Phosphorus-based SAHA analogues as histone deacetylase inhibitors.

Galina V. Kapustin; György Fejér; Jennifer L. Gronlund; Dewey G. McCafferty; Edward Seto; Felicia A. Etzkorn

doi:10.1021/ol035056n

Phosphorus-based SAHA analogues as histone deacetylase inhibitors.

Galina V. Kapustin
, György Fejér
, Jennifer L. Gronlund
, Dewey G. McCafferty
, Edward Seto
, Felicia A. Etzkorn^*

^*Corresponding author for this work

School of Biomedical Sciences

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

Abstract

[structure: see text] Three analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC(50) = 0.57-6.1 mM), HDAC8 (IC(50) = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC(50) = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Antiproliferative activity against A2780 cancer cells (IC(50) = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

Original language	English
Pages (from-to)	3053-3056
Number of pages	0
Journal	Org Lett
Volume	5
Issue number	17
DOIs	https://doi.org/10.1021/ol035056n
Publication status	Published - 21 Aug 2003

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Antineoplastic Agents
Bacterial Proteins
Cell Nucleus
Enzyme Inhibitors
Female
HeLa Cells
Histone Deacetylase Inhibitors
Humans
Hydroxamic Acids
Inhibitory Concentration 50
Organophosphorus Compounds
Ovarian Neoplasms
Recombinant Proteins
Tumor Cells
Cultured
Vorinostat

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title = "Phosphorus-based SAHA analogues as histone deacetylase inhibitors.",

abstract = "[structure: see text] Three analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC(50) = 0.57-6.1 mM), HDAC8 (IC(50) = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC(50) = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Antiproliferative activity against A2780 cancer cells (IC(50) = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.",

keywords = "Antineoplastic Agents, Bacterial Proteins, Cell Nucleus, Enzyme Inhibitors, Female, HeLa Cells, Histone Deacetylase Inhibitors, Humans, Hydroxamic Acids, Inhibitory Concentration 50, Organophosphorus Compounds, Ovarian Neoplasms, Recombinant Proteins, Tumor Cells, Cultured, Vorinostat",

author = "Kapustin, \{Galina V.\} and Gy{\"o}rgy Fej{\'e}r and Gronlund, \{Jennifer L.\} and McCafferty, \{Dewey G.\} and Edward Seto and Etzkorn, \{Felicia A.\}",

year = "2003",

month = aug,

day = "21",

doi = "10.1021/ol035056n",

language = "English",

volume = "5",

pages = "3053--3056",

journal = "Org Lett",

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TY - JOUR

T1 - Phosphorus-based SAHA analogues as histone deacetylase inhibitors.

AU - Kapustin, Galina V.

AU - Fejér, György

AU - Gronlund, Jennifer L.

AU - McCafferty, Dewey G.

AU - Seto, Edward

AU - Etzkorn, Felicia A.

PY - 2003/8/21

Y1 - 2003/8/21

N2 - [structure: see text] Three analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC(50) = 0.57-6.1 mM), HDAC8 (IC(50) = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC(50) = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Antiproliferative activity against A2780 cancer cells (IC(50) = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

AB - [structure: see text] Three analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC(50) = 0.57-6.1 mM), HDAC8 (IC(50) = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC(50) = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Antiproliferative activity against A2780 cancer cells (IC(50) = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.

KW - Antineoplastic Agents

KW - Bacterial Proteins

KW - Cell Nucleus

KW - Enzyme Inhibitors

KW - Female

KW - HeLa Cells

KW - Histone Deacetylase Inhibitors

KW - Humans

KW - Hydroxamic Acids

KW - Inhibitory Concentration 50

KW - Organophosphorus Compounds

KW - Ovarian Neoplasms

KW - Recombinant Proteins

KW - Tumor Cells

KW - Cultured

KW - Vorinostat

U2 - 10.1021/ol035056n

DO - 10.1021/ol035056n

M3 - Article

SN - 1523-7060

VL - 5

SP - 3053

EP - 3056

JO - Org Lett

JF - Org Lett

IS - 17

ER -

Phosphorus-based SAHA analogues as histone deacetylase inhibitors.

Abstract

UN SDGs

Keywords

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