Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

Jai Seo; Ekaruth Srisook; Jin Son Hyo; Onyou Hwang; Young Nam Cha; Yoon Chi Dae

doi:10.1016/j.bmcl.2005.05.033

Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

Jai Seo, Ekaruth Srisook, Jin Son Hyo, Onyou Hwang, Young Nam Cha, Yoon Chi Dae

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

10 Scopus citations

Abstract

Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH₄ synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH₄ production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH₄ production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH₄ production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH ₄-dependent dimerization of the newly synthesized iNOS monomer.

Original language	English (US)
Pages (from-to)	3369-3373
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	14
DOIs	https://doi.org/10.1016/j.bmcl.2005.05.033
State	Published - Jul 15 2005
Externally published	Yes

Keywords

Inhibition of NO
Inhibition of tetrahydrobiopterin
NAMDA
Nitric oxide
Nitric oxide synthase

ASJC Scopus subject areas

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

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title = "Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide",

abstract = "Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.",

keywords = "Inhibition of NO, Inhibition of tetrahydrobiopterin, NAMDA, Nitric oxide, Nitric oxide synthase",

author = "Jai Seo and Ekaruth Srisook and Hyo, {Jin Son} and Onyou Hwang and Cha, {Young Nam} and Dae, {Yoon Chi}",

year = "2005",

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doi = "10.1016/j.bmcl.2005.05.033",

language = "English (US)",

volume = "15",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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AU - Seo, Jai

AU - Srisook, Ekaruth

AU - Hyo, Jin Son

AU - Hwang, Onyou

AU - Cha, Young Nam

AU - Dae, Yoon Chi

PY - 2005/7/15

Y1 - 2005/7/15

N2 - Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.

AB - Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.

KW - Inhibition of NO

KW - Inhibition of tetrahydrobiopterin

KW - NAMDA

KW - Nitric oxide

KW - Nitric oxide synthase

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