scholarly journals Modification of N-terminal α-amine of proteins via biomimetic ortho-quinone-mediated oxidation

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Siyao Wang ◽  
Qingqing Zhou ◽  
Xiaoping Chen ◽  
Rong-Hua Luo ◽  
Yunxue Li ◽  
...  

AbstractNaturally abundant quinones are important molecules, which play essential roles in various biological processes due to their reduction potential. In contrast to their universality, the investigation of reactions between quinones and proteins remains sparse. Herein, we report the development of a convenient strategy to protein modification via a biomimetic quinone-mediated oxidation at the N-terminus. By exploiting unique reactivity of an ortho-quinone reagent, the α-amine of protein N-terminus is oxidized to generate aldo or keto handle for orthogonal conjugation. The applications have been demonstrated using a range of proteins, including myoglobin, ubiquitin and small ubiquitin-related modifier 2 (SUMO2). The effect of this method is further highlighted via the preparation of a series of 17 macrophage inflammatory protein 1β (MIP-1β) analogs, followed by preliminary anti-HIV activity and cell viability assays, respectively. This method offers an efficient and complementary approach to existing strategies for N-terminal modification of proteins.

2020 ◽  
Author(s):  
Ping Wang ◽  
Siyao Wang ◽  
Qingqing Zhou ◽  
Yunxue Li ◽  
Xiaoping Chen ◽  
...  

Abstract Naturally abundant quinones are important molecules, which play essential roles in various biological processes due to their reduction potential. In contrast to their universality, the reactions between quinones and proteins remain sparse. Herein, we report the development of unprecedented strategy to protein modification via a biomimetic quinone-mediated oxidation at the N-terminus. By exploiting unique reactivity of an ortho-quinone reagent, the α-amine of protein N-terminus was oxidized to generate aldo or keto handle for orthogonal conjugation. Its applications have been demonstrated using a range of proteins, including myoglobin and ubiquitin. The effect of this method was further highlighted via the preparation of a series of 17 MIP-1β analogs, followed by preliminary anti-HIV activity and cell viability assays, respectively. This method offers a fast, efficient and complementary approach to existing strategies for protein N-terminus modification.


2003 ◽  
Vol 123 (1) ◽  
pp. 106-109 ◽  
Author(s):  
Evangelos Terpos ◽  
Marianna Politou ◽  
Richard Szydlo ◽  
John M. Goldman ◽  
Jane F. Apperley ◽  
...  

2000 ◽  
Vol 193 (1) ◽  
pp. 35-50 ◽  
Author(s):  
Hiroyuki Yoneyama ◽  
Kenjiro Matsuno ◽  
Yanyun Zhang ◽  
Masako Murai ◽  
Meiji Itakura ◽  
...  

We have studied the recruitment and roles of distinct dendritic cell (DC) precursors from the circulation into Propionibacterium acnes–induced granulomas in mouse liver. During infection, F4/80−B220−CD11c+ DC precursors appeared in the circulation, migrated into the perisinusoidal space, and matured within newly formed granulomas. Recruited DCs later migrated to the portal area to interact with T cells in what we term “portal tract–associated lymphoid tissue” (PALT). Macrophage inflammatory protein 1α attracted blood DC precursors to the sinusoidal granuloma, whereas secondary lymphoid organ chemokine (SLC) attracted mature DCs to the newly identified PALT. Anti-SLC antibody diminished PALT expansion while exacerbating granuloma formation. Therefore, circulating DC precursors can migrate into a solid organ like liver, and participate in the granulomatous reaction in response to specific chemokines.


2002 ◽  
Vol 185 (1) ◽  
pp. 123-126 ◽  
Author(s):  
Anita W. Rijneveld ◽  
Germie P. van den Dobbelsteen ◽  
Sandrine Florquin ◽  
Theodore J. Standiford ◽  
Peter Speelman ◽  
...  

2004 ◽  
Vol 13 (3) ◽  
pp. 205-207 ◽  
Author(s):  
Rosaria Alba Merendino ◽  
Giuseppe Di Pasquale ◽  
Filippo De Luca ◽  
Laura Di Pasquale ◽  
Edoardo Ferlazzo ◽  
...  

MODERATE-severe depression (MSD) is linked to overexpression of proinflammatory cytokines and chemokines. Fractalkine (FKN) and macrophage inflammatory protein-1 alpha (MIP-1α) are, respectively, members of CX3C and C-C chemokines, and both are involved in recruiting and activating mononuclear phagocytes in the central nervous system. We analysed the presence of FKN and MIP-1α in sera of untreated MSD patients and healthy donors. High FKN levels were observed in all MSD patients as compared with values only detectable in 26% of healthy donors. MIP-1α was measurable in 20% of patients, while no healthy donors showed detectable chemokine levels. In conclusion, we describe a previously unknown involvement of FKN in the pathogenesis of MSD, suggesting that FKN may represent a target for a specific immune therapy of this disease.


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