Synthesis of hydrophilic HYNIC-[1,2,4,5]tetrazine conjugates and their use in antibody pretargeting with Tc-99m

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art_GARCIA_Synthesis_of_hydrophilic_HYNIC1245tetrazine_conjugates_and_their_use_2018.PDF (1.94 MB)
Citações na Scopus
16
Tipo de produção
article
Data de publicação
2018
Editora
ROYAL SOC CHEMISTRY
DOI
Indexadores
Scopus
Web of Science
PubMed
Título da Revista
ISSN da Revista
Título do Volume
Autores
GARCIA, Maria Fernanda
GALLAZZI, Fabio
FERNANDEZ, Marcelo
CAMACHO, Ximena
COUTO, Marcos
CARRION, Federico
Autor de Grupo de pesquisa
Editores
Coordenadores
Organizadores
Citação
ORGANIC & BIOMOLECULAR CHEMISTRY, v.16, n.29, p.5275-5285, 2018
Projetos de Pesquisa
Unidades Organizacionais
Fascículo
Resumo
Pretargeted imaging, based on the highly reactive process between [1,2,4,5]tetrazines with trans-cyclooctene (TCO), appears as an attractive strategy to overcome disadvantages associated with traditional radioimmunoconjugates. To be successful, the radiolabeled component should react in vivo with the conjugated antibody and the non reactive excess clear fast from the organism. Herein, we explore the in vivo effects of hydrophilic linker incorporation into [1,2,4,5]tetrazine systems bearing a 6-hydrazinonicotinyl (HYNIC) moiety for technetium-99m coordination. Incorporation of a polypeptide chain containing hydrophilic aminoacids, resulted in a derivative with renal clearance. Pretargeted bevacizumab imaging was used as proof of concept.
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URI
https://observatorio.fm.usp.br/handle/OPI/28074
Referências
  1. Agard NJ, 2004, J AM CHEM SOC, V126, P15046, DOI 10.1021/ja0449981
  2. Altai M, 2017, J NUCL MED, V58, P1553, DOI 10.2967/jnumed.117.189944
  3. Blackman ML, 2008, J AM CHEM SOC, V130, P13518, DOI 10.1021/ja8053805
  4. Boerman OC, 2003, J NUCL MED, V44, P400
  5. Borjesson PKE, 2006, CLIN CANCER RES, V12, P2133, DOI 10.1158/1078-0432.CCR-05-2137
  6. Camacho X., 2014, J ANAL ONCOL, P53
  7. Camacho X, 2013, ONCOLOGY-BASEL, V84, P200, DOI 10.1159/000338961
  8. Couturier O, 2005, EUR J NUCL MED MOL I, V32, P601, DOI 10.1007/s00259-005-1803-2
  9. Denk C, 2016, BIOCONJUGATE CHEM, V27, P1707, DOI 10.1021/acs.bioconjchem.6b00234
  10. Devaraj NK, 2009, ANGEW CHEM INT EDIT, V48, P7013, DOI 10.1002/anie.200903233
  11. Devaraj NK, 2008, BIOCONJUGATE CHEM, V19, P2297, DOI 10.1021/bc8004446
  12. Garcia MF, 2016, BIOORGAN MED CHEM, V24, P1209, DOI 10.1016/j.bmc.2016.01.046
  13. Ferrara N, 2003, NAT MED, V9, P669, DOI 10.1038/nm0603-669
  14. Flook AM, 2014, J MED CHEM, V57, P9010, DOI 10.1021/jm501114v
  15. Garcia MF, 2014, CURR RADIOPHARM, V7, P84, DOI 10.2174/1874471007666141128160449
  16. Gnanasegaran G, 2014, EUR J NUCL MED MOL I, V41, pS26, DOI 10.1007/s00259-013-2643-0
  17. Goldenberg DM, 2007, ONCOGENE, V26, P3734, DOI 10.1038/sj.onc.1210373
  18. Goldenberg DM, 2012, EXPERT OPIN BIOL TH, V12, P1173, DOI 10.1517/14712598.2012.693472
  19. Goldenberg DM, 2003, CANCER IMMUNOL IMMUN, V52, P281, DOI 10.1007/s00262-002-0348-5
  20. GOODWIN DA, 1988, J NUCL MED, V29, P226
  21. Hacker MC, 2011, PRINCIPLES OF REGENERATIVE MEDICINE, 2ND EDITION, P587, DOI 10.1016/B978-0-12-381422-7.10033-1
  22. Hamoudeh M, 2008, ADV DRUG DELIVER REV, V60, P1329, DOI 10.1016/j.addr.2008.04.013
  23. Janzer M, 2016, BIOCONJUGATE CHEM, V27, P2441, DOI 10.1021/acs.bioconjchem.6b00397
  24. Karver MR, 2011, BIOCONJUGATE CHEM, V22, P2263, DOI 10.1021/bc200295y
  25. Keinanen O, 2016, ACS MED CHEM LETT, V7, P62, DOI 10.1021/acsmedchemlett.5b00330
  26. Lappchen T, 2017, NUCL MED BIOL, V55, P19, DOI 10.1016/j.nucmedbio.2017.09.001
  27. Liu GZ, 2002, J NUCL MED, V43, P384
  28. Liu S, 2008, ADV DRUG DELIVER REV, V60, P1347, DOI 10.1016/j.addr.2008.04.006
  29. Maggi A, 2016, ORG BIOMOL CHEM, V14, P7544, DOI 10.1039/c6ob01411a
  30. Meszaros LK, 2010, INORG CHIM ACTA, V363, P1059, DOI 10.1016/j.ica.2010.01.009
  31. Meyer JP, 2017, J MED CHEM, V60, P8201, DOI 10.1021/acs.jmedchem.7b01108
  32. Meyer JP, 2016, BIOCONJUGATE CHEM, V27, P298, DOI 10.1021/acs.bioconjchem.5b00504
  33. MORTON DB, 1985, VET REC, V116, P431, DOI 10.1136/vr.116.16.431
  34. Prescher JA, 2005, NAT CHEM BIOL, V1, P13, DOI 10.1038/nchembio0605-13
  35. Presta LG, 1997, CANCER RES, V57, P4593
  36. Quinn T, 2010, GIORN ITAL DERMAT V, V145, P245
  37. Rossin R., 2010, ANGEW CHEM, V122, P3447
  38. Rossin R, 2014, MOL PHARMACEUT, V11, P3090, DOI 10.1021/mp500275a
  39. Rossin R, 2013, J NUCL MED, V54, P1989, DOI 10.2967/jnumed.113.123745
  40. Ruhrberg C, 2002, GENE DEV, V16, P2684, DOI 10.1101/gad.242002
  41. Sharkey RM, 2005, CLIN CANCER RES, V11, p7109S, DOI 10.1158/1078-0432.CCR-1004-0009
  42. Sletten EM, 2009, ANGEW CHEM INT EDIT, V48, P6974, DOI 10.1002/anie.200900942
  43. Steiner M, 2011, CLIN CANCER RES, V17, P6406, DOI 10.1158/1078-0432.CCR-11-0483
  44. Stollman TH, 2009, CANCER BIOTHER RADIO, V24, P195, DOI 10.1089/cbr.2008.0574
  45. Surfraz MBU, 2008, DALTON T, P2920, DOI 10.1039/b805110k
  46. Surfraz MBU, 2007, J MED CHEM, V50, P1418, DOI 10.1021/jm0612741
  47. Surfraz MBU, 2010, TETRAHEDRON, V66, P2037, DOI 10.1016/j.tet.2010.01.038
  48. van de Watering FCJ, 2014, FRONT MED, V1, DOI 10.3389/fmed.2014.00044
  49. van Dongen GAMS, 2007, ONCOLOGIST, V12, P1379, DOI 10.1634/theoncologist.12-12-1379
  50. Vito A, 2016, PLOS ONE, V11, DOI 10.1371/journal.pone.0167425
  51. Weis SM, 2011, NAT MED, V17, P1359, DOI 10.1038/nm.2537
  52. Weissleder R, 2006, SCIENCE, V312, P1168, DOI 10.1126/science.1125949
  53. Weissleder R, 2008, NATURE, V452, P580, DOI 10.1038/nature06917
  54. Witmer AN, 2002, J HISTOCHEM CYTOCHEM, V50, P767, DOI 10.1177/002215540205000603
  55. Yamaguchi R, 1998, HEPATOLOGY, V28, P68, DOI 10.1002/hep.510280111
  56. Yang JQ, 2010, BIOORGAN MED CHEM, V18, P6695, DOI 10.1016/j.bmc.2010.07.061
  57. Yazdani A, 2017, DALTON T, V46, P14691, DOI 10.1039/c7dt01497j
  58. Yazdani A, 2016, J MED CHEM, V59, P9381, DOI 10.1021/acs.jmedchem.6b00938
  59. Zeglis BM, 2015, MOL PHARMACEUT, V12, P3575, DOI 10.1021/acs.molpharmaceut.5b00294
  60. Zeglis BM, 2013, J NUCL MED, V54, P1389, DOI 10.2967/jnumed.112.115840

Coleções
Artigos e Materiais de Revistas Científicas - FM/MDR
Artigos e Materiais de Revistas Científicas - HC/ICESP
Artigos e Materiais de Revistas Científicas - LIM/21
Artigos e Materiais de Revistas Científicas - LIM/24
Artigos e Materiais de Revistas Científicas - LIM/43