带有吡啶丙氧基取代基的非外周八取代锌 (II) 酞菁 - 抗菌、抗癌光动力和声动力活性。
Non-peripheral octasubstituted zinc(II) phthalocyanines bearing pyridinepropoxy substituents - Antibacterial, anticancer photodynamic and sonodynamic activity.
发表日期:2024 Sep 30
作者:
Marcin Wysocki, Daniel Ziental, Zekeriya Biyiklioglu, Malgorzata Jozkowiak, Hüseyin Baş, Jolanta Dlugaszewska, Hanna Piotrowska-Kempisty, Emre Güzel, Lukasz Sobotta
来源:
JOURNAL OF INORGANIC BIOCHEMISTRY
摘要:
通过取代邻苯二甲腈的环化合成了具有 3- 和 4- 吡啶丙氧基取代基的新型非外围八取代锌 (II) 酞菁并进行了进一步表征。然后评估它们对细菌和癌细胞的光动力和声动力活性。此外,还评估了对常见人类酶的抑制活性。在光照射下测量单线态氧的生成(使用 1,3-二苯基异苯并呋喃 - DPBF 作为单线态氧的非特异性化学猝灭剂),而在超声波(1 MHz,3 W)下评估 DPBF 在敏化剂存在下的稳定性。两种酞菁在 DMSO 中均表现出高光稳定性,在 DMF 中表现出中等稳定性,而在 DMF 中则表现出中等的声稳定性。两种化合物的计算光诱导单线态氧产生量子产率相似,在 DMF 中振荡于 0.33 左右,在 DMSO 中振荡于 0.67 左右。声动力方式显示 1 MHz 时具有中等高的 DPBF 分解。光动力和声动力方式均显着减少了细菌,针对 MRSA 和表皮葡萄球菌的细菌减少量达到 >3 对数。两种化合物均显示出约。下咽肿瘤 (FaDu) 的活力降低 50%。此外,在鳞状细胞癌 (SCC-25) 中观察到存活率降低高达 60%。总之,这种基于酞菁的高效敏化剂的分子构建是光动力和声动力应用的潜在治疗方法。版权所有 © 2024 作者。由爱思唯尔公司出版。保留所有权利。
The novel non-peripheral octa-substituted zinc(II) phthalocyanines with 3- and 4-pyridinepropoxy substituents were synthesized via cyclization of substituted phthalonitriles and further characterized. Their photodynamic and sonodynamic activity were then assessed toward bacteria and cancer cells. Additionally, inhibition activity against common human enzymes was evaluated. The singlet oxygen generation (with 1,3-diphenylisobenzofuran - DPBF as an unspecific chemical quencher of singlet oxygen) were measured under light irradiation, whereas under ultrasounds (1 MHz, 3 W) the stability of DPBF in the presence of sensitizer was evaluated. Both phthalocyanines revealed high photostability in DMSO and moderate in DMF, whereas the sonostability in DMF was moderate. Calculated light-induced singlet oxygen generation quantum yields were similar for both compounds and oscillated around 0.33 in DMF and 0.67 in DMSO. Sonodynamic manner revealed moderately high DPBF decomposition upon 1 MHz. Significant bacterial reduction was noted in both photodynamic and sonodynamic manner, reaching >3 log reduction against MRSA and S. epidermidis. Both compounds showed ca. 50 % viability reduction toward hypopharyngeal tumor (FaDu). Moreover, up to 60 % viability reduction was observed in squamous cell carcinoma (SCC-25). In summary, this molecular building of the efficient phthalocyanine-based sensitizer is a potential therapeutic for photodynamic and sonodynamic applications.Copyright © 2024 The Author(s). Published by Elsevier Inc. All rights reserved.