Copper(II) complexes with N′-methylsarcosinamide selective for human bladder cancer cells

Neven Smrečki; Tomislav Rončević; Ozren Jović; Boris Marko Kukovec; Ana Maravić; Goran Gajski; Vedrana Čikeš-Čulić

doi:10.1016/j.ica.2019.01.013

Copper(II) complexes with N′-methylsarcosinamide selective for human bladder cancer cells

Neven Smrečki
, Tomislav Rončević
, Ozren Jović
, Boris Marko Kukovec
, Ana Maravić
, Goran Gajski
, Vedrana Čikeš-Čulić

Research output: Contribution to journal › Article › peer-review

Abstract

Two copper(II) complexes, [CuCl₂(SarMeam)₂] · H₂O (1) and [Cu(NO₃)₂(SarMeam)₂] (2) were obtained by reactions of N′-methylsarcosinamide (SarMeam) with copper(II) chloride and copper(II) nitrate in aqueous solutions. The complexes were characterized by X-ray crystallography, IR and UV-Vis spectroscopy, thermal analysis (TG-DTA) and DFT calculations. The octahedral coordination environments around the copper(II) ions in complexes 1 and 2 consisted of two N,O-bidentate N′-methylsarcosinamide ligands and two chloride or nitrate ions, respectively, forming trans isomers. The [CuCl(H₂O)(SarMeam)₂]⁺ and [Cu(H₂O)₂(SarMeam)₂]²⁺ species formed upon dissolution of 1 by successive substitution of coordinated chloride ions with water molecules, while dissolution of 2 led exclusively to the formation of [Cu(H₂O)₂(SarMeam)₂]²⁺. [Cu(OH)(H₂O)(SarMeam)₂]⁺ species formed in basic solutions by deprotonation of coordinated ligands and then transformed to a planar [Cu(SarMeam_−H)₂]. Complexes 1 and 2 decomposed in highly acidic or basic solutions, giving [Cu(H₂O)₆]²⁺ or Cu(OH)₂, respectively. The water-soluble complexes 1 and 2 were biologically evaluated and tested on human bladder cancer T24 and UM-UC-3 cell lines and a panel of Gram-negative and Gram-positive bacteria. They showed excellent potency towards human bladder cancer T24 cell line and no activity against bacterial strains. At the same time no toxicity was noticed on normal human cells, as observed by the cell viability and comet assay on peripheral blood leukocytes.

Original language	English
Pages (from-to)	312-320
Number of pages	9
Journal	Inorganica Chimica Acta
Volume	488
DOIs	https://doi.org/10.1016/j.ica.2019.01.013
Publication status	Published - 24 Mar 2019
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Antitumor activity
Copper(II) complexes
Crystal structure
DFT calculations
N′-Methylsarcosinamide
Spectrophotometric potentiometric titration

Access to Document

10.1016/j.ica.2019.01.013

Cite this

@article{875ecd58d28945ecba9ba7dda4859989,

title = "Copper(II) complexes with N′-methylsarcosinamide selective for human bladder cancer cells",

abstract = "Two copper(II) complexes, [CuCl2(SarMeam)2] · H2O (1) and [Cu(NO3)2(SarMeam)2] (2) were obtained by reactions of N′-methylsarcosinamide (SarMeam) with copper(II) chloride and copper(II) nitrate in aqueous solutions. The complexes were characterized by X-ray crystallography, IR and UV-Vis spectroscopy, thermal analysis (TG-DTA) and DFT calculations. The octahedral coordination environments around the copper(II) ions in complexes 1 and 2 consisted of two N,O-bidentate N′-methylsarcosinamide ligands and two chloride or nitrate ions, respectively, forming trans isomers. The [CuCl(H2O)(SarMeam)2]+ and [Cu(H2O)2(SarMeam)2]2+ species formed upon dissolution of 1 by successive substitution of coordinated chloride ions with water molecules, while dissolution of 2 led exclusively to the formation of [Cu(H2O)2(SarMeam)2]2+. [Cu(OH)(H2O)(SarMeam)2]+ species formed in basic solutions by deprotonation of coordinated ligands and then transformed to a planar [Cu(SarMeam−H)2]. Complexes 1 and 2 decomposed in highly acidic or basic solutions, giving [Cu(H2O)6]2+ or Cu(OH)2, respectively. The water-soluble complexes 1 and 2 were biologically evaluated and tested on human bladder cancer T24 and UM-UC-3 cell lines and a panel of Gram-negative and Gram-positive bacteria. They showed excellent potency towards human bladder cancer T24 cell line and no activity against bacterial strains. At the same time no toxicity was noticed on normal human cells, as observed by the cell viability and comet assay on peripheral blood leukocytes.",

keywords = "Antitumor activity, Copper(II) complexes, Crystal structure, DFT calculations, N′-Methylsarcosinamide, Spectrophotometric potentiometric titration",

author = "Neven Smre{\v c}ki and Tomislav Ron{\v c}evi{\'c} and Ozren Jovi{\'c} and Kukovec, \{Boris Marko\} and Ana Maravi{\'c} and Goran Gajski and Vedrana {\v C}ike{\v s}-{\v C}uli{\'c}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = mar,

day = "24",

doi = "10.1016/j.ica.2019.01.013",

language = "English",

volume = "488",

pages = "312--320",

journal = "Inorganica Chimica Acta",

issn = "0020-1693",

}

TY - JOUR

T1 - Copper(II) complexes with N′-methylsarcosinamide selective for human bladder cancer cells

AU - Smrečki, Neven

AU - Rončević, Tomislav

AU - Jović, Ozren

AU - Kukovec, Boris Marko

AU - Maravić, Ana

AU - Gajski, Goran

AU - Čikeš-Čulić, Vedrana

PY - 2019/3/24

Y1 - 2019/3/24

N2 - Two copper(II) complexes, [CuCl2(SarMeam)2] · H2O (1) and [Cu(NO3)2(SarMeam)2] (2) were obtained by reactions of N′-methylsarcosinamide (SarMeam) with copper(II) chloride and copper(II) nitrate in aqueous solutions. The complexes were characterized by X-ray crystallography, IR and UV-Vis spectroscopy, thermal analysis (TG-DTA) and DFT calculations. The octahedral coordination environments around the copper(II) ions in complexes 1 and 2 consisted of two N,O-bidentate N′-methylsarcosinamide ligands and two chloride or nitrate ions, respectively, forming trans isomers. The [CuCl(H2O)(SarMeam)2]+ and [Cu(H2O)2(SarMeam)2]2+ species formed upon dissolution of 1 by successive substitution of coordinated chloride ions with water molecules, while dissolution of 2 led exclusively to the formation of [Cu(H2O)2(SarMeam)2]2+. [Cu(OH)(H2O)(SarMeam)2]+ species formed in basic solutions by deprotonation of coordinated ligands and then transformed to a planar [Cu(SarMeam−H)2]. Complexes 1 and 2 decomposed in highly acidic or basic solutions, giving [Cu(H2O)6]2+ or Cu(OH)2, respectively. The water-soluble complexes 1 and 2 were biologically evaluated and tested on human bladder cancer T24 and UM-UC-3 cell lines and a panel of Gram-negative and Gram-positive bacteria. They showed excellent potency towards human bladder cancer T24 cell line and no activity against bacterial strains. At the same time no toxicity was noticed on normal human cells, as observed by the cell viability and comet assay on peripheral blood leukocytes.

AB - Two copper(II) complexes, [CuCl2(SarMeam)2] · H2O (1) and [Cu(NO3)2(SarMeam)2] (2) were obtained by reactions of N′-methylsarcosinamide (SarMeam) with copper(II) chloride and copper(II) nitrate in aqueous solutions. The complexes were characterized by X-ray crystallography, IR and UV-Vis spectroscopy, thermal analysis (TG-DTA) and DFT calculations. The octahedral coordination environments around the copper(II) ions in complexes 1 and 2 consisted of two N,O-bidentate N′-methylsarcosinamide ligands and two chloride or nitrate ions, respectively, forming trans isomers. The [CuCl(H2O)(SarMeam)2]+ and [Cu(H2O)2(SarMeam)2]2+ species formed upon dissolution of 1 by successive substitution of coordinated chloride ions with water molecules, while dissolution of 2 led exclusively to the formation of [Cu(H2O)2(SarMeam)2]2+. [Cu(OH)(H2O)(SarMeam)2]+ species formed in basic solutions by deprotonation of coordinated ligands and then transformed to a planar [Cu(SarMeam−H)2]. Complexes 1 and 2 decomposed in highly acidic or basic solutions, giving [Cu(H2O)6]2+ or Cu(OH)2, respectively. The water-soluble complexes 1 and 2 were biologically evaluated and tested on human bladder cancer T24 and UM-UC-3 cell lines and a panel of Gram-negative and Gram-positive bacteria. They showed excellent potency towards human bladder cancer T24 cell line and no activity against bacterial strains. At the same time no toxicity was noticed on normal human cells, as observed by the cell viability and comet assay on peripheral blood leukocytes.

KW - Antitumor activity

KW - Copper(II) complexes

KW - Crystal structure

KW - DFT calculations

KW - N′-Methylsarcosinamide

KW - Spectrophotometric potentiometric titration

UR - https://www.scopus.com/pages/publications/85061281645

U2 - 10.1016/j.ica.2019.01.013

DO - 10.1016/j.ica.2019.01.013

M3 - Article

AN - SCOPUS:85061281645

SN - 0020-1693

VL - 488

SP - 312

EP - 320

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

ER -

Copper(II) complexes with N′-methylsarcosinamide selective for human bladder cancer cells

Abstract

UN SDGs

Keywords

Access to Document

Other files and links

Fingerprint

Cite this