Improved Stability and Photodynamic Activity of Water-Soluble 5,15-Diazaporphyrins Incorporated in β-(1,3-1,6)-d-Glucan with On-Off Switch.
aggregation
fluorescent probes
host-guest systems
polysaccharide
porphyrinoids
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
03 Feb 2020
03 Feb 2020
Historique:
received:
12
11
2019
revised:
10
12
2019
pubmed:
13
12
2019
medline:
13
12
2019
entrez:
13
12
2019
Statut:
ppublish
Résumé
5,15-Diazaporphyrins, which have a large absorption at wavelengths over 600 nm, were dissolved in water by complex formation with β-(1,3-1,6)-d-glucans. Aqueous solutions of these complexes were relatively stable compared with their trimethyl-β-cyclodextrin-complexed analogues. β-Glucan-complexed diazaporphyrins showed quenched fluorescence and had low singlet-oxygen-generation abilities owing to random self-aggregation. However, external stimuli, such as the presence of liposomes or intracellular uptake, restored the fluorescence and singlet-oxygen-generation abilities of β-glucan-complexed diazaporphyrins. Consequently, β-glucan-complexed diazaporphyrins showed very high photodynamic activities toward HeLa cells.
Identifiants
pubmed: 31828944
doi: 10.1002/asia.201901582
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
365-370Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
T. J. Dougherty, C. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, Q. Peng, J. Natl. Cancer Inst. 1998, 90, 889-905.
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.
S. Yano, S. Hirohara, M. Obata, Y. Hagiya, S. Ogura, A. Ikeda, H. Kataoka, M. Tanaka, T. Joh, J. Photochem. Photobiol. C 2011, 12, 46-67.
A. Ben Mihoub, L. Larue, A. Moussaron, Z. Youssef, L. Colombeau, F. Baros, C. Frochot, R. Vanderesse, S. Acherar, Molecules 2018, 23, 1936.
K. Langa, J. Mosinger, D. M. Wagnerová, Coord. Chem. Rev. 2004, 248, 321-350.
B. Horiguchi, T. Nakaya, M. Ueda, K. Sugikawa, T. Mizuta, T. Haino, N. Kawata, A. Ikeda, Eur. J. Org. Chem. 2018, 2138-2143.
A. Ikeda, S. Satake, T. Mae, M. Ueda, K. Sugikawa, H. Shigeto, H. Funabashi, A. Kuroda, ACS Med. Chem. Lett. 2017, 8, 555-559.
S. Satake, H. Shinmori, S. Kawabata, K. Sugikawa, H. Funabashi, A. Kuroda, A. Ikeda, Org. Biomol. Chem. 2019, 17, 3141-3149.
J. Li, Y. Aizawa, K. Hiramoto, E. Kasahara, D. Tsuruta, T. Suzuki, A. Ikeda, H. Azuma, T. Nagasaki, Biomed. Pharmacother. 2015, 69, 201-207.
A. Ikeda, M. Akiyama, K. Sugikawa, K. Koumoto, Y. Kagoshima, J. Li, T. Suzuki, T. Nagasaki, Org. Biomol. Chem. 2017, 15, 1990-1997.
A. Ikeda, T. Iizuka, N. Maekubo, R. Aono, J. Kikuchi, M. Akiyama, T. Konishi, T. Ogawa, N. Ishida-Kitagawa, H. Tatebe, K. Shiozaki, ACS Med. Chem. Lett. 2013, 4, 752-756.
T. Hasegawa, T. Fujisawa, M. Numata, C. Li, A.-H. Bae, S. Haraguchi, K. Sakurai, S. Shinkai, Chem. Lett. 2005, 34, 1118-1119.
S. Hino, R. Funada, K. Sugikawa, K. Koumoto, T. Suzuki, T. Nagasaki, A. Ikeda, Photochem. Photobiol. Sci. 2019, 18, 2854-2858.
M. Numata, M. Asai, K. Kaneko, T. Hasegawa, N. Fujita, Y. Kitada, K. Sakurai, S. Shinkai, Chem. Lett. 2004, 33, 232-233.
T. Hasegawa, T. Fujisawa, M. Numata, M. Umeda, T. Matsumoto, T. Kimura, S. Okumura, K. Sakurai, S. Shinkai, Chem. Commun. 2004, 2150-2151.
M. Numata, M. Asai, K. Kaneko, A.-H. Bae, T. Hasegawa, K. Sakurai, S. Shinkai, J. Am. Chem. Soc. 2005, 127, 5875-5884.
M. Numata, T. Hasegawa, T. Fujisawa, K. Sakurai, S. Shinkai, Org. Lett. 2004, 6, 4447-4450.
C. Li, M. Numata, A.-H. Bae, K. Sakurai, S. Shinkai, J. Am. Chem. Soc. 2005, 127, 4548-4549.
S. Haraguchi, M. Numata, C. Li, Y. Nakano, F. Michiya, S. Shinkai, Chem. Lett. 2009, 38, 254-255.
K. Komatsu, K. Fujiwara, Y. Murata, T. Braun, J. Chem. Soc. Perkin Trans. 1 1999, 2963-2966.
C. R. Miller, B. Bondurant, S. D. McLean, K. A. McGovern, D. F. O'Brien, Biochemistry 1998, 37, 12875-12883.
Y. Doi, A. Ikeda, M. Akiyama, M. Nagano, T. Shigematsu, T. Ogawa, T. Takeya, T. Nagasaki, Chem. Eur. J. 2008, 14, 8892-8897.
A. Ikeda, T. Mae, K. Sugikawa, K. Komaguchi, T. Konishi, T. Hirao, T. Haino, ChemistrySelect 2017, 2, 11322-11327.
S. Mieda, A. Ikeda, Y. Shigeri, W. Shinoda, J. Phys. Chem. C 2014, 118, 12555-12561.
J. Sunamoto, K. Iwamoto, H. Kondo, S. Shinkai, J. Biochem. 1980, 88, 1219-1226.
K. Iwamoto, J. Sunamoto, J. Biochem. 1982, 91, 975-979.
M. Takada, T. Yuzuriha, K. Katayama, K. Iwamoto, J. Sunamoto, Biochim. Biophys. Acta Gen. Subj. 1984, 802, 237-244.
D. Kessel, Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1986, 49, 901-907.
D. Kessel, Photochem. Photobiol. 1986, 44, 193-196.