Thiazole Functionalization of Thiosemicarbazone for Cu(II) Complexation: Moving toward Highly Efficient Anticancer Drugs with Promising Oral Bioavailability DOI Creative Commons

Song-Yu Luo,

Chun-Mei Zeng,

Ping Xu

и другие.

Molecules, Год журнала: 2024, Номер 29(16), С. 3832 - 3832

Опубликована: Авг. 13, 2024

In this work, we report the synthesis of a new thiosemicarbazone-based drug N′-(di(pyridin-2-yl)methylene)-4-(thiazol-2-yl)piperazine-1-carbothiohydrazide (HL) featuring thiazole spectator for efficient coordination with Cu(II) to give [CuCl(L)]2 (1) and [Cu(NO3)(L)]2 (2). Both 1 2 exhibit dimeric structures ascribed presence di-2-pyridylketone moieties that demonstrate dual functions chelation intermolecular bridging. HL, 1, are highly toxic against hepatocellular carcinoma cell lines Hep-G2, PLC/PRF/5, HuH-7 half maximal inhibitory concentration (IC50) values as low 3.26 nmol/mL (HL), 2.18 (1), 2.54 × 10−5 (2) PLC/PRF/5. While free ligand HL may elicit its anticancer effect via sequestration bio-relevant metal ions (i.e., Fe3+ Cu2+), also capable generating cytotoxic reactive oxygen species (ROS) inhibit cancer proliferation. Our preliminary pharmacokinetic studies revealed oral administration (per os, PO) has significantly longer half-life t1/2 21.61 ± 9.4 h, nearly doubled compared intravenous (i.v.) 11.88 1.66 certifying an effective chemotherapeutic PO administration.

Язык: Английский

Availability of π–Cation Radical in the Oxidative Products of Oxidovanadium Porphyrin: Significance for DNA Binding and Antibacterial Activity DOI
Ijaz Ullah Muzaddadi, Arumugam Murugan, Shankhadeep Saha

и другие.

Applied Organometallic Chemistry, Год журнала: 2024, Номер 38(12)

Опубликована: Авг. 29, 2024

ABSTRACT Oxidovanadium meso ‐tetrakis(3,4,5‐trimethoxyphenyl) porphyrin [VO(T(OMe)3PP)] (Complex 1 ) was prepared. The oxidation product of Complex has been characterized by cyclic voltammetry (CV), UV–visible spectrophotometer, electron paramagnetic resonance (EPR) and nuclear magnetic (NMR) the addition SbCl 5 to . There is a one‐electron in that creates π–cation radicals CV data. This supported an IR spectrophotometer. Subsequent EPR spectra verified initiation monoradical, which subsequently transforms into triplet state where S = 1. DNA binding antibacterial analysis with have also analysed. In DNA‐binding analysis, data confirm interaction between DNA. Furthermore, fact more effective at killing bacteria shows metal ion's chelation ligand makes it lipophilic.

Язык: Английский

Процитировано

1
Thiazole Functionalization of Thiosemicarbazone for Cu(II) Complexation: Moving toward Highly Efficient Anticancer Drugs with Promising Oral Bioavailability DOI Creative Commons

Song-Yu Luo,

Chun-Mei Zeng,

Ping Xu

и другие.

Molecules, Год журнала: 2024, Номер 29(16), С. 3832 - 3832

Опубликована: Авг. 13, 2024

In this work, we report the synthesis of a new thiosemicarbazone-based drug N′-(di(pyridin-2-yl)methylene)-4-(thiazol-2-yl)piperazine-1-carbothiohydrazide (HL) featuring thiazole spectator for efficient coordination with Cu(II) to give [CuCl(L)]2 (1) and [Cu(NO3)(L)]2 (2). Both 1 2 exhibit dimeric structures ascribed presence di-2-pyridylketone moieties that demonstrate dual functions chelation intermolecular bridging. HL, 1, are highly toxic against hepatocellular carcinoma cell lines Hep-G2, PLC/PRF/5, HuH-7 half maximal inhibitory concentration (IC50) values as low 3.26 nmol/mL (HL), 2.18 (1), 2.54 × 10−5 (2) PLC/PRF/5. While free ligand HL may elicit its anticancer effect via sequestration bio-relevant metal ions (i.e., Fe3+ Cu2+), also capable generating cytotoxic reactive oxygen species (ROS) inhibit cancer proliferation. Our preliminary pharmacokinetic studies revealed oral administration (per os, PO) has significantly longer half-life t1/2 21.61 ± 9.4 h, nearly doubled compared intravenous (i.v.) 11.88 1.66 certifying an effective chemotherapeutic PO administration.

Язык: Английский

Процитировано

0