Chiral AuI- and AuIII-isothiourea complexes: synthesis, characterization and application

Danila Gasperini; Mark Greenhalgh; Rehan Imad; Shehzaib Siddiqui; Anum Malik; Fizza Arshad; Muhammad Iqbal Choudhary; Abdullah  Al-Majid; David  Cordes; Alexandra Slawin; Steven Nolan; Andrew D. Smith

doi:10.1002/chem.201804653

Chiral Au^I- and Au^III-isothiourea complexes: synthesis, characterization and application

Danila Gasperini, Mark Greenhalgh, Rehan Imad, Shehzaib Siddiqui, Anum Malik, Fizza Arshad, Muhammad Iqbal Choudhary, Abdullah Al-Majid, David Cordes, Alexandra Slawin, Steven Nolan, Andrew D. Smith

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

Abstract

During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold‐isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air‐ and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)‐isothiourea carbonyl complexes. The novel gold(I)‐ and gold(III)‐isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically‐relevant enzymes.

Original language	English
Journal	Chemistry - A European Journal
Volume	Early View
Early online date	21 Dec 2018
DOIs	https://doi.org/10.1002/chem.201804653
Publication status	E-pub ahead of print - 21 Dec 2018

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

SDG 3 Good Health and Well-being

Keywords

Gold
Coordination chemistry
N ligands
Homogeneous catalysis
Bioinorganic chemistry

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10.1002/chem.201804653

Gasperini_et_al-2018-Chemistry_-_A_European_Journal(2)
Copyright © 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/chem.201804653
Accepted author manuscript, 1.89 MB

Cite this

@article{b69c546f1f874734bde746d677c5d802,

title = "Chiral AuI- and AuIII-isothiourea complexes: synthesis, characterization and application",

abstract = "During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold‐isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air‐ and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)‐isothiourea carbonyl complexes. The novel gold(I)‐ and gold(III)‐isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically‐relevant enzymes.",

keywords = "Gold, Coordination chemistry, N ligands, Homogeneous catalysis, Bioinorganic chemistry",

author = "Danila Gasperini and Mark Greenhalgh and Rehan Imad and Shehzaib Siddiqui and Anum Malik and Fizza Arshad and Choudhary, \{Muhammad Iqbal\} and Abdullah Al-Majid and David Cordes and Alexandra Slawin and Steven Nolan and Smith, \{Andrew D.\}",

note = "ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. SPN thanks King Abdullah University of Science and Technology (Award No. SR-2015-CCF-1974-03) and King Saud University for support.",

year = "2018",

month = dec,

day = "21",

doi = "10.1002/chem.201804653",

language = "English",

volume = "Early View",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley \& Sons, Ltd",

}

TY - JOUR

T1 - Chiral AuI- and AuIII-isothiourea complexes

T2 - synthesis, characterization and application

AU - Gasperini, Danila

AU - Greenhalgh, Mark

AU - Imad, Rehan

AU - Siddiqui, Shehzaib

AU - Malik, Anum

AU - Arshad, Fizza

AU - Choudhary, Muhammad Iqbal

AU - Al-Majid, Abdullah

AU - Cordes, David

AU - Slawin, Alexandra

AU - Nolan, Steven

AU - Smith, Andrew D.

N1 - ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. SPN thanks King Abdullah University of Science and Technology (Award No. SR-2015-CCF-1974-03) and King Saud University for support.

PY - 2018/12/21

Y1 - 2018/12/21

N2 - During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold‐isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air‐ and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)‐isothiourea carbonyl complexes. The novel gold(I)‐ and gold(III)‐isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically‐relevant enzymes.

AB - During an investigation into the potential union of Lewis basic isothiourea organocatalysis and gold catalysis, the formation of gold‐isothiourea complexes was observed. These novel gold complexes were formed in high yield and were found to be air‐ and moisture stable. A series of neutral and cationic chiral gold(I) and gold(III) complexes bearing enantiopure isothiourea ligands was therefore synthesized and fully characterized. The steric and electronic properties of the isothiourea ligands was assessed through calculation of their percent buried volume and the synthesis and analysis of novel iridium(I)‐isothiourea carbonyl complexes. The novel gold(I)‐ and gold(III)‐isothiourea complexes have been applied in preliminary catalytic and biological studies, and display promising preliminary levels of catalytic activity and potency towards cancerous cell lines and clinically‐relevant enzymes.

KW - Gold

KW - Coordination chemistry

KW - N ligands

KW - Homogeneous catalysis

KW - Bioinorganic chemistry

UR - https://www.scopus.com/pages/publications/85059011049

U2 - 10.1002/chem.201804653

DO - 10.1002/chem.201804653

M3 - Article

SN - 0947-6539

VL - Early View

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

Chiral Au^I- and Au^III-isothiourea complexes: synthesis, characterization and application

Abstract

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Keywords

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RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications