4.7 Article

Cell permeability of Py-Im-polyamide-fluorescein conjugates: Influence of molecular size and Py/Im content

期刊

BIOORGANIC & MEDICINAL CHEMISTRY
卷 18, 期 2, 页码 978-983

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.07.018

关键词

Polyamide; DNA binder; Flow cytometry; Cell permeability

资金

  1. Ministry of Education, Culture, Sports, Science, and Technology, Japan
  2. Academia Showcase for Japan Chemical Innovation Institute
  3. JST
  4. CREST

向作者/读者索取更多资源

In order to investigate the influence of molecular size and pyrrole (Py)/imidazole (Im) content on the cell permeability of Py-Im-polyamide-fluorescein conjugates we systematically designed the Py-polyamides and Im-polyamides. Flow cytometric analysis revealed that Py-polyamides, even those with large molecular size, P-15 and P-18, showed good cellular uptake, but Im-polyamides showed very poor uptake. Fluorescence microscopy revealed that conjugate P-6 exhibited nuclear localization, while P-18 showed less nuclear stain but intracellular localization, suggesting that increased molecular size is one of the determinants in reducing nuclear access. Furthermore, results for hairpin polyamide conjugates H-1, H-2, and H-3 containing different Py/Im content indicated that cellular uptake increases as the Im residue is reduced. It appears that Py-Im-polyamide has general properties regardless of whether they have a linear or a hairpin structure. (C) 2009 Elsevier Ltd. All rights reserved.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.7
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Biochemistry & Molecular Biology

Biomimetic DNA Nanotechnology to Understand and Control Cellular Responses

Soumya Sethi, Hiroshi Sugiyama, Masayuki Endo

Summary: DNA nanotechnology is a promising toolkit for mimicking cell-cell and cell-matrix interactions, aiding in understanding and manipulating cellular functions. Future innovations in the field can be inspired by exploring the potentials of DNA-based nanostructures and addressing current challenges.

CHEMBIOCHEM (2022)

Article Biochemistry & Molecular Biology

Strong and Specific Recognition of CAG/CTG Repeat DNA (5'-dWGCWGCW-3') by a Cyclic Pyrrole-Imidazole Polyamide

Yuki Hirose, Tomo Ohno, Sefan Asamitsu, Kaori Hashiya, Toshikazu Bando, Hiroshi Sugiyama

Summary: A cyclic pyrrole-imidazole polyamide (cPIP) was synthesized to bind to the abnormal expanded CAG/CTG repeat DNA sequences, showing high binding affinity and specificity for its target DNA sequence.

CHEMBIOCHEM (2022)

Article Biochemistry & Molecular Biology

Photo-Cross-Linking between BrU and Pyrene Residues in an RNA/DNA Hybrid

Ryu Tashiro, Ji Hye Yum, Soyoung Park, Hiroshi Sugiyama

Summary: The study showed that the photoreactivity of U-Br changes dramatically from hydrogen abstraction to cross-linking by changing the conformation of the duplex from the B-form to the A-form. Among three A-form structures, the largest amount of cross-linked products was observed when U-Br was incorporated into the RNA strand and the pyrene was conjugated to the 5 ' end of the DNA. These results indicate that the contact manner of pyrene was different between A- and B-form duplexes.

CHEMBIOCHEM (2022)

Article Biochemistry & Molecular Biology

A Hexameric Ribozyme Nanostructure Formed by Double-Decker Assembly of a Pair of Triangular Ribozyme Trimers

Kai Yu, Kumi Hidaka, Hiroshi Sugiyama, Masayuki Endo, Shigeyoshi Matsumura, Yoshiya Ikawa

Summary: Naturally occurring ribozymes with modular architecture are promising for designing and assembling three-dimensional RNA nanostructures with catalytic abilities. In this study, RNA nanostructures with polygonal-shaped ribozyme oligomers were constructed using unit RNAs from the Tetrahymena group I intron, and ribozyme trimers with a triangular shape were dimerized by introducing pillar units. The resulting double-decker nanostructures containing six ribozyme units showed higher catalytic activity than the parent ribozyme trimers.

CHEMBIOCHEM (2022)

Article Biochemistry & Molecular Biology

Dissection of nanoconfinement and proximity effects on the binding events in DNA origami nanocavity

Sagun Jonchhe, Shankar Pandey, Christian Beneze, Tomoko Emura, Hiroshi Sugiyama, Masayuki Endo, Hanbin Mao

Summary: Researchers found that a DNA nanobowl significantly increased the stability of a human telomeric G-quadruplex and its binding with a ligand. By minimizing the proximity effect and attributing the increased affinity to the nanoconfinement effect, they provided insights into the mechanisms of binding events in nanocavities.

NUCLEIC ACIDS RESEARCH (2022)

Article Chemistry, Multidisciplinary

Inhibition of GLI-Mediated Transcription by Cyclic Pyrrole-Imidazole Polyamide in Cancer Stem Cells

Vinodh J. Sahayasheela, Zutao Yu, Yuki Hirose, Ganesh N. Pandian, Toshikazu Bando, Hiroshi Sugiyama

Summary: Research suggests that targeting Gli-mediated transcription to inhibit the proliferation of cancer stem cells may be a promising strategy.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2022)

Article Biochemistry & Molecular Biology

Characterization of 2-Fluoro-2'-deoxyadenosine in Duplex, G-Quadruplex and i-Motif

Shingo Hirashima, Hiroshi Sugiyama, Soyoung Park

Summary: This study characterized 2FA-containing DNA molecules and found that they have similar structure and properties to native adenine due to their small size, but exhibit unique features due to their high electronegativity. This provides valuable information for future applications of 2FA-modified DNA.

CHEMBIOCHEM (2022)

Article Biochemistry & Molecular Biology

N-terminal Cationic Modification of Linear Pyrrole-Imidazole Polyamide Improves Its Binding to DNA

Junnosuke Hatanaka, Yuki Hirose, Kaori Hashiya, Toshikazu Bando, Hiroshi Sugiyama

Summary: In this study, we synthesized linear pyrrole-imidazole polyamides (PIPs) that can selectively bind to DNA. These linear PIPs have lower molecular weights compared to commonly used hairpin PIPs. The binding affinity of the PIPs to DNA was improved by modifying the N-terminus of the linear PIPs. These findings provide insights for the design of effective linear PIPs.

CHEMBIOCHEM (2022)

Article Materials Science, Multidisciplinary

Photoinitiator-Free Two-Photon Polymerization of Biocompatible Materials for 3D Micro/Nanofabrication

Atsushi Nakayama, Yasuaki Kumamoto, Masafumi Minoshima, Kazuya Kikuchi, Atsushi Taguchi, Katsumasa Fujita

Summary: This study demonstrates the use of photopolymerization without photoinitiators to fabricate 3D structures using biocompatible materials. The material properties of poly(ethylene glycol) diacrylate (PEGda) and collagen are preserved, making them suitable for applications with live cells.

ADVANCED OPTICAL MATERIALS (2022)

Article Chemistry, Multidisciplinary

Development of a Versatile Protein Labeling Tool for Live-Cell Imaging Using Fluorescent β-Lactamase Inhibitors

Masafumi Minoshima, Taro Umeno, Kohei Kadooka, Margaux Roux, Namiko Yamada, Kazuya Kikuchi

Summary: To understand protein function in live cells, it is important to monitor protein dynamics and sense their environment in real-time. We developed a versatile chemical protein-labeling tool that efficiently forms stable carbamoylated complexes with beta-lactamase, allowing long-term visualization of labeled proteins in live cells. The use of an alpha-fluorinated carboxylate ester-based prodrug enables cell membrane permeability and stable labeling of intracellular proteins. Combining this labeling tool with a pH-activatable fluorescent probe enables visual monitoring of lysosomal protein translocation during autophagy.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Multidisciplinary Sciences

RNA G-quadruplex organizes stress granule assembly through DNAPTP6 in neurons

Sefan Asamitsu, Yasushi Yabuki, Kazuya Matsuo, Moe Kawasaki, Yuki Hirose, Gengo Kashiwazaki, Anandhakumar Chandran, Toshikazu Bando, Dan Ohtan Wang, Hiroshi Sugiyama, Norifumi Shioda

Summary: In this study, DNAPTP6 was identified as an RNA binding protein that plays a critical role in coordinating the assembly of stress granules (SGs) in a rG4-dependent manner. The recruitment of mRNAs into SGs through DNAPTP6 promotes RNA self-assembly and DNAPTP6 phase separation, which is essential for neuronal function.

SCIENCE ADVANCES (2023)

Article Chemistry, Multidisciplinary

Efficient visible/NIR light-driven uncaging of hydroxylated thiazole orange-based caged compounds in aqueous media

Ryu Hashimoto, Masafumi Minoshima, Souhei Sakata, Fumihito Ono, Hirokazu Ishii, Yuki Watakabe, Tomomi Nemoto, Saeko Yanaka, Koichi Kato, Kazuya Kikuchi

Summary: In this study, visible-light-sensitive protecting groups with high uncaging cross sections were developed for precise control of bioactivity. Two-photon photolysis reactions were achieved using near-infrared laser, and green-light illumination enabled optical control of biological functions.

CHEMICAL SCIENCE (2022)

Article Biochemistry & Molecular Biology

Targeted elimination of mutated mitochondrial DNA by a multi-functional conjugate capable of sequence-specific adenine alkylation

Takuya Hidaka, Kaori Hashiya, Toshikazu Bando, Ganesh N. Pandian, Hiroshi Sugiyama

Summary: This study constructed a class of compounds that can selectively alkylate mutant mitochondrial DNA, with the potential to treat mitochondrial diseases. These compounds have programmability and can be used to target pathogenic mutations associated with mitochondrial diseases in future studies.

CELL CHEMICAL BIOLOGY (2022)

Article Chemistry, Multidisciplinary

A selective hybrid fluorescent sensor for fructose detection based on a phenylboronic acid and BODIPY-based hydrophobicity probe

Gengo Kashiwazaki, Ryo Watanabe, Akihiro Nishikawa, Koyori Kawamura, Takashi Kitayama, Takao Hibi

Summary: Researchers have designed and synthesized a novel fluorescent probe for fructose detection, which shows a linear fluorescence response within the concentration range of 100-1000 μM and a low detection limit of 32 μM. This probe offers a simple and sensitive method for fructose determination.

RSC ADVANCES (2022)

Article Chemistry, Multidisciplinary

Nanoscopic observation of a DNA crystal surface and its dynamic formation and degradation using atomic force microscopy

Haruhiko Eki, Katsuhiko Abe, Hiroshi Sugiyama, Masayuki Endo

Summary: This study used atomic force microscopy to directly observe the formation and degradation of tensegrity triangle DNA crystals at a molecular level, visualizing the dynamic process and characterizing them with nanoscale resolution.

CHEMICAL COMMUNICATIONS (2021)

暂无数据