Triphenylphosphonium conjugates of 1,2,3-triazolyl nucleoside analogues. Synthesis and cytotoxicity evaluation

Strobykina, I. Yu.; Andreeva, O. V.; Belenok, M. G.; Semenova, Marina N.; Семенов, В. В.; Chuprov‐Netochin, Roman N.; Sapunova, Аnastasiia S.; Voloshina, Alexandra D.; Dobrynin, Alexey B.; Семенов, В. Э.; Катаев, В. Е.

doi:10.1007/s00044-020-02629-x

Cited by 8 publications

(4 citation statements)

References 31 publications

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“…In current study, GC-MS analysis of the BS, SSU, GSU and CSU samples showed 25, 12, 23, and 21 compounds including pyridines, piperidines, indole alkaloids, monoterpenes, xanthophylls, esters, sterols, alkanes, amides, carbohydrates, etc. These results in accordance with other studies focused on bioactivity of compounds derived from brittle stars and sea urchins (Nuzzo et al, 2017;Francis and Chakraborty, 2020a;Francis and Chakraborty, 2020b;Strobykina et al, 2020).…”

Section: Discussionsupporting

confidence: 93%

Antioxidant and anticholinesterase properties of Echinometra mathaei and Ophiocoma erinaceus venoms from the Persian Gulf

Dehghani,

Rashedinia,

Mohebbi

et al. 2024

Front. Chem.

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Introduction: The Persian Gulf is home to a diverse range of marine life, including various species of fish, crustaceans, mollusks, and echinoderms. This study investigates the potential therapeutic properties of venoms from echinoderms in the Persian Gulf, specifically their ability to inhibit cholinesterases (Acetylcholinesterase and butyrylcholinesterase) and act as antioxidants.Methods: Four venoms from two echinoderm species, including the spine, gonad, and coelomic fluids of sea urchins, as well as brittle star venoms, were analyzed using various methods, including LD50 determination, protein analysis, antioxidant assays, GC-MS for secondary metabolite identification, and molecular docking simulations.Results and discussion: The study’s results revealed the LD50 of the samples as follows: 2.231 ± 0.09, 1.03 ± 0.05, 1.12 ± 0.13, and 6.04 ± 0.13 mg/mL, respectively. Additionally, the protein levels were 44.037 ± 0.002, 74.223 ± 0.025, 469.97 ± 0.02, and 104.407 ± 0.025 μg/mL, respectively. SDS-PAGE and total protein studies indicated that at least part of the venom was proteinaceous. Furthermore, the study found that the brittle star samples exhibited significantly higher antioxidant activity compared to other samples, including the standard ascorbic acid, at all tested concentrations. GC-MS analysis identified 12, 23, 21, and 25 compounds in the samples, respectively. These compounds had distinct chemical and bioactive structures, including alkaloids, terpenes, and steroids.Conclusion: These venoms displayed strong cholinesterase inhibitory and antioxidant activities, likely attributed to their protein content and the presence of alkaloids, terpenes, and steroids. Notably, the alkaloid compound C7 was identified as a promising candidate for further research in Alzheimer’s disease therapy. In conclusion, echinoderms in the Persian Gulf may hold significant potential for discovering novel therapeutic agents.

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Section: Discussionsupporting

confidence: 93%

Antioxidant and anticholinesterase properties of Echinometra mathaei and Ophiocoma erinaceus venoms from the Persian Gulf

Dehghani,

Rashedinia,

Mohebbi

et al. 2024

Front. Chem.

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“…This effect fosters the accumulation of cationic molecules [ 17 , 47 , 48 ], hence inducing high selectivity for mitocans holding a (more or less) lipophilic cation such as a rhodamine scaffold. The same effect applies for triphenylphosphonium cations [ 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ] and to a small extent for quaternary ammonium ions [ 58 , 59 , 60 ], zwitterionic N -oxides [ 60 , 61 ] and triterpenes substituted with BODIPYs [ 62 , 63 , 64 , 65 , 66 ] or a safirinium moiety [ 67 ]. However, the presence of a cationic center is not alone decisive for achieving high cytotoxic effects [ 60 ].…”

Section: Resultsmentioning

confidence: 98%

Mitocanic Di- and Triterpenoid Rhodamine B Conjugates

et al. 2020

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The combination of the “correct” triterpenoid, the “correct” spacer and rhodamine B (RhoB) seems to be decisive for the ability of the conjugate to accumulate in mitochondria. So far, several triterpenoid rhodamine B conjugates have been prepared and screened for their cytotoxic activity. To obtain cytotoxic compounds with EC50 values in a low nano-molar range combined with good tumor/non-tumor selectivity, the Rho B unit has to be attached via an amine spacer to the terpenoid skeleton. To avoid spirolactamization, secondary amines have to be used. First results indicate that a homopiperazinyl spacer is superior to a piperazinyl spacer. Hybrids derived from maslinic acid or tormentic acid are superior to those from oleanolic, ursolic, glycyrrhetinic or euscaphic acid. Thus, a tormentic acid-derived RhoB conjugate 32, holding a homopiperazinyl spacer can be regarded, at present, as the most promising candidate for further biological studies.

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“…[157] The SARs elucidated that hybrids with two substituents on the phenyl ring and at least one of them was hydroxyl or methoxy could increase the activity; [157] 4H-pyrano[2,3-d]pyrimidine moiety was critical for the activity, and replacement by imidazole, benzothiazole, coumarin, indole, isosteviol, epigallocatechin-3-gallate, pyrimidine, quinoline or sulfonamide resulted in the loss of activity. [158][159][160][161][162][163][164][165][166][167][168] In particular, 2.9 µM, MTT assay) was more potent than doxorubicin (IC 50 :…”

Section: Indole-pyridine/quinoline Hybridsmentioning

confidence: 99%

“…[ 157 ] The SARs elucidated that hybrids with two substituents on the phenyl ring and at least one of them was hydroxyl or methoxy could increase the activity; [ 157 ] 4 H ‐pyrano[2,3‐d]pyrimidine moiety was critical for the activity, and replacement by imidazole, benzothiazole, coumarin, indole, isosteviol, epigallocatechin‐3‐gallate, pyrimidine, quinoline or sulfonamide resulted in the loss of activity. [ 158–168 ] In particular, hybrids 128a,b (IC 50 : 1.36 and 1.67 µM) were not inferior to doxorubicin (IC 50 : 5.12 µM), lapatinib (IC 50 : 1.21 µM), and erlotinib (IC 50 : 2.74 µM) against MCF‐7 breast cancer cells and exhibited substantial dual EGFR/HER2 inhibitory activity (IC 50 : 160–290 nM). Xylopyranose‐1,2,3‐triazole‐thienopyrimidine hybrid 129 (IC 50 : 2.9 µM, MTT assay) was more potent than doxorubicin (IC 50 : 6.7 µM) against MCF‐7 breast cancer cells, [ 169 ] and galactose‐1,2,3‐triazole‐podophyllotoxin hybrid 130 (IC 50 : 1.25 µM, MTT assay) also demonstrated promising antiproliferative activity against MCF‐7 breast cancer cells.…”

Section: 23‐triazole Acted As a Linkermentioning

confidence: 99%

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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Triphenylphosphonium conjugates of 1,2,3-triazolyl nucleoside analogues. Synthesis and cytotoxicity evaluation

Cited by 8 publications

References 31 publications

Antioxidant and anticholinesterase properties of Echinometra mathaei and Ophiocoma erinaceus venoms from the Persian Gulf

Antioxidant and anticholinesterase properties of Echinometra mathaei and Ophiocoma erinaceus venoms from the Persian Gulf

Mitocanic Di- and Triterpenoid Rhodamine B Conjugates

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

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