Gold(I) Complexes with P-Donor Ligands and Their Biological Evaluation

被引：1

作者：

Richert, Monika ^{[1
]}

Mikstacka, Renata ^{[1
]}

Walczyk, Mariusz ^{[2
]}

Cieslak, Marcin Janusz ^{[3
]}

Kazmierczak-Baranska, Julia ^{[3
]}

Krolewska-Golinska, Karolina ^{[3
]}

Muziol, Tadeusz Mikolaj ^{[2
]}

Biniak, Stanislaw ^{[2
]}

机构：

[1] Nicolaus Copernicus Univ Torun, Fac Pharm, Coll Med Bydgoszcz, Jurasza 2, PL-85094 Bydgoszcz, Poland

[2] Nicolaus Copernicus Univ Torun, Fac Chem, Gagarina 7, PL-87100 Torun, Poland

[3] Polish Acad Sci, Ctr Mol & Macromol Studies, Sienkiewicza 112, PL-90363 Lodz, Poland

来源：

PROCESSES | 2021年 / 9卷 / 12期

关键词：

gold(I) phosphines complex; anticancer drug; cytotoxic effect; NADPH activity; THIOREDOXIN REDUCTASE; CANCER-CELLS; CATALYZED AMINATION; ANTICANCER ACTIVITY; METAL-COMPLEXES; AURANOFIN; PHOSPHINE; CYTOTOXICITY; LIPOPHILICITY; COORDINATION;

D O I：

10.3390/pr9122100

中图分类号：

TQ [化学工业];

学科分类号：

0817 ;

摘要：

Gold(I) complexes with phosphine ligands-[Au(TrippyPhos)Cl] (1) (TrippyPhos = 1-[2-[bis(tert-butyl)phosphino]phenyl]-3,5-diphenyl-1H-pyrazole), [Au(BippyPhos)Cl]Greek ano teleia0.5CH(2)Cl(2) (2) (BippyPhos = 5-(di-tert-butylphosphino)-1 ', 3 ', 5 '-triphenyl-1 ' H-[1,4 ']bipyrazole), and [Au(meCgPPh)Cl] (3) (meCgPPh = 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane-were investigated as types of bioactive gold metallodrugs. Complexes (1)-(3) were characterized using IR, H-1, C-13, P-31 NMR spectroscopy, elemental analysis and mass spectrometry (FAB-MS). Complexes of (1) and (2) exhibited substantial in vitro cytotoxicity (IC50 = 0.5-7.0 mu M) against both the cisplatin-sensitive and -resistant variants of the A2780 human ovarian carcinoma cell line, as well as against the A549 human lung carcinoma, K562 chronic myelogenous leukemia, and HeLa (human cervix carcinoma) cells. However, among the compounds studied, complex (2) showed the most promising biological properties: the highest stability in biologically relevant media, selectivity towards cancer cells over the non-cancer cells (HUVEC, human umbilical vein endothelial cells), and the highest inhibitory effect on cytosolic NADPH-dependent reductases in A2780 and A2780cis cells among the gold complexes under analysis.

引用

页数：18

共 69 条

[1] Gold(I)-Phosphine-N-Heterocycles: Biological Activity and Specific (Ligand) Interactions on the C-Terminal HIVNCp7 Zinc Finger [J].

Abbehausen, Camilla ;

Peterson, Erica J. ;

de Paiva, Raphael E. F. ;

Corbi, Pedro P. ;

Formiga, Andre L. B. ;

Qu, Yun ;

Farrell, Nicholas P. .

INORGANIC CHEMISTRY, 2013, 52 (19) :11280-11287

[2] Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].

Adjabeng, G ;

Brenstrum, T ;

Frampton, CS ;

Robertson, AJ ;

Hillhouse, J ;

McNulty, J ;

Capretta, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086

[3] Far-infrared absorption spectra of synthetically-prepared, ligated metal clusters with Au6, Au8, Au9 and Au6Pd metal cores [J].

Alvino, Jason F. ;

Bennett, Trystan ;

Anderson, David ;

Donoeva, Baira ;

Ovoshchnikov, Daniil ;

Adnan, Rohul H. ;

Appadoo, Dominique ;

Golovko, Vladimir ;

Andersson, Gunther ;

Metha, Gregory F. .

RSC ADVANCES, 2013, 3 (44) :22140-22149

[4] ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) [J].

Barnes, CL .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1997, 30 (01) :568-568

[5]

Bats J.W., 2017, REFCODE GASLUK CCDC

[6]

Berners-Price S.J., 1988, Bioinorg. Chem, P27, DOI DOI 10.1007/3-540-50130-4

[7]

Brandenburg K, 2001, RELEASE 2 1E

[8] Coordination chemistry of 1,3,5-triaza-7-phosphaadamantane (PTA) and derivatives. Part II. The quest for tailored ligands, complexes and related applications [J].

Bravo, Jorge ;

Bolano, Sandra ;

Gonsalvi, Luca ;

Peruzzini, Maurizio .

COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :555-607

[9] The histone deacetylase inhibitor SAHA arrests cancer cell growth, up-regulates thioredoxin-binding protein-2, and down-regulates thioredoxin [J].

Butler, LM ;

Zhou, XB ;

Xu, WS ;

Scher, HI ;

Rifkind, RA ;

Marks, PA ;

Richon, VM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (18) :11700-11705

[10] The impact of lipophilicity on environmental processes, drug delivery and bioavailability of food components [J].

Chmiel, Tomasz ;

Mieszkowska, Anna ;

Kempinska-Kupczyk, Dagmara ;

Kot-Wasik, Agata ;

Namiesnik, Jacek ;

Mazerska, Zofia .

MICROCHEMICAL JOURNAL, 2019, 146 :393-406

← 1 2 3 4 5 6 7 →