Synthesis, crystal and solution structures and antimicrobial screening of palladium(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands

Bugarčić, Živadin D.; Divac, Vera M.; Kostić, Marina D.; Janković, Nenad; Heinemann, Frank W.; Radulović, Niko S.; Stojanović-Radić, Zorica

doi:10.1016/j.jinorgbio.2014.11.002

Cited by 14 publications

(7 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Results presented in this paper are the first investigation of biological activity of such fused bicyclic seleno-hydantoin and its Pd(II) complex on cancer cell lines. Cytotoxic character of Pd(II) complexes, hydantoins and seleno-derivatives is proved and well explained in numerous articles (Kushev et al 2002;Sabo et al 2004;Ananda Kumar et al 2009;Basappa et al 2009;Mudit et al 2009;Varbanov et al 2010;Matovic et al 2013;Hmuda et al 2014;Kosaric et al 2014;Bugarcic et al 2015). Comparing with results obtained in this article, many of tested Pd(II) complexes, seleno-organic compounds, hydantoins and their combinations exerted considerable cytotoxicity on cancer cell lines.…”

Section: Discussionsupporting

confidence: 74%

“…Moreover, bicyclic hydantoins are also studied (Ananda Kumar et al 2009;Basappa et al 2009). Although seleno-organic compounds (Kosaric et al 2014;Bugarcic et al 2015) and Pd(II) complexes of hydantoins are investigated (Kushev et al 2002;Varbanov et al 2010), according to our knowledge there are no records regarding antitumor activities of bicyclic selenohydantoins and their Pd(II) complexes.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

Živanović

Košarić²,

Šmit³

et al. 2017

gpb

View full text Add to dashboard Cite

Selenium and palladium containing compounds separately exert multifunctional effects on cells. While selenium containing compounds usually exert antioxidative properties, palladium(II) containing compounds are cytotoxic and prooxidative. Here we investigated biological effects of bicyclic seleno-hydantoin cis-7a-ethyl-5-methyl-5-phenylselanylmethyl-tetrahydro-pyrrolo[1,2-c] imidazole-1,3-dione (Hid-Se), and its palladium(II) complex, trans-bis-(cis-7a-ethyl-5-methyl-5-phenylselanylmethyl-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dionato) palladium(II) chloride ((Hid-Se) 2 Pd) on human colon HCT-116 and breast MDA-MB-231 cancer cell lines. Hid-Se and (Hid-Se) 2 Pd showed prooxidative and cytotoxic character. In all performed experiments (Hid-Se) 2 Pd proved to be more active, i.e. this substance exerted greater prooxidative effect, cytotoxicity and influence on cell migration potential. Even though Hid-Se and (Hid-Se) 2 Pd enhanced migration of HCT-116 cells, very important feature of these substances is the strong antimigratory potential on metastatic MDA-MB-231 cells.

show abstract

Section: Discussionsupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

Živanović

Košarić²,

Šmit³

et al. 2017

gpb

View full text Add to dashboard Cite

show abstract

“…The cyclic tertiary ∆ 4 ‐alkenol with a trisubstituted double bond 10 also gave the six‐membered cyclic ether ( 10a ). Quantum‐chemical calculations on the phenylselenoetherification of (Z) and (E)‐hex‐4‐en‐1‐ols ( 3 and 4 ) have shown that the cyclization of (Z)‐hex‐4‐en‐1‐ol ( 3 ) is kinetically controlled by the activation energy to afford the five‐membered cyclic ether ( 3a ), while the cyclization of the (E)‐alkenol ( 4 ) is thermodynamically controlled to yield the more stable six‐membered tetrahydropyran cyclic ether ( 4a ). As expected, the γ,δ‐unsaturated carboxylic acid 9 yields the corresponding seleno‐substituted lactone 9a , showing the efficiency of the procedure when using unsaturated carboxylic acids instead of alkenols.…”

Section: Resultsmentioning

confidence: 99%

A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids

Kostić

Verdía

Fernández-Stefanuto

et al. 2019

J of Physical Organic Chem

View full text Add to dashboard Cite

A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with absolute regioselectivity, using primary, secondary, tertiary, and aromatic alcohols, as well as monosubstituted, disubstituted, and trisubstituted alkenols. This procedure provides a new method for the synthesis of substituted tetrahydrofurans and tetrahydropyrans ethers, the precursors of many biologically active metabolites, avoiding the use of toxic and corrosive catalysts. There are no previous reports of seleniummediated cyclofuncionalization reactions in ionic liquids. Taking into the account the good results obtained with [MMIM][MSO 4 ], its ease preparation, low viscosity, low price, and its capacity to be recovered and reused, it was selected as the solvent/catalyzer. Quantum-chemical calculations (MP2(fc)/ 6-311 + G**//B3LYP/6-311 + G**) has shown that the intramolecular cyclization is promoted by the hydrogen bond formed between the ionic liquid anion and the hydroxyl group of the alkenol.

show abstract

“…13,30,31 Besides the synthetic part of the investigation, selected examples of the cyclic ethers have been subjected to screening of the biological properties, preferentially antiproliferative and antioxidative activities, 32 as well as to their complexation with transition metal ions (palladium and platinum) and investigation of the medical potential of the obtained complexes. 33,34 The results of these studies have revealed the ability of the organoselenium-functionalized cyclic ethers to serve as reducers of reactive oxygen species (ROS) and anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile

Mihajlović

Divac

Kostic

et al. 2022

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

Terpenic alcohols linalool, nerolidol and α-terpineol were subjected to the PhSe-induced cyclization, where corresponding cyclic ethers were obtained. The heterocyclic product derived from α-terpineol is a derivate of the natural product eucalyptol, while linalool cyclization produces precursors of the natural product karahanaenone. All three cyclic ether products have an organoselenium moiety in the side chain, which can represent a significant source of bioactivities. Biological evaluation of obtained products, in vitro cytotoxicity and redox status parameters, was performed on two model systems: HCT-116 – immortalized colon cancer cell line, and MRC-5 – healthy fibroblasts isolated from lung pleura. The results indicate a strong prooxidative character of all compounds on colon cancer HCT-116 and healthy MRC-5 cells in the highest applied concentrations. Selectivity towards cancer cells was not observed, except when nerolidol-derived product was used for longer exposure time. A biological evaluation was conducted to establish the quantitative relationship between enhanced radical species formation and cell viability.

show abstract

Synthesis, crystal and solution structures and antimicrobial screening of palladium(II) complexes with 2-(phenylselanylmethyl)oxolane and 2-(phenylselanylmethyl)oxane as ligands

Cited by 14 publications

References 40 publications

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

Novel seleno-hydantoin palladium(II) complex – antimigratory, cytotoxic and prooxidative potential on human colon HCT-116 and breast MDA-MB-231 cancer cells

A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids

Selenium-functionalized cyclic ethers derived from natural terpenic alcohols – biological in vitro profile

Contact Info

Product

Resources

About