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Fine-tuning the side-chain length of iridium(III) complexes for enhanced Photophysical properties in Cancer Theranostics 微调铱(III)配合物的侧链长度以增强癌症治疗的光物理特性
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-12 DOI: 10.1016/j.jinorgbio.2024.112760
Tao Shao , Zhihui Feng , Yu Shen , Dandan Chen , Pan Xiang , Qiong Zhang , Shao Ma , Yupeng Tian , Xiaohe Tian
Cyclometalated iridium(III) complexes have emerged as versatile candidates for cancer theranostics, offering integrated diagnostic imaging and potent singlet oxygen (1O2) generation for photodynamic therapy (PDT). However, their application has been limited by subdued photoluminescence, primarily due to intramolecular motion-induced excited energy dissipation. In this study, we address these limitations through the design and synthesis of five novel iridium(III) complexes: IrC2, IrC4, IrC6, IrC8, and IrC12. Our approach employs meticulous side-chain extending strategy to modulate side-chain length, thereby reducing intramolecular motion and significantly enhancing both one- and three-photon emissions and 1O2 production in the aggregated state. Detailed photophysical investigations, supported by crystallographic insights, reveal that side-chain elongation substantially amplifies these properties. Among the synthesized complexes, IrC8 stands out as a superior candidate for image-guided photodynamic therapy in cellular and 3D tumor spheroid models. This investigation pioneers the simultaneous enhancement of dual-photon emissions and PDT efficacy through a novel side-chain extension strategy in iridium(III) complexes, paving the way for their translational application in clinical theranostics.
环金属化铱(III)复合物已成为癌症治疗的多功能候选物质,可提供综合诊断成像和强效单线态氧(1O2)生成,用于光动力疗法(PDT)。然而,主要由于分子内运动引起的激发能量耗散,它们的应用一直受到光致发光不足的限制。在本研究中,我们通过设计和合成五种新型铱(III)配合物来解决这些局限性:IrC2、IrC4、IrC6、IrC8 和 IrC12。我们的方法采用了细致的侧链延长策略来调节侧链长度,从而减少了分子内运动,并显著增强了聚集态的单光子和三光子发射以及 1O2 生成。详细的光物理研究以及对晶体学的深入了解表明,侧链的拉长大大增强了这些特性。在合成的复合物中,IrC8 脱颖而出,成为在细胞和三维肿瘤球体模型中进行图像引导光动力疗法的理想候选物质。这项研究开创性地在铱(III)复合物中通过新型侧链延伸策略同时增强了双光子发射和光动力疗法的疗效,为其在临床治疗学中的转化应用铺平了道路。
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引用次数: 0
Copper(II) complexes containing hydrazone and bipyridine/phenanthroline ligands for anticancer application against breast cancer cells 含腙和联吡啶/菲罗啉配体的铜(II)配合物用于乳腺癌细胞的抗癌应用。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-12 DOI: 10.1016/j.jinorgbio.2024.112759
Dorothy Priyanka Dorairaj , Prashant Kumar , Haritha Rajasekaran , Nattamai Bhuvanesh , Sodio C.N. Hsu , Ramasamy Karvembu
In this work, mixed ligand Cu(II) complexes containing hydrazone and bipyridine ligands (CB1-CB5), or hydrazone and phenanthroline ligands (CP1-CP5) have been synthesized and characterized by spectroscopic and analytical techniques. Single crystal X-ray structure of complex CB1 revealed that two nitrogen atoms from bipyridine, one carbonyl oxygen, one azomethine nitrogen and one hydroxyl oxygen from the hydrazone ligand coordinated to Cu(II) ion, adopting a distorted square pyramidal geometry. Interaction of these complexes with calf thymus (CT) DNA and bovine serum albumin (BSA) was analyzed by absorption and emission studies. Further, the in vitro anticancer activity of the complexes was investigated exclusively against the breast cancer cells namely MCF7, T47D and MDA MB 231, and a normal breast MCF 10a cell line. The phenanthroline bearing complexes (CP1-CP5) displayed better activity than their bipyridine counterparts as seen from the IC50 values. In addition, the most active complex CP1 having an IC50 value of 5.8 ± 0.3 μM against T47D cancer cells was investigated for its mode of cell death through acridine orange/ethidium bromide(AO/EB), 4′,6-diamidino-2-phenylindole (DAPI) and Annexin-V fluorescein isothiocyanate (FITC) staining assays which revealed apoptosis. Lastly, the cell cycle analysis revealed that complex CP1 induced cell death in T47D cancer cells at the G0/G1 phase.
本研究合成了含有腙和联吡啶配体(CB1-CB5)或腙和菲罗啉配体(CP1-CP5)的混合配体铜(II)配合物,并利用光谱和分析技术对其进行了表征。络合物 CB1 的单晶 X 射线结构显示,双吡啶的两个氮原子、一个羰基氧、一个偶氮甲基氮以及腙配体的一个羟基氧与 Cu(II)离子配位,呈扭曲的正方形金字塔几何结构。通过吸收和发射研究分析了这些配合物与小牛胸腺(CT)DNA 和牛血清白蛋白(BSA)的相互作用。此外,还专门针对乳腺癌细胞 MCF7、T47D 和 MDA MB 231 以及正常乳腺细胞 MCF 10a 进行了体外抗癌活性研究。从 IC50 值可以看出,含菲罗啉的复合物(CP1-CP5)比双吡啶复合物具有更好的活性。此外,通过吖啶橙/溴化乙锭(AO/EB)、4',6-二脒基-2-苯基吲哚(DAPI)和附件素-V 异硫氰酸荧光素(FITC)染色检测,研究了对 T47D 癌细胞最具活性的复合物 CP1 的细胞凋亡模式,其 IC50 值为 5.8 ± 0.3 μM。最后,细胞周期分析表明,复合物 CP1 能诱导处于 G0/G1 期的 T47D 癌细胞死亡。
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引用次数: 0
Two bis-maltol-polyamines: Synthesis, characterization and studies of their palladium(II) complexes exploring their potential anticancer activity 两种双麦芽酚多胺:其钯(II)配合物的合成、表征和研究,探索其潜在的抗癌活性。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-09 DOI: 10.1016/j.jinorgbio.2024.112758
Daniele Paderni , Eleonora Macedi , Enrica Sordini , Stefano Amatori , Patrizia Rossi , Mauro Formica , Luca Giorgi , Paola Paoli , Mirco Fanelli , Vieri Fusi
The interest in the antineoplastic and binding properties shown by the bis-maltol polyamine family, particularly Malten and Maltonis, prompted us to study the Pd2+ complexes of these latter from both a biological and metallo-receptor point of view. The Malten-Pd2+ complex can lodge hard species such as Sr2+ in its coordination-driven preorganized pocket, as confirmed by X-ray diffraction. UV–Vis and NMR data showed that Malten-Pd2+ forms even at acidic pH and exists in aqueous solution in a wide range of pH. The mononuclear complex is stable enough not to release Pd2+ in solution for a long period of time (at least one week), thus Malten-Pd2+, similarly to Maltonis-Pd2+, is suitable to be tested in biological analyses. Studies on the U937 cell line revealed that the effect on cell survival reduction induced by Malten is partially lost in Malten-Pd2+, while no differences where monitored between the effects of Maltonis-Pd2+ and Maltonis, suggesting that the availability of free maltol moieties, that is retained in Maltonis-Pd2+, but not in Malten-Pd2+, is crucial to guarantee the biological activity of these compounds.
我们对双麦芽酚多胺家族,特别是 Malten 和 Maltonis 所表现出的抗肿瘤和结合特性很感兴趣,这促使我们从生物学和金属受体的角度研究后者的 Pd2+ 复合物。正如 X 射线衍射所证实的那样,Malten-Pd2+ 复合物能在其配位驱动的预组织口袋中吸附 Sr2+ 等硬物。紫外-可见光和核磁共振数据显示,即使在酸性 pH 值下,Malten-Pd2+ 也能形成,并在很宽的 pH 值范围内存在于水溶液中。这种单核复合物足够稳定,在溶液中长期(至少一周)不会释放 Pd2+,因此 Malten-Pd2+ 与 Maltonis-Pd2+ 类似,适合用于生物分析测试。对 U937 细胞系的研究表明,Malten 诱导的降低细胞存活率的效应在 Malten-Pd2+ 中部分消失,而 Maltonis-Pd2+ 和 Maltonis 的效应之间没有监测到差异,这表明游离麦芽酚分子的可用性(在 Maltonis-Pd2+ 中保留而在 Malten-Pd2+ 中不保留)对于保证这些化合物的生物活性至关重要。
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引用次数: 0
AIE-based ruthenium complexes as photosensitizers for specifically photo-inactivate gram-positive bacteria 以 AIE 为基础的钌复合物作为光敏剂,专门用于光灭活革兰氏阳性细菌。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-06 DOI: 10.1016/j.jinorgbio.2024.112755
Hai-Yan Huang , Run-Yu Xue , Su-Xin Xiao , Li-Ting Huang , Xiang-Wen Liao , Jin-Tao Wang , Xue-Min Duan , Ru-Jian Yu , Yan-Shi Xiong
The emergence of multidrug-resistant bacterial have caused severe burden for public health. Particularly, Staphylococcus aureus as one of ESKAPE pathogens have induced various infectious diseases and resulted in increasing deaths. Developing new antibacterial agents is still urgent and challenging. Fortunately, in this study, based on aggregation-induced emission (AIE) ruthenium complexes were designed and synthesized, which realized the high efficiency of reactive oxygen species generation and remarkably killed S. aureus unlike conventional antibiotics action. Significantly, owing to good singlet oxygen production ability, Ru1 at only 4 μg/mL of concentration displayed good antibacterial photodynamic therapy effect upon white light irradiation and could deplete essential coenzyme NADH to disrupt intracellular redox balance. Also, the electrostatic interaction between Ru1 and bacteria enhanced the possibility of antibacterial. Under light irradiation, Ru1 could efficiently inhibit the biofilm growth and avoid the development of drug-resistant. Furthermore, Ru1 possessed excellent biocompatibility and displayed remarkable therapy effect in treating mice-wound infections in vivo. These findings indicated that AIE-based ruthenium complexes as new antibacterial agent had great potential in photodynamic therapy of bacteria and addressing the drug-resistance crisis.
耐多药细菌的出现给公共卫生造成了严重负担。特别是金黄色葡萄球菌作为 ESKAPE 病原体之一,诱发了各种传染病,导致越来越多的人死亡。开发新的抗菌剂仍然是一项紧迫而又具有挑战性的任务。幸运的是,本研究设计并合成了基于聚集诱导发射(AIE)的钌复合物,它实现了活性氧的高效生成,与传统抗生素的作用不同,能显著杀灭金黄色葡萄球菌。值得注意的是,由于具有良好的单线态氧生成能力,在白光照射下,浓度仅为 4 μg/mL 的 Ru1 就能显示出良好的光动力抗菌治疗效果,并能消耗细胞内必需的辅酶 NADH,从而破坏细胞内的氧化还原平衡。此外,Ru1 与细菌之间的静电作用也增强了抗菌的可能性。在光照射下,Ru1 能有效抑制生物膜的生长,避免耐药性的产生。此外,Ru1 还具有良好的生物相容性,在治疗体内小鼠伤口感染方面具有显著疗效。这些研究结果表明,基于 AIE 的钌复合物作为新型抗菌剂,在光动力治疗细菌和解决耐药性危机方面具有巨大潜力。
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引用次数: 0
Synthesis, anticancer activity, and mechanistic investigations of aryl-alkyl diorganotin arylformylhydrazone complexes 芳基-烷基二甘草亭芳基甲酰腙复合物的合成、抗癌活性和机理研究。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-06 DOI: 10.1016/j.jinorgbio.2024.112756
Wujiu Jiang , Qing Luo , Wei Huang , Yuxing Tan , Yiyuan Peng
Diorganotin acylhydrazone complexes with mitochondrial targeting demonstrate significant potential as replacements for platinum-based complexes due to their potent anticancer properties. Twelve methylphenyltin arylformylhydrazone complexes have been synthesized by microwave “one-pot” reaction. The complexes have been characterized by FT-IR, multinuclear NMR (1H, 13C, and 119Sn), TGA, and HRMS. Crystal structures were determined for 10 out of the 12 complexes under study. Structures 1 through 8, 10 and 12 possessed a central symmetric structure of a di-nuclear Sn2O2 tetrahedral ring. All complexes were tested for their inhibitory activity against human cell lines NCI-H460, MCF-7, and HepG2. Complex 8 exhibited the most effective inhibitory effect on HepG2 cells, with an IC50 value of 1.34 ± 0.04 μM. Preliminary studies on the anticancer mechanism suggest that complex 8 induces apoptosis in HepG2 cells via the mitochondrial pathway, accompanied by G2/M phase cell cycle arrest.
具有线粒体靶向性的二甘醇锡酰基腙复合物因其强大的抗癌特性而显示出替代铂基复合物的巨大潜力。我们通过微波 "一锅 "反应合成了十二种甲基苯基锡芳基腙复合物。通过傅立叶变换红外光谱、多核核磁共振(1H、13C 和 119Sn)、热重分析和 HRMS 对这些复合物进行了表征。在所研究的 12 个复合物中,有 10 个已确定了晶体结构。结构 1 至 8、10 和 12 具有二核 Sn2O2 四面体环的中心对称结构。测试了所有复合物对人类细胞系 NCI-H460、MCF-7 和 HepG2 的抑制活性。复合物 8 对 HepG2 细胞具有最有效的抑制作用,其 IC50 值为 1.34 ± 0.04 μM。对其抗癌机制的初步研究表明,复合物 8 可通过线粒体途径诱导 HepG2 细胞凋亡,并伴随 G2/M 期细胞周期的停滞。
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引用次数: 0
Ruthenium complexes with abiraterone acetate as antiproliferative agents 与醋酸阿比特龙的钌配合物作为抗增殖剂。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-05 DOI: 10.1016/j.jinorgbio.2024.112754
Anastasia A. Antonets , Ekaterina V. Spitsyna , Vladimir Yu. Tyurin , Dmitrii M. Mazur , Dmitry S. Yakovlev , Denis A. Babkov , Mariya S. Pshenichnikova , Alexander A. Spasov , Elena R. Milaeva , Alexey A. Nazarov
This study is dedicated to the development of multimodal anticancer agents. We have obtained ruthenium complexes conjugated with the steroid-type antitumor drug abiraterone acetate in order to take advantage of the dual antitumor properties of both ruthenium and abiraterone. The compounds exhibit good antiproliferative activity against cancer cells, with selectivity over primary fibroblasts. Real-time cell analysis revealed that compound dichlorido(η66-p-cymene)(abiraterone acetate)ruthenium(II) had pronounced antiproliferation activity compared to abiraterone acetate. Flow cytometric studies on the mechanism of cell death have revealed that the most active compound induces apoptosis more effectively than abiraterone acetate. Our findings demonstrate the potential of this novel dual-action compound as promising candidates for further development as anticancer agents.
这项研究致力于开发多模式抗癌剂。为了利用钌和阿比特龙的双重抗肿瘤特性,我们获得了与类固醇型抗肿瘤药物醋酸阿比特龙共轭的钌复合物。这些化合物对癌细胞具有良好的抗增殖活性,并对原代成纤维细胞具有选择性。实时细胞分析表明,与醋酸阿比特龙相比,二氯(η66-p-亚甲基)(醋酸阿比特龙)钌(II)化合物具有明显的抗增殖活性。关于细胞死亡机制的流式细胞仪研究显示,活性最强的化合物比醋酸阿比特龙更有效地诱导细胞凋亡。我们的研究结果表明,这种新型双效化合物具有作为抗癌药物进一步开发的潜力。
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引用次数: 0
Corrigendum to "Monomeric copper(II) complexes with unsymmetrical salen environment: Synthesis, characterization and study of biological activities" [Journal of Inorganic Biochemistry 253 (2024) 112497]. 具有非对称沙林环境的单体铜(II)配合物:合成、表征和生物活性研究" [《无机生物化学杂志》253 (2024) 112497]。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-04 DOI: 10.1016/j.jinorgbio.2024.112753
Deepika Mohapatra, Sushree Aradhana Patra, Pratikshya Das Pattanayak, Gurunath Sahu, Takashi Nakamura, Takahiro Sasamori, Rupam Dinda
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引用次数: 0
Antibacterial profile and antiproliferative activities over human tumor cells of new silver(I) complexes containing two distinct trifluoromethyl uracil isomers 含有两种不同的三氟甲基尿嘧啶异构体的新型银(I)复合物对人类肿瘤细胞的抗菌谱和抗增殖活性。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-01 DOI: 10.1016/j.jinorgbio.2024.112752
Gabriele de Menezes Pereira , Julia H. Bormio Nunes , Vinicius Souza Macedo , Douglas Henrique Pereira , Kaio Eduardo Buglio , Daniele D. Affonso , Ana Lucia T.G. Ruiz , João Ernesto de Carvalho , Silmara Cristina L. Frajácomo , Wilton R. Lustri , Carmen Silvia Passos Lima , Fernando R.G. Bergamini , Alexandre Cuin , Norberto Masciocchi , Pedro Paulo Corbi
New silver(I) complexes of 5-(trifluoromethyl)uracil (5TFMU) and 6-(trifluoromethyl)uracil (6TFMU) isomers were synthesized, characterized, and evaluated as antibacterial and antiproliferative agents. Based on elemental and thermogravimetric analyses, the Ag-5TFMU and Ag-6TFMU species are formulated as AgC5H2F3N2O2 and Ag2C5HF3N2O2, respectively. Infrared and 13C solid-state nuclear magnetic resonance spectroscopies suggest coordination of the trifluoromethyluracil isomers to silver by both nitrogen and oxygen atoms. Confirmation of their structure and connectivity was achieved, in the absence of single crystals of suitable quality, by state-of-the-art structural powder diffraction methods. In Ag-5TFMU, the organic ligand is tridentate and two distinct metal coordination environments are found (linear AgN2 as well as C2v AgO4 geometries), whereas Ag-6TFMU contains a complex polymeric structure with tetradentate dianionic 6TFMU moieties and five distinct AgX2 (X = N, O) fragments, further stabilized by ancillary (longer) AgO contacts. These species presented modest activity over Gram-positive and Gram-negative bacterial strains, whereas Ag-6TFMU was active over a set of tumor cells, with the best activity over prostate (PC-3) and kidney cell lines and selectivity indices of 4.6 and 1.3, respectively. On the other hand, Ag-5TFMU was active over all considered tumor cells except MCF-7 (breast cancer). The best activity was found for PC-3 cells, but no selectivity was observed. The Ag-5TFMU and Ag-6TFMU species also reduced the proliferation of tongue squamous cell carcinoma cell lines SCC − 4 and SCC-15. Preliminary biophysical assays by circular dichroism suggest that the Ag-5TFMU complex interacts with DNA by intercalation, an effect not seen in Ag-6TFMU.
合成了 5-(三氟甲基)尿嘧啶(5TFMU)和 6-(三氟甲基)尿嘧啶(6TFMU)异构体的新银(I)配合物,对其进行了表征,并将其作为抗菌剂和抗增殖剂进行了评估。根据元素分析和热重分析,Ag-5TFMU 和 Ag-6TFMU 分别配制成 AgC5H2F3N2O2 和 Ag2C5HF3N2O2。红外光谱和 13C 固态核磁共振光谱显示,三氟甲基尿嘧啶异构体通过氮原子和氧原子与银配位。在没有适当质量的单晶体的情况下,我们采用最先进的结构粉末衍射方法确认了它们的结构和连接性。在 Ag-5TFMU 中,有机配体是三位的,并且发现了两种不同的金属配位环境(线性 AgN2 和 C2v AgO4 几何结构),而 Ag-6TFMU 则包含一种复杂的聚合物结构,其中有四位的二离子 6TFMU 分子和五个不同的 AgX2(X = N、O)片段,并通过辅助的(较长的)Ag...O 接触进一步稳定。这些物种对革兰氏阳性和革兰氏阴性细菌菌株具有适度的活性,而 Ag-6TFMU 对一系列肿瘤细胞具有活性,其中对前列腺(PC-3)和肾细胞系的活性最好,选择性指数分别为 4.6 和 1.3。另一方面,除 MCF-7(乳腺癌)外,Ag-5TFMU 对所有考虑的肿瘤细胞都有活性。PC-3 细胞的活性最好,但没有观察到选择性。Ag-5TFMU 和 Ag-6TFMU 还能减少舌鳞状细胞癌细胞系 SCC - 4 和 SCC-15 的增殖。通过圆二色性进行的初步生物物理分析表明,Ag-5TFMU 复合物通过插层作用与 DNA 发生相互作用,而 Ag-6TFMU 则没有这种效果。
{"title":"Antibacterial profile and antiproliferative activities over human tumor cells of new silver(I) complexes containing two distinct trifluoromethyl uracil isomers","authors":"Gabriele de Menezes Pereira ,&nbsp;Julia H. Bormio Nunes ,&nbsp;Vinicius Souza Macedo ,&nbsp;Douglas Henrique Pereira ,&nbsp;Kaio Eduardo Buglio ,&nbsp;Daniele D. Affonso ,&nbsp;Ana Lucia T.G. Ruiz ,&nbsp;João Ernesto de Carvalho ,&nbsp;Silmara Cristina L. Frajácomo ,&nbsp;Wilton R. Lustri ,&nbsp;Carmen Silvia Passos Lima ,&nbsp;Fernando R.G. Bergamini ,&nbsp;Alexandre Cuin ,&nbsp;Norberto Masciocchi ,&nbsp;Pedro Paulo Corbi","doi":"10.1016/j.jinorgbio.2024.112752","DOIUrl":"10.1016/j.jinorgbio.2024.112752","url":null,"abstract":"<div><div>New silver(I) complexes of 5-(trifluoromethyl)uracil (5TFMU) and 6-(trifluoromethyl)uracil (6TFMU) isomers were synthesized, characterized, and evaluated as antibacterial and antiproliferative agents. Based on elemental and thermogravimetric analyses, the Ag-5TFMU and Ag-6TFMU species are formulated as AgC<sub>5</sub>H<sub>2</sub>F<sub>3</sub>N<sub>2</sub>O<sub>2</sub> and Ag<sub>2</sub>C<sub>5</sub>HF<sub>3</sub>N<sub>2</sub>O<sub>2</sub>, respectively. Infrared and <sup>13</sup>C solid-state nuclear magnetic resonance spectroscopies suggest coordination of the trifluoromethyluracil isomers to silver by both nitrogen and oxygen atoms. Confirmation of their structure and connectivity was achieved, in the absence of single crystals of suitable quality, by state-of-the-art structural powder diffraction methods. In Ag-5TFMU, the organic ligand is tridentate and two distinct metal coordination environments are found (linear AgN<sub>2</sub> as well as <em>C</em><sub><em>2v</em></sub> AgO<sub>4</sub> geometries), whereas Ag-6TFMU contains a complex polymeric structure with tetradentate dianionic 6TFMU moieties and <em>five</em> distinct AgX<sub>2</sub> (X = N, O) fragments, further stabilized by ancillary (longer) Ag<sup>…</sup>O contacts. These species presented modest activity over Gram-positive and Gram-negative bacterial strains, whereas Ag-6TFMU was active over a set of tumor cells, with the best activity over prostate (PC-3) and kidney cell lines and selectivity indices of 4.6 and 1.3, respectively. On the other hand, Ag-5TFMU was active over all considered tumor cells except MCF-7 (breast cancer). The best activity was found for PC-3 cells, but no selectivity was observed. The Ag-5TFMU and Ag-6TFMU species also reduced the proliferation of tongue squamous cell carcinoma cell lines SCC − 4 and SCC-15. Preliminary biophysical assays by circular dichroism suggest that the Ag-5TFMU complex interacts with DNA by intercalation, an effect not seen in Ag-6TFMU.</div></div>","PeriodicalId":364,"journal":{"name":"Journal of Inorganic Biochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142374875","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis, structures, and cytotoxicity insights of organotin(IV) complexes with thiazole-appended pincer ligand 有机锡(IV)与噻唑添加钳配体配合物的合成、结构和细胞毒性研究。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-09-30 DOI: 10.1016/j.jinorgbio.2024.112750
Tushar S. Basu Baul , Swmkwr Brahma , Rupen Tamang , Andrew Duthie , Biplob Koch , Sean Parkin
Diorganotin complexes of the compositions [Me2Sn(L)] (1), [n-Bu2Sn(L)] (2), [Ph2Sn(L)]⋅C6H6 (3), [Bz2Sn(L)]⋅C6H6 (4) and [n-Oct2Sn(L)] (5) were synthesized by reacting R2SnO (R = Me, n-Bu, Ph, Bz or n-Oct) with the N2,N6-di(thiazol-2-yl)pyridine-2,6-dicarboxamide (H2L, where H2 denotes the two acidic protons) in refluxing toluene. Additionally, the mono-n-butyltin complex [n-BuSn(HL)Cl2]·H2O (6) was synthesized from n-BuSnCl3 and H2L in acetonitrile. Compounds were characterized by FT-IR, 1H, 13C and 119Sn NMR spectroscopy, while their solid-state structures were examined using single-crystal X-ray diffraction studies. In diorganotin compounds 15, the dianionic tridentate ligands (Npy, N, N) act as κ-N3 chelators. In 6, the L moiety (O, Npy, N) acts as a κ-ON2 tridentate chelator, with involvement of one of the carboxamide oxygen atoms. The coordination polyhedron around the Sn(IV) ion is completed either by two axial Sn-R ligands in compounds 15 or by n-Bu and Cl ligands in compound 6, giving rise to distorted trigonal bipyramid or octahedral structures, respectively. The tin NMR results show that the penta-coordinated structures of compounds 15 and the hexacoordinated structure of compound 6, observed in the solid-state, are retained in solution. The in vitro antitumor activities of 15 were tested on T-47D breast cancer cells. Of these, diphenyltin compound 3 showed the highest anti-proliferative effect, with an IC50 of 10 ± 1.60 μM. Compound 3 exhibited selective toxicity, potentially inducing apoptosis via reactive oxygen species generation and nuclear changes, indicating promise as a breast cancer treatment. This study is the first to explore thiazole-appended organotin compounds for cytotoxicity.
通过将 R2SnO(R = Me、n-Bu、Ph、Bz 或 n-Oct)与 N2,N6-二(噻唑-2-基)吡啶-2,6-二甲酰胺(H2L,其中 H2 表示两个酸性质子)在回流甲苯中反应而合成。此外,正丁基锡化合物[n-BuSn(HL)Cl2]-H2O(6)也是由正丁基锡化合物 H2L 在乙腈中合成的。化合物的表征采用了傅立叶变换红外光谱、1H、13C 和 119Sn NMR 光谱,其固态结构则采用了单晶 X 射线衍射研究。在二氧化甘油锡化合物 1-5 中,二阴离子三叉配体(Npy、N-、N-)起着κ-N3 螯合剂的作用。在 6 中,L 离子(O、Npy、N-)作为κ-ON2 三叉螯合剂,其中一个羧酰胺氧原子参与其中。围绕 Sn(IV)离子的配位多面体在化合物 1-5 中由两个轴向 Sn-R 配体完成,或在化合物 6 中由 n-Bu 和 Cl 配体完成,分别形成扭曲的三叉二面体或八面体结构。锡核磁共振结果表明,固态下观察到的化合物 1-5 的五配位结构和化合物 6 的六配位结构在溶液中得以保留。在 T-47D 乳腺癌细胞上测试了 1-5 化合物的体外抗肿瘤活性。其中,二苯基锡化合物 3 的抗增殖作用最强,IC50 为 10 ± 1.60 μM。化合物 3 显示出选择性毒性,可能通过活性氧生成和核变化诱导细胞凋亡,显示出治疗乳腺癌的前景。这项研究首次探索了噻唑类有机锡化合物的细胞毒性。
{"title":"Synthesis, structures, and cytotoxicity insights of organotin(IV) complexes with thiazole-appended pincer ligand","authors":"Tushar S. Basu Baul ,&nbsp;Swmkwr Brahma ,&nbsp;Rupen Tamang ,&nbsp;Andrew Duthie ,&nbsp;Biplob Koch ,&nbsp;Sean Parkin","doi":"10.1016/j.jinorgbio.2024.112750","DOIUrl":"10.1016/j.jinorgbio.2024.112750","url":null,"abstract":"<div><div>Diorganotin complexes of the compositions [Me<sub>2</sub>Sn(L)] (<strong>1</strong>), [<em>n</em>-Bu<sub>2</sub>Sn(L)] (<strong>2</strong>), [Ph<sub>2</sub>Sn(L)]⋅C<sub>6</sub>H<sub>6</sub> (<strong>3</strong>), [Bz<sub>2</sub>Sn(L)]⋅C<sub>6</sub>H<sub>6</sub> (<strong>4</strong>) and [<em>n</em>-Oct<sub>2</sub>Sn(L)] (<strong>5</strong>) were synthesized by reacting R<sub>2</sub>SnO (R = Me, <em>n</em>-Bu, Ph, Bz or <em>n</em>-Oct) with the <em>N</em><sup><em>2</em></sup>,<em>N</em><sup><em>6</em></sup>-di(thiazol-2-yl)pyridine-2,6-dicarboxamide (H<sub>2</sub>L, where H<sub>2</sub> denotes the two acidic protons) in refluxing toluene. Additionally, the mono-<em>n</em>-butyltin complex [<em>n</em>-BuSn(HL)Cl<sub>2</sub>]·H<sub>2</sub>O (<strong>6</strong>) was synthesized from <em>n</em>-BuSnCl<sub>3</sub> and H<sub>2</sub>L in acetonitrile. Compounds were characterized by FT-IR, <sup>1</sup>H, <sup>13</sup>C and <sup>119</sup>Sn NMR spectroscopy, while their solid-state structures were examined using single-crystal X-ray diffraction studies. In diorganotin compounds <strong>1</strong>–<strong>5</strong>, the dianionic tridentate ligands (N<sub>py</sub>, N<sup>−</sup>, N<sup>−</sup>) act as κ-<em>N</em><sup><em>3</em></sup> chelators. In <strong>6</strong>, the L moiety (O, N<sub>py</sub>, N<sup>−</sup>) acts as a κ-<em>ON</em><sup><em>2</em></sup> tridentate chelator, with involvement of one of the carboxamide oxygen atoms. The coordination polyhedron around the Sn(IV) ion is completed either by two axial Sn-R ligands in compounds <strong>1</strong>–<strong>5</strong> or by <em>n</em>-Bu and Cl ligands in compound <strong>6</strong>, giving rise to distorted trigonal bipyramid or octahedral structures, respectively. The tin NMR results show that the penta-coordinated structures of compounds <strong>1</strong>–<strong>5</strong> and the hexacoordinated structure of compound <strong>6</strong>, observed in the solid-state, are retained in solution. The <em>in vitro</em> antitumor activities of <strong>1</strong>–<strong>5</strong> were tested on T-47D breast cancer cells. Of these, diphenyltin compound <strong>3</strong> showed the highest anti-proliferative effect, with an IC<sub>50</sub> of 10 ± 1.60 μM. Compound <strong>3</strong> exhibited selective toxicity, potentially inducing apoptosis via reactive oxygen species generation and nuclear changes, indicating promise as a breast cancer treatment. This study is the first to explore thiazole-appended organotin compounds for cytotoxicity.</div></div>","PeriodicalId":364,"journal":{"name":"Journal of Inorganic Biochemistry","volume":null,"pages":null},"PeriodicalIF":3.8,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142387008","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Non-peripheral octasubstituted zinc(II) phthalocyanines bearing pyridinepropoxy substituents – Antibacterial, anticancer photodynamic and sonodynamic activity 具有吡啶丙氧基取代基的非外周八代锌(II)酞菁--抗菌、抗癌光动力和声动力活性。
IF 3.8 2区 化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-09-30 DOI: 10.1016/j.jinorgbio.2024.112751
Marcin Wysocki , Daniel Ziental , Zekeriya Biyiklioglu , Malgorzata Jozkowiak , Hüseyin Baş , Jolanta Dlugaszewska , Hanna Piotrowska-Kempisty , Emre Güzel , Lukasz Sobotta
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.
通过取代酞腈的环化反应合成了具有 3-和 4-吡啶丙氧基取代基的新型非外周八取代锌(II)酞菁,并对其进行了进一步表征。然后评估了它们对细菌和癌细胞的光动力和声动力活性。此外,还评估了它们对人类常见酶的抑制活性。在光照射下测量了单线态氧的生成(1,3-二苯基异苯并呋喃-DPBF 作为单线态氧的非特异性化学淬灭剂),而在超声波(1 MHz, 3 W)下则评估了 DPBF 在敏化剂存在下的稳定性。这两种酞菁在二甲基亚砜中的光稳定性较高,在 DMF 中的光稳定性适中,而在 DMF 中的超声稳定性适中。两种化合物的光诱导单线态氧生成量子产率的计算结果相似,在 DMF 中为 0.33,在 DMSO 中为 0.67。声动力学方法显示,在 1 MHz 频率下,DPBF 的分解率适中。光动力和声动力方式都能显著减少细菌数量,对 MRSA 和表皮葡萄球菌的减少量大于 3 log。这两种化合物对下咽肿瘤(FaDu)的存活率降低了约 50%。此外,在鳞状细胞癌(SCC-25)中也观察到了高达 60% 的存活率降低。总之,这种基于酞菁的高效敏化剂分子结构是光动力和声动力应用的一种潜在疗法。
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Journal of Inorganic Biochemistry
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