Novel phenoxyacetylthiosemicarbazide derivatives as novel ligands in cancer diseases

Kozyra, Paweł; Adamczuk, Grzegorz; Karczmarzyk, Zbigniew; Matysiak, Joanna; Podkościelna, Beata; Humeniuk, Ewelina; Wysocki, Waldemar; Korga-Plewko, Agnieszka; Senczyna, Bogusław; Pitucha, Monika

doi:10.1016/j.taap.2023.116634

Cited by 2 publications

(7 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 1-18 were obtained in the reaction of phenoxyacetic acid hydrazide with the appropriate isothiocyanate at the boiling point of MeOH. The anticancer potential of the compounds against prostate and melanoma human cancer cells has been proved [31].…”

Section: Set Of Analyzed Compoundsmentioning

confidence: 99%

“…Molecules 2023, 28, x FOR PEER REVIEW 3 of 14 % plasma-protein binding (% PPB) of these compounds. Thiosemicarbazides are described as anticancer agents [28][29][30][31]. Some of them target topoisomerase II alpha and indoleamine-2,3-dioxygenase 1 (IDO 1) [29], others induce apoptosis in cancer cells via JNK signaling in human breast cancer cells [30].…”

Section: Set Of Analyzed Compoundsmentioning

confidence: 99%

“…The MeOH concentration ranged from 0.4 to 0.9 (v/v), at 0.1 intervals (Table S1 in the Supplementary Materials). Details are provided in Kozyra et al [31].…”

Section: C-18 Chromatographymentioning

confidence: 99%

“…The aim of the presented investigation was the lipophilicity estimation of 1-aryl-4-(phenoxy)acetylthiosemicarbazides to predict their oral absorption, and the assessment of % plasma-protein binding (% PPB) of these compounds. Thiosemicarbazides are described as anticancer agents [28][29][30][31]. Some of them target topoisomerase II alpha and indoleamine-2,3-dioxygenase 1 (IDO 1) [29], others induce apoptosis in cancer cells via JNK signaling in human breast cancer cells [30].…”

Section: Introductionmentioning

confidence: 99%

“…1 -The values were taken from Kozyra et al[31].Figure 2. Retention of the investigated compounds on C-18, IAM, Chol, and IAM (log k HSA and AGP stationary phases (log k, 15% propan-2-ol).…”

mentioning

confidence: 99%

See 4 more Smart Citations

Retention Behavior of Anticancer Thiosemicarbazides in Biomimetic Chromatographic Systems and In Silico Calculations

Studziński,

Kozyra,

Pitucha

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

Chromatographic methods, apart from in silico ones, are commonly used rapid techniques for the evaluation of certain properties of biologically active compounds used for their prediction of pharmacokinetic processes. Thiosemicarbazides are compounds possessing anticancer, antimicrobial, and other valuable biological activities. The aim of the investigation was to estimate the lipophilicity of 1-aryl-4-(phenoxy)acetylthiosemicarbazides, to predict their oral adsorption and the assessment of their % plasma–protein binding (%PPB). RP-HPLC chromatographic techniques with five diversified HPLC systems, including columns with surface-bonded octadecylsilanes (C-18), phosphatidylcholine (immobilized artificial membrane, IAM), cholesterol (Chol), and α1-acid glycoprotein (AGP) and human serum albumin (HSA), were applied. The measured lipophilicity of all investigated compounds was within the range recommended for potential drug candidates. However, some derivatives are strongly bonded to HSA (%PPB ≈ 100%), which may limit some pharmacokinetic processes. HPLC determined lipophilicity descriptors were compared with those obtained by various computational approaches.

show abstract

Section: Set Of Analyzed Compoundsmentioning

confidence: 99%

Section: Set Of Analyzed Compoundsmentioning

confidence: 99%

“…The MeOH concentration ranged from 0.4 to 0.9 (v/v), at 0.1 intervals (Table S1 in the Supplementary Materials). Details are provided in Kozyra et al [31].…”

Section: C-18 Chromatographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…1 -The values were taken from Kozyra et al[31].Figure 2. Retention of the investigated compounds on C-18, IAM, Chol, and IAM (log k HSA and AGP stationary phases (log k, 15% propan-2-ol).…”

mentioning

confidence: 99%

See 3 more Smart Citations

Retention Behavior of Anticancer Thiosemicarbazides in Biomimetic Chromatographic Systems and In Silico Calculations

Studziński,

Kozyra,

Pitucha

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

N-Substituted 2-(Benzenosulfonyl)-1-Carbotioamide Derivatives Exert Antimicrobial and Cytotoxic Effects via Aldehyde Dehydrogenase Pathway: Synthesis, In Silico and In Vitro Studies

Walczak-Nowicka,

Biernasiuk,

Ziemichód

et al. 2023

Pharmaceuticals

Self Cite

View full text Add to dashboard Cite

A series of N-Substituted 2-(benzenosulfonyl)-1-carbotioamide derivatives (WZ1–WZ4) were synthesized and characterized using spectral methods. A comprehensive activity study was performed for each compound. All compounds were tested for antibacterial activity. Moreover, in silico studies were carried out to determine the anticancer potential of the designed WZ1–WZ4 ligands. Based on molecular docking, aldehyde dehydrogenase was selected as a molecular target. The obtained data were compared with experimental data in vitro tests. Novel hybrids of the thiosemicarbazide scaffold and sulfonyl groups may have promising anticancer activity via the aldehyde dehydrogenase pathway. The best candidate for further studies appears to be WZ2, due to its superior selectivity in comparison to the other tested compounds.

show abstract

Novel phenoxyacetylthiosemicarbazide derivatives as novel ligands in cancer diseases

Cited by 2 publications

References 57 publications

Retention Behavior of Anticancer Thiosemicarbazides in Biomimetic Chromatographic Systems and In Silico Calculations

Retention Behavior of Anticancer Thiosemicarbazides in Biomimetic Chromatographic Systems and In Silico Calculations

N-Substituted 2-(Benzenosulfonyl)-1-Carbotioamide Derivatives Exert Antimicrobial and Cytotoxic Effects via Aldehyde Dehydrogenase Pathway: Synthesis, In Silico and In Vitro Studies

Contact Info

Product

Resources

About