
| container_title | Journal of medicinal chemistry |
| container_volume | 60 |
| creator | Islam, Md Kamrul Kim, Soyeon Kim, Hee-Kyung Park, Subin Lee, Gang-Ho Kang, Hyo Jeung Jung, Jae-Chang Park, Joon-Suk Kim, Tae-Jeong Chang, Yongmin |
| description | A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophilic, stable complex with Mn
, this new Mn chelate was rapidly taken up by liver hepatocytes and excreted by the kidneys and biliary system. The kinetic inertness and R
relaxivity of the complex were much higher than those of mangafodipir trisodium (MnDPDP), a clinically approved liver-specific MRI contrast agent. The diagnostic utility of this new Mn complex in MRI was demonstrated by high-sensitivity tumor detection in an animal model of liver cancer. |
| doi_str_mv | 10.1021/acs.jmedchem.6b01799 |
| format | article |
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, this new Mn chelate was rapidly taken up by liver hepatocytes and excreted by the kidneys and biliary system. The kinetic inertness and R
relaxivity of the complex were much higher than those of mangafodipir trisodium (MnDPDP), a clinically approved liver-specific MRI contrast agent. The diagnostic utility of this new Mn complex in MRI was demonstrated by high-sensitivity tumor detection in an animal model of liver cancer.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/acs.jmedchem.6b01799</identifier><identifier>PMID: 28301142</identifier><language>eng</language><publisher>United States</publisher><subject>Aniline Compounds - chemistry ; Aniline Compounds - pharmacokinetics ; Animals ; Benzothiazoles - chemistry ; Benzothiazoles - pharmacokinetics ; Cell Line, Tumor ; Chelating Agents - chemistry ; Chelating Agents - pharmacokinetics ; Contrast Media - chemistry ; Contrast Media - pharmacokinetics ; Coordination Complexes - analogs & derivatives ; Coordination Complexes - pharmacokinetics ; Edetic Acid - chemistry ; Hepatocytes - pathology ; Humans ; Liver - cytology ; Liver - diagnostic imaging ; Liver - pathology ; Liver Neoplasms - diagnostic imaging ; Liver Neoplasms - pathology ; Magnetic Resonance Imaging - methods ; Male ; Manganese - chemistry ; Manganese - pharmacokinetics ; Mice, Inbred BALB C ; Mice, Nude</subject><ispartof>Journal of medicinal chemistry, 2017-04, Vol.60 (7), p.2993-3001</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c307t-3d98c89bb7a256d18b1cd94f5923d850080f556bdb2156da6b1c1ab55fa7329f3</citedby><cites>FETCH-LOGICAL-c307t-3d98c89bb7a256d18b1cd94f5923d850080f556bdb2156da6b1c1ab55fa7329f3</cites><orcidid>0000-0002-0585-8714</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28301142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Islam, Md Kamrul</creatorcontrib><creatorcontrib>Kim, Soyeon</creatorcontrib><creatorcontrib>Kim, Hee-Kyung</creatorcontrib><creatorcontrib>Park, Subin</creatorcontrib><creatorcontrib>Lee, Gang-Ho</creatorcontrib><creatorcontrib>Kang, Hyo Jeung</creatorcontrib><creatorcontrib>Jung, Jae-Chang</creatorcontrib><creatorcontrib>Park, Joon-Suk</creatorcontrib><creatorcontrib>Kim, Tae-Jeong</creatorcontrib><creatorcontrib>Chang, Yongmin</creatorcontrib><title>Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophilic, stable complex with Mn
, this new Mn chelate was rapidly taken up by liver hepatocytes and excreted by the kidneys and biliary system. The kinetic inertness and R
relaxivity of the complex were much higher than those of mangafodipir trisodium (MnDPDP), a clinically approved liver-specific MRI contrast agent. The diagnostic utility of this new Mn complex in MRI was demonstrated by high-sensitivity tumor detection in an animal model of liver cancer.</description><subject>Aniline Compounds - chemistry</subject><subject>Aniline Compounds - pharmacokinetics</subject><subject>Animals</subject><subject>Benzothiazoles - chemistry</subject><subject>Benzothiazoles - pharmacokinetics</subject><subject>Cell Line, Tumor</subject><subject>Chelating Agents - chemistry</subject><subject>Chelating Agents - pharmacokinetics</subject><subject>Contrast Media - chemistry</subject><subject>Contrast Media - pharmacokinetics</subject><subject>Coordination Complexes - analogs & derivatives</subject><subject>Coordination Complexes - pharmacokinetics</subject><subject>Edetic Acid - chemistry</subject><subject>Hepatocytes - pathology</subject><subject>Humans</subject><subject>Liver - cytology</subject><subject>Liver - diagnostic imaging</subject><subject>Liver - pathology</subject><subject>Liver Neoplasms - diagnostic imaging</subject><subject>Liver Neoplasms - pathology</subject><subject>Magnetic Resonance Imaging - methods</subject><subject>Male</subject><subject>Manganese - chemistry</subject><subject>Manganese - pharmacokinetics</subject><subject>Mice, Inbred BALB C</subject><subject>Mice, Nude</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNo9kc1u2zAQhImiQe2meYOi4NE9yOGPfqij7LpJAAcJCucsrKiVTEOiXJEOGr9GXzgM7OS0h_lmBtgh5Dtnc84Evwbt5rsea73Ffp5WjGd5_olMeSJYFCsWfyZTxoSIRCrkhHx1bscYk1zIL2QilGScx2JK_t-DbcGiQ7oc-n2H_-jQ0JXfvnRosTbQG4se_Qig0RtNC21qOlv92hQ_owXa4-C3Bo5Dh7SwpgswnS2CFtLs7tCCRwqOAn0cPFpvoKNr84xjtIGxDXm2pfd_7t7g0OA8LdpAfSMXDXQOr873kjz9Xm2Wt9H64eZuWawjLVnmI1nnSqu8qjIQSVpzVXFd53GT5ELWKmFMsSZJ0qquBA86pEHnUCVJA5kUeSMvyeyUux-Hvwd0vuyN09h14R_DwZVcZUqJOJMyoPEJ1ePg3IhNuR9ND-NLyVn5NkcZ5ijf5yjPcwTbj3PDoQrah-n9__IV30yKWA</recordid><startdate>20170413</startdate><enddate>20170413</enddate><creator>Islam, Md Kamrul</creator><creator>Kim, Soyeon</creator><creator>Kim, Hee-Kyung</creator><creator>Park, Subin</creator><creator>Lee, Gang-Ho</creator><creator>Kang, Hyo Jeung</creator><creator>Jung, Jae-Chang</creator><creator>Park, Joon-Suk</creator><creator>Kim, Tae-Jeong</creator><creator>Chang, Yongmin</creator><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><orcidid>https://orcid.org/0000-0002-0585-8714</orcidid></search><sort><creationdate>20170413</creationdate><title>Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent</title><author>Islam, Md Kamrul ; Kim, Soyeon ; Kim, Hee-Kyung ; Park, Subin ; Lee, Gang-Ho ; Kang, Hyo Jeung ; Jung, Jae-Chang ; Park, Joon-Suk ; Kim, Tae-Jeong ; Chang, Yongmin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c307t-3d98c89bb7a256d18b1cd94f5923d850080f556bdb2156da6b1c1ab55fa7329f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aniline Compounds - chemistry</topic><topic>Aniline Compounds - pharmacokinetics</topic><topic>Animals</topic><topic>Benzothiazoles - chemistry</topic><topic>Benzothiazoles - pharmacokinetics</topic><topic>Cell Line, Tumor</topic><topic>Chelating Agents - chemistry</topic><topic>Chelating Agents - pharmacokinetics</topic><topic>Contrast Media - chemistry</topic><topic>Contrast Media - pharmacokinetics</topic><topic>Coordination Complexes - analogs & derivatives</topic><topic>Coordination Complexes - pharmacokinetics</topic><topic>Edetic Acid - chemistry</topic><topic>Hepatocytes - pathology</topic><topic>Humans</topic><topic>Liver - cytology</topic><topic>Liver - diagnostic imaging</topic><topic>Liver - pathology</topic><topic>Liver Neoplasms - diagnostic imaging</topic><topic>Liver Neoplasms - pathology</topic><topic>Magnetic Resonance Imaging - methods</topic><topic>Male</topic><topic>Manganese - chemistry</topic><topic>Manganese - pharmacokinetics</topic><topic>Mice, Inbred BALB C</topic><topic>Mice, Nude</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Islam, Md Kamrul</creatorcontrib><creatorcontrib>Kim, Soyeon</creatorcontrib><creatorcontrib>Kim, Hee-Kyung</creatorcontrib><creatorcontrib>Park, Subin</creatorcontrib><creatorcontrib>Lee, Gang-Ho</creatorcontrib><creatorcontrib>Kang, Hyo Jeung</creatorcontrib><creatorcontrib>Jung, Jae-Chang</creatorcontrib><creatorcontrib>Park, Joon-Suk</creatorcontrib><creatorcontrib>Kim, Tae-Jeong</creatorcontrib><creatorcontrib>Chang, Yongmin</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Islam, Md Kamrul</au><au>Kim, Soyeon</au><au>Kim, Hee-Kyung</au><au>Park, Subin</au><au>Lee, Gang-Ho</au><au>Kang, Hyo Jeung</au><au>Jung, Jae-Chang</au><au>Park, Joon-Suk</au><au>Kim, Tae-Jeong</au><au>Chang, Yongmin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>2017-04-13</date><risdate>2017</risdate><volume>60</volume><issue>7</issue><spage>2993</spage><epage>3001</epage><pages>2993-3001</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophilic, stable complex with Mn
, this new Mn chelate was rapidly taken up by liver hepatocytes and excreted by the kidneys and biliary system. The kinetic inertness and R
relaxivity of the complex were much higher than those of mangafodipir trisodium (MnDPDP), a clinically approved liver-specific MRI contrast agent. The diagnostic utility of this new Mn complex in MRI was demonstrated by high-sensitivity tumor detection in an animal model of liver cancer.</abstract><cop>United States</cop><pmid>28301142</pmid><doi>10.1021/acs.jmedchem.6b01799</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-0585-8714</orcidid></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2017-04, Vol.60 (7), p.2993-3001 |
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| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Aniline Compounds - chemistry Aniline Compounds - pharmacokinetics Animals Benzothiazoles - chemistry Benzothiazoles - pharmacokinetics Cell Line, Tumor Chelating Agents - chemistry Chelating Agents - pharmacokinetics Contrast Media - chemistry Contrast Media - pharmacokinetics Coordination Complexes - analogs & derivatives Coordination Complexes - pharmacokinetics Edetic Acid - chemistry Hepatocytes - pathology Humans Liver - cytology Liver - diagnostic imaging Liver - pathology Liver Neoplasms - diagnostic imaging Liver Neoplasms - pathology Magnetic Resonance Imaging - methods Male Manganese - chemistry Manganese - pharmacokinetics Mice, Inbred BALB C Mice, Nude |
| title | Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent |
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