Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

Sae Kwang Ku; Jee Hyun Lee; O. Yuseok; Wonhwa Lee; Gyu Yong Song; Jong Sup Bae

doi:10.1016/j.bmcl.2015.07.079

Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

Sae Kwang Ku
, Jee Hyun Lee
, O. Yuseok
, Wonhwa Lee
, Gyu Yong Song
, Jong Sup Bae

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

7 Scopus citations

Abstract

In this Letter, we investigated the barrier protective effects of 3-N-(MeO)_n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)₃-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.

Original language	English
Pages (from-to)	4304-4307
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2015.07.079
State	Published - 1 Oct 2015
Externally published	Yes

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

SDG 3 Good Health and Well-being

Keywords

3-N-Cinnamoyl carbazole
3-O-Cinnamoyl carbazole
HMGB1
Vascular barrier integrity

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10.1016/j.bmcl.2015.07.079

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title = "Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives",

abstract = "In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.",

keywords = "3-N-Cinnamoyl carbazole, 3-O-Cinnamoyl carbazole, HMGB1, Vascular barrier integrity",

author = "Ku, \{Sae Kwang\} and Lee, \{Jee Hyun\} and O. Yuseok and Wonhwa Lee and Song, \{Gyu Yong\} and Bae, \{Jong Sup\}",

year = "2015",

month = oct,

day = "1",

doi = "10.1016/j.bmcl.2015.07.079",

language = "English",

volume = "25",

pages = "4304--4307",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

AU - Ku, Sae Kwang

AU - Lee, Jee Hyun

AU - Yuseok, O.

AU - Lee, Wonhwa

AU - Song, Gyu Yong

AU - Bae, Jong Sup

PY - 2015/10/1

Y1 - 2015/10/1

N2 - In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.

AB - In this Letter, we investigated the barrier protective effects of 3-N-(MeO)n-cinnamoyl carbazoles (BS 1; n = 1, BS 2; n = 2, BS 3; n = 3) and 3-O-(MeO)3-cinnamoyl carbazole (BS 4) against high-mobility group box 1 (HMGB1)-mediated vascular disruptive responses in human umbilical vein endothelial cells (HUVECs) and in mice for the first time. Data showed that BS 2, BS 3, and BS 4, but not BS 1, inhibited HMGB1-mediated vascular disruptive responses and transendothelial migration of human neutrophils to HUVECs. BS 2, BS3, and BS 4 also suppressed HMGB1-induced hyperpermeability and leukocyte migration in mice. Interestingly, the barrier protective effects of BS 3 and BS 4 were better than those of BS 2. These results suggest that the number of methoxy groups substituted on the cinnamamide or cinnamate moiety of the 9H-3-carbazole derivative is an important pharmacophore for the barrier protective effects of these compounds.

KW - 3-N-Cinnamoyl carbazole

KW - 3-O-Cinnamoyl carbazole

KW - HMGB1

KW - Vascular barrier integrity

UR - https://www.scopus.com/pages/publications/84945485815

U2 - 10.1016/j.bmcl.2015.07.079

DO - 10.1016/j.bmcl.2015.07.079

M3 - Article

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AN - SCOPUS:84945485815

SN - 0960-894X

VL - 25

SP - 4304

EP - 4307

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Vascular barrier protective effects of 3-N- or 3-O-cinnamoyl carbazole derivatives

Abstract

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Keywords

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