Pro-organic radical contrast agents ("pro-ORCAs") for real-time MRI of pro-drug activation in biological systems.


Journal

Polymer chemistry
ISSN: 1759-9954
Titre abrégé: Polym Chem
Pays: England
ID NLM: 101562526

Informations de publication

Date de publication:
07 Aug 2020
Historique:
entrez: 1 4 2021
pubmed: 2 4 2021
medline: 2 4 2021
Statut: ppublish

Résumé

Nitroxide-based organic-radical contrast agents (ORCAs) are promising as safe, next-generation magnetic resonance imaging (MRI) tools. Nevertheless, stimuli-responsive ORCAs that enable MRI monitoring of prodrug activation have not been reported; such systems could open new avenues for prodrug validation and image-guided drug delivery. Here, we introduce a novel "pro-ORCA" concept that addresses this challenge. By covalent conjugation of nitroxides and drug molecules (doxorubicin, DOX) to the same brush-arm star polymer (BASP) through chemically identical cleavable linkers, we demonstrate that pro-ORCA and prodrug activation,

Identifiants

pubmed: 33790990
doi: 10.1039/d0py00558d
pmc: PMC8009311
mid: NIHMS1610607
doi:

Types de publication

Journal Article

Langues

eng

Pagination

4768-4779

Subventions

Organisme : NCI NIH HHS
ID : R01 CA220468
Pays : United States

Déclaration de conflit d'intérêts

Conflicts of interest There are no conflicts to declare.

Références

Nano Lett. 2006 Nov;6(11):2427-30
pubmed: 17090068
Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7066-7070
pubmed: 29624828
J Nucl Med. 2016 Dec;57(12):1833-1837
pubmed: 27738007
Quant Imaging Med Surg. 2011 Dec;1(1):35-40
pubmed: 23256052
J Med Chem. 1999 Sep 9;42(18):3657-67
pubmed: 10479297
Small. 2016 Sep;12(33):4563-71
pubmed: 27351167
ACS Macro Lett. 2019 Apr 16;8(4):473-478
pubmed: 31289694
J Biol Inorg Chem. 2014 Feb;19(2):127-31
pubmed: 24414380
J Am Chem Soc. 2014 Apr 23;136(16):5896-9
pubmed: 24724706
Macromolecules. 2010 Dec 28;43(24):10326-10335
pubmed: 21532937
Angew Chem Int Ed Engl. 2010 Dec 17;49(51):9960-4
pubmed: 21082634
Bioconjug Chem. 2011 Oct 19;22(10):1879-903
pubmed: 21830812
Chem Commun (Camb). 2009 Jan 7;(1):53-5
pubmed: 19081996
Am J Clin Oncol. 2002 Feb;25(1):60-4
pubmed: 11823699
Proc Natl Acad Sci U S A. 2009 Jul 7;106(27):11394-9
pubmed: 19564622
N Engl J Med. 2010 Jul 22;363(4):301-4
pubmed: 20551152
Cancer Res. 2010 Mar 15;70(6):2180-90
pubmed: 20215497
Angew Chem Int Ed Engl. 2009;48(23):4174-9
pubmed: 19408274
Curr Opin Chem Biol. 2015 Oct;28:29-38
pubmed: 26056952
Proc Natl Acad Sci U S A. 2016 Apr 12;113(15):E2104-13
pubmed: 27036008
J Am Chem Soc. 2013 Aug 7;135(31):11657-62
pubmed: 23865715
Acc Chem Res. 2011 Oct 18;44(10):1123-34
pubmed: 21692448
Chem Soc Rev. 2010 Feb;39(2):464-73
pubmed: 20111771
ACS Macro Lett. 2014 Sep 16;3(9):854-857
pubmed: 25243099
Cancer Res. 2010 Oct 1;70(19):7553-61
pubmed: 20702603
Chem Rev. 2019 Jan 23;119(2):957-1057
pubmed: 30350585
Magn Reson Med. 2006 Nov;56(5):1011-8
pubmed: 17029236
ACS Macro Lett. 2017 Feb 21;6(2):176-180
pubmed: 35632889
ACS Macro Lett. 2018 Apr 17;7(4):472-476
pubmed: 30271675
Bioconjug Chem. 2010 Aug 18;21(8):1404-7
pubmed: 20715846
ACS Macro Lett. 2017 Sep 19;6(9):963-968
pubmed: 35650899
J Control Release. 2010 Sep 1;146(2):219-27
pubmed: 20403397
ACS Nano. 2018 Nov 27;12(11):11343-11354
pubmed: 30387988
Bioconjug Chem. 2019 Sep 18;30(9):2264-2286
pubmed: 31380621
Cancer Res. 2010 Sep 15;70(18):7031-41
pubmed: 20685894
J Am Chem Soc. 2012 Sep 26;134(38):15724-7
pubmed: 22974177
Angew Chem Int Ed Engl. 2014 Apr 22;53(17):4469-74
pubmed: 24644015
Nat Rev Mater. 2017;2:
pubmed: 29075517
Sci Transl Med. 2018 Jan 31;10(426):
pubmed: 29386357
J Cereb Blood Flow Metab. 2008 Jun;28(6):1165-74
pubmed: 18270519
Ann Oncol. 2017 Dec 1;28(suppl_12):xii33-xii43
pubmed: 29253115
N Engl J Med. 2007 Aug 16;357(7):720-2
pubmed: 17699829
Nat Med. 2007 Mar;13(3):372-7
pubmed: 17322898
ACS Nano. 2012 Aug 28;6(8):7281-94
pubmed: 22809405
Chem Rev. 2015 Oct 14;115(19):10967-1011
pubmed: 26463640
Acc Chem Res. 2011 Oct 18;44(10):841
pubmed: 22004477
J Am Chem Soc. 2015 Feb 11;137(5):2056-66
pubmed: 25629952
Acc Chem Res. 2011 Oct 18;44(10):969-78
pubmed: 21675721
World J Gastroenterol. 2015 Dec 21;21(47):13400-2
pubmed: 26715826
Annu Rev Genomics Hum Genet. 2011;12:217-44
pubmed: 21721939
J Control Release. 2012 Jun 10;160(2):117-34
pubmed: 22484195
J Am Chem Soc. 2016 Dec 21;138(50):16380-16387
pubmed: 27998081
ACS Nano. 2019 Jan 22;13(1):176-186
pubmed: 30592401
Acc Chem Res. 2015 Nov 17;48(11):2935-46
pubmed: 26513450
Chem Soc Rev. 2019 Feb 4;48(3):771-813
pubmed: 30575832
Langmuir. 2014 Jul 29;30(29):8898-906
pubmed: 24979524
Biomaterials. 2012 Sep;33(26):6186-93
pubmed: 22687759
Acc Chem Res. 2008 Dec;41(12):1630-40
pubmed: 18698851
Macromol Biosci. 2015 Jun;15(6):788-98
pubmed: 25677802
Adv Mater. 2018 Jan;30(3):
pubmed: 29210480
Nat Commun. 2014 Mar 04;5:3384
pubmed: 24594970
Pediatr Radiol. 2008 May;38(5):489-96; quiz 602-3
pubmed: 17943276
Mol Pharm. 2018 Aug 6;15(8):2973-2983
pubmed: 29771534
J Immunol. 2017 Jan 1;198(1):31-39
pubmed: 27994166
Chem Mater. 2014 Mar 25;26(6):2105-2112
pubmed: 24748722
Nat Biomed Eng. 2018 Sep;2(9):707
pubmed: 31015683
Nat Commun. 2014 Nov 18;5:5460
pubmed: 25403521
Mol Pharm. 2010 Dec 6;7(6):1959-73
pubmed: 20957997
J Am Chem Soc. 2016 Sep 28;138(38):12494-501
pubmed: 27626288
J Am Chem Soc. 2016 Sep 14;138(36):11501-4
pubmed: 27580971
Nat Commun. 2014 Aug 26;5:4712
pubmed: 25158161
Nat Commun. 2017 Mar 10;8:14702
pubmed: 28281530
Biomaterials. 2010 Sep;31(27):7132-8
pubmed: 20580427
ACS Cent Sci. 2017 Jul 26;3(7):800-811
pubmed: 28776023
Acc Chem Res. 2011 Oct 18;44(10):1029-38
pubmed: 21545096
Chem Soc Rev. 2018 Jan 2;47(1):28-52
pubmed: 29057403

Auteurs

Hung V-T Nguyen (HV)

Department of Chemistry, Massachusetts Institute of Technology (MIT).
David H. Koch Institute for Integrative Cancer Research, MIT, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.
These authors contributed equally.

Alexandre Detappe (A)

David H. Koch Institute for Integrative Cancer Research, MIT, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.
Centre Paul Strauss, 3 Rue de la Porte de l'Hopital, 67000 Strasbourg, France.
These authors contributed equally.

Peter Harvey (P)

Department of Biological Engineering, MIT.

Nolan Gallagher (N)

Department of Chemistry, Massachusetts Institute of Technology (MIT).

Clelia Mathieu (C)

Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.

Michael P Agius (MP)

Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.

Oksana Zavidij (O)

Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.

Wencong Wang (W)

Department of Chemistry, Massachusetts Institute of Technology (MIT).

Yivan Jiang (Y)

Department of Chemistry, Massachusetts Institute of Technology (MIT).

Andrzej Rajca (A)

Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588, United States.

Alan Jasanoff (A)

Department of Biological Engineering, MIT.
Department of Brain and Cognitive Sciences, MIT.
Department of Nuclear Science and Engineering, MIT.

Irene M Ghobrial (IM)

Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.

P Peter Ghoroghchian (PP)

David H. Koch Institute for Integrative Cancer Research, MIT, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Department of Medical Oncology, Dana-Farber Cancer Institute, 450 Brookline Avenue, Boston, Massachusetts 02215, United States.
Harvard Medical School, 25 Shattuck Street, Boston, Massachusetts 02115, United States.

Jeremiah A Johnson (JA)

Department of Chemistry, Massachusetts Institute of Technology (MIT).
David H. Koch Institute for Integrative Cancer Research, MIT, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Classifications MeSH