A heavy-atom-free π-extended N-confused porphyrin as a photosensitizer for photodynamic therapy

被引:15
作者
Babu, Balaji [1 ]
Mack, John [1 ]
Nyokong, Tebello [1 ]
机构
[1] Rhodes Univ, Inst Nanotechnol Innovat, Dept Chem, Makhanda, South Africa
基金
新加坡国家研究基金会;
关键词
MAGNETIC CIRCULAR-DICHROISM; GREEN LIGHT; DYES; ISOMER; RED;
D O I
10.1039/d1nj00112d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis and characterization of a novel 1,3-diethyl-2-thiobarbituric-acid-substituted N-confused porphyrin (NCP-TB) is reported, along with a study of its photodynamic activity against MCF-7 cells using 530 (110 mW cm(-2)) and 660 nm (280 mW cm(-2)) Thorlabs light-emitting diodes for 30 min. The singlet oxygen quantum yield for NCP-TB is 0.38 compared to 0.23 for the parent unsubstituted N-confused porphyrin (NCP) due to the presence of a sulfur atom. NCP-TB exhibits enhanced PDT activity compared to NCP at both wavelengths. A significantly lower IC50 value of 5.2 mu M was obtained at 530 nm (14.7 mu M at 660 nm) despite a smaller light dose, due to a large red shift of the intense B band into the green region of the spectrum. 2 ',7 '-Dichlorofluorescein diacetate (DCFDA) assays demonstrate that there is intracellular generation of reactive oxygen species upon exposure to light.
引用
收藏
页码:5654 / 5658
页数:5
相关论文
共 34 条
  • [1] Solvent Effects on the UV-Vis Absorption Properties and Tautomerisnn of N-Confused Tetraphenylporphyrin
    Aleman, Elvin A.
    Joseph, Jojo
    Modarelli, David A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 11031 - 11038
  • [2] Arias HR, 2001, MOL PHARMACOL, V60, P497
  • [3] Sn(iv) N-confused porphyrins as photosensitizer dyes for photodynamic therapy in the near IR region
    Babu, Balaji
    Mack, John
    Nyokong, Tebello
    [J]. DALTON TRANSACTIONS, 2020, 49 (43) : 15180 - 15183
  • [4] Berridge MV, 2005, BIOTECHNOL ANN REV, V11, P127, DOI 10.1016/S1387-2656(05)11004-7
  • [5] TETRA-P-TOLYLPORPHYRIN WITH AN INVERTED PYRROLE RING - A NOVEL ISOMER OF PORPHYRIN
    CHMIELEWSKI, PJ
    LATOSGRAZYNSKI, L
    RACHLEWICZ, K
    GLOWIAK, T
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (07): : 779 - 781
  • [6] Green light is effective and less painful than red light in photodynamic therapy of facial solar keratoses
    Fritsch, C
    Stege, H
    Saalmann, G
    Goerz, G
    Ruzicka, T
    Krutmann, J
    [J]. PHOTODERMATOLOGY PHOTOIMMUNOLOGY & PHOTOMEDICINE, 1997, 13 (5-6) : 181 - 185
  • [7] N-CONFUSED PORPHYRIN - A NEW ISOMER OF TETRAPHENYLPORPHYRIN
    FURUTA, H
    ASANO, T
    OGAWA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) : 767 - 768
  • [8] An efficient one-flask synthesis of N-confused tetraphenylporphyrin
    Geier, GR
    Haynes, DM
    Lindsey, JS
    [J]. ORGANIC LETTERS, 1999, 1 (09) : 1455 - 1458
  • [9] Clinical photodynamic therapy for superficial cancer in the oesophagus and the bronchi: 514 nm compared with 630 nm light irradiation after sensitization with Photofrin II
    Grosjean, P
    Wagnieres, G
    Fontolliet, C
    van den Bergh, H
    Monnier, P
    [J]. BRITISH JOURNAL OF CANCER, 1998, 77 (11) : 1989 - 1995
  • [10] CORRELATION OF BIOLOGICAL ACTIVITY OF PHENOXYACETIC ACIDS WITH HAMMETT SUBSTITUENT CONSTANTS AND PARTITION COEFFICIENTS
    HANSCH, C
    MALONEY, PP
    FUJITA, T
    [J]. NATURE, 1962, 194 (4824) : 178 - &