Straightforward synthetic route to gold(i)-thiolato glycoconjugate complexes bearing NHC ligands (NHC = N-heterocyclic carbene) and their promising anticancer activity

被引:25
|
作者
Safir Filho, Mauro [1 ]
Scattolin, Thomas [2 ,3 ]
Dao, Pascal [1 ]
Tzouras, Nikolaos, V [2 ,3 ]
Benhida, Rachid [1 ,4 ]
Saab, Marina [2 ,3 ]
Van Hecke, Kristof [2 ,3 ]
Lippmann, Petra [5 ]
Martin, Anthony R. [1 ,6 ]
Ott, Ingo [5 ]
Nolan, Steven P. [2 ,3 ]
机构
[1] Univ Cote dAzur, Inst Chim Nice, UMR7272, CNRS, Nice, France
[2] Univ Ghent, Dept Chem, Krygslaan 281,S-3, B-9000 Ghent, Belgium
[3] Univ Ghent, Ctr Sustainable Chem, Krygslaan 281,S-3, B-9000 Ghent, Belgium
[4] Mohammed VI Polytech Univ, Chem & Biochem Sci Green Proc Engn CBS GPE, Lot 660, Hay Moulay Rachid, Benguerir, Morocco
[5] Tech Univ Carolo Wilhelmina Braunschweig, Inst Med & Pharmaceut Chem, Beethovenstr 55, D-38106 Braunschweig, Germany
[6] Univ Montpellier, Inst Biomol Max Mousseron, CNRS, ENSCM,UMR5247, Montpellier, France
关键词
AURANOFIN; CYTOTOXICITY; INHIBITION; AU(I);
D O I
10.1039/d1nj02117f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and eco-friendly route to gold-NHC complexes bearing different thiosugars is reported. The reaction between [Au(NHC)Cl] precursors, the thiosugars and a weak base proceeds under air using technical grade acetone under mild conditions (60 degrees C, 1 h). The one-pot synthesis of the same complexes starting from the corresponding imidazolium salts was also investigated. The obtained complexes showed strong cytotoxic activities against selected cancer cell lines with IC50 values in the submicromolar to low micromolar concentration range.
引用
收藏
页码:9995 / 10001
页数:7
相关论文
共 50 条
  • [1] Straightforward synthesis of [Cu(NHC)(alkynyl)] and [Cu(NHC)(thiolato)] complexes (NHC = N-heterocyclic carbene)
    Ibni Hashim, Ishfaq
    Scattolin, Thomas
    Tzouras, Nikolaos V.
    Bourda, Laurens
    Van Hecke, Kristof
    Ritacco, Ida
    Caporaso, Lucia
    Cavallo, Luigi
    Nolan, Steven P.
    Cazin, Catherine S. J.
    DALTON TRANSACTIONS, 2021, 51 (01) : 231 - 240
  • [2] Catalytic activity of (NHC)-copper(I) complexes (NHC = N-heterocyclic carbene)
    Diez-Gonzalez, Silvia
    Scott, Natalie M.
    Stevens, Edwin D.
    Nolan, Steven P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3230 - U3230
  • [3] A general synthetic route to [Cu(X)(NHC)] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes
    Santoro, Orlando
    Collado, Alba
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    Cazin, Catherine S. J.
    CHEMICAL COMMUNICATIONS, 2013, 49 (89) : 10483 - 10485
  • [4] Synthetic routes to [Au(NHC)(OH)] (NHC = N-heterocyclic carbene) complexes
    Gomez-Suarez, Adrian
    Ramon, Ruben S.
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    DALTON TRANSACTIONS, 2012, 41 (18) : 5461 - 5463
  • [5] Straightforward synthesis of [Au(NHC)X] (NHC = N-heterocyclic carbene, X = Cl, Br, I) complexes
    Collado, Alba
    Gomez-Suarez, Adrian
    Martin, Anthony R.
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    CHEMICAL COMMUNICATIONS, 2013, 49 (49) : 5541 - 5543
  • [6] The anticancer activity of an air-stable Pd(i)-NHC (NHC = N-heterocyclic carbene) dimer
    Scattolin, Thomas
    Bortolamiol, Enrica
    Palazzolo, Stefano
    Caligiuri, Isabella
    Perin, Tiziana
    Canzonieri, Vincenzo
    Demitri, Nicola
    Rizzolio, Flavio
    Cavallo, Luigi
    Dereli, Busra
    Mane, Manoj V.
    Nolan, Steven P.
    Visentin, Fabiano
    CHEMICAL COMMUNICATIONS, 2020, 56 (81) : 12238 - 12241
  • [7] A general synthetic route to mixed NHC-phosphane palladium(0) complexes (NHC = N-heterocyclic carbene)
    Fantasia, Serena
    Nolan, Steven P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (23) : 6987 - 6993
  • [8] Anticancer, antimicrobial and antiparasitical activities of copper(I) complexes based on N-heterocyclic carbene (NHC) ligands bearing aryl substituents
    Touj, Nedra
    Al Nasr, Ibrahim S.
    Koko, Waleed S.
    Khan, Tariq A.
    Ozdemir, Ismail
    Yasar, Sedat
    Mansour, Lamjed
    Alresheedi, Faisal
    Hamdi, Naceur
    JOURNAL OF COORDINATION CHEMISTRY, 2020, 73 (20-22) : 2889 - 2905
  • [9] Synthesis, characterization and anticancer activity of palladium allyl complexes bearing benzimidazole-based N-heterocyclic carbene (NHC) ligands
    Scattolin, Thomas
    Piccin, Andrea
    Mauceri, Matteo
    Rizzolio, Flavio
    Demitri, Nicola
    Canzonieri, Vincenzo
    Visentin, Fabiano
    POLYHEDRON, 2021, 207
  • [10] Silver N-Heterocyclic Carbene (NHC) Complexes as Antimicrobial and/or Anticancer Agents
    Ceramella, Jessica
    Catalano, Alessia
    Mariconda, Annaluisa
    D'Amato, Assunta
    Aquila, Saveria
    Saturnino, Carmela
    Rosano, Camillo
    Sinicropi, Maria Stefania
    Longo, Pasquale
    PHARMACEUTICALS, 2025, 18 (01)