Highly Phototoxic Transplatin-Modified Distyryl-BODIPY Photosensitizers for Photodynamic Therapy.
Antineoplastic Agents
/ chemistry
Boron Compounds
/ chemistry
Cell Proliferation
/ drug effects
Cell Survival
/ drug effects
Cisplatin
/ chemistry
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
Humans
Molecular Structure
Photochemotherapy
Photosensitizing Agents
/ chemistry
Singlet Oxygen
/ metabolism
Structure-Activity Relationship
Cancer
intramolecular charge transfer
photophysics
photosensitizer
singlet oxygen
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
17 02 2021
17 02 2021
Historique:
received:
08
09
2020
revised:
14
10
2020
pubmed:
10
11
2020
medline:
4
11
2021
entrez:
9
11
2020
Statut:
ppublish
Résumé
We report the synthesis of the first transplatin-BODIPY conjugates for application in photodynamic therapy (PDT). The distyryl BODIPYs containing two iodine atoms were designed to absorb in the red region, easily undergo intersystem crossing for efficient singlet oxygen generation, and additionally offer the possibility for coordination with mono-activated transplatin. We were able to demonstrate that coordination of the BODIPYs with a mono-activated transplatin increases the phototoxic index of the photosensitizers significantly, giving rise to highly phototoxic distyryl BODIPY derivatives, of which one was shown to have the highest ever reported phototoxic index against any cell line. Furthermore, the photophysical mechanism of singlet oxygen generation in distyryl BODIPYs undergoing intramolecular charge transfer was studied experimentally and using time-dependent density functional theory.
Identifiants
pubmed: 33164336
doi: 10.1002/cmdc.202000702
doi:
Substances chimiques
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
0
Antineoplastic Agents
0
Boron Compounds
0
Photosensitizing Agents
0
transplatin
14913-33-8
Singlet Oxygen
17778-80-2
Cisplatin
Q20Q21Q62J
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
694-701Subventions
Organisme : University of Zurich
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
P. Agostinis, K. Berg, K. A. Cengel, T. H. Foster, A. W. Girotti, S. O. Gollnick, S. M. Hahn, M. R. Hamblin, A. Juzeniene, D. Kessel, M. Korbelik, J. Moan, P. Mroz, D. Nowis, J. Piette, B. C. Wilson, J. Golab, Ca-Cancer J. Clin. 2011, 61, 250-281.
D. E. J. G. J. Dolmans, D. Fukumura, R. K. Jain, Nat. Rev. Cancer 2003, 3, 380-387.
M. Ethirajan, Y. Chen, P. Joshi, R. K. Pandey, Chem. Soc. Rev. 2011, 40, 340-362.
A. Oniszczuk, K. A. Wojtunik-Kulesza, T. Oniszczuk, K. Kasprzak, Biomed. Pharmacother. 2016, 83, 912-929.
C. A. Robertson, D. H. Evans, H. Abrahamse, J. Photochem. Photobiol. B 2009, 96, 1-8.
M. Tampa, M.-I. Sarbu, C. Matei, C.-I. Mitran, M.-I. Mitran, C. Caruntu, C. Constantin, M. Neagu, S.-R. Georgescu, Oncol. Lett. 2019, 17, 4085-4093.
D. van Straten, V. Mashayekhi, H. S. de Bruijn, S. Oliveira, D. J. Robinson, Cancers 2017, 9, 19.
S. A. McFarland, A. Mandel, R. Dumoulin-White, G. Gasser, Curr. Opin. Chem. Biol. 2020, 56, 23-27.
M. C. DeRosa, R. J. Crutchley, Coord. Chem. Rev. 2002, 233, 351-371.
F. Wilkinson, W. P. Helman, A. B. Ross, J. Phys. Chem. Ref. Data 1993, 22, 113-262.
Z. Zhou, J. Song, L. Nie, X. Chen, Chem. Soc. Rev. 2016, 45, 6597-6626.
I. Yoon, J. Z. Li, Y. K. Shim, Clin. Endosc. 2013, 46, 7-23.
H. Abrahamse, M. R. Hamblin, Biochem. J. 2016, 473, 347-364.
A. Naik, R. Rubbiani, G. Gasser, B. Spingler, Angew. Chem. Int. Ed. 2014, 53, 6938-6941;
Angew. Chem. 2014, 126, 7058-7061.
S. G. Bown, Philos. Trans. R. Soc. London Ser. A 2013, 371, 20120371.
A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung, K. Burgess, Chem. Soc. Rev. 2013, 42, 77-88.
A. Gorman, J. Killoran, C. O′Shea, T. Kenna, W. M. Gallagher, D. F. O′Shea, J. Am. Chem. Soc. 2004, 126, 10619-10631.
J. Wang, Q. Gong, L. Wang, E. Hao, L. Jiao, J. Porphyrins Phthalocyanines 2019, 1-33.
C. S. Kue, S. Y. Ng, S. H. Voon, A. Kamkaew, L. Y. Chung, L. V. Kiew, H. B. Lee, Photochem. Photobiol. Sci. 2018, 17, 1691-1708.
H. Lu, J. Mack, Y. Yang, Z. Shen, Chem. Soc. Rev. 2014, 43, 4778-4823.
A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932.
M. L. Agazzi, M. B. Ballatore, A. M. Durantini, E. N. Durantini, A. C. Tomé, J. Photochem. Photobiol. C 2019, 40, 21-48.
T. Yogo, Y. Urano, Y. Ishitsuka, F. Maniwa, T. Nagano, J. Am. Chem. Soc. 2005, 127, 12162-12163.
S. G. Awuah, Y. You, RSC Adv. 2012, 2, 11169-11183.
Y. P. Rey, D. G. Abradelo, N. Santschi, C. A. Strassert, R. Gilmour, Eur. J. Org. Chem. 2017, 2170-2178.
Y. Zhang, Z. Yang, X. Zheng, L. Yang, N. Song, L. Zhang, L. Chen, Z. Xie, Dyes Pigm. 2020, 178, 108348.
N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172.
A. Onkelinx, F. C. De Schryver, L. Viaene, M. Van der Auweraer, K. Iwai, M. Yamamoto, M. Ichikawa, H. Masuhara, M. Maus, W. Rettig, J. Am. Chem. Soc. 1996, 118, 2892-2902.
M. Kollmannsberger, K. Rurack, U. Resch-Genger, J. Daub, J. Phys. Chem. A 1998, 102, 10211-10220.
L. Gai, J. Mack, H. Lu, H. Yamada, D. Kuzuhara, G. Lai, Z. Li, Z. Shen, Chem. Eur. J. 2014, 20, 1091-1102.
Z. R. Grabowski, K. Rotkiewicz, W. Rettig, Chem. Rev. 2003, 103, 3899-4032.
K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. Int. Ed. 2001, 40, 385-387;
Angew. Chem. 2001, 113, 396-399.
M. Baruah, W. Qin, C. Flors, J. Hofkens, R. A. L. Vallée, D. Beljonne, M. Van der Auweraer, W. M. De Borggraeve, N. Boens, J. Phys. Chem. A 2006, 110, 5998-6009.
E. Deniz, G. C. Isbasar, Ö. A. Bozdemir, L. T. Yildirim, A. Siemiarczuk, E. U. Akkaya, Org. Lett. 2008, 10, 3401-3403.
N. Epelde-Elezcano, V. Martínez-Martínez, E. Peña-Cabrera, C. F. A. Gómez-Durán, I. L. Arbeloa, S. Lacombe, RSC Adv. 2016, 6, 41991-41998.
N. Epelde-Elezcano, E. Palao, H. Manzano, A. Prieto-Castañeda, A. R. Agarrabeitia, A. Tabero, A. Villanueva, S. de la Moya, I. López-Arbeloa, V. Martínez-Martínez, M. J. Ortiz, Chem. Eur. J. 2017, 23, 4837-4848.
W. Hu, X.-F. Zhang, X. Lu, S. Lan, D. Tian, T. Li, L. Wang, S. Zhao, M. Feng, J. Zhang, Dyes Pigm. 2018, 149, 306-314.
L. Wang, J. Bai, Y. Qian, New J. Chem. 2019, 43, 16829-16834.
X.-F. Zhang, Y. Zhang, B. Xu, J. Photochem. Photobiol. A 2017, 349, 197-206.
R. Rubbiani, W. Wu, A. Naik, M. Larocca, L. Schneider, R. Padrutt, V. Babu, C. König, D. Hinger, C. Maake, G. Gasser, S. Ferrari, B. Spingler, Chem. Commun. 2020, 56, 14373-14376.
L. Schneider, M. Larocca, W. Wu, V. Babu, R. Padrutt, E. Slyshkina, C. König, S. Ferrari, B. Spingler, Photochem. Photobiol. Sci. 2019, 18, 2792-2803.
L. R. Kelland, C. F. J. Barnard, K. J. Mellish, M. Jones, P. M. Goddard, M. Valenti, A. Bryant, B. A. Murrer, K. R. Harrap, Cancer Res. 1994, 54, 5618-5622.
Z. Guo, Y. Zou, H. He, J. Rao, S. Ji, X. Cui, H. Ke, Y. Deng, H. Yang, C. Chen, Y. Zhao, H. Chen, Adv. Mater. 2016, 28, 10155-10164.
Y. Liu, Z. Li, L. Chen, Z. Xie, Dyes Pigm. 2017, 141, 5-12.
M. K. Raza, S. Gautam, A. Garai, K. Mitra, P. Kondaiah, A. R. Chakravarty, Inorg. Chem. 2017, 56, 11019-11029.
M. K. Raza, S. Gautam, P. Howlader, A. Bhattacharyya, P. Kondaiah, A. R. Chakravarty, Inorg. Chem. 2018, 57, 14374-14385.
X. Xue, C. Qian, H. Fang, H.-K. Liu, H. Yuan, Z. Guo, Y. Bai, W. He, Angew. Chem. Int. Ed. 2019, 58, 12661-12666.
W. M. Gallagher, L. T. Allen, C. O′Shea, T. Kenna, M. Hall, A. Gorman, J. Killoran, D. F. O′Shea, Brit. J. Cancer 2005, 92, 1702-1710.
A. K. Chandra, N. J. Turro, A. L. Lyons, Jr., P. Stone, J. Am. Chem. Soc. 1978, 100, 4964-4968.
C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr. 2016, B72, 171-179.
J. H. Gibbs, Z. Zhou, D. Kessel, F. R. Fronczek, S. Pakhomova, M. G. H. Vicente, J. Photochem. Photobiol. B 2015, 145, 35-47.
P. Zhang, C. K. C. Chiu, H. Huang, Y. P. Y. Lam, A. Habtemariam, T. Malcomson, M. J. Paterson, G. J. Clarkson, P. B. O′Connor, H. Chao, P. J. Sadler, Angew. Chem. Int. Ed. 2017, 56, 14898-14902;
Angew. Chem. 2017, 129, 15094-15098.
H. H. Wasserman, K. Stiller, M. B. Floyd, Tetrahedron Lett. 1968, 9, 3277-3280.
I. Gürol, M. Durmuş, V. Ahsen, T. Nyokong, Dalton Trans. 2007, 3782-3791.
Y. Zorlu, F. Dumoulin, M. Durmuş, V. Ahsen, Tetrahedron 2010, 66, 3248-3258.
J. Xu, L. Zhu, Q. Wang, L. Zeng, X. Hu, B. Fu, Z. Sun, Tetrahedron 2014, 70, 5800-5805.
C. A. Cohn, C. E. Pedigo, S. N. Hylton, S. R. Simon, M. A. A. Schoonen, Geochem. Trans. 2009, 10, 8.
P. M. Antoni, A. Naik, I. Albert, R. Rubbiani, S. Gupta, P. Ruiz-Sanchez, P. Munikorn, J. M. Mateos, V. Luginbuehl, P. Thamyongkit, U. Ziegler, G. Gasser, G. Jeschke, B. Spingler, Chem. Eur. J. 2015, 21, 1179-1183.
R. P. Rastogi, S. P. Singh, D.-P. Häder, R. P. Sinha, Biochem. Biophys. Res. Commun. 2010, 397, 603-607.
B. Spingler, S. Schnidrig, T. Todorova, F. Wild, CrystEngComm 2012, 14, 751-757.
CrysAlisPro, vers. 1.171.40, Rigaku Oxford Corporation, 2019.
G. M. Sheldrick, Acta Crystallogr. 2015, A71, 3-8.
G. M. Sheldrick, Acta Crystallogr. 2015, C71, 3-8.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
C. F. Macrae, L. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shields, J. S. Stevens, M. Towler, P. A. Wood, J. Appl. Crystallogr. 2020, 53, 226-235.