Antitumor Activity of Ionic Liquids Based on Ampicillin

Ricardo Ferraz; João Costa-Rodrigues; Maria H. Fernandes; Miguel Santos; I. M. Marrucho; Luis P. N. Rebelo; Cristina Prudêncio; João Paulo da Costa de Noronha; Zeljko Petrovski; Luís Alexandre Almeida Fernandes Cobra Branco

doi:10.1002/cmdc.201500142

Antitumor Activity of Ionic Liquids Based on Ampicillin

Ricardo Ferraz, João Costa-Rodrigues, Maria H. Fernandes, Miguel Santos, I. M. Marrucho, Luis P. N. Rebelo, Cristina Prudêncio, João Paulo da Costa de Noronha, Zeljko Petrovski, Luís Alexandre Almeida Fernandes Cobra Branco

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Abstract

Significant antiproliferative effects against various tumor cell lines were observed with novel ampicillin salts as ionic liquids. The combination of anionic ampicillin with appropriate ammonium, imidazolium, phosphonium, and pyridinium cations yielded active pharmaceutical ingredient ionic liquids (API-ILs) that show potent antiproliferative activities against five different human cancer cell lines: T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon). Some API-ILs showed IC50 values between 5 and 42nM, activities that stand in dramatic contrast to the negligible cytotoxic activity level shown by the ampicillin sodium salt. Moreover, very low cytotoxicity against two primary cell linesskin (SF) and gingival fibroblasts (GF)indicates that the majority of these API-ILs are nontoxic to normal human cell lines. The most promising combination of antitumor activity and low toxicity toward healthy cells was observed for the 1-hydroxyethyl-3-methylimidazolium-ampicillin pair ([C2OHMIM][Amp]), making this the most suitable lead API-IL for future studies.

Original language	English
Pages (from-to)	1480-1483
Journal	Chemmedchem
Volume	10
Issue number	9
DOIs	https://doi.org/10.1002/cmdc.201500142
Publication status	Published - Sept 2015

Keywords

active pharmaceutical ingredients
ampicillin
antitumor agents
ionic liquids
toxicity

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

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ChemMedchem_galery_proofsAccepted author manuscript, 556 KBLicence: CC BY-NC

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@article{b58340a656a2493cb5efc91a94da1788,

title = "Antitumor Activity of Ionic Liquids Based on Ampicillin",

abstract = "Significant antiproliferative effects against various tumor cell lines were observed with novel ampicillin salts as ionic liquids. The combination of anionic ampicillin with appropriate ammonium, imidazolium, phosphonium, and pyridinium cations yielded active pharmaceutical ingredient ionic liquids (API-ILs) that show potent antiproliferative activities against five different human cancer cell lines: T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon). Some API-ILs showed IC50 values between 5 and 42nM, activities that stand in dramatic contrast to the negligible cytotoxic activity level shown by the ampicillin sodium salt. Moreover, very low cytotoxicity against two primary cell linesskin (SF) and gingival fibroblasts (GF)indicates that the majority of these API-ILs are nontoxic to normal human cell lines. The most promising combination of antitumor activity and low toxicity toward healthy cells was observed for the 1-hydroxyethyl-3-methylimidazolium-ampicillin pair ([C2OHMIM][Amp]), making this the most suitable lead API-IL for future studies.",

keywords = "active pharmaceutical ingredients , ampicillin , antitumor agents , ionic liquids , toxicity",

author = "Ricardo Ferraz and Jo{\~a}o Costa-Rodrigues and Fernandes, {Maria H.} and Miguel Santos and Marrucho, {I. M.} and Rebelo, {Luis P. N.} and Cristina Prud{\^e}ncio and Noronha, {Jo{\~a}o Paulo da Costa de} and Zeljko Petrovski and Branco, {Lu{\'i}s Alexandre Almeida Fernandes Cobra}",

year = "2015",

month = sep,

doi = "10.1002/cmdc.201500142",

language = "English",

volume = "10",

pages = "1480--1483",

journal = "Chemmedchem",

issn = "1860-7179",

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

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}

TY - JOUR

T1 - Antitumor Activity of Ionic Liquids Based on Ampicillin

AU - Ferraz, Ricardo

AU - Costa-Rodrigues, João

AU - Fernandes, Maria H.

AU - Santos, Miguel

AU - Marrucho, I. M.

AU - Rebelo, Luis P. N.

AU - Prudêncio, Cristina

AU - Noronha, João Paulo da Costa de

AU - Petrovski, Zeljko

AU - Branco, Luís Alexandre Almeida Fernandes Cobra

PY - 2015/9

Y1 - 2015/9

N2 - Significant antiproliferative effects against various tumor cell lines were observed with novel ampicillin salts as ionic liquids. The combination of anionic ampicillin with appropriate ammonium, imidazolium, phosphonium, and pyridinium cations yielded active pharmaceutical ingredient ionic liquids (API-ILs) that show potent antiproliferative activities against five different human cancer cell lines: T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon). Some API-ILs showed IC50 values between 5 and 42nM, activities that stand in dramatic contrast to the negligible cytotoxic activity level shown by the ampicillin sodium salt. Moreover, very low cytotoxicity against two primary cell linesskin (SF) and gingival fibroblasts (GF)indicates that the majority of these API-ILs are nontoxic to normal human cell lines. The most promising combination of antitumor activity and low toxicity toward healthy cells was observed for the 1-hydroxyethyl-3-methylimidazolium-ampicillin pair ([C2OHMIM][Amp]), making this the most suitable lead API-IL for future studies.

AB - Significant antiproliferative effects against various tumor cell lines were observed with novel ampicillin salts as ionic liquids. The combination of anionic ampicillin with appropriate ammonium, imidazolium, phosphonium, and pyridinium cations yielded active pharmaceutical ingredient ionic liquids (API-ILs) that show potent antiproliferative activities against five different human cancer cell lines: T47D (breast), PC3 (prostate), HepG2 (liver), MG63 (osteosarcoma), and RKO (colon). Some API-ILs showed IC50 values between 5 and 42nM, activities that stand in dramatic contrast to the negligible cytotoxic activity level shown by the ampicillin sodium salt. Moreover, very low cytotoxicity against two primary cell linesskin (SF) and gingival fibroblasts (GF)indicates that the majority of these API-ILs are nontoxic to normal human cell lines. The most promising combination of antitumor activity and low toxicity toward healthy cells was observed for the 1-hydroxyethyl-3-methylimidazolium-ampicillin pair ([C2OHMIM][Amp]), making this the most suitable lead API-IL for future studies.

KW - active pharmaceutical ingredients

KW - ampicillin

KW - antitumor agents

KW - ionic liquids

KW - toxicity

U2 - 10.1002/cmdc.201500142

DO - 10.1002/cmdc.201500142

M3 - Article

C2 - 26190053

SN - 1860-7179

VL - 10

SP - 1480

EP - 1483

JO - Chemmedchem

JF - Chemmedchem

IS - 9

ER -

Antitumor Activity of Ionic Liquids Based on Ampicillin

Abstract

Keywords

UN SDGs

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