Toward multifunctional anticancer therapeutics: post-synthetic carbonate functionalisation of asymmetric Au(<scp>i</scp>) bis-N-heterocyclic carbenes

Sen, Sajal; Perrin, Mark W.; Sedgwick, Adam; Dunsky, Evie Y.; Lynch, Vincent M.; He, Xiao‐Peng; Sessler, Jonathan L.; Arambula, Jonathan F.

doi:10.1039/d0cc03339a

Cited by 12 publications

(20 citation statements)

References 38 publications

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“…6A ). Under analogous conditions our previously reported carbonate bonded naphthalimide system proved unstable, 8 leading us to infer that complex 9 would be suitable for use in vitro .…”

Section: Resultsmentioning

confidence: 70%

“…2A) cumulated in the development of both carbonate and carbamate linker strategies. 7,8 However, carbamates and carbonates are known to be more susceptible to hydrolysis than amides in biological environments. 9 Unfortunately, complex 1 did not allow access to Au(I) bis NHC targets containing less labile amide linkers.…”

Section: Syntheses and Characterizationmentioning

confidence: 99%

“…In previous work, and in accord with the literature, 33,34 we found that attachment of a naphthalimide moiety to an Au(I) bis-NHC motif facilitated binding to bovine serum albumin (BSA). 8 However, our previous studies centred around a carbonatelinked complex that was found to undergo slow hydrolysis, even ex vivo. Complex 9, prepared using the present amide linking protocol, was expected to be stable against hydrolysis.…”

Section: Non-covalent Binding Between Hsa and Au(i) Bis-nhcmentioning

confidence: 99%

“…5,6 Post-synthetic functionalization provides an attractive means for creating new Au(I) bis-NHC derivatives. 7,8 Oen this involves the use of chemical tethers to link Au(I) bis-NHCs to other moieties. However, a number of previously reported linkers, including esters and carbonates, proved susceptible to degradation in biological milieus leading to reduced efficacy.…”

Section: Introductionmentioning

confidence: 99%

“… 21 Recently, a strategy designed to enhance non-covalent binding interactions between HSA and Au( i ) bis-NHCs was reported by our lab. 8 However, covalent binding was not achieved. More broadly, we are not aware of any systematic studies that compare the relative benefits of covalent vs. non-covalent binding using a similar drug motif.…”

Section: Introductionmentioning

confidence: 99%

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Covalent and non-covalent albumin binding of Au(i) bis-NHCsviapost-synthetic amide modification

et al. 2021

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“…6A ). Under analogous conditions our previously reported carbonate bonded naphthalimide system proved unstable, 8 leading us to infer that complex 9 would be suitable for use in vitro .…”

Section: Resultsmentioning

confidence: 70%

Section: Syntheses and Characterizationmentioning

confidence: 99%

Section: Non-covalent Binding Between Hsa and Au(i) Bis-nhcmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Covalent and non-covalent albumin binding of Au(i) bis-NHCsviapost-synthetic amide modification

et al. 2021

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Synthetic Strategies for the Preparation of Gold‐based Anticancer Agents

Gukathasan

Awuah

2022

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Gold (Au) complexes attained an exceptional reach as new metal‐based anticancer agents in recent years. The FDA‐approved Au I complex auranofin [(2,3,4,6‐tetra‐ O ‐acetyl‐1‐thio‐β‐ d ‐glucopyranose (triethylphosphoranylidene)gold(I)] displays efficacious chemotherapeutic potential in phase I and II clinical trials for both liquid and solid tumors. Ignited by the success of auranofin as an anticancer agent, new designs and synthetic processes toward Au I and Au III complexes for unique biomedical applications are actively ongoing. In the past few years, Au III complexes have become attractive as premised on promising antitumor preclinical studies despite bottlenecks associated with stability and biological target identification. Advancement of gold complexes to the clinic will require agents with improved anticancer potency, unambiguous biological target, pharmacokinetic profile, and optimal stability. Thus, ligand tuning and innovative synthetic chemistry coupled with rigorous biological characterization are crucial. In this article, an overview of known synthetic strategies for the synthesis of gold anticancer complexes is presented. Primary focus on the synthesis of Au I and Au III complexes along with anticancer outcomes is outlined. This article presents medicinal inorganic chemists with an armory of synthetic tools and purification protocols to readily access highly potent gold anticancer agents.

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Gold Complexes in Anticancer Therapy: From New Design Principles to Particle‐Based Delivery Systems

2023

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The discovery of the medicinal properties of gold complexes has fuelled the design and synthesis of new anticancer metallodrugs, which have received special attention due to their unique modes of action. Current research in the development of gold compounds with therapeutic properties is predominantly focused on the molecular design of drug leads with superior pharmacological activities, e.g., by introducing targeting features. Moreover, intensive research aims at improving the physicochemical properties of gold compounds, such as chemical stability and solubility in the physiological environment. In this regard, the encapsulation of gold compounds in nanocarriers or their chemical grafting onto targeted delivery vectors could lead to new nanomedicines that eventually reach clinical applications. Herein, we provide an overview of the state‐of‐the‐art progress of gold anticancer compounds, andmore importantly we thoroughly revise the development of nanoparticle‐based delivery systems for gold chemotherapeutics.

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Toward multifunctional anticancer therapeutics: post-synthetic carbonate functionalisation of asymmetric Au(i) bis-N-heterocyclic carbenes

Abstract: A post-synthetic strategy is reported that permits functionalization of Au(i)–bis NHCs via carbonate formation and synthesis of a potential multifunctional anticancer therapeutic.

Cited by 12 publications

References 38 publications

Covalent and non-covalent albumin binding of Au(i) bis-NHCsviapost-synthetic amide modification

Covalent and non-covalent albumin binding of Au(i) bis-NHCsviapost-synthetic amide modification

Synthetic Strategies for the Preparation of Gold‐based Anticancer Agents

Gold Complexes in Anticancer Therapy: From New Design Principles to Particle‐Based Delivery Systems

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