Synthesis of a DOTA- C -glyco bifunctional chelating agent and preliminary in vitro and in vivo study of [ 68 Ga]Ga-DOTA- C -glyco-RGD

The design of bifunctional chelating agents (BFCA) allowing straightforward radiometal labelling of biomolecules is a current challenge. We report herein the development of a bifunctional chelating agent based on a DOTA chelator linked to a -glycosyl compound, taking advantage of the robustness and...

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Veröffentlicht in:	RSC advances 2021-02, Vol.11 (13), p.7672-7681
Hauptverfasser:	Mangin, Floriane, Collet, Charlotte, Jouan-Hureaux, Valérie, Maskali, Fatiha, Roeder, Emilie, Pierson, Julien, Selmeczi, Katalin, Marie, Pierre-Yves, Boura, Cédric, Pellegrini-Moïse, Nadia, Lamandé-Langle, Sandrine
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Schlagworte:	Biomolecules Carbohydrates Chelating agents Chelation Chemical compounds Chemical Sciences Chemistry In vivo methods and tests Quality control
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creator	Mangin, Floriane Collet, Charlotte Jouan-Hureaux, Valérie Maskali, Fatiha Roeder, Emilie Pierson, Julien Selmeczi, Katalin Marie, Pierre-Yves Boura, Cédric Pellegrini-Moïse, Nadia Lamandé-Langle, Sandrine
description	The design of bifunctional chelating agents (BFCA) allowing straightforward radiometal labelling of biomolecules is a current challenge. We report herein the development of a bifunctional chelating agent based on a DOTA chelator linked to a -glycosyl compound, taking advantage of the robustness and hydrophilicity of this type of carbohydrate derivative. This new BFCA was coupled with success by CuAAC with c(RGDfK) for α β integrin targeting. As attested by evaluation, the conjugate DOTA- -glyco-c(RGDfC) demonstrated high affinity for α β integrins (IC of 42 nM). [ Ga]Ga-DOTA- -glyco-c(RGDfK) was radiosynthesized straightforwardly and showed high hydrophilic property (log = -3.71) and stability (>120 min). Preliminary PET study of U87MG engrafted mice gave evidence of an interesting tumor-to-non-target area ratio. All these data indicate that [ Ga]Ga-DOTA- -glyco-c(RGDfK) allows monitoring of α β expression and could thus be used for cancer diagnosis. The DOTA- -glycoside BFCA reported here could also be used with various ligands and chelating other (radio)metals opening a broad scope of applications in imaging modalities and therapy.
doi_str_mv	10.1039/d0ra09274f
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We report herein the development of a bifunctional chelating agent based on a DOTA chelator linked to a -glycosyl compound, taking advantage of the robustness and hydrophilicity of this type of carbohydrate derivative. This new BFCA was coupled with success by CuAAC with c(RGDfK) for α β integrin targeting. As attested by evaluation, the conjugate DOTA- -glyco-c(RGDfC) demonstrated high affinity for α β integrins (IC of 42 nM). [ Ga]Ga-DOTA- -glyco-c(RGDfK) was radiosynthesized straightforwardly and showed high hydrophilic property (log = -3.71) and stability (>120 min). Preliminary PET study of U87MG engrafted mice gave evidence of an interesting tumor-to-non-target area ratio. All these data indicate that [ Ga]Ga-DOTA- -glyco-c(RGDfK) allows monitoring of α β expression and could thus be used for cancer diagnosis. The DOTA- -glycoside BFCA reported here could also be used with various ligands and chelating other (radio)metals opening a broad scope of applications in imaging modalities and therapy.</description><subject>Biomolecules</subject><subject>Carbohydrates</subject><subject>Chelating agents</subject><subject>Chelation</subject><subject>Chemical compounds</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>In vivo methods and tests</subject><subject>Quality control</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdUV1LIzEUDYuySvXFHyABnxRG8zkfL0JpbRUKgus-LUu4nUnayDSpyUyhf2B_9860Kmpe7s29J-fek4PQGSXXlPDipiIBSMEyYX6gY0ZEmjCSFgef8iN0GuML6U4qKUvpT3TEpWC8S4_Rv19b1yx1tBF7gwGPH5-HCR7hZFFvS4_n1rSubKx3UONyqWtorFtgWGjXYHAVXgdd25V1ELbYOryxTfC7xu6y8Tg2bbXtuf_gNMdT-DuF5OuQ5Gk6PkGHBuqoT9_iAP2e3D2P7pPZ4_RhNJwlJedZk5SdnkoWUoIWNBNkXoGomDGSi1SDLIFVOZnnLJMcMirBCANECMoZB1poyQfods-7bucrXZWdjAC1Wge76hQoD1Z97Ti7VAu_UXlaiKIjGqDLPcHy27P74Uz1NcKplFmWbXrsxduw4F9bHRv14tvQ_WRUTBSEMk7yfqWrPaoMPsagzQctJaq3WI3J03Bn8aQDn3_e_wP6bij_D6G6np8</recordid><startdate>20210217</startdate><enddate>20210217</enddate><creator>Mangin, Floriane</creator><creator>Collet, Charlotte</creator><creator>Jouan-Hureaux, Valérie</creator><creator>Maskali, Fatiha</creator><creator>Roeder, Emilie</creator><creator>Pierson, Julien</creator><creator>Selmeczi, Katalin</creator><creator>Marie, Pierre-Yves</creator><creator>Boura, Cédric</creator><creator>Pellegrini-Moïse, Nadia</creator><creator>Lamandé-Langle, Sandrine</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>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-8569-5793</orcidid><orcidid>https://orcid.org/0000-0002-9669-6967</orcidid><orcidid>https://orcid.org/0000-0003-3291-3309</orcidid><orcidid>https://orcid.org/0000-0001-5576-3011</orcidid><orcidid>https://orcid.org/0000-0002-5439-8881</orcidid><orcidid>https://orcid.org/0000-0001-9227-8920</orcidid><orcidid>https://orcid.org/0000-0003-1127-7067</orcidid><orcidid>https://orcid.org/0000-0002-3594-3960</orcidid></search><sort><creationdate>20210217</creationdate><title>Synthesis of a DOTA- C -glyco bifunctional chelating agent and preliminary in vitro and in vivo study of [ 68 Ga]Ga-DOTA- C -glyco-RGD</title><author>Mangin, Floriane ; Collet, Charlotte ; Jouan-Hureaux, Valérie ; Maskali, Fatiha ; Roeder, Emilie ; Pierson, Julien ; Selmeczi, Katalin ; Marie, Pierre-Yves ; Boura, Cédric ; Pellegrini-Moïse, Nadia ; Lamandé-Langle, Sandrine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-c206d5955ae41740bda4d2ff5346ea5ca2d80b82753a715af4fa0441323a19e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biomolecules</topic><topic>Carbohydrates</topic><topic>Chelating agents</topic><topic>Chelation</topic><topic>Chemical compounds</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>In vivo methods and tests</topic><topic>Quality control</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mangin, Floriane</creatorcontrib><creatorcontrib>Collet, Charlotte</creatorcontrib><creatorcontrib>Jouan-Hureaux, Valérie</creatorcontrib><creatorcontrib>Maskali, Fatiha</creatorcontrib><creatorcontrib>Roeder, Emilie</creatorcontrib><creatorcontrib>Pierson, Julien</creatorcontrib><creatorcontrib>Selmeczi, Katalin</creatorcontrib><creatorcontrib>Marie, Pierre-Yves</creatorcontrib><creatorcontrib>Boura, Cédric</creatorcontrib><creatorcontrib>Pellegrini-Moïse, Nadia</creatorcontrib><creatorcontrib>Lamandé-Langle, Sandrine</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>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</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>Mangin, Floriane</au><au>Collet, Charlotte</au><au>Jouan-Hureaux, Valérie</au><au>Maskali, Fatiha</au><au>Roeder, Emilie</au><au>Pierson, Julien</au><au>Selmeczi, Katalin</au><au>Marie, Pierre-Yves</au><au>Boura, Cédric</au><au>Pellegrini-Moïse, Nadia</au><au>Lamandé-Langle, Sandrine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a DOTA- C -glyco bifunctional chelating agent and preliminary in vitro and in vivo study of [ 68 Ga]Ga-DOTA- C -glyco-RGD</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2021-02-17</date><risdate>2021</risdate><volume>11</volume><issue>13</issue><spage>7672</spage><epage>7681</epage><pages>7672-7681</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The design of bifunctional chelating agents (BFCA) allowing straightforward radiometal labelling of biomolecules is a current challenge. We report herein the development of a bifunctional chelating agent based on a DOTA chelator linked to a -glycosyl compound, taking advantage of the robustness and hydrophilicity of this type of carbohydrate derivative. This new BFCA was coupled with success by CuAAC with c(RGDfK) for α β integrin targeting. As attested by evaluation, the conjugate DOTA- -glyco-c(RGDfC) demonstrated high affinity for α β integrins (IC of 42 nM). [ Ga]Ga-DOTA- -glyco-c(RGDfK) was radiosynthesized straightforwardly and showed high hydrophilic property (log = -3.71) and stability (>120 min). Preliminary PET study of U87MG engrafted mice gave evidence of an interesting tumor-to-non-target area ratio. All these data indicate that [ Ga]Ga-DOTA- -glyco-c(RGDfK) allows monitoring of α β expression and could thus be used for cancer diagnosis. The DOTA- -glycoside BFCA reported here could also be used with various ligands and chelating other (radio)metals opening a broad scope of applications in imaging modalities and therapy.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35423261</pmid><doi>10.1039/d0ra09274f</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-8569-5793</orcidid><orcidid>https://orcid.org/0000-0002-9669-6967</orcidid><orcidid>https://orcid.org/0000-0003-3291-3309</orcidid><orcidid>https://orcid.org/0000-0001-5576-3011</orcidid><orcidid>https://orcid.org/0000-0002-5439-8881</orcidid><orcidid>https://orcid.org/0000-0001-9227-8920</orcidid><orcidid>https://orcid.org/0000-0003-1127-7067</orcidid><orcidid>https://orcid.org/0000-0002-3594-3960</orcidid><oa>free_for_read</oa></addata></record>
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subjects	Biomolecules Carbohydrates Chelating agents Chelation Chemical compounds Chemical Sciences Chemistry In vivo methods and tests Quality control
title	Synthesis of a DOTA- C -glyco bifunctional chelating agent and preliminary in vitro and in vivo study of [ 68 Ga]Ga-DOTA- C -glyco-RGD
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