Precursor-directed generation of indolocarbazoles with topoisomerase IIα inhibitory activity

Cong Wang; Adeep Monger; Liping Wang; Peng Fu; Pawinee Piyachaturawat; Arthit Chairoungdua; Weiming Zhu

doi:10.3390/md16050168

Precursor-directed generation of indolocarbazoles with topoisomerase IIα inhibitory activity

Cong Wang, Adeep Monger, Liping Wang, Peng Fu, Pawinee Piyachaturawat, Arthit Chairoungdua, Weiming Zhu

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

17 Citations (Scopus)

Abstract

One new indolocarbazole, 3-hydroxy-K252d (3), together with the recently reported 3-hydroxyholyrine A (1) and 3-N-acetyl-3-hydroxyholyrine A (2), were obtained by feeding a culture of the marine-derived Streptomyces strain OUCMDZ-3118 with 5-hydroxy-L-tryptophan. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 potently induced apoptosis of gastric cancer cells by inhibiting topoisomerase IIα enzyme activity and reducing the expression of antiapoptosis protein level. Compound 3 displayed moderate cytotoxicity against the A549 and MCF-7 cell lines with IC₅₀ values of 1.2 ± 0.05 µM, 1.6 ± 0.09 µM, respectively.

Original language	English
Article number	168
Journal	Marine Drugs
Volume	16
Issue number	5
DOIs	https://doi.org/10.3390/md16050168
Publication status	Published - May 2018
Externally published	Yes

Keywords

Cytotoxicities
Indolocarbazole
Marine-derived Streptomyces
Streptomyces sp. OUCMDZ-3118
Topoisomerase IIα enzyme activity

UN SDGs

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

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10.3390/md16050168

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title = "Precursor-directed generation of indolocarbazoles with topoisomerase IIα inhibitory activity",

abstract = "One new indolocarbazole, 3-hydroxy-K252d (3), together with the recently reported 3-hydroxyholyrine A (1) and 3-N-acetyl-3-hydroxyholyrine A (2), were obtained by feeding a culture of the marine-derived Streptomyces strain OUCMDZ-3118 with 5-hydroxy-L-tryptophan. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 potently induced apoptosis of gastric cancer cells by inhibiting topoisomerase IIα enzyme activity and reducing the expression of antiapoptosis protein level. Compound 3 displayed moderate cytotoxicity against the A549 and MCF-7 cell lines with IC50 values of 1.2 ± 0.05 µM, 1.6 ± 0.09 µM, respectively.",

keywords = "Cytotoxicities, Indolocarbazole, Marine-derived Streptomyces, Streptomyces sp. OUCMDZ-3118, Topoisomerase IIα enzyme activity",

author = "Cong Wang and Adeep Monger and Liping Wang and Peng Fu and Pawinee Piyachaturawat and Arthit Chairoungdua and Weiming Zhu",

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month = may,

doi = "10.3390/md16050168",

language = "English",

volume = "16",

journal = "Marine Drugs",

issn = "1660-3397",

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T1 - Precursor-directed generation of indolocarbazoles with topoisomerase IIα inhibitory activity

AU - Wang, Cong

AU - Monger, Adeep

AU - Wang, Liping

AU - Fu, Peng

AU - Piyachaturawat, Pawinee

AU - Chairoungdua, Arthit

AU - Zhu, Weiming

PY - 2018/5

Y1 - 2018/5

N2 - One new indolocarbazole, 3-hydroxy-K252d (3), together with the recently reported 3-hydroxyholyrine A (1) and 3-N-acetyl-3-hydroxyholyrine A (2), were obtained by feeding a culture of the marine-derived Streptomyces strain OUCMDZ-3118 with 5-hydroxy-L-tryptophan. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 potently induced apoptosis of gastric cancer cells by inhibiting topoisomerase IIα enzyme activity and reducing the expression of antiapoptosis protein level. Compound 3 displayed moderate cytotoxicity against the A549 and MCF-7 cell lines with IC50 values of 1.2 ± 0.05 µM, 1.6 ± 0.09 µM, respectively.

AB - One new indolocarbazole, 3-hydroxy-K252d (3), together with the recently reported 3-hydroxyholyrine A (1) and 3-N-acetyl-3-hydroxyholyrine A (2), were obtained by feeding a culture of the marine-derived Streptomyces strain OUCMDZ-3118 with 5-hydroxy-L-tryptophan. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 potently induced apoptosis of gastric cancer cells by inhibiting topoisomerase IIα enzyme activity and reducing the expression of antiapoptosis protein level. Compound 3 displayed moderate cytotoxicity against the A549 and MCF-7 cell lines with IC50 values of 1.2 ± 0.05 µM, 1.6 ± 0.09 µM, respectively.

KW - Cytotoxicities

KW - Indolocarbazole

KW - Marine-derived Streptomyces

KW - Streptomyces sp. OUCMDZ-3118

KW - Topoisomerase IIα enzyme activity

UR - http://www.scopus.com/inward/record.url?scp=85047176616&partnerID=8YFLogxK

U2 - 10.3390/md16050168

DO - 10.3390/md16050168

M3 - Article

C2 - 29772796

AN - SCOPUS:85047176616

SN - 1660-3397

VL - 16

JO - Marine Drugs

JF - Marine Drugs

IS - 5

M1 - 168

ER -

Precursor-directed generation of indolocarbazoles with topoisomerase IIα inhibitory activity

Abstract

Keywords

UN SDGs

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