Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

Hao He; Li Ping Bai; Zhi Hong JIANG

doi:10.1016/j.bmcl.2011.12.143

Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

Hao He, Li Ping Bai, Zhi Hong JIANG^*

^*Corresponding author for this work

School of Chinese Medicine

Research output: Contribution to journal › Journal article › peer-review

30 Citations (Scopus)

Abstract

The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.

Original language	English
Pages (from-to)	1582-1586
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2011.12.143
Publication status	Published - 15 Feb 2012

Scopus Subject Areas

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

User-Defined Keywords

Alkannin
G-quadruplex
Glycosylation
Shikonin
Telomeric

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10.1016/j.bmcl.2011.12.143

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title = "Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin",

abstract = "The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.",

keywords = "Alkannin, G-quadruplex, Glycosylation, Shikonin, Telomeric",

author = "Hao He and Bai, {Li Ping} and JIANG, {Zhi Hong}",

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TY - JOUR

T1 - Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

AU - He, Hao

AU - Bai, Li Ping

AU - JIANG, Zhi Hong

PY - 2012/2/15

Y1 - 2012/2/15

N2 - The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.

AB - The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity.

KW - Alkannin

KW - G-quadruplex

KW - Glycosylation

KW - Shikonin

KW - Telomeric

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U2 - 10.1016/j.bmcl.2011.12.143

DO - 10.1016/j.bmcl.2011.12.143

M3 - Journal article

C2 - 22281188

AN - SCOPUS:84856678408

SN - 0960-894X

VL - 22

SP - 1582

EP - 1586

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

ER -

Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

Abstract

Scopus Subject Areas

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