Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity

Mavurapu Satyanarayana; Young Ah Kim; Suzanne G. Rzuczek; Daniel S. Pilch; Angela A. Liu; Leroy F. Liu; Joseph E. Rice; Edmond J. LaVoie

doi:10.1016/j.bmcl.2010.03.086

Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity

Mavurapu Satyanarayana
, Young Ah Kim
, Suzanne G. Rzuczek
, Daniel S. Pilch
, Angela A. Liu
, Leroy F. Liu
, Joseph E. Rice
, Edmond J. LaVoie

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

28 Citations (Scopus)

Abstract

A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC₅₀ values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.

Original language	English
Pages (from-to)	3150-3154
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2010.03.086
Publication status	Published - May 15 2010
Externally published	Yes

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Antitumor
Athymic nude mice
Cytotoxicity
G-quadruplex DNA
G-quadruplex RNA
G-quadruplex ligands
Hexaoxazoles
MDA-MB-435 xenograft
Macrocycles

ASJC Scopus subject areas

Drug Discovery
Molecular Medicine
Molecular Biology
Biochemistry
Clinical Biochemistry
Pharmaceutical Science
Organic Chemistry

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10.1016/j.bmcl.2010.03.086

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title = "Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity",

abstract = "A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC50 values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.",

keywords = "Antitumor, Athymic nude mice, Cytotoxicity, G-quadruplex DNA, G-quadruplex RNA, G-quadruplex ligands, Hexaoxazoles, MDA-MB-435 xenograft, Macrocycles",

author = "Mavurapu Satyanarayana and Kim, \{Young Ah\} and Rzuczek, \{Suzanne G.\} and Pilch, \{Daniel S.\} and Liu, \{Angela A.\} and Liu, \{Leroy F.\} and Rice, \{Joseph E.\} and LaVoie, \{Edmond J.\}",

year = "2010",

month = may,

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doi = "10.1016/j.bmcl.2010.03.086",

language = "English",

volume = "20",

pages = "3150--3154",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

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T2 - Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity

AU - Satyanarayana, Mavurapu

AU - Kim, Young Ah

AU - Rzuczek, Suzanne G.

AU - Pilch, Daniel S.

AU - Liu, Angela A.

AU - Liu, Leroy F.

AU - Rice, Joseph E.

AU - LaVoie, Edmond J.

PY - 2010/5/15

Y1 - 2010/5/15

N2 - A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC50 values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.

AB - A series of 24-membered macrocyclic hexaoxazoles containing one or two aminoalkyl substituents was synthesized and evaluated for cytotoxicity and for their ability to selectively stabilize G-quadruplex DNA and RNA. The most cytotoxic analog 4a, with IC50 values of 25 and 130 nM using KB3-1 and RPMI 8402 cells, is efficacious in vivo in athymic nude mice with a human tumor xenograft from the breast cancer cell line MDA-MB-435.

KW - Antitumor

KW - Athymic nude mice

KW - Cytotoxicity

KW - G-quadruplex DNA

KW - G-quadruplex RNA

KW - G-quadruplex ligands

KW - Hexaoxazoles

KW - MDA-MB-435 xenograft

KW - Macrocycles

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DO - 10.1016/j.bmcl.2010.03.086

M3 - Article

C2 - 20409709

AN - SCOPUS:77952065213

SN - 0960-894X

VL - 20

SP - 3150

EP - 3154

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

Macrocyclic hexaoxazoles: Influence of aminoalkyl substituents on RNA and DNA G-quadruplex stabilization and cytotoxicity

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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