Synthesis, characterization and anticancer evaluation of phosphinogold(I) thiocarbohydrate complexes

Christian K. Adokoh; James Darkwa; Henok H. Kinfe

doi:10.1016/j.poly.2017.09.010

Synthesis, characterization and anticancer evaluation of phosphinogold(I) thiocarbohydrate complexes

Christian K. Adokoh, James Darkwa, Henok H. Kinfe

Chemical Sciences

University of Johannesburg

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

9 Citations (Scopus)

Abstract

Several novel thiocarbohydrate phosphinogold(I) complexes were prepared via the reaction of n-gluconamidoalkyl thiol (L1–L7) {where L1–L4 = n-gluconamidoalkyl thiol (n = 1–4), L5–L7 = acetylated n-gluconamidoalkyl thiol (n = 1–3)} with the gold precursors [AuCl(PPh₃)], [Au₂Cl₂(dppe)], [Au₂Cl₂(dppp)] and [Au₂Cl₂(dppb)], leading to the new gold(I) complexes [Au(L1)(PPh₃)] (1–4), [Au(L5)(PPh₃)] (5–7), [Au₂(L1)₂(dppe)] (8–11), [Au₂(L5)₂(dppx)] (12–14), [(Au₂(L6)₂)(dppx)] (15–17), [Au₂(L7)₂(dppx)] (18–20), {where dppe = 1,2-bis(diphenylphosphino)ethane (x = e), dppp = 1,3-bis(diphenylphosphino)propane (x = p) and dppb = 1,4-bis-(diphenylphosphino)butane (x = b)}. These gold complexes were characterized by a combination of NMR and infrared spectroscopy, microanalysis and mass spectrometry. Complexes 8, 12, 14–16 (IC₅₀ values between 0.003 and 1.8 μM) are all active against MCF7, HCT116 and PC3 cells. Complex 8 recorded the highest IC₅₀ value of 0.003 μM against PC3. Complex 14 was found to be selective towards both MCF7 and PC3 cells with a TS value of 142.1, while compounds 15 and 16 were highly selective toward PC3 cells with TS values of 970.0 and 937.5, respectively.

Original language	English
Pages (from-to)	57-67
Number of pages	11
Journal	Polyhedron
Volume	138
DOIs	https://doi.org/10.1016/j.poly.2017.09.010
Publication status	Published - 2017

Keywords

Cytotoxicity
SRB assay
Thiocarbohydrate phosphinogold(I) complex
Tumor-specificity
n-Gluconamidoalkyl thiol

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

UN SDGs

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

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10.1016/j.poly.2017.09.010

Cite this

@article{2d935656c47d44428ab8284f183b3108,

title = "Synthesis, characterization and anticancer evaluation of phosphinogold(I) thiocarbohydrate complexes",

abstract = "Several novel thiocarbohydrate phosphinogold(I) complexes were prepared via the reaction of n-gluconamidoalkyl thiol (L1–L7) {where L1–L4 = n-gluconamidoalkyl thiol (n = 1–4), L5–L7 = acetylated n-gluconamidoalkyl thiol (n = 1–3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)] and [Au2Cl2(dppb)], leading to the new gold(I) complexes [Au(L1)(PPh3)] (1–4), [Au(L5)(PPh3)] (5–7), [Au2(L1)2(dppe)] (8–11), [Au2(L5)2(dppx)] (12–14), [(Au2(L6)2)(dppx)] (15–17), [Au2(L7)2(dppx)] (18–20), {where dppe = 1,2-bis(diphenylphosphino)ethane (x = e), dppp = 1,3-bis(diphenylphosphino)propane (x = p) and dppb = 1,4-bis-(diphenylphosphino)butane (x = b)}. These gold complexes were characterized by a combination of NMR and infrared spectroscopy, microanalysis and mass spectrometry. Complexes 8, 12, 14–16 (IC50 values between 0.003 and 1.8 μM) are all active against MCF7, HCT116 and PC3 cells. Complex 8 recorded the highest IC50 value of 0.003 μM against PC3. Complex 14 was found to be selective towards both MCF7 and PC3 cells with a TS value of 142.1, while compounds 15 and 16 were highly selective toward PC3 cells with TS values of 970.0 and 937.5, respectively.",

keywords = "Cytotoxicity, SRB assay, Thiocarbohydrate phosphinogold(I) complex, Tumor-specificity, n-Gluconamidoalkyl thiol",

author = "Adokoh, {Christian K.} and James Darkwa and Kinfe, {Henok H.}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.poly.2017.09.010",

language = "English",

volume = "138",

pages = "57--67",

journal = "Polyhedron",

issn = "0277-5387",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - Synthesis, characterization and anticancer evaluation of phosphinogold(I) thiocarbohydrate complexes

AU - Adokoh, Christian K.

AU - Darkwa, James

AU - Kinfe, Henok H.

PY - 2017

Y1 - 2017

N2 - Several novel thiocarbohydrate phosphinogold(I) complexes were prepared via the reaction of n-gluconamidoalkyl thiol (L1–L7) {where L1–L4 = n-gluconamidoalkyl thiol (n = 1–4), L5–L7 = acetylated n-gluconamidoalkyl thiol (n = 1–3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)] and [Au2Cl2(dppb)], leading to the new gold(I) complexes [Au(L1)(PPh3)] (1–4), [Au(L5)(PPh3)] (5–7), [Au2(L1)2(dppe)] (8–11), [Au2(L5)2(dppx)] (12–14), [(Au2(L6)2)(dppx)] (15–17), [Au2(L7)2(dppx)] (18–20), {where dppe = 1,2-bis(diphenylphosphino)ethane (x = e), dppp = 1,3-bis(diphenylphosphino)propane (x = p) and dppb = 1,4-bis-(diphenylphosphino)butane (x = b)}. These gold complexes were characterized by a combination of NMR and infrared spectroscopy, microanalysis and mass spectrometry. Complexes 8, 12, 14–16 (IC50 values between 0.003 and 1.8 μM) are all active against MCF7, HCT116 and PC3 cells. Complex 8 recorded the highest IC50 value of 0.003 μM against PC3. Complex 14 was found to be selective towards both MCF7 and PC3 cells with a TS value of 142.1, while compounds 15 and 16 were highly selective toward PC3 cells with TS values of 970.0 and 937.5, respectively.

AB - Several novel thiocarbohydrate phosphinogold(I) complexes were prepared via the reaction of n-gluconamidoalkyl thiol (L1–L7) {where L1–L4 = n-gluconamidoalkyl thiol (n = 1–4), L5–L7 = acetylated n-gluconamidoalkyl thiol (n = 1–3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)] and [Au2Cl2(dppb)], leading to the new gold(I) complexes [Au(L1)(PPh3)] (1–4), [Au(L5)(PPh3)] (5–7), [Au2(L1)2(dppe)] (8–11), [Au2(L5)2(dppx)] (12–14), [(Au2(L6)2)(dppx)] (15–17), [Au2(L7)2(dppx)] (18–20), {where dppe = 1,2-bis(diphenylphosphino)ethane (x = e), dppp = 1,3-bis(diphenylphosphino)propane (x = p) and dppb = 1,4-bis-(diphenylphosphino)butane (x = b)}. These gold complexes were characterized by a combination of NMR and infrared spectroscopy, microanalysis and mass spectrometry. Complexes 8, 12, 14–16 (IC50 values between 0.003 and 1.8 μM) are all active against MCF7, HCT116 and PC3 cells. Complex 8 recorded the highest IC50 value of 0.003 μM against PC3. Complex 14 was found to be selective towards both MCF7 and PC3 cells with a TS value of 142.1, while compounds 15 and 16 were highly selective toward PC3 cells with TS values of 970.0 and 937.5, respectively.

KW - Cytotoxicity

KW - SRB assay

KW - Thiocarbohydrate phosphinogold(I) complex

KW - Tumor-specificity

KW - n-Gluconamidoalkyl thiol

UR - http://www.scopus.com/inward/record.url?scp=85030175122&partnerID=8YFLogxK

U2 - 10.1016/j.poly.2017.09.010

DO - 10.1016/j.poly.2017.09.010

M3 - Article

AN - SCOPUS:85030175122

SN - 0277-5387

VL - 138

SP - 57

EP - 67

JO - Polyhedron

JF - Polyhedron

ER -

Synthesis, characterization and anticancer evaluation of phosphinogold(I) thiocarbohydrate complexes

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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