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Article ; Online: Cell surface expression of human RP105 depends on N-glycosylation of MD-1.

Biswas, Mrityunjoy / Yamazaki, Tatsuya / Tomono, Susumu / Karnan, Sivasundaram / Takagi, Hidekazu / Ichimonji, Isao / Inui, Masanori / Nagaoka, Fumiaki / Hosokawa, Yoshitaka / Akashi-Takamura, Sachiko

FEBS letters

2022

Abstract: ... its two N-glycosylation sites, N96 and N156. Cell surface expression of RP105 decreased in the presence ... but not pre-expressed RP105. Thus, the N-glycans of MD-1 may represent targets for SLE therapy. ...

Abstract	For its cell surface expression, radioprotective 105 (RP105) - an orphan Toll-like receptor - must form a complex with a soluble glycoprotein called myeloid differentiation 1 (MD-1). The number of RP105-negative cells is significantly increased in patients with systemic lupus erythematosus (SLE); however, to elucidate the mechanism underlying this increase, how RP105 is expressed on the cell surface depending on MD-1 should be investigated. We demonstrated that RP105 exhibits two forms depending on MD-1 and its two N-glycosylation sites, N96 and N156. Cell surface expression of RP105 decreased in the presence of mutant MD-1 (N96Q/N156Q). Nonglycosylated MD-1 decreased the de novo cell surface expression of RP105 but not pre-expressed RP105. Thus, the N-glycans of MD-1 may represent targets for SLE therapy.
Language	English
Publishing date	2022-07-18
Publishing country	England
Document type	Journal Article
ZDB-ID	212746-5
ISSN	1873-3468 ; 0014-5793
ISSN (online)	1873-3468
ISSN	0014-5793
DOI	10.1002/1873-3468.14452
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Article ; Online: ANKRD22 is an N-myristoylated hairpin-like monotopic membrane protein specifically localized to lipid droplets.

Utsumi, Toshihiko / Hosokawa, Takuro / Shichita, Mayu / Nishiue, Misato / Iwamoto, Natsuko / Harada, Haruna / Kiwado, Aya / Yano, Manami / Otsuka, Motoaki / Moriya, Koko

Scientific reports

2021 Volume 11, Issue 1, Page(s) 19233

Abstract: The membrane topology and intracellular localization of ANKRD22, a novel human N-myristoylated ... tumor necrosis factor (GLCTNF) and assessment of their susceptibility to protein N-glycosylation revealed that ANKRD22 ... is synthesized on the endoplasmic reticulum (ER) membrane as an N-myristoylated hairpin-like ...

Abstract	The membrane topology and intracellular localization of ANKRD22, a novel human N-myristoylated protein with a predicted single-pass transmembrane domain that was recently reported to be overexpressed in cancer, were examined. Immunofluorescence staining of COS-1 cells transfected with cDNA encoding ANKRD22 coupled with organelle markers revealed that ANKRD22 localized specifically to lipid droplets (LD). Analysis of the intracellular localization of ANKRD22 mutants C-terminally fused to glycosylatable tumor necrosis factor (GLCTNF) and assessment of their susceptibility to protein N-glycosylation revealed that ANKRD22 is synthesized on the endoplasmic reticulum (ER) membrane as an N-myristoylated hairpin-like monotopic membrane protein with the amino- and carboxyl termini facing the cytoplasm and then sorted to LD. Pro98 located at the center of the predicted membrane domain was found to be essential for the formation of the hairpin-like monotopic topology of ANKRD22. Moreover, the hairpin-like monotopic topology, and positively charged residues located near the C-terminus were demonstrated to be required for the sorting of ANKRD22 from ER to LD. Protein N-myristoylation was found to positively affect the LD localization. Thus, multiple factors, including hairpin-like monotopic membrane topology, C-terminal positively charged residues, and protein N-myristoylation cooperatively affected the intracellular targeting of ANKRD22 to LD.
MeSH term(s)	Animals ; COS Cells ; Cell-Free System ; Chlorocebus aethiops ; Humans ; Insecta ; Lipid Droplets/metabolism ; Membrane Proteins/chemistry ; Membrane Proteins/genetics ; Membrane Proteins/metabolism ; Mutation ; Myristic Acid/metabolism ; Protein Processing, Post-Translational
Chemical Substances	ANKRD22 protein, human ; Membrane Proteins ; Myristic Acid (0I3V7S25AW)
Language	English
Publishing date	2021-09-28
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2615211-3
ISSN	2045-2322 ; 2045-2322
ISSN (online)	2045-2322
ISSN	2045-2322
DOI	10.1038/s41598-021-98486-8
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Article ; Online: Associations of plasma aprepitant and its N-dealkylated metabolite with cachexia status and clinical responses in head and neck cancer patients.

Suzuki, Yusuke / Naito, Takafumi / Shibata, Kaito / Hosokawa, Seiji / Kawakami, Junichi

Cancer chemotherapy and pharmacology

2023 Volume 91, Issue 6, Page(s) 481–490

Abstract: ... cancer. This study aimed to characterize plasma aprepitant and its N-dealkylated metabolite (ND-AP) based ...

Abstract	Purpose: Oral aprepitant has a large interindividual variation in clinical responses in advanced cancer. This study aimed to characterize plasma aprepitant and its N-dealkylated metabolite (ND-AP) based on the cachexia status and clinical responses in head and neck cancer patients. Methods: Fifty-three head and neck cancer patients receiving cisplatin-based chemotherapy with oral aprepitant were enrolled. Plasma concentrations of total and free aprepitant and ND-AP were determined at 24 h after a 3-day aprepitant treatment. The clinical responses to aprepitant and degrees of cachexia status were assessed using a questionnaire and Glasgow Prognostic Score (GPS). Results: Serum albumin level was negatively correlated with the plasma concentrations of total and free aprepitant but not ND-AP. The serum albumin level had a negative correlation with the metabolic ratio of aprepitant. The patients with GPS 1 or 2 had higher plasma concentrations of total and free aprepitant than those with GPS 0. No difference was observed in the plasma concentration of ND-AP between the GPS classifications. The plasma interleukin-6 level was higher in patients with GPS 1 or 2 than 0. The absolute plasma concentration of free ND-AP was higher in patients without the delayed nausea, and its concentration to determine the occurrence was 18.9 ng/mL. The occurrence of delayed nausea had no relation with absolute plasma aprepitant. Conclusion: Cancer patients with a lower serum albumin and progressive cachectic condition had a higher plasma aprepitant level. In contrast, plasma free ND-AP but not aprepitant was related to the antiemetic efficacy of oral aprepitant.
MeSH term(s)	Humans ; Aprepitant ; Vomiting/drug therapy ; Cachexia/drug therapy ; Cachexia/etiology ; Morpholines ; Antiemetics ; Nausea/drug therapy ; Cisplatin ; Head and Neck Neoplasms/complications ; Head and Neck Neoplasms/drug therapy ; Dexamethasone ; Antineoplastic Agents/adverse effects
Chemical Substances	Aprepitant (1NF15YR6UY) ; Morpholines ; Antiemetics ; Cisplatin (Q20Q21Q62J) ; Dexamethasone (7S5I7G3JQL) ; Antineoplastic Agents
Language	English
Publishing date	2023-05-04
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	6820-2
ISSN	1432-0843 ; 0344-5704 ; 0943-9404
ISSN (online)	1432-0843
ISSN	0344-5704 ; 0943-9404
DOI	10.1007/s00280-023-04537-4
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Article ; Online: Cell surface expression of human RP105 depends on N‐glycosylation of MD‐1

FEBS Letters. 2022 Dec., v. 596, no. 24 p.3211-3231

2022

Abstract: ... its two N‐glycosylation sites, N96 and N156. Cell surface expression of RP105 decreased in the presence ... but not pre‐expressed RP105. Thus, the N‐glycans of MD‐1 may represent targets for SLE therapy. ...

Abstract	For its cell surface expression, radioprotective 105 (RP105) – an orphan Toll‐like receptor – must form a complex with a soluble glycoprotein called myeloid differentiation 1 (MD‐1). The number of RP105‐negative cells is significantly increased in patients with systemic lupus erythematosus (SLE); however, to elucidate the mechanism underlying this increase, how RP105 is expressed on the cell surface depending on MD‐1 should be investigated. We demonstrated that RP105 exhibits two forms depending on MD‐1 and its two N‐glycosylation sites, N96 and N156. Cell surface expression of RP105 decreased in the presence of mutant MD‐1 (N96Q/N156Q). Nonglycosylated MD‐1 decreased the de novo cell surface expression of RP105 but not pre‐expressed RP105. Thus, the N‐glycans of MD‐1 may represent targets for SLE therapy.
Keywords	Toll-like receptors ; glycoproteins ; glycosylation ; humans ; lupus erythematosus ; mutants ; therapeutics
Language	English
Dates of publication	2022-12
Size	p. 3211-3231.
Publishing place	John Wiley & Sons, Ltd
Document type	Article ; Online
Note	JOURNAL ARTICLE
ZDB-ID	212746-5
ISSN	1873-3468 ; 0014-5793
ISSN (online)	1873-3468
ISSN	0014-5793
DOI	10.1002/1873-3468.14452
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis of the C1–C17 Segment of Bafilomycin N

Sato, Haruka / Hosokawa, Seijiro

Synlett

2019 Volume 30, Issue 05, Page(s) 577–580

Abstract: The C1–C17 segment of bafilomycin N has been synthesized. The C1–C11 segment was synthesized ... by the anti -selective vinylogous Mukaiyama aldol reaction with a chiral vinylketene silyl N O -acetal and ...

Abstract	The C1–C17 segment of bafilomycin N has been synthesized. The C1–C11 segment was synthesized by the anti -selective vinylogous Mukaiyama aldol reaction with a chiral vinylketene silyl N O -acetal and the Horner–Wadsworth–Emmons reaction, whereas C12–C17 was constructed by the syn -selective vinylogous Mukaiyama aldol reaction and the Jung’s semipinacol rearrangement. Those segments were connected by the Stille coupling to afford the C1–C17 segment.
Keywords	bafilomycin ; vinylogous Mukaiyama aldol reaction ; vinylketene silyl ; , ; -acetal ; polypropionate ; semipinacol rearrangement ; Stille coupling
Language	English
Publishing date	2019-02-21
Publisher	© Georg Thieme Verlag
Publishing place	Stuttgart ; New York
Document type	Article
ZDB-ID	2042012-2
ISSN	1437-2096 ; 0936-5214
ISSN (online)	1437-2096
ISSN	0936-5214
DOI	10.1055/s-0037-1611727
Database	Thieme publisher's database

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Article ; Online: Remote Asymmetric Induction Using Acetate-Type Vinylketene Silyl N,O-Acetals.

Sagawa, Naoya / Sato, Haruka / Hosokawa, Seijiro

Organic letters

2017 Volume 19, Issue 1, Page(s) 198–201

Abstract: ... vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived ...

Abstract	Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and l-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl
Language	English
Publishing date	2017-01-06
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.6b03476
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Article ; Online: Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals.

Sagawa, Naoya / Moriya, Hiroki / Hosokawa, Seijiro

Organic letters

2017 Volume 19, Issue 1, Page(s) 250–253

Abstract: Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal ...

Abstract	Stereoselective vinylogous Mukaiyama aldol reactions using the Z,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary, derived from (E)-3-pentenoic acid and l-valine, have been achieved. The reaction proceeded smoothly to give a syn adduct in high stereoselectivity. Since the products possess structures including δ-alkoxy-γ-methyl-α,β-unsaturated imide, this reaction would be applicable to synthesize polyketides in a short procedure.
Language	English
Publishing date	2017-01-06
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.6b03549
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Article ; Online: Gomisin N Decreases Inflammatory Cytokine Production in Human Periodontal Ligament Cells.

Hosokawa, Yoshitaka / Hosokawa, Ikuko / Shindo, Satoru / Ozaki, Kazumi / Matsuo, Takashi

Inflammation

2017 Volume 40, Issue 2, Page(s) 360–365

Abstract: Gomisin N, which is a lignan isolated from Schisandra chinensis, has some pharmacological effects ... However, the anti-inflammatory effects of gomisin N on periodontal disease are uncertain. The aim of this study was to examine ... the effect of gomisin N on inflammatory mediator production in tumor necrosis factor (TNF)-α-stimulated human ...

Abstract	Gomisin N, which is a lignan isolated from Schisandra chinensis, has some pharmacological effects. However, the anti-inflammatory effects of gomisin N on periodontal disease are uncertain. The aim of this study was to examine the effect of gomisin N on inflammatory mediator production in tumor necrosis factor (TNF)-α-stimulated human periodontal ligament cells (HPDLC). Gomisin N inhibited interleukin (IL)-6, IL-8, CC chemokine ligand (CCL) 2, and CCL20 production in TNF-α-stimulated HPDLC in a dose-dependent manner. Moreover, we revealed that gomisin N could suppress extracellular signal-regulated kinase (ERK) and c-Jun N terminal kinase (JNK) phosphorylation in TNF-α-stimulated HPDLC though protein kinase B (Akt) phosphorylation was not suppressed by gomisin N treatment. In summary, gomisin N might exert anti-inflammatory effects by attenuating cytokine production in periodontal ligament cells via inhibiting the TNF-α-stimulated ERK and JNK pathways activation.
MeSH term(s)	Anti-Inflammatory Agents/pharmacology ; Cells, Cultured ; Cyclooctanes/pharmacology ; Cytokines/antagonists & inhibitors ; Cytokines/biosynthesis ; Dose-Response Relationship, Drug ; Humans ; Inflammation Mediators ; Lignans/pharmacology ; MAP Kinase Signaling System/drug effects ; Periodontal Ligament/cytology ; Periodontal Ligament/drug effects ; Periodontal Ligament/metabolism ; Phosphorylation/drug effects ; Polycyclic Compounds/pharmacology ; Tumor Necrosis Factor-alpha
Chemical Substances	Anti-Inflammatory Agents ; Cyclooctanes ; Cytokines ; Inflammation Mediators ; Lignans ; Polycyclic Compounds ; Tumor Necrosis Factor-alpha ; schizandrin B (02XA4X3KZW)
Language	English
Publishing date	2017-04
Publishing country	United States
Document type	Journal Article
ZDB-ID	434408-x
ISSN	1573-2576 ; 0360-3997
ISSN (online)	1573-2576
ISSN	0360-3997
DOI	10.1007/s10753-016-0482-4
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Article ; Online: Remote Asymmetric Induction Reactions using a E, E-Vinylketene Silyl N, O-Acetal and the Wide Range Stereocontrol Strategy for the Synthesis of Polypropionates.

Hosokawa, Seijiro

Accounts of chemical research

2018 Volume 51, Issue 5, Page(s) 1301–1314

Abstract: ... silyl N, O-acetal 1, which is commensurate to an anti-selective vinylogous Mukaiyama aldol reaction ... asymmetric induction reaction based on the E, E-vinylketene N, O-acetal 1, which includes syn-selective ...

Abstract	The construction of libraries of acyclic polyketides remains a challenging topic, mostly due to the difficulties associated with finding the right balance between diversity and brevity for the synthetic routes leading to polyketides. Recently, relatively short methods have been developed and applied to the synthesis of natural products. However, these short routes often suffer from limited diversity with respect to the arrangement of functional groups and stereochemistry, as these usually require reactions that direct multiple functional groups simultaneously in one step. Therefore, methods that combine a small number of reaction steps with structural diversity remain an attractive research target for the construction of acyclic polyketide libraries. In 2004, we reported a remote asymmetric induction reaction using chiral vinylketene silyl N, O-acetal 1, which is commensurate to an anti-selective vinylogous Mukaiyama aldol reaction. Ever since, this reaction has been applied to the synthesis of numerous natural products, as this synthetic route is short and efficient on account of the simultaneous introduction of both asymmetric centers and the multiply functionalized carbon chain. Recently, we have developed a variety of this remote asymmetric induction reaction based on the E, E-vinylketene N, O-acetal 1, which includes syn-selective vinylogous Mukaiyama aldol reactions, as well as alkylation, acylation, and bromination reaction. These reactions provide polypropionates in a highly stereoselective manner. The proposed transition states of these reactions are discussed in this Account. Additionally, we have developed a new short synthesis of polypropionates by combining reactions for the remote asymmetric induction and the functionalization of double bonds (wide-range stereocontrol, WRS). The remote asymmetric induction reaction simultaneously constructs the stereogenic centers at the central part of the products and introduces the α,β-unsaturated imide, while the new strategy is based on the initial construction of the central part of the molecule and a subsequent functionalization of the surroundings (WRS). This strategy successfully furnished stereoisomers in a few steps, and the stereodivergent synthesis of 2,4,6-trimethyloctanoic acid derivatives was accomplished. This strategy should also be feasible to construct an acyclic polyketide library. Moreover, we applied this method to the concise synthesis of natural products. In this Account, the development of remote asymmetric induction reactions and the new WRS strategy are described. Applications of the WRS strategy as well as reactions for the stereodivergent synthesis of polypropionates and natural products are also described. The aforementioned acyclic polyketide library should be constructed in the future with the help of the WRS strategy and become a powerful tool in drug discovery.
Language	English
Publishing date	2018-05-04
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1483291-4
ISSN	1520-4898 ; 0001-4842
ISSN (online)	1520-4898
ISSN	0001-4842
DOI	10.1021/acs.accounts.8b00125
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Article ; Online: Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost.

Iwamoto, Takahiro / Hosokawa, Atsushi / Nakamura, Masaharu

Chemical communications (Cambridge, England)

2019 Volume 55, Issue 78, Page(s) 11683–11686

Abstract: ... we demonstrate that such an endergonic reaction can be promoted with light-energy as a driving force; N ...

Abstract	Intermolecular addition reactions are generally accompanied by an entropic penalty due to the decrease of molecular numbers during the reaction, which sometimes makes the reaction endergonic. Here we demonstrate that such an endergonic reaction can be promoted with light-energy as a driving force; N-methylamines were added to aromatic ketones to produce aminoalcohols under UV-light irradiation. The reaction represents an obvious example showing that the photochemical approach is effective to offset such an entropic cost, and thereby to drive thermodynamically uphill addition reactions. Moreover the present reactions are highly expedient from the synthetic view point, being transition-metal-catalyst-free, scalable, highly atom economical, and regioselective. The product amines can be converted in one step to functional multi-arylated enamines, which are potentially valuable compounds in electronic materials.
Language	English
Publishing date	2019-09-12
Publishing country	England
Document type	Journal Article
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/c9cc06011a
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