PEGylated Purpurin 18 with Improved Solubility: Potent Compounds for Photodynamic Therapy of Cancer.

PEGylated purpurin 18 apoptosis cancer cells cytotoxicity flow cytometry live-cell fluorescence microscopy photodynamic therapy photosensitizer phototoxicity singlet oxygen

Journal

Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009

Informations de publication

Date de publication:
06 Dec 2019
Historique:
received: 30 09 2019
revised: 29 11 2019
accepted: 01 12 2019
entrez: 11 12 2019
pubmed: 11 12 2019
medline: 6 5 2020
Statut: epublish

Résumé

Purpurin 18 derivatives with a polyethylene glycol (PEG) linker were synthesized as novel photosensitizers (PSs) with the goal of using them in photodynamic therapy (PDT) for cancer. These compounds, derived from a second-generation PS, exhibit absorption at long wavelengths; considerable singlet oxygen generation and, in contrast to purpurin 18, have higher hydrophilicity due to decreased logP. Together, these properties make them potentially ideal PSs. To verify this, we screened the developed compounds for cell uptake, intracellular localization, antitumor activity and induced cell death type. All of the tested compounds were taken up into cancer cells of various origin and localized in organelles known to be important PDT targets, specifically, mitochondria and the endoplasmic reticulum. The incorporation of a zinc ion and PEGylation significantly enhanced the photosensitizing efficacy, decreasing IC

Identifiants

pubmed: 31817655
pii: molecules24244477
doi: 10.3390/molecules24244477
pmc: PMC6943672
pii:
doi:

Substances chimiques

Porphyrins 0
Singlet Oxygen 17778-80-2
purpurin 18 25465-77-4

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Subventions

Organisme : The Ministry of Education, Youth and Sports
ID : LO1220, LO1601, LM2015063
Organisme : CZ.02.1.01/0.0/0.0/16_013/0001799
ID : CZ.02.1.01/0.0/0.0/16_013/0001799
Organisme : OP VVV [2.16/3.1.00/24503]
ID : OP VVV [2.16/3.1.00/24503]
Organisme : Specific university research MSMT
ID : No 21-SVV/2019
Organisme : Martina Roeselová foundation
ID : Martina Roeselová foundation
Organisme : L'Oréal -UNESCO for Women in Science 2019
ID : L'Oréal -UNESCO for Women in Science 2019

Références

J Chem Inf Model. 2014 Dec 22;54(12):3284-301
pubmed: 25382374
Biomaterials. 2017 Oct;141:199-209
pubmed: 28689116
Proc Natl Acad Sci U S A. 1988 Jul;85(13):4582-6
pubmed: 3387428
Retrovirology. 2014 May 20;11:37
pubmed: 24886575
Int J Mol Sci. 2014 May 08;15(5):8091-105
pubmed: 24815070
J Mater Chem B. 2019 Sep 18;7(36):5465-5477
pubmed: 31414695
Biochim Biophys Acta. 2007 Nov;1768(11):2748-56
pubmed: 17692283
Photodiagnosis Photodyn Ther. 2005 Jun;2(2):91-106
pubmed: 25048669
Org Biomol Chem. 2016 Jan 21;14(3):1049-64
pubmed: 26633562
Bioorg Med Chem. 2009 Feb 1;17(3):1297-306
pubmed: 19121946
Mol Cancer Ther. 2017 Jun;16(6):1124-1132
pubmed: 28292934
Front Pharmacol. 2016 Nov 15;7:434
pubmed: 27895586
Adv Drug Deliv Rev. 2004 Jan 13;56(1):53-76
pubmed: 14706445
J Natl Cancer Inst. 1998 Jun 17;90(12):889-905
pubmed: 9637138
Phys Chem Chem Phys. 2010 Oct 14;12(38):12229-36
pubmed: 20714577
Lasers Surg Med. 2004;34(1):62-72
pubmed: 14755426
Cancer Biol Ther. 2010 Sep 1;10(5):471-82
pubmed: 20592494
Sci Rep. 2017 Oct 17;7(1):13375
pubmed: 29042620
Biochem Biophys Res Commun. 2002 Mar 8;291(4):813-9
pubmed: 11866438
Photochem Photobiol. 1988 Nov;48(5):579-82
pubmed: 3241831
Anticancer Res. 2016 Sep;36(9):4493-501
pubmed: 27630287
Bioconjug Chem. 2008 Mar;19(3):705-13
pubmed: 18269224
Oncol Lett. 2015 Feb;9(2):551-556
pubmed: 25621023
J Fluoresc. 2004 Jul;14(4):465-72
pubmed: 15617389
J Photochem Photobiol B. 2017 Mar;168:175-184
pubmed: 28236685
Indian J Biochem Biophys. 2005 Feb;42(1):7-12
pubmed: 23923575
J Photochem Photobiol B. 2009 Jul 17;96(1):1-8
pubmed: 19406659
Photodiagnosis Photodyn Ther. 2009 Jun;6(2):94-6
pubmed: 19683209
J Photochem Photobiol B. 2009 Aug 3;96(2):101-8
pubmed: 19464192
J Control Release. 2006 Mar 10;111(1-2):153-64
pubmed: 16423422
Bioconjug Chem. 2009 Feb;20(2):274-82
pubmed: 19191565
Mol Pharm. 2011 Aug 1;8(4):1186-97
pubmed: 21702452
Int J Clin Exp Med. 2014 Dec 15;7(12):4867-76
pubmed: 25663983
Acta Naturae. 2015 Jan-Mar;7(1):109-16
pubmed: 25927008
Photochem Photobiol. 1999 Oct;70(4):391-475
pubmed: 10546544
PLoS One. 2017 Apr 20;12(4):e0176208
pubmed: 28426740
Beilstein J Org Chem. 2019 Aug 13;15:1933-1944
pubmed: 31501660
J Med Chem. 2015 Nov 12;58(21):8658-70
pubmed: 26457363
Cancer Res. 2001 Oct 1;61(19):7155-62
pubmed: 11585749
Cancer Res. 1985 Nov;45(11 Pt 1):5328-34
pubmed: 4053007
Invest New Drugs. 2013 Feb;31(1):192-9
pubmed: 22688292
Cancer Lett. 2003 May 30;195(1):73-80
pubmed: 12767514
Cancer Biol Ther. 2006 Sep;5(9):1111-6
pubmed: 16880732
Photochem Photobiol Sci. 2004 Feb;3(2):231-5
pubmed: 14872242
J Med Chem. 2016 May 26;59(10):4999-5010
pubmed: 27136389
Cancer Res. 1997 Sep 15;57(18):4000-7
pubmed: 9307285
Photochem Photobiol. 1997 Aug;66(2):224-8
pubmed: 9277141
BMC Struct Biol. 2003 Jul 7;3:6
pubmed: 12846933
RSC Adv. 2019 Jun 11;9(32):18359-18370
pubmed: 35515266
J Immunol Methods. 1995 Jul 17;184(1):39-51
pubmed: 7622868
Int J Mol Sci. 2008 May;9(5):864-871
pubmed: 19325790
J Med Chem. 2010 May 27;53(10):4018-27
pubmed: 20441223
Molecules. 2015 Oct 27;20(10):19526-39
pubmed: 26516829
Br J Cancer. 1995 Mar;71(3):549-55
pubmed: 7880738
Photochem Photobiol Sci. 2008 Apr;7(4):433-41
pubmed: 18385885
Adv Pharm Bull. 2016 Jun;6(2):227-33
pubmed: 27478785
PLoS One. 2017 Oct 10;12(10):e0185984
pubmed: 29016698
Photochem Photobiol Sci. 2011 May;10(5):792-801
pubmed: 21479313
Mol Pharm. 2014 Sep 2;11(9):3164-73
pubmed: 25077598
Bioorg Med Chem. 2004 Sep 15;12(18):4853-60
pubmed: 15336264
Integr Med Res. 2013 Sep;2(3):106-111
pubmed: 28664061
J Org Chem. 2012 Dec 7;77(23):10638-47
pubmed: 23126407
Photochem Photobiol. 1988 Aug;48(2):157-63
pubmed: 3222325
CA Cancer J Clin. 2011 Jul-Aug;61(4):250-81
pubmed: 21617154
Org Biomol Chem. 2006 Oct 21;4(20):3815-21
pubmed: 17024289
Tetrahedron. 2007 Apr 30;63(18):3840-3849
pubmed: 17479170
J Mater Chem B. 2018 Jul 14;6(26):4301-4307
pubmed: 32254506
Photochem Photobiol. 2001 Mar;73(3):290-6
pubmed: 11281026
Photochem Photobiol Sci. 2002 Apr;1(4):283-7
pubmed: 12661969
Eur J Med Chem. 2016 Nov 29;124:284-298
pubmed: 27597406
Drug Des Devel Ther. 2018 Nov 16;12:3961-3972
pubmed: 30510404
J Pharm Biomed Anal. 1995 Jun;13(7):823-8
pubmed: 8562605
J Biol Chem. 2013 Dec 20;288(51):36579-88
pubmed: 24214973
J Med Chem. 2007 Apr 19;50(8):1754-67
pubmed: 17371002
Cancers (Basel). 2011;3(2):2516-39
pubmed: 23914299
Cancer Chemother Pharmacol. 2006 Apr;57(4):500-6
pubmed: 16075277
Anticancer Res. 2011 Mar;31(3):763-9
pubmed: 21498693

Auteurs

Vladimíra Pavlíčková (V)

Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 3, 166 28 Prague 6, Czech Republic.

Silvie Rimpelová (S)

Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 3, 166 28 Prague 6, Czech Republic.

Michal Jurášek (M)

Department of Chemistry of Natural Compounds, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Kamil Záruba (K)

Department of Analytical Chemistry, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Jan Fähnrich (J)

Department of Analytical Chemistry, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Ivana Křížová (I)

Department of Biotechnology, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Jiří Bejček (J)

Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 3, 166 28 Prague 6, Czech Republic.

Zdeňka Rottnerová (Z)

Central laboratories, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Vojtěch Spiwok (V)

Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 3, 166 28 Prague 6, Czech Republic.

Pavel Drašar (P)

Department of Chemistry of Natural Compounds, University of Chemistry and Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic.

Tomáš Ruml (T)

Department of Biochemistry and Microbiology, University of Chemistry and Technology in Prague, Technická 3, 166 28 Prague 6, Czech Republic.

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