Abstract
Some metal radionuclides can be used in diagnostic methods for imaging, such as single-photon emission computed tomography (99mTc, 111In) and positron emission tomography (PET) (44Sc, 64Cu, 68Ga), as well as for therapeutic applications (47Sc, 90Y, 177Lu, 212Pb, 212/213Bi, 225Ac). A chelator, e.g., a ligand that binds a radiometal ion into a strong stable coordination complex, is an important component of a radiopharmaceutical (RP) based on radio metals. In the past decade, as part of the search for new highly effective chelating molecules, the number of studies related to the production of picolinate ligands and the characterization of their complexes with diagnostic and therapeutic radionuclides has sharply increased. Moreover, conjugates with biomolecules based on these chelators have already been synthesized and studied. In this review, data on the binding of cations of radionuclides by picolinate-containing ligands of various types, as well as their conjugates, are systematized and analyzed.
Similar content being viewed by others
Notes
Additional studies with Bi3+ cations are required.
REFERENCES
Deal, K.A., Davis, I.A., Mirzadeh, S., Kennel, S.J., and Brechbiel, M.W., J. Med. Chem., 1999, vol. 42, no. 15, p. 2988.
Koike, T., Mahatma, A.B., and Kimura, E., Inorg. Chem., 1991, vol. 30, no. 6, p. 1270.
Pippin, C.G., Kumar, K., Mirzadeh, S., and Gansow, O.A., Chemistry, 1990, vol. 23, no. 11, p. 227.
Molnár, E., Camus, N., Patinec, V., Rolla, G.A., Botta, M., Tircsó, G., Kálmán, F.K., Fodor, T., Tripier, R., and Platas-Iglesias, C., Inorg. Chem., 2014, vol. 53, no. 10, p. 5136.
Guillou, A., Galland, M., Roux, A., Varadi, B., Gogolak, R.A., le Saëc, P., Faivre-Chauvet, A., Beyler, M., Bucher, C., Tircsó, G., Patinec, V., Maury, O., and Tripier, R., J. Inorg. Biochem., 2020, vol. 205, 110978.
Guillou, A., Lima, L.M.P., Roger, M., Esteban-Gomez, D., Delgado, R., Platas-Iglesias, C., Patinec, V., and Tripier, R., Eur. J. Inorg. Chem., 2017, vol. 18, p. 2435.
Roger, M., Lima, L.M.P., Frindel, M., Platas-Iglesias, C., Gestin, J.-F., Delgado, R., Patinec, V., and Tripier, R., Inorg. Chem., 2013, vol. 52, no. 9, p. 5246.
Lima, L.M.P., Esteban-Gomez, D., Delgado, R., Platas-Iglesias, C., and Tripier, R., Inorg. Chem., 2012, vol. 51, no. 12, p. 6916.
Aluicio-Sarduy, E., Thiele, N.A., Martin, K.E., Vaughn, B.A., Devaraj, J., Olson, A.P., Barnhart, T.E., Wilson, J.J., Boros, E., and Engle, J.W., Chemistry, 2020, vol. 26, no. 6, p. 1238.
Regueiro-Figueroa, M., Bensenane, B., Ruscsak, E., Esteban-Gomez, D., Charbonnihre, L.J., Tircsj, G., Tjth, I., de Blas, A., Rodriguez-Blas, T., and Platas-Iglesias, C., Inorg. Chem., 2011, vol. 50, p. 4125.
Lima, L.M.P., Beyler, M., Delgado, R., Platas-Iglesias, C., and Tripier, R., Inorg. Chem., 2015, vol. 54, p. 7045.
Lima, L.M.P., Beyler, M., and Oukhatar, F., le Saëc, P., Faivre-Chauvet, A., Platas-Iglesias, C., and Delgado, R., Chem. Commun., 2014, vol. 50, p. 12371.
Pálinkás, Z., Roca-Sabio, A., Mato-Iglesias, M., Esteban-Gómez, D., Platas-Iglesias, C., de Blas, A., Rodríguez-Blas, T., and Tóth, E., Inorg. Chem., 2009, vol. 48, no. 18, p. 8878.
le Fur, M., Beyler, M., Molnár, E., Fougère, O., Esteban-Gómez, D., Tircsó, G., Platas-Iglesias, C., Lepareur, N., Rousseaux, O., and Tripier, R., Chem. Commun., 2017, vol. 53, p. 9534.
Le Fur, M., Beyler, M., Molnár, E., Fougère, O., Esteban-Gómez, D., Tircsó, G., Platas-Iglesias, C., Lepareur, N., Rousseaux, O., and Tripier, R., Inorg. Chem., 2018, vol. 57, no. 4, p. 2051.
Roca-Sabio, A., Bonnet, C.S., Mato-Iglesias, M., Esteban-Gómez, D., Tóth, E., de Blas, A., Rodríguez-Blas, T., and Platas-Iglesias, C., Inorg. Chem., 2012, vol. 51, no. 20, p. 10893.
Lima, L.M.P., Halime, Z., Marion, R., Camus, N., Delgado, R., Platas-Iglesias, C., and Tripier, R., Inorg. Chem., 2014, vol. 53, no. 10, p. 5269.
Frindel, M., le Saëc, P., Beyler, M., Navarro, A.-S., Saï-Maurel, C., Alliot, C., Chérel, M., Gestin, J.-F., Faivre-Chauvet, A., and Tripier, R., RSC Adv., 2017, vol. 7, p. 9272.
Roca-Sabio, A., Mato-Iglesias, M., Esteban-Gómez, D., de Blas, A., Rodríguez-Blas, T., and Platas-Iglesias, C., Dalton Trans., 2011, vol. 40, p. 384.
Roca-Sabio, A., Mato-Iglesias, M., Esteban-Gómez, D., Tóth, E., de Blas, A., Platas-Iglesias, C., and Rodríguez-Blas, T., J. Am. Chem. Soc., 2009, vol. 131, no. 9, p. 3331.
Hu, A., MacMillan, S.N., and Wilson, J.J., J. Am. Chem. Soc., 2020, vol. 142, no. 31, p. 13500.
Sinenko, I.L., Kalmykova, T.P., Likhosherstova, D.V., Egorova, B.V., Zubenko, A.D., Vasiliev, A.N., Ermolaev, S.V., Lapshina, E.V., Ostapenko, V.S., Fedorova, O.A., and Kalmykov, S.N., J. Radioanal. Nucl. Chem., 2019, vol. 321, p. 531.
Woo, S.K., Jang, S.J., Seo, M.J., Park, J.H., Kim, B.S., Kim, E.J., Lee, Y.J., Lee, T.S., An, G.I., Song, I.H., Seo, Y., Kim, K.I., and Kang, J.H., J. Nucl. Med., 2019, vol. 60, no. 1, p. 26.
Bevilacqua, A., Gelb, R.I., Hebard, W.B., and Zompa, L.J., Inorg. Chem., 1987, vol. 26, no. 16, p. 2699.
van der Merve, M.J., Boeyens, J.C.A., and Hancock, R.D., Inorg. Chem., 1985, vol. 24, p. 1208.
Martell, A.E. and Smith, R.M., Critical Stability Constants, New York: Springer, 1974, vol. 1, p. 20.
Eder, M., Schafer, M., Bauder-Wust, U., Hull, W.-E., Wangler, C., Mier, W., Haberkorn, U., and Eisenhut, M., Bioconjugate Chem., 2012, vol. 23, p. 688.
Bass, L.A., Wang, Mu., Welch, M.J., and Anderson, C.J., Bioconjugate Chem., 2000, vol. 11, no. 4, p. 527.
Odendaal, Y., Fiamengo, A.L., Ferdani, R., Wadas, T.J., Hill, D.C., Peng, Y., Heroux, K.J., Golen, J.A., Rheingold, A.L., Anderson, C.J., Weisman, G.R., and Wong, E.H., Inorg. Chem., 2011, vol. 50, p. 3078.
Pandya, D.N., Dale, A.V., Kim, J.Y., Lee, H., Su, H.Y., An, G., and Yoo, J., Bioconjugate Chem., 2012, vol. 23, p. 330.
Esteves, C.V., Lamosa, P., Delgado, R., Costa, J., Désogère, P., Rousselin, Y., Goze, C., and Denat, F., Inorg. Chem., 2013, vol. 52, p. 5138.
Boswell, C.A., Sun, X., Niu, W., Weisman, G.R., Wong, E.H., Rheingold, A.L., and Anderson, C.J., J. Med. Chem., 2004, vol. 47, p. 1465.
Lewis, E.A., Boyle, R.W., and Archibald, S.J., Chem. Commun., 2004, p. 2212.
Sprague, J.E., Peng, Y., Fiamengo, A.L., Woodin, K.S., Southwick, E.A., Weisman, G.R., Wong, E.H., Golen, J.A., Rheingold, A.L., and Anderson, C.J., J. Med. Chem., 2007, vol. 50, p. 2527.
Boswell, C.A., Regino, C.A.S., Baidoo, K.E., Wong, K.J., Bumb, A., Xu, H., Milenic, D.E., Kelley, J.A., Lai, C.C., and Brechbiel, M.W., Bioconjugate Chem., 2008, vol. 19, p. 1476.
Boros, E., Rybak-Akimova, E., Holland, J.P., Rietz, T., Rotile, N., Blasi, F., Day, H., Latifi, R., and Caravan, P., Mol. Pharm., 2014, vol. 11, p. 617.
Weisman, G.R., Rogers, M.E., Wong, E.H., Jasinski, J.P., and Paight, E.S., J. Am. Chem. Soc., 1990, vol. 112, p. 8604.
Hubin, T.J., McCormick, J.M., Collinson, S.R., Buchalova, M., Perkins, C.M., Alcock, N.W., Kahol, P.K., Raghunathan, A., and Busch, D.H., J. Am. Chem. Soc., 2000, vol. 122, p. 2512.
Hubin, T.J., McCormick, J.M., Collinson, S.R., Alcock, N.W., and Busch, D.H., Chem. Commun., 1998, p. 1675.
Ferreiros-Martinez, R., Esteban-Gómez, D., Platas-Iglesias, C., de Blas, A., and Rodríguez-Blas, T., Dalton Trans., 2008, vol. 42, p. 5754.
Boros, E., Ferreira, C., Cawthray, J., Price, E., Patrick, B., Wester, D., Adam, M., and Orvig, C., J. Am. Chem. Soc., 2010, vol. 132, p. 15726.
Boros, E., Cawthray, J.F., Ferreira, C.L., Patrick, B.O., Adam, M.J., and Orvig, C., Inorg. Chem., 2012, vol. 51, p. 6279.
Damu, K.V., Salim Shaikjee, M., Michael, J.P., Howard, A.S., and Hancock, R.D., Inorg. Chem., 1986, vol. 25, no. 22, p. 3879.
Thiele, N.A., Brown, V., Kelly, J.M., Amor-Coarasa, A., Jermilova, U., MacMillan, S.N., Nikolopoulou, A., Ponnala, S., Ramogida, C.F., Robertson, A.K.H., Rodríguez-Rodríguez, C., Schaffer, P., Williams, C., Jr., Babich, J.W., Radchenko, V., and Wilson, J.J., Angew. Chem., Int. Ed., 2017, vol. 56, no. 46, p. 14712.
Fedorov, Yu.V., Fedorova, O.A., Kalmykov, S.N., Oshchepkov, M.S., Nelubina, YuV., Arkhipov, D.E., Egorova, B.V., and Zubenko, A.D., Polyhedron, 2017, vol. 124, p. 229.
Egorova, B.V., Matazova, E.V., Mitrofanov, A.A., Aleshin, G.Yu., Trigub, A.L., Zubenko, A.D., Fedorova, O.A., Fedorov, YuV., and Kalmykov, S.N., Nucl. Med. Biol., 2018, vol. 60, p. 1.
Pellissier, A., Bretonniere, Y., Chatterton, N., Pecaut, J., Delangle, P., and Mazzanti, M., Inorg. Chem., 2007, vol. 46, no. 9, p. 3714.
Bretonniere, Y., Mazzanti, M., Pecaut, J., Dunand, F.A., and Merbach, A.E., Inorg. Chem., 2001, vol. 40, no. 26, p. 6737.
Price, E.W., Cawthray, J.F., Bailey, G.A., Ferreira, C.L., Boros, E., Adam, M.J., and Orvig, C., J. Am. Chem. Soc., 2012, vol. 134, no. 20, p. 8670.
Price, E.W., Zeglis, B.M., Cawthray, J.F., Ramogida, C.F., Ramos, N., Lewis, J.S., Adam, M.J., and Orvig, C., J. Am. Chem. Soc., 2013, vol. 135, no. 34, p. 12707.
Kálmán, F.K., Végh, A., Regueiro-Figueroa, M., Tóth, E., Platas-Iglesias, C., and Tircsó, G., Inorg. Chem., 2015, vol. 54, no. 5, p. 2345.
Price, E.W., Cawthray, J.F., Adam, M.J., and Orvig, C., Dalton Trans., 2014, vol. 43, p. 7176.
Price, E.W., Zeglis, B.M., Cawthray, J.F., Lewis, J.S., Adam, M.J., and Orvig, C., Inorg. Chem., 2014, vol. 53, no. 19, p. 10412.
Bailey, G.A., Price, E.W., Zeglis, B.M., Ferreira, C.L., Boros, E., Lacasse, M.J., Patrick, B.O., Lewis, J.S., Adam, M.J., and Orvig, C., Inorg. Chem., 2012, vol. 51, no. 22, p. 12575.
Price, E.W., Zeglis, B.M., Lewis, J.S., Adam, M.J., and Orvig, C., Dalton Trans., 2014, vol. 43, p. 119.
Spreckelmeyer, S., Ramogida, C.F., Rousseau, J., Arane, K., Bratanovic, I., Colpo, N., Jermilova, U., Dias, G.M., Dude, I., Jaraquemada-Peláez, M., Bénard, F., Schaffer, P., and Orvig, C., Bioconjugate Chem., 2017, vol. 28, no. 8, p. 2145.
Li, L., Jaraquemada-Peláez, M., Aluicio-Sarduy, E., Wang, X., Barnhart, T.E., Cai, W., Radchenko, V., Schaffer, P., Engle, J.W., and Orvig, C., Dalton Trans., 2020, vol. 49, p. 5547.
Li, L., Jaraquemada-Peláez, M., Kuo, H.-T., Merkens, H., Choudhary, N., Gitschtaler, K., Jermilova, U., Colpo, N., Uribe-Muñoz, C., Radchenko, V., Schaffer, P., Lin, K.-S., Bénard, F., and Orvig, C., Bioconjugate Chem., 2019, vol. 30, no. 5, p. 1539.
Hu, A., Keresztes, I., MacMillan, S.N., Yang, Y., Ding, E., Zipfel, W.R., DiStasio, R.A., Jr., Babich, J.W., and Wilson, J.J., Inorg. Chem., 2020, vol. 59, no. 7, p. 51161.
Bretonnier, Y., Mazzanti, M., Pecaut, J., Dunand, F.A., and Merbach, A.E., Chem. Commun., 2001, vol. 7, p. 621.
Boros, E., Lin, Y.-H.S., Ferreira, C.L., Patrick, B.O., Hafeli, U.O., Adam, M.J., and Orvig, C., Dalton Trans., 2011, vol. 40, no. 23, p. 6253.
Boros, E., Ferreira, C.L., Patrick, B.O., Adam, M.J., and Orvig, C., Nucl. Med. Biol., 2011, vol. 38, p. 1165.
McMurry, T.J., Pippin, C.G., Wu, C., Deal, K.A., Brechbiel, M.W., Mirzadeh, S., and Gansow, O.A., J. Med. Chem., 1998, vol. 41, p. 3546.
Boros, E., Ferreira, C.L., Yapp, D.T.T., Gill, R.K., Price, E.W., Adam, M.J., and Orvig, C., Nucl. Med. Biol., 2012, vol. 39, no. 6, p. 785.
Singh, A.N., Liu, W., Hao, G., Kumar, A., Gupta, A., Oz, O.K., Hsieh, J.-T., and Sun, X., Bioconjugate Chem., 2011, vol. 22, p. 1650.
Li, Z.B., Chen, K., and Chen, X., Eur. J. Nucl. Med. Mol. Imaging, 2008, vol. 35, p. 1100.
Martell, A.E., Motekaitis, R.J., Clarke, E.T., Delgado, R., Sun, Y., and Ma, R., Supramol. Chem., 1996, vol. 6, nos. 3–4, p. 353.
Platas-Iglesias, C., Mato-Iglesias, M., Djanashvili, K., Müller, R.N., Elst, L.V., Peters, J.A., de Blas, A., and Rodríguez-Blas, T., Chemistry, 2004, vol. 10, no. 14, p. 3579.
Jaraquemada-Peláez, M., Wang, X., Clough, T.J., Cao, Y., Choudhary, N., Emler, K., Patricka, B.O., and Orvig, C., Dalton Trans., 2017, vol. 46, p. 14647.
Price, E.W., Edwards, K.J., Carnazza, K.E., Carlin, S.D., Zeglis, B.M., Adam, M.J., Orvig, C., and Lewis, J.S., Nucl. Med. Biol., 2016, vol. 43, no. 9, p. 566.
Li, L., Jaraquemada-Peláez, M., Aluicio-Sarduy, E., Wang, X., Jiang, D., Sakheie, M., Kuo, H.-T., Barnhart, T.E., Cai, W., Radchenko, V., Schaffer, P., Lin, K.-S., Engle, J.W., Bénard, F., and Orvig, C., Inorg. Chem., 2020, vol. 59, no. 3, p. 1985.
Funding
This study was supported by the Russian Foundation for Basic Research (project no. 19-33-90136).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.
Additional information
Translated by V. Mittova
About this article
Cite this article
Kalmykova, T.P., Egorova, B.V. & Kalmykov, S.N. Ligands Bearing Picolinate Groups as Potential Chelators for Application in Nuclear Medicine. Moscow Univ. Chem. Bull. 77, 1–37 (2022). https://doi.org/10.3103/S0027131422010047
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.3103/S0027131422010047