Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies

Chi-Fung Yeung; Sik-Him Tang; Zhe Yang; Tsun-Yin Li; Ka-Kit Li; Yuen-Man Chan; Hau-Lam Shek; Kai-Wa Io; King-Ting Tam; Shek-Man Yiu; Man-Kit Tse; Chun-Yuen Wong

doi:10.3390/molecules27051709

Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies

Chi-Fung Yeung, Sik-Him Tang, Zhe Yang, Tsun-Yin Li, Ka-Kit Li, Yuen-Man Chan, Hau-Lam Shek, Kai-Wa Io, King-Ting Tam, Shek-Man Yiu, Man-Kit Tse, Chun-Yuen Wong^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

2 Citations (Scopus)

95 Downloads (CityUHK Scholars)

Abstract

Mononuclear and dinuclear Ru(II) complexes cis-[Ru(k²-dppm)(bpy)Cl₂] (1), cis-[Ru(k²-dppe)(bpy)Cl₂] (2) and [Ru₂(bpy)₂(μ-dpam)₂(μ-Cl)₂](Cl)₂ ([3](Cl)₂) were prepared from the reactions between cis(Cl), cis(S)-[Ru(bpy)(dmso-S)₂Cl₂] and diphosphine/diarsine ligands (bpy = 2,2 '-bipyridine; dppm = 1,1-bis(diphenylphosphino)methane; dppe = 1,2-bis(diphenylphosphino)ethane; dpam = 1,1-bis(diphenylarsino)methane). While methoxy-substituted ruthenafuran [Ru(bpy)(k²-dppe)(C^{^}O)]⁺ ([7]⁺; C^{^}O = anionic bidentate [C(OMe)CHC(Ph)O]^- chelate) was obtained as the only product in the reaction between 2 and phenyl ynone HC≡C(C=O)Ph in MeOH, replacing 2 with 1 led to the formation of both methoxy-substituted ruthenafuran [Ru(bpy)(k²-dppm)(C^{^}O)]⁺ ([4]⁺) and phosphonium-ring-fused bicyclic ruthenafuran [Ru(bpy)(P^{^}C^{^}O)Cl]⁺ ([5]⁺; P^{^}C^{^}O = neutral tridentate [(Ph)₂PCH₂P(Ph)₂CCHC(Ph)O] chelate). All of these aforementioned metallafuran complexes were derived from Ru(II)-vinylidene intermediates. The potential applications of these metallafuran complexes as anticancer agents were evaluated by in vitro cytotoxicity studies against cervical carcinoma (HeLa) cancer cell line. All the ruthenafuran complexes were found to be one order of magnitude more cytotoxic than cisplatin, which is one of the metal-based anticancer agents being widely used currently.

Original language	English
Article number	1709
Journal	Molecules
Volume	27
Issue number	5
Online published	5 Mar 2022
DOIs	https://doi.org/10.3390/molecules27051709
Publication status	Published - Mar 2022

Funding

The work described in this paper was supported by the Research Grants Council of Hong Kong SAR (CityU 11305920 and T42-103/16-N) and City University of Hong Kong (7005604).

UN SDGs

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

SDG 3 Good Health and Well-being

Research Keywords

ruthenium
alkyne activation
metallafuran
cytotoxicity
UNCONVENTIONAL ALKYNE ACTIVATIONS
RUTHENIUM COMPLEXES
TERMINAL ALKYNES
GOLD CATALYSIS
METAL
VINYLIDENE
CYCLOISOMERIZATION
HETEROCYCLES
STRATEGY
NITROGEN

Publisher's Copyright Statement

This full text is made available under CC-BY 4.0. https://creativecommons.org/licenses/by/4.0/

RGC Funding Information

RGC-funded

Access Output

10.3390/molecules27051709

97231873.pdfFinal Published version, 3.24 MBLicence: CC BY

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{b05ca08787d74e2c849a82b001531cd5,

title = "Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies",

abstract = "Mononuclear and dinuclear Ru(II) complexes cis-[Ru(k2-dppm)(bpy)Cl2] (1), cis-[Ru(k2-dppe)(bpy)Cl2] (2) and [Ru2(bpy)2(μ-dpam)2(μ-Cl)2](Cl)2 ([3](Cl)2) were prepared from the reactions between cis(Cl), cis(S)-[Ru(bpy)(dmso-S)2Cl2] and diphosphine/diarsine ligands (bpy = 2,2 '-bipyridine; dppm = 1,1-bis(diphenylphosphino)methane; dppe = 1,2-bis(diphenylphosphino)ethane; dpam = 1,1-bis(diphenylarsino)methane). While methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppe)(C^O)]+ ([7]+; C^O = anionic bidentate [C(OMe)CHC(Ph)O]- chelate) was obtained as the only product in the reaction between 2 and phenyl ynone HC≡C(C=O)Ph in MeOH, replacing 2 with 1 led to the formation of both methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppm)(C^O)]+ ([4]+) and phosphonium-ring-fused bicyclic ruthenafuran [Ru(bpy)(P^C^O)Cl]+ ([5]+; P^C^O = neutral tridentate [(Ph)2PCH2P(Ph)2CCHC(Ph)O] chelate). All of these aforementioned metallafuran complexes were derived from Ru(II)-vinylidene intermediates. The potential applications of these metallafuran complexes as anticancer agents were evaluated by in vitro cytotoxicity studies against cervical carcinoma (HeLa) cancer cell line. All the ruthenafuran complexes were found to be one order of magnitude more cytotoxic than cisplatin, which is one of the metal-based anticancer agents being widely used currently.",

keywords = "ruthenium, alkyne activation, metallafuran, cytotoxicity, UNCONVENTIONAL ALKYNE ACTIVATIONS, RUTHENIUM COMPLEXES, TERMINAL ALKYNES, GOLD CATALYSIS, METAL, VINYLIDENE, CYCLOISOMERIZATION, HETEROCYCLES, STRATEGY, NITROGEN",

author = "Chi-Fung Yeung and Sik-Him Tang and Zhe Yang and Tsun-Yin Li and Ka-Kit Li and Yuen-Man Chan and Hau-Lam Shek and Kai-Wa Io and King-Ting Tam and Shek-Man Yiu and Man-Kit Tse and Chun-Yuen Wong",

year = "2022",

month = mar,

doi = "10.3390/molecules27051709",

language = "English",

volume = "27",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "5",

}

TY - JOUR

T1 - Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set

T2 - Synthesis and Cytotoxicity Studies

AU - Yeung, Chi-Fung

AU - Tang, Sik-Him

AU - Yang, Zhe

AU - Li, Tsun-Yin

AU - Li, Ka-Kit

AU - Chan, Yuen-Man

AU - Shek, Hau-Lam

AU - Io, Kai-Wa

AU - Tam, King-Ting

AU - Yiu, Shek-Man

AU - Tse, Man-Kit

AU - Wong, Chun-Yuen

PY - 2022/3

Y1 - 2022/3

N2 - Mononuclear and dinuclear Ru(II) complexes cis-[Ru(k2-dppm)(bpy)Cl2] (1), cis-[Ru(k2-dppe)(bpy)Cl2] (2) and [Ru2(bpy)2(μ-dpam)2(μ-Cl)2](Cl)2 ([3](Cl)2) were prepared from the reactions between cis(Cl), cis(S)-[Ru(bpy)(dmso-S)2Cl2] and diphosphine/diarsine ligands (bpy = 2,2 '-bipyridine; dppm = 1,1-bis(diphenylphosphino)methane; dppe = 1,2-bis(diphenylphosphino)ethane; dpam = 1,1-bis(diphenylarsino)methane). While methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppe)(C^O)]+ ([7]+; C^O = anionic bidentate [C(OMe)CHC(Ph)O]- chelate) was obtained as the only product in the reaction between 2 and phenyl ynone HC≡C(C=O)Ph in MeOH, replacing 2 with 1 led to the formation of both methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppm)(C^O)]+ ([4]+) and phosphonium-ring-fused bicyclic ruthenafuran [Ru(bpy)(P^C^O)Cl]+ ([5]+; P^C^O = neutral tridentate [(Ph)2PCH2P(Ph)2CCHC(Ph)O] chelate). All of these aforementioned metallafuran complexes were derived from Ru(II)-vinylidene intermediates. The potential applications of these metallafuran complexes as anticancer agents were evaluated by in vitro cytotoxicity studies against cervical carcinoma (HeLa) cancer cell line. All the ruthenafuran complexes were found to be one order of magnitude more cytotoxic than cisplatin, which is one of the metal-based anticancer agents being widely used currently.

AB - Mononuclear and dinuclear Ru(II) complexes cis-[Ru(k2-dppm)(bpy)Cl2] (1), cis-[Ru(k2-dppe)(bpy)Cl2] (2) and [Ru2(bpy)2(μ-dpam)2(μ-Cl)2](Cl)2 ([3](Cl)2) were prepared from the reactions between cis(Cl), cis(S)-[Ru(bpy)(dmso-S)2Cl2] and diphosphine/diarsine ligands (bpy = 2,2 '-bipyridine; dppm = 1,1-bis(diphenylphosphino)methane; dppe = 1,2-bis(diphenylphosphino)ethane; dpam = 1,1-bis(diphenylarsino)methane). While methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppe)(C^O)]+ ([7]+; C^O = anionic bidentate [C(OMe)CHC(Ph)O]- chelate) was obtained as the only product in the reaction between 2 and phenyl ynone HC≡C(C=O)Ph in MeOH, replacing 2 with 1 led to the formation of both methoxy-substituted ruthenafuran [Ru(bpy)(k2-dppm)(C^O)]+ ([4]+) and phosphonium-ring-fused bicyclic ruthenafuran [Ru(bpy)(P^C^O)Cl]+ ([5]+; P^C^O = neutral tridentate [(Ph)2PCH2P(Ph)2CCHC(Ph)O] chelate). All of these aforementioned metallafuran complexes were derived from Ru(II)-vinylidene intermediates. The potential applications of these metallafuran complexes as anticancer agents were evaluated by in vitro cytotoxicity studies against cervical carcinoma (HeLa) cancer cell line. All the ruthenafuran complexes were found to be one order of magnitude more cytotoxic than cisplatin, which is one of the metal-based anticancer agents being widely used currently.

KW - ruthenium

KW - alkyne activation

KW - metallafuran

KW - cytotoxicity

KW - UNCONVENTIONAL ALKYNE ACTIVATIONS

KW - RUTHENIUM COMPLEXES

KW - TERMINAL ALKYNES

KW - GOLD CATALYSIS

KW - METAL

KW - VINYLIDENE

KW - CYCLOISOMERIZATION

KW - HETEROCYCLES

KW - STRATEGY

KW - NITROGEN

UR - http://www.scopus.com/inward/record.url?scp=85126408404&partnerID=8YFLogxK

UR - http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=LinksAMR&SrcApp=PARTNER_APP&DestLinkType=FullRecord&DestApp=WOS&KeyUT=000768512400001

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85126408404&origin=recordpage

U2 - 10.3390/molecules27051709

DO - 10.3390/molecules27051709

M3 - RGC 21 - Publication in refereed journal

C2 - 35268810

SN - 1420-3049

VL - 27

JO - Molecules

JF - Molecules

IS - 5

M1 - 1709

ER -

Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies

Abstract

Funding

UN SDGs

Research Keywords

Publisher's Copyright Statement

RGC Funding Information

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

GRF: Constructing Metalated Heterocycles via Alkyne Cycloisomerization: Mechanism and Application

TBRS: A Compact System for Terahertz Imaging and Spectroscopy

Cite this

Ruthenafuran Complexes Supported by the Bipyridine-is(diphenylphosphino)methane Ligand Set: Synthesis and Cytotoxicity Studies

Abstract

Funding

UN SDGs

Research Keywords

Publisher's Copyright Statement

RGC Funding Information

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

Projects

GRF: Constructing Metalated Heterocycles via Alkyne Cycloisomerization: Mechanism and Application

TBRS: A Compact System for Terahertz Imaging and Spectroscopy

Cite this