Synthesis and photodynamic activity of new 5-[(E)-2-(3-alkoxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-2-phenyl-3H-indoles.
cytotoxicity
indole
photodynamic effect
pyrazole
reactive oxygen species
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
05 Jul 2024
05 Jul 2024
Historique:
revised:
31
05
2024
received:
16
04
2024
accepted:
17
06
2024
medline:
6
7
2024
pubmed:
6
7
2024
entrez:
5
7
2024
Statut:
aheadofprint
Résumé
A series of new indole-pyrazole hybrids 8a-m were synthesized through the palladium-catalyzed ligandless Heck coupling reaction from easily accessible unsubstituted, methoxy- or fluoro-substituted 4-ethenyl-1H-pyrazoles and 5-bromo-3H-indoles. These compounds exerted cytotoxicity to melanoma G361 cells when irradiated with blue light (414 nm) and no cytotoxicity in the dark at concentrations up to 10 µM, prompting us to explore their photodynamic effects. The photodynamic properties of the example compound 8d were further investigated in breast cancer MCF-7 cells. Evaluation revealed comparable anticancer activities of 8d in both breast and melanoma cancer cell lines within the submicromolar range. The treatment induced a massive generation of reactive oxygen species, leading to different types of cell death depending on the compound concentration and the irradiation intensity.
Identifiants
pubmed: 38969965
doi: 10.1002/ardp.202400282
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2400282Subventions
Organisme : Research Council of Lithuania
ID : S-MIP-23-51
Organisme : The project National Institute for Cancer Research, Programme EXCELES
ID : LX22NPO5102
Organisme : Doctoral Fund of Kaunas University of Technology
ID : A-410
Organisme : Palacký University Olomouc
ID : IGA_PrF_2024_005
Informations de copyright
© 2024 The Author(s). Archiv der Pharmazie published by Wiley‐VCH GmbH on behalf of Deutsche Pharmazeutische Gesellschaft.
Références
M. A. Corsello, J. Kim, N. K. Garg, Chem. Sci. 2017, 8, 5836.
A. Dorababu, RSC Med. Chem. 2020, 11, 1335.
S. Kumar, Ritika, Futur. J. Pharm. Sci. 2020, 6, 121.
M.‐Z. Zhang, Q. Chen, G.‐F. Yang, Eur. J. Med. Chem. 2015, 89, 421.
N. Kaushik, N. Kaushik, P. Attri, N. Kumar, C. Kim, A. Verma, E. Choi, Molecules 2013, 18, 6620.
I. Mancini, J. Vigna, D. Sighel, A. Defant, Molecules 2022, 27, 4948.
M. M. Heravi, V. Zadsirjan, RSC Adv. 2020, 10, 44247.
N. Kerru, L. Gummidi, S. Maddila, K. K. Gangu, S. B. Jonnalagadda, Molecules 2020, 25, 1909.
D. Sunil, P. Kamath, Curr. Top. Med. Chem. 2017, 17, 959.
E. Mahmoud, A. M. Hayallah, S. Kovacic, D. Abdelhamid, M. Abdel‐Aziz, Pharm. Rep. 2022, 74, 570. https://doi.org/10.1007/s43440-022-00370-3
F. Song, Y. Bian, J. Liu, Z. Li, L. Zhao, J. Fang, Y. Lai, M. Zhou, Curr. Top. Med. Chem. 2021, 21, 377.
A. Yver, Ann. Oncol. 2016, 27, 1165.
A. Rekowska, P. Rola, M. Wójcik‐Superczyńska, I. Chmielewska, P. Krawczyk, J. Milanowski, Curr. Oncol. 2022, 29, 3531.
Z.‐Z. Li, V. K. R. Tangadanchu, N. Battini, R. R. Y. Bheemanaboina, Z.‐L. Zang, S.‐L. Zhang, C.‐H. Zhou, Eur. J. Med. Chem. 2019, 179, 723.
F. Yang, X.‐E. Jian, L. Chen, Y.‐F. Ma, Y.‐X. Liu, W.‐W. You, P.‐L. Zhao, New J. Chem. 2021, 45, 21869.
M. Iškauskienė, A. Kadlecová, J. Voller, L. Janovská, V. Malinauskienė, A. Žukauskaitė, A. Šačkus, Arch. Pharm. 2021, 354, 2100001.
G. Campiani, C. Cavella, J. D. Osko, M. Brindisi, N. Relitti, S. Brogi, A. P. Saraswati, S. Federico, G. Chemi, S. Maramai, G. Carullo, B. Jaeger, A. Carleo, R. Benedetti, F. Sarno, S. Lamponi, P. Rottoli, E. Bargagli, C. Bertucci, D. Tedesco, D. Herp, J. Senger, G. Ruberti, F. Saccoccia, S. Saponara, B. Gorelli, M. Valoti, B. Kennedy, H. Sundaramurthi, S. Butini, M. Jung, K. M. Roach, L. Altucci, P. Bradding, D. W. Christianson, S. Gemma, A. Prasse, J. Med. Chem. 2021, 64, 9960.
X.‐L. Xu, C.‐L. Yu, W. Chen, Y.‐C. Li, L.‐J. Yang, Y. Li, H.‐B. Zhang, X.‐D. Yang, Org. Biomol. Chem. 2015, 13, 1550.
A. Kryshchyshyn, D. Kaminskyy, O. Karpenko, A. Gzella, P. Grellier, R. Lesyk, Eur. J. Med. Chem. 2019, 174, 292.
K. Fabitha, M. Chandrakanth, R. N. Pramod, C. G. Arya, Y. Li, J. Banothu, ChemistrySelect 2022, 7, e202201064. https://doi.org/10.1002/slct.202201064
M. Hawash, S. G. Ergun, D. C. Kahraman, A. Olgac, E. Hamel, R. Cetin‐Atalay, S. N. Baytas, J. Mol. Struct. 2023, 1285, 135477.
A. Q. Ramle, N. N. M. Y. Chan, M. P. Ng, C. H. Tan, K. S. Sim, E. R. T. Tiekink, C. C. Fei, Mol. Divers. 2023. https://doi.org/10.1007/s11030-023-10662-2
G. Varvuolytė, L. Malina, A. Bieliauskas, B. Hošíková, H. Simerská, H. Kolářová, N. Kleizienė, V. Kryštof, A. Šačkus, A. Žukauskaitė, Dyes Pigm. 2020, 183, 108666.
F. Huber, J. Roesslein, K. Gademann, Org. Lett. 2019, 21, 2560.
A. J. Smith, D. Dimitrova, J. N. Arokianathar, K. F. Clark, D. L. Poole, S. G. Leach, J. A. Murphy, Chem. Sci. 2020, 11, 12364.
A. Alagumalai, M. F. M. K., P. Vellimalai, M. C. Sil, J. Nithyanandhan, ACS Appl. Mater. Interfaces 2016, 8, 35353.
S. Kumar, D. L. Watkins, T. Fujiwara, Chem. Commun. 2009, 4369.
B. H. Kim, H. S. Freeman, J. Mater. Chem. 2012, 22, 20403.
H. Wölfle, H. Kopacka, K. Wurst, P. Preishuber‐Pflügl, B. Bildstein, J. Organomet. Chem. 2009, 694, 2493.
M. Tomasulo, S. Sortino, F. M. Raymo, Org. Lett. 2005, 7, 1109.
E. A. Owens, N. Bruschi, J. G. Tawney, M. Henary, Dyes Pigm. 2015, 113, 27.
R. M. Boehme, T. Andries, K. H. Dötz, B. Thiele, K. Guenther, Chemosphere 2010, 80, 813.
E. Brambilla, S. Leoni, G. Abbiati, V. Pirovano, E. Rossi, Eur. J. Org. Chem. 2021, 2021, 2440.
S. Li, X. Li, T. Zhang, J. Zhu, K. Liu, D. Wang, F. Meng, Bioorg. Chem. 2021, 111, 104840.
D. Bora, A. Kaushal, N. Shankaraiah, Eur. J. Med. Chem. 2021, 215, 113263.
J. Ueda, S. Harada, M. Kobayashi, M. Yanagawa, T. Nemoto, Eur. J. Org. Chem. 2021, 2021, 3999.
B. K. Chan, E. Seward, M. Lainchbury, T. F. Brewer, L. An, T. Blench, M. W. Cartwright, G. K. Y. Chan, E. F. Choo, J. Drummond, R. L. Elliott, E. Gancia, L. Gazzard, B. Hu, G. E. Jones, X. Luo, A. Madin, S. Malhotra, J. G. Moffat, J. Pang, L. Salphati, C. J. Sneeringer, C. E. Stivala, B. Wei, W. Wang, P. Wu, T. P. Heffron, ACS Med. Chem. Lett. 2022, 13, 84.
B. Razmienė, V. Vojáčková, E. Řezníčková, L. Malina, V. Dambrauskienė, M. Kubala, R. Bajgar, H. Kolářová, A. Žukauskaitė, E. Arbačiauskienė, A. Šačkus, V. Kryštof, Bioorg. Chem. 2022, 119, 105570.
N. A. M. Pereira, M. Laranjo, J. Pina, A. S. R. Oliveira, J. D. Ferreira, C. Sánchez‐Sánchez, J. Casalta‐Lopes, A. C. Gonçalves, A. B. Sarmento‐Ribeiro, M. Piñeiro, J. S. Seixas de Melo, M. F. Botelho, T. M. V. D. Pinho e Melo, Eur. J. Med. Chem. 2018, 146, 395.
N. A. M. Pereira, M. Laranjo, B. F. O. Nascimento, J. C. S. Simões, J. Pina, B. D. P. Costa, G. Brites, J. Braz, J. S. Seixas de Melo, M. Pineiro, M. F. Botelho, T. M. V. D. Pinho e Melo, RSC Med. Chem. 2021, 12, 615.
C. Ni, J. Hu, Chem. Soc. Rev. 2016, 45, 5441.
E. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315.
G. Chandra, D. V. Singh, G. K. Mahato, S. Patel, Chem. Pap. 2023, 77, 4085.
S. Casa, M. Henary, Molecules 2021, 26, 1160.
R. Borchardt, E. Kerns, C. Lipinski, D. Thakker, B. Wang, Pharmaceutical Profiling in Drug Discovery for Lead Selection, Alexandria, VA: American Assoc. Of Pharm. Scientists, 2005.
E. Arbačiauskienė, G. Vilkauskaitė, G. A. Eller, W. Holzer, A. Šačkus, Tetrahedron 2009, 65, 7817.
N. Petek, U. Grošelj, J. Svete, F. Požgan, D. Kočar, B. Štefane, Catalysts 2020, 10, 981.
A. Bieliauskas, S. Krikštolaitytė, W. Holzer, A. Šačkus, ARKIVOC 2018, 2018, 296.
K. Kazlauskas, G. Kreiza, E. Arbačiauskienė, A. Bieliauskas, V. Getautis, A. Šačkus, S. Juršėnas, J. Phys. Chem. C 2014, 118, 25261.
A. Urbonavičius, G. Fortunato, E. Ambrazaitytė, E. Plytninkienė, A. Bieliauskas, V. Milišiūnaitė, R. Luisi, E. Arbačiauskienė, S. Krikštolaitytė, A. Šačkus, Molecules 2022, 27, 3752.
G. Varvuolytė, A. Bieliauskas, N. Kleizienė, A. Žukauskaitė, A. Šačkus, Molbank 2024, 2024, M1782.
A. B. Braun, I. Wehl, D. K. Kölmel, U. Schepers, S. Bräse, Chem. Eur. J. 2019, 25, 7998.
W. R. Dolbier, Guide to Fluorine NMR for Organic Chemists, Hoboken, NJ: John Wiley & Sons, Inc, 2016.
R. Bajgar, H. Kolářová, P. Kolář, K. Pížová, A. Hanáková. Patent No. CZ28377U1 Czech Republic, 2015.
S. Kwiatkowski, B. Knap, D. Przystupski, J. Saczko, E. Kędzierska, K. Knap‐Czop, J. Kotlińska, O. Michel, K. Kotowski, J. Kulbacka, Biomed. Pharmacother. 2018, 106, 1098.
L. Žárská, Z. Malá, K. Langová, L. Malina, S. Binder, R. Bajgar, H. Kolářová, Photodiagn. Photodyn. Ther. 2021, 34, 102224.
Y. Ou‐Yang, Y. Zheng, K. E. Mills, Front. Med. 2023, 10, 1089361. https://doi.org/10.3389/fmed.2023.1089361
D. Bartusik‐Aebisher, M. Osuchowski, M. Adamczyk, J. Stopa, G. Cieślar, A. Kawczyk‐Krupka, D. Aebisher, Front. Oncol. 2022, 12, 1024576. https://doi.org/10.3389/fonc.2022.1024576
E. Ostańska, D. Aebisher, D. Bartusik‐Aebisher, Biomed. Pharmacother. 2021, 137, 111302.
M. Czarnecka‐Czapczyńska, D. Aebisher, P. Oleś, B. Sosna, M. Krupka‐Olek, K. Dynarowicz, W. Latos, G. Cieślar, A. Kawczyk‐Krupka, Biomed. Pharmacother. 2021, 144, 112342.
E. C. Aniogo, B. Plackal Adimuriyil George, H. Abrahamse, Cancer Cell. Int. 2019, 19, 91.
D. Arora, S. Hall, S. Anoopkumar‐Dukie, R. Morrison, A. McFarland, A. V. Perkins, A. K. Davey, G. D. Grant, Toxicol. Mech. Methods 2018, 28, 410.
S. Hall, C. McDermott, S. Anoopkumar‐Dukie, A. McFarland, A. Forbes, A. Perkins, A. Davey, R. Chess‐Williams, M. Kiefel, D. Arora, G. Grant, Toxins 2016, 8, 236.
X. Cao, X. Deng, W. S. May, Blood 2003, 102, 2605.
E. H. Kim, S.‐W. Wong, J. Martinez, Cell Death Differ. 2019, 26, 25.
M. Feoktistova, M. Leverkus, FEBS. J. 2015, 282, 19.
C. Garrido, L. Galluzzi, M. Brunet, P. E. Puig, C. Didelot, G. Kroemer, Cell Death Differ. 2006, 13, 1423.
B. J. Soltys, R. S. Gupta, Exp. Cell Res. 1996, 222, 16.
A. Hoter, M. E. El‐Sabban, H. Y. Naim, Int. J. Mol. Sci. 2018, 19, 2560.
H. Hattori, Y.‐C. Liu, I. Tohnai, M. Ueda, T. Kaneda, T. Kobayashi, K. Tanabe, K. Ohtsuka, Cell Struct. Funct. 1992, 17, 77.
C. J. Gomer, S. W. Ryter, A. Ferrario, N. Rucker, S. Wong, A. M. Fisher, Cancer Res. 1996, 56, 2355.
C. I. Holmberg, S. A. Illman, M. Kallio, A. Mikhailov, L. Sistonen, Cell Stress Chaperones 2000, 5, 219.
A. D. Lackner, A. V. Samant, F. D. Toste, J. Am. Chem. Soc. 2013, 135, 14090.
V. Savickienė, A. Bieliauskas, S. Belyakov, A. Šačkus, E. Arbačiauskienė, J. Heterocycl. Chem. 2024, 61, 927.