Loading…

Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity

Intracellular delivery is crucial not only in achieving effective oligonucleotide therapeutics but also for a wide variety of therapeutic strategies. In this study to elucidate the effects of the number of incorporated arginine residues on cell membrane permeability, we designed a series of peptide...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry letters 2018-03, Vol.47 (3), p.381-384
Main Authors: Sugai, Hiroka, Nakase, Ikuhiko, Sakamoto, Seiji, Nishio, Akihiro, Inagaki, Masahito, Nishijima, Masaki, Yamayoshi, Asako, Araki, Yasuyuki, Ishibashi, Satoru, Yokota, Takanori, Inoue, Yoshihisa, Wada, Takehiko
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3
cites cdi_FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3
container_end_page 384
container_issue 3
container_start_page 381
container_title Chemistry letters
container_volume 47
creator Sugai, Hiroka
Nakase, Ikuhiko
Sakamoto, Seiji
Nishio, Akihiro
Inagaki, Masahito
Nishijima, Masaki
Yamayoshi, Asako
Araki, Yasuyuki
Ishibashi, Satoru
Yokota, Takanori
Inoue, Yoshihisa
Wada, Takehiko
description Intracellular delivery is crucial not only in achieving effective oligonucleotide therapeutics but also for a wide variety of therapeutic strategies. In this study to elucidate the effects of the number of incorporated arginine residues on cell membrane permeability, we designed a series of peptide ribonucleic acids (PRNAs) that alternatingly incorporated 4, 8, or 12 arginine residues (PRR1-3) in the PRNA backbone for experimental verifications. Indeed, the cellular uptake efficiency and the aggregation properties turned out to be critical functions of the number of incorporated arginine residues. Thus, the optimized PRR2 that incorporates 8 arginines showed the most efficient cellular uptake ability, much higher than that of octaarginine, without accompanying cytotoxicity or aggregation.
doi_str_mv 10.1246/cl.171186
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2241365969</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2241365969</sourcerecordid><originalsourceid>FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3</originalsourceid><addsrcrecordid>eNplkc1u1DAURi0EEkNhwRtYYkOlZojt_NjLMCq0UgXViK4jx74Onrp2sB2J7HgHXoOn6pM01VSwYHUX99xz9elD6C0pt4RWzQfltqQlhDfP0IawihdlS-rnaFOypinaktKX6FVKh7IsuWB0g_5cw5StBry3Q_CzcmAV7pTV-P31_kt3ev_rdxdH660HfLEM0eq0xefGgMoJB4P_LveQrJ4h4c5liF5m60e34EufY9CzAo1zwI9K_FGq2_UX4OBxN44RxhUO_gzvwLnZyYhvpixv4QxLr_FuySGHn1bZvLxGL4x0Cd48zRN08-n82-6iuPr6-XLXXRWqIlUudA2i1UNpuODc1KRmwBhUAx0aJQSVTEsiKZeaaN4OghimmKoqKkytgQ-KnaB3R-8Uw481U-4PYV4zudRTWhHW1KIRK3V6pFQMKUUw_RTtnYxLT8r-sYxeuf5Yxso2T-x3uLNqNQVlIS8HOUn_z_7_4QPHDJIY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2241365969</pqid></control><display><type>article</type><title>Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity</title><source>Oxford Journals Online</source><creator>Sugai, Hiroka ; Nakase, Ikuhiko ; Sakamoto, Seiji ; Nishio, Akihiro ; Inagaki, Masahito ; Nishijima, Masaki ; Yamayoshi, Asako ; Araki, Yasuyuki ; Ishibashi, Satoru ; Yokota, Takanori ; Inoue, Yoshihisa ; Wada, Takehiko</creator><creatorcontrib>Sugai, Hiroka ; Nakase, Ikuhiko ; Sakamoto, Seiji ; Nishio, Akihiro ; Inagaki, Masahito ; Nishijima, Masaki ; Yamayoshi, Asako ; Araki, Yasuyuki ; Ishibashi, Satoru ; Yokota, Takanori ; Inoue, Yoshihisa ; Wada, Takehiko</creatorcontrib><description>Intracellular delivery is crucial not only in achieving effective oligonucleotide therapeutics but also for a wide variety of therapeutic strategies. In this study to elucidate the effects of the number of incorporated arginine residues on cell membrane permeability, we designed a series of peptide ribonucleic acids (PRNAs) that alternatingly incorporated 4, 8, or 12 arginine residues (PRR1-3) in the PRNA backbone for experimental verifications. Indeed, the cellular uptake efficiency and the aggregation properties turned out to be critical functions of the number of incorporated arginine residues. Thus, the optimized PRR2 that incorporates 8 arginines showed the most efficient cellular uptake ability, much higher than that of octaarginine, without accompanying cytotoxicity or aggregation.</description><identifier>ISSN: 0366-7022</identifier><identifier>EISSN: 1348-0715</identifier><identifier>DOI: 10.1246/cl.171186</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><subject>Agglomeration ; Backbone ; Cell membranes ; Cytotoxicity ; Peptides ; Residues ; Ribonucleic acid ; RNA ; Toxicity</subject><ispartof>Chemistry letters, 2018-03, Vol.47 (3), p.381-384</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Chemical Society of Japan 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3</citedby><cites>FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Sugai, Hiroka</creatorcontrib><creatorcontrib>Nakase, Ikuhiko</creatorcontrib><creatorcontrib>Sakamoto, Seiji</creatorcontrib><creatorcontrib>Nishio, Akihiro</creatorcontrib><creatorcontrib>Inagaki, Masahito</creatorcontrib><creatorcontrib>Nishijima, Masaki</creatorcontrib><creatorcontrib>Yamayoshi, Asako</creatorcontrib><creatorcontrib>Araki, Yasuyuki</creatorcontrib><creatorcontrib>Ishibashi, Satoru</creatorcontrib><creatorcontrib>Yokota, Takanori</creatorcontrib><creatorcontrib>Inoue, Yoshihisa</creatorcontrib><creatorcontrib>Wada, Takehiko</creatorcontrib><title>Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity</title><title>Chemistry letters</title><description>Intracellular delivery is crucial not only in achieving effective oligonucleotide therapeutics but also for a wide variety of therapeutic strategies. In this study to elucidate the effects of the number of incorporated arginine residues on cell membrane permeability, we designed a series of peptide ribonucleic acids (PRNAs) that alternatingly incorporated 4, 8, or 12 arginine residues (PRR1-3) in the PRNA backbone for experimental verifications. Indeed, the cellular uptake efficiency and the aggregation properties turned out to be critical functions of the number of incorporated arginine residues. Thus, the optimized PRR2 that incorporates 8 arginines showed the most efficient cellular uptake ability, much higher than that of octaarginine, without accompanying cytotoxicity or aggregation.</description><subject>Agglomeration</subject><subject>Backbone</subject><subject>Cell membranes</subject><subject>Cytotoxicity</subject><subject>Peptides</subject><subject>Residues</subject><subject>Ribonucleic acid</subject><subject>RNA</subject><subject>Toxicity</subject><issn>0366-7022</issn><issn>1348-0715</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNplkc1u1DAURi0EEkNhwRtYYkOlZojt_NjLMCq0UgXViK4jx74Onrp2sB2J7HgHXoOn6pM01VSwYHUX99xz9elD6C0pt4RWzQfltqQlhDfP0IawihdlS-rnaFOypinaktKX6FVKh7IsuWB0g_5cw5StBry3Q_CzcmAV7pTV-P31_kt3ev_rdxdH660HfLEM0eq0xefGgMoJB4P_LveQrJ4h4c5liF5m60e34EufY9CzAo1zwI9K_FGq2_UX4OBxN44RxhUO_gzvwLnZyYhvpixv4QxLr_FuySGHn1bZvLxGL4x0Cd48zRN08-n82-6iuPr6-XLXXRWqIlUudA2i1UNpuODc1KRmwBhUAx0aJQSVTEsiKZeaaN4OghimmKoqKkytgQ-KnaB3R-8Uw481U-4PYV4zudRTWhHW1KIRK3V6pFQMKUUw_RTtnYxLT8r-sYxeuf5Yxso2T-x3uLNqNQVlIS8HOUn_z_7_4QPHDJIY</recordid><startdate>20180305</startdate><enddate>20180305</enddate><creator>Sugai, Hiroka</creator><creator>Nakase, Ikuhiko</creator><creator>Sakamoto, Seiji</creator><creator>Nishio, Akihiro</creator><creator>Inagaki, Masahito</creator><creator>Nishijima, Masaki</creator><creator>Yamayoshi, Asako</creator><creator>Araki, Yasuyuki</creator><creator>Ishibashi, Satoru</creator><creator>Yokota, Takanori</creator><creator>Inoue, Yoshihisa</creator><creator>Wada, Takehiko</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20180305</creationdate><title>Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity</title><author>Sugai, Hiroka ; Nakase, Ikuhiko ; Sakamoto, Seiji ; Nishio, Akihiro ; Inagaki, Masahito ; Nishijima, Masaki ; Yamayoshi, Asako ; Araki, Yasuyuki ; Ishibashi, Satoru ; Yokota, Takanori ; Inoue, Yoshihisa ; Wada, Takehiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Agglomeration</topic><topic>Backbone</topic><topic>Cell membranes</topic><topic>Cytotoxicity</topic><topic>Peptides</topic><topic>Residues</topic><topic>Ribonucleic acid</topic><topic>RNA</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sugai, Hiroka</creatorcontrib><creatorcontrib>Nakase, Ikuhiko</creatorcontrib><creatorcontrib>Sakamoto, Seiji</creatorcontrib><creatorcontrib>Nishio, Akihiro</creatorcontrib><creatorcontrib>Inagaki, Masahito</creatorcontrib><creatorcontrib>Nishijima, Masaki</creatorcontrib><creatorcontrib>Yamayoshi, Asako</creatorcontrib><creatorcontrib>Araki, Yasuyuki</creatorcontrib><creatorcontrib>Ishibashi, Satoru</creatorcontrib><creatorcontrib>Yokota, Takanori</creatorcontrib><creatorcontrib>Inoue, Yoshihisa</creatorcontrib><creatorcontrib>Wada, Takehiko</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sugai, Hiroka</au><au>Nakase, Ikuhiko</au><au>Sakamoto, Seiji</au><au>Nishio, Akihiro</au><au>Inagaki, Masahito</au><au>Nishijima, Masaki</au><au>Yamayoshi, Asako</au><au>Araki, Yasuyuki</au><au>Ishibashi, Satoru</au><au>Yokota, Takanori</au><au>Inoue, Yoshihisa</au><au>Wada, Takehiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity</atitle><jtitle>Chemistry letters</jtitle><date>2018-03-05</date><risdate>2018</risdate><volume>47</volume><issue>3</issue><spage>381</spage><epage>384</epage><pages>381-384</pages><issn>0366-7022</issn><eissn>1348-0715</eissn><abstract>Intracellular delivery is crucial not only in achieving effective oligonucleotide therapeutics but also for a wide variety of therapeutic strategies. In this study to elucidate the effects of the number of incorporated arginine residues on cell membrane permeability, we designed a series of peptide ribonucleic acids (PRNAs) that alternatingly incorporated 4, 8, or 12 arginine residues (PRR1-3) in the PRNA backbone for experimental verifications. Indeed, the cellular uptake efficiency and the aggregation properties turned out to be critical functions of the number of incorporated arginine residues. Thus, the optimized PRR2 that incorporates 8 arginines showed the most efficient cellular uptake ability, much higher than that of octaarginine, without accompanying cytotoxicity or aggregation.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/cl.171186</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0366-7022
ispartof Chemistry letters, 2018-03, Vol.47 (3), p.381-384
issn 0366-7022
1348-0715
language eng
recordid cdi_proquest_journals_2241365969
source Oxford Journals Online
subjects Agglomeration
Backbone
Cell membranes
Cytotoxicity
Peptides
Residues
Ribonucleic acid
RNA
Toxicity
title Peptide Ribonucleic Acid (PRNA)–Arginine Hybrids. Effects of Arginine Residues Alternatingly Introduced to PRNA Backbone on Aggregation, Cellular Uptake, and Cytotoxicity
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T20%3A09%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Peptide%20Ribonucleic%20Acid%20(PRNA)%E2%80%93Arginine%20Hybrids.%20Effects%20of%20Arginine%20Residues%20Alternatingly%20Introduced%20to%20PRNA%20Backbone%20on%20Aggregation,%20Cellular%20Uptake,%20and%20Cytotoxicity&rft.jtitle=Chemistry%20letters&rft.au=Sugai,%20Hiroka&rft.date=2018-03-05&rft.volume=47&rft.issue=3&rft.spage=381&rft.epage=384&rft.pages=381-384&rft.issn=0366-7022&rft.eissn=1348-0715&rft_id=info:doi/10.1246/cl.171186&rft_dat=%3Cproquest_cross%3E2241365969%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c414t-d5e97db0f8988f5153e33e4b2b6c992a3da1a28ad1d87b91f3c3c4429f5de8bc3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2241365969&rft_id=info:pmid/&rfr_iscdi=true