The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Andy G. Harry; James Murphy; William E. Butler; Rachel Tiedt; Áine Mooney; Jennifer C. Manton; Mary T. Pryce; Norma O'Donovan; Naomi Walsh; John Crown; Dilip K. Rai; Peter T.M. Kenny

doi:10.1016/j.jorganchem.2012.11.041

The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Andy G. Harry, James Murphy, William E. Butler, Rachel Tiedt, Áine Mooney, Jennifer C. Manton, Mary T. Pryce, Norma O'Donovan, Naomi Walsh, John Crown, Dilip K. Rai, Peter T.M. Kenny

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

9 Citations (Scopus)

Abstract

N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethynyl-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(OEt), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of ¹H NMR, ¹³C NMR, DEPT-135 and ¹H-¹³C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC₅₀ values in the range of 3.2-7.2 μM.

Original language	English
Pages (from-to)	86-92
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	734
DOIs	https://doi.org/10.1016/j.jorganchem.2012.11.041
Publication status	Published - 15 Jun 2013
Externally published	Yes

Keywords

Bioorganometallic chemistry
Cytotoxicity
Dipeptides
Ferrocene
Lung cancer

UN SDGs

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

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10.1016/j.jorganchem.2012.11.041

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Harry, A. G., Murphy, J., Butler, W. E., Tiedt, R., Mooney, Á., Manton, J. C., Pryce, M. T., O'Donovan, N., Walsh, N., Crown, J., Rai, D. K., & Kenny, P. T. M. (2013). The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters. Journal of Organometallic Chemistry, 734, 86-92. https://doi.org/10.1016/j.jorganchem.2012.11.041

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title = "The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters",

abstract = "N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethynyl-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(OEt), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of 1H NMR, 13C NMR, DEPT-135 and 1H-13C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.2-7.2 μM.",

keywords = "Bioorganometallic chemistry, Cytotoxicity, Dipeptides, Ferrocene, Lung cancer",

author = "Harry, {Andy G.} and James Murphy and Butler, {William E.} and Rachel Tiedt and {\'A}ine Mooney and Manton, {Jennifer C.} and Pryce, {Mary T.} and Norma O'Donovan and Naomi Walsh and John Crown and Rai, {Dilip K.} and Kenny, {Peter T.M.}",

year = "2013",

month = jun,

day = "15",

doi = "10.1016/j.jorganchem.2012.11.041",

language = "English",

volume = "734",

pages = "86--92",

journal = "Journal of Organometallic Chemistry",

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Harry, AG, Murphy, J, Butler, WE, Tiedt, R, Mooney, Á, Manton, JC, Pryce, MT, O'Donovan, N, Walsh, N, Crown, J, Rai, DK & Kenny, PTM 2013, 'The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters', Journal of Organometallic Chemistry, vol. 734, pp. 86-92. https://doi.org/10.1016/j.jorganchem.2012.11.041

TY - JOUR

T1 - The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

AU - Harry, Andy G.

AU - Murphy, James

AU - Butler, William E.

AU - Tiedt, Rachel

AU - Mooney, Áine

AU - Manton, Jennifer C.

AU - Pryce, Mary T.

AU - O'Donovan, Norma

AU - Walsh, Naomi

AU - Crown, John

AU - Rai, Dilip K.

AU - Kenny, Peter T.M.

PY - 2013/6/15

Y1 - 2013/6/15

N2 - N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethynyl-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(OEt), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of 1H NMR, 13C NMR, DEPT-135 and 1H-13C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.2-7.2 μM.

AB - N-{6-(Ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters 2-8 were prepared by coupling 6-(ferrocenyl) ethynyl-2-naphthoic acid 1 to the amino acid ethyl ester GABA(OEt) and the dipeptide ethyl esters GlyGly(OEt), GlyAla(OEt), SarGly(OEt), SarAla(OEt), ProGly(OEt) and ProAla(OEt) using the standard N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of 1H NMR, 13C NMR, DEPT-135 and 1H-13C COSY (HMQC) spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and cyclic voltammetry (CV). Compounds, 2-8 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.2-7.2 μM.

KW - Bioorganometallic chemistry

KW - Cytotoxicity

KW - Dipeptides

KW - Ferrocene

KW - Lung cancer

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DO - 10.1016/j.jorganchem.2012.11.041

M3 - Article

AN - SCOPUS:84876671848

SN - 0022-328X

VL - 734

SP - 86

EP - 92

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

The synthesis, structural characterization and in vitro anti-cancer activity of novel N-{6-(ferrocenyl) ethynyl-2-naphthoyl} amino acid and dipeptide ethyl esters

Abstract

Keywords

UN SDGs

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