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Synthesis 2020; 52(07): 1087-1095
DOI: 10.1055/s-0039-1691540
paper
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches to the Bifunctional Chelators for Radio­nuclides Based On Pyridine-Containing Azacrown Compounds

Anastasia D. Zubenko  ∗
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   eMail: nastya.mutasova@yandex.ru
,
Anna A. Shchukina
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   eMail: nastya.mutasova@yandex.ru
b   D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, 125047 Moscow, Russian Federation
,
Olga A. Fedorova
a   A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, 119991 Moscow, Russian Federation   eMail: nastya.mutasova@yandex.ru
b   D. I. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, 125047 Moscow, Russian Federation
› InstitutsangabenThe work was supported by Russian Science Foundation (grant No 16-13-10226). The characterization of the products was performed with the financial support from the Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS.
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Publikationsverlauf

Received: 11. Oktober 2019

Accepted after revision: 03. Dezember 2019

Publikationsdatum:
16. Dezember 2019 (online)

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Abstract

Synthetic ways to introduce functional groups (CO2Me, CO2H, OCH2CO2H, OCH2C≡CH, CH2OH, CH2Cl, CH2N3) into the pyridine ring of pyridine-containing azacrown compounds are described. These groups were introduced at position-4 of the pyridine ring, while keeping the macrocyclic carboxylate groups available for metal chelation. The derivatives were obtained by macrocyclization reaction of 4-substituted, trimethyl pyridine-2,4,6-tricarboxylate or by modification of methyl ester group in pyridine fragment of macrocycles. Obtained derivatives can be applied for preparing radiotherapeutic agents by conjugation to different vector biomolecules for targeted drug delivery to cancer cells without damaging healthy tissue.

Key words

bifunctional chelators - azacrown compounds - macro­cyclization - radiopharmaceuticals - bioconjugation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691540.
  • Supporting Information
 

  • References

  • 1 Bourgeois M, Bailly C, Frindel M, Guerard F, Chérel M, Faivre-Chauvet A, Bodet-Milin C. Expert Opin. Biol. Ther. 2017; 17: 813
    CrossrefPubMed
  • 2 Cai Z, Anderson CJ. J. Labelled Compd. Radiopharm. 2014; 57: 224
    CrossrefPubMed
  • 3 Ramogida CF, Orvig C. Chem. Commun. 2013; 49: 4720
    CrossrefPubMed
  • 4 Velikyan I. Theranostics 2012; 2: 424
    CrossrefPubMed
  • 5 Price EW, Orvig C. Chem. Soc. Rev. 2014; 43: 260
    CrossrefPubMed
  • 6 Liu S. Adv. Drug Deliv. Rev. 2008; 60: 1347
    CrossrefPubMed
  • 7 Lattuada L, Barge A, Cravotto G, Giovenzana GB, Tei L. Chem. Soc. Rev. 2011; 40: 3019
    CrossrefPubMed
  • 8 Läppchen T, Kiefer Y, Holland JP, Bartholomä MD. Nucl. Med. Biol. 2018; 60: 45
    CrossrefPubMed
  • 9 Li L, Jaraquemada-Peláez MD. G, Kuo HT, Merkens H, Choudhary N, Gitschalter K, Schaffer P. Bioconjugate Chem. 2019; 30: 1539
    CrossrefPubMed
  • 10 Giannini G, Milazzo FM, Battistuzzi G, Rosi A, Anastasi AM, Petronzelli F, Albertoni C, Tei L, Leone L, Salvini L, De Santis R. Bioorg. Med. Chem. 2019; 27: 3248
    CrossrefPubMed
  • 11 Pandey U, Gamre N, Lohar SP, Dash A. Appl. Radiat. Isot. 2017; 127: 1
    CrossrefPubMed
  • 12 Weinmann C, Holland JP, Läppchen T, Scherer H, Maus S, Stemler T, Bartholomä MD. Org. Biomol. Chem. 2018; 16: 7503
    CrossrefPubMed
  • 13 Banerjee SR, Pullambhatla M, Foss CA, Nimmagadda S, Ferdani R, Anderson CJ, Pomper MG. J. Med. Chem. 2014; 57: 2657
    CrossrefPubMed
  • 14 Dumont RA, Deininger F, Haubner R, Maecke HR, Weber WA, Fani M. J. Nucl. Med. 2011; 52: 1276
    CrossrefPubMed
  • 15 Cutler CS, Hennkens HM, Sisay N, Huclier-Markai S, Jurisson SS. Chem. Rev. 2013; 113: 858
    CrossrefPubMed
  • 16 Bartholomä MD. Inorg. Chim. Acta 2012; 389: 36
    Crossref
  • 17 Tsionou MI, Knapp CE, Foley CA, Munteanu CR, Cakebread A, Imberti C, Ma MT. RSC Adv. 2017; 7: 49586
    CrossrefPubMed
  • 18 Felten AS, Petry N, Henry B, Pellegrini-Moïse N, Selmeczi K. New J. Chem. 2016; 40: 1507
    Crossref
  • 19 Zha Z, Song J, Choi SR, Wu Z, Ploessl K, Smith M, Kung H. Bioconjugate Chem. 2016; 27: 1314
    CrossrefPubMed
  • 20 Silversides JD, Smith R, Archibald SJ. Dalton Trans. 2011; 40: 6289
    CrossrefPubMed
  • 21 Mewis RE, Archibald SJ. Coord. Chem. Rev. 2010; 254: 1686
    Crossref
  • 22 Kang CS, Sun X, Jia F, Song HA, Chen Y, Lewis M, Chong HS. Bioconjugate Chem. 2012; 23: 1775
    CrossrefPubMed
  • 23 Parus JL, Pawlak D, Mikolajczak R, Duatti A. Curr. Radiopharm. 2015; 8: 86
    CrossrefPubMed
  • 24 Blom E, Långström B, Velikyan I. Bioconjugate Chem. 2009; 20: 1146
    CrossrefPubMed
  • 25 D’huyvetter M, Aerts A, Xavier C, Vaneycken I, Devoogdt N, Gijs M, Caveliers V. Contrast Media Mol. Imaging 2012; 7: 254
    CrossrefPubMed
  • 26 Spang P, Herrmann C, Roesch F. Semin. Nucl. Med. 2016; 46: 373
    CrossrefPubMed
  • 27 Dadwal M, Kang CS, Song HA, Sun X, Dai A, Baidoo KE, Brechbiel MW, Chong HS. Bioorg. Med. Chem. Lett. 2011; 21: 7513
    CrossrefPubMed
  • 28 Hassfjell S, Brechbiel MW. Chem. Rev. 2001; 101: 2019
    CrossrefPubMed
  • 29 Fedorov Y, Fedorova O, Peregudov A, Kalmykov S, Egorova B, Arkhipov D, Zubenko A, Oshchepkov M. J. Phys. Org. Chem. 2016; 29: 244
    Crossref
  • 30 Fedorov YV, Fedorova OA, Kalmykov SN, Oshchepkov MS, Nelubina YV, Arkhipov DE, Egorova BV, Zubenko AD. Polyhedron 2017; 124: 229
    Crossref
  • 31 Egorova BV, Matazova EV, Mitrofanov AA, Aleshin GY, Trigub AL, Zubenko AD, Fedorova OA, Fedorov YV, Kalmykov SN. Nucl. Med. Biol. 2018; 60: 1
    CrossrefPubMed
  • 32 Jamous M, Haberkorn U, Mier W. Molecules 2013; 18: 3379
    CrossrefPubMed
  • 33 Lymperis E, Kaloudi A, Sallegger W, Bakker IL, Krenning EP, De Jong M, Maina T, Nock BA. Bioconjugate Chem. 2018; 29: 1774
    CrossrefPubMed
  • 34 Eppard E, De La Fuente A, Mohr N, Allmeroth M, Zentel R, Miederer M, Pektor S, Rösch F. EJNMMI Res. 2018; 8: 16
    CrossrefPubMed
  • 35 Muller C, Farkas R, Borgna F, Schmid RM, Benesova M, Schibli R. Bioconjugate Chem. 2017; 28: 2372
    CrossrefPubMed
  • 36 Calce E, Monfregola L, De Luca S. Int. J. Pept. Res. Ther. 2013; 19: 199
    Crossref
  • 37 de la Reberdière A, Lachaud F, Chuburu F, Cadiou C, Lemercier G. Tetrahedron Lett. 2012; 53: 6115
    Crossref
  • 38 Jamous M, Haberkorn U, Mier W. Tetrahedron Lett. 2012; 53: 810
  • 39 Kubicek V, Havlickova J, Kotek J, Tircso G, Hermann P, Toth E, Lukes I. Inorg. Chem. 2010; 49: 10960
    CrossrefPubMed
  • 40 Leygue N, Enel M, Diallo A, Mestre-Voegtlé B, Galaup C, Picard C. Eur. J. Org. Chem. 2019; 2899
  • 41 Weekley CM, Kenkel I, Lippert R, Wei S, Lieb D, Cranwell T, Ivanović-Burmazović I. Inorg. Chem. 2017; 56: 6076
    CrossrefPubMed
  • 42 Lin Y, Favre-Réguillon A, Pellet-Rostaing S, Lemaire M. Tetrahedron Lett. 2007; 48: 3463
    Crossref
  • 43 Le Bihan T, Navarro AS, Le Bris N, Le Saec P, Gouard S, Haddad F, Tripier R. Org. Biomol. Chem. 2018; 16: 4261
    CrossrefPubMed
  • 44 Chakraborty S, Goswami D, Chakravarty R, Mohammed SK, Sarma HD, Dash A. Chem. Biol. Drug Des. 2018; 92: 1618
    CrossrefPubMed
  • 45 Désogère P, Rousselin Y, Poty S, Bernhard C, Goze C, Boschetti F, Denat F. Eur. J. Org. Chem. 2014; 7831
  • 46 Förster C, Schubert M, Pietzsch HJ, Steinbach J. Molecules 2011; 16: 5228
    CrossrefPubMed
  • 47 Suzuki H, Kanai A, Uehara T, Gomez FL. G, Hanaoka H, Arano Y. Bioorg. Med. Chem. 2012; 20: 978
    CrossrefPubMed
  • 48 Huang Y, Liu Y, Liu S, Wu R, Wu Z. Eur. J. Org. Chem. 2018; 1546
  • 49 Chong HS, Sun X, Dong P, Kang CS. Eur. J. Org. Chem. 2011; 6641
  • 50 Hoareau R, Scott PJ. H. Tetrahedron Lett. 2013; 54: 5755
    Crossref
  • 51 Wardle NJ, Herlihy AH, So PW, Bell JD, Bligh SA. Bioorg. Med. Chem. 2007; 15: 4714
    CrossrefPubMed
  • 52 Korendovych IV, Cho M, Makhlynets OV, Butler PL, Staples RJ, Rybak-Akimova EV. J. Org. Chem. 2008; 73: 4771
    CrossrefPubMed
  • 53 Gryko D, Gryko DT, Sierzputowska-Gracz H, Piątek P, Jurczak J. Helv. Chim. Acta 2004; 87: 156
    Crossref
  • 54 Dabrowa K, Niedbala P, Majdecki M, Duszewski P, Jurczak J. Org. Lett. 2015; 17: 4774
    CrossrefPubMed
  • 55 Molecular & Diagnostic Imaging in Prostate Cancer . Schatten H. Springer International Publishing AG; Cham (Switzerland): 2018
    Google Scholar
  • 56 Rasheed OK, McDouall JJ. W, Muryn CA, Raftery J, Vitorica-Yrezabal IJ, Quayle P. Dalton Trans. 2017; 46: 5229
    CrossrefPubMed
  • 57 Baptiste B, Douat-Casassus C, Laxmi-Reddy K, Godde F, Huc I. J. Org. Chem. 2010; 75: 7175
    CrossrefPubMed
  • 58 Zubenko AD, Egorova BV, Kalmykov SN, Shepel NE, Karnoukhova VA, Fedyanin IV, Fedorov YV, Fedorova OA. Tetrahedron 2019; 75: 2848
    Crossref
  • 60 Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
    CrossrefPubMed
  • 61 Bock VD, Hiemstra H, Van Maarseveen JH. Eur. J. Org. Chem. 2006; 51
    • 62a Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
      CrossrefPubMed
    • 62b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
      CrossrefPubMed
    • 63a Berg R, Straub BF. Beilstein J. Org. Chem. 2013; 9: 2715
      CrossrefPubMed
    • 63b Schöffler A, Makarem A, Rominger A, Straub BF. Beilstein J. Org. Chem. 2016; 12: 1566
      CrossrefPubMed
  • 64 Wu C, Li D, Yang L. J. Mater. Chem. B 2015; 3: 1470
    CrossrefPubMed
  • 65 Le Bihan T, Le Bris N, Bernard H, Platas-Iglesias C, Tripier R. Eur. J. Org. Chem. 2019; 5955
  • 66 Banerjee SR, Schaffer P, Babich JW, Valliant JF, Zubieta J. Dalton Trans. 2005; 3886
    PubMed
  • 67 Shelkov R, Melman A. Eur. J. Org. Chem. 2005; 1397
  • 68 Yu K.-K, Li K, Hou J.-T, Yu X.-Q. Tetrahedron Lett. 2013; 54: 5771
    Crossref