Medicinal Applications of Gold(I/III)-Based Complexes Bearing N-Heterocyclic Carbene and Phosphine Ligands

被引:84
作者
Dominelli, Bruno [1 ]
Correia, Joao D. G. [2 ]
Kuehn, Fritz E. [1 ]
机构
[1] Tech Univ Munich, Catalysis Res Ctr, Dept Chem, Mol Catalysis, Lichtenbergstr 4, D-85748 Garching, Germany
[2] Univ Lisbon, Inst Super Tecn, Ctr Ciencias & Tecnol Nucl, Campus Tecnol & Nucl,Estr Nacl 10,Km 139-7, P-2695066 Bobadela Lrs, Portugal
关键词
Gold(I/III) complexes; N-Heterocyclic carbenes; Phosphines; Medicinal applications; IN-VITRO CYTOTOXICITY; GOLD(I) COMPLEXES; METAL-COMPLEXES; ANTICANCER AGENTS; STRUCTURAL-CHARACTERIZATION; BIOLOGICAL-ACTIVITIES; POTENTIAL ANTICANCER; LUMINESCENT RE(I); NHC COMPLEXES; DERIVATIVES;
D O I
10.1016/j.jorganchem.2018.04.023
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Phosphines are the most studied ligands on gold-based metallodrugs, whereas N-heterocyclic carbenes (NHCs) have been emerging in the past years as potential alternative ligands for medicinal applications. Indeed, in both cases, phosphine and NHC allow the preparation of a plethora of transition metal-based complexes with attractive properties for medicinal applications. This review offers an update on phosphine and NHC ligands used in gold complexes with potential anti-cancer, anti-bacterial, anti-parasitic (malaria, leishmaniasis and trypanosomasis) and anti-viral (HIV-1) activity. Structural information about diverse ligands is discussed and the biological activity of the corresponding homo-metallic Au(I), Au(III) and hetero-metallic complexes is summarized in tables and discussed as well. Additionally, these complexes are compared with reference compounds and facts about mechanistic studies and luminescence properties are highlighted. The main target of this review is to find trends in ligand design for medicinal purposes. Particularly, questions about the balance between lipophilicity and hydrophilicity, the presence of functional groups, the utilization of multinuclear complexes and the comparison of neutral versus cationic complexes will be addressed. (C) 2018 Elsevier B.V. All rights reserved.
引用
收藏
页码:153 / 164
页数:12
相关论文
共 87 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]   Auranofin efficacy against MDR Streptococcus pneumoniae and Staphylococcus aureus infections [J].
Aguinagalde, Leire ;
Diez-Martinez, Roberto ;
Yuste, Jose ;
Royo, Inmaculada ;
Gil, Carmen ;
Lasa, Inigo ;
Martin-Fontecha, Mar ;
Marin-Ramos, Nagore Isabel ;
Ardanuy, Carmen ;
Linares, Josefina ;
Garcia, Pedro ;
Garcia, Ernesto ;
Sanchez-Puelles, Jose M. .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2015, 70 (09) :2608-2617
[3]   Synthesis and Evaluation of Polymeric Gold Glyco-Conjugates as Anti-Cancer Agents [J].
Ahmed, Marya ;
Mamba, Saul ;
Yang, Xiao-Hong ;
Darkwa, James ;
Kumar, Piyush ;
Narain, Ravin .
BIOCONJUGATE CHEMISTRY, 2013, 24 (06) :979-986
[4]   Synthesis, characterization, in vitro cytotoxicity and DNA interaction study of phosphanegold(I) complexes with dithiocarbamate ligands [J].
Al-Jaroudi, Said S. ;
Altaf, Muhammad ;
Seliman, Adam A. ;
Yadav, Shipra ;
Arjmand, Farukh ;
Alhoshani, Ali ;
Korashy, Hesham M. ;
Ahmad, Saeed ;
Isab, Anvarhusein A. .
INORGANICA CHIMICA ACTA, 2017, 464 :37-48
[5]   In vitro Biological Activities of Gold(I) and Gold(III) Bis (N-Heterocyclic Carbene) Complexes [J].
Al-Majid, Abdullah M. ;
Choudhary, Muhammad Iqbal ;
Yousuf, Sammer ;
Jabeen, Almas ;
Imad, Rehan ;
Javeed, Kulsoom ;
Shaikh, Nimra Naveed ;
Collado, Alba ;
Sioriki, Eleni ;
Nahra, Fady ;
Nolan, Steven P. .
CHEMISTRYSELECT, 2017, 2 (19) :5316-5320
[6]   Gold-NHC complexes as potent bioactive compounds [J].
Al-Majid, Abdullah M. ;
Yousuf, Sammer ;
Choudhary, M. Iqbal ;
Nahra, Fady ;
Nolan, Steven P. .
CHEMISTRYSELECT, 2016, 1 (01) :76-80
[7]   Anticancer Agents: Does a Phosphonium Behave Like a Gold(I) Phosphine Complex? Let a "Smart" Probe Answer! [J].
Ali, Moussa ;
Dondaine, Lucile ;
Adolle, Anais ;
Sampaio, Carla ;
Chotard, Florian ;
Richard, Philippe ;
Denat, Franck ;
Bettaieb, Ali ;
Le Gendre, Pierre ;
Laurens, Veronique ;
Goze, Christine ;
Paul, Catherine ;
Bodio, Ewen .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) :4521-4528
[8]   The synthesis, spectroscopic characterization and anticancer activity of new mono and binuclear phosphanegold(I) dithiocarbamate complexes [J].
Altaf, Muhammad ;
Monim-ul-Mehboob, M. ;
Isab, Anvarhusein A. ;
Dhuna, Vikram ;
Bhatia, Gaurav ;
Dhuna, Kshitija ;
Altuwaijri, Saleh .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (01) :377-385
[9]   Synthesis and Biological Activity of Gold(I) N-Heterocyclic Carbene Complexes with Long Aliphatic Side Chains [J].
Arcau, Julia ;
Andermark, Vincent ;
Rodrigues, Mafalda ;
Giannicchi, Ilaria ;
Perez-Garcia, Lluisa ;
Ott, Ingo ;
Rodriguez, Laura .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, (35) :6117-6125
[10]   Nimesulide Silver Metallodrugs, Containing the Mitochondriotropic, Triaryl Derivatives of Pnictogen; Anticancer Activity against Human Breast Cancer Cells [J].
Banti, Christina N. ;
Papatriantafyllopoulou, Constantina ;
Manoli, Maria ;
Tasiopoulos, Anastasios J. ;
Hadjikakou, Sotiris K. .
INORGANIC CHEMISTRY, 2016, 55 (17) :8681-8696