Article
Chemistry, Multidisciplinary
George J. Saunders, Andrei K. Yudin
Summary: The passive membrane permeability of macrocycles can be greatly improved by incorporating heterocyclic grafts. However, the permeability does not scale linearly with the number of heterocycles, highlighting the subtleties of the conformation-property relationship in this class of molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Ruihong Liu, Dongzhi Liu, Fancui Meng, Wei Li, Lichang Wang, Xueqin Zhou
Summary: The peptide secondary conformation strongly influences the arrangement of artificial photosynthetic supramolecules, affecting the formation of nanosheets, nanospheres, and nanotubes from a porphyrin-hexapeptide supramolecule. The alpha-helix conformation with strong intramolecular hydrogen bond interaction leads to the formation of nanosheets, while the beta-sheet conformation with weak intermolecular interaction results in the formation of nanospheres or nanotubes. These findings provide insights for developing artificial photosynthesis systems by regulating the aggregate structures of porphyrin-peptide supramolecular systems.
Article
Chemistry, Organic
Nicolas D'Imperio, Valentina Pelliccioli, Sara Grecchi, Alberto Bossi, Francesca Vasile, Silvia Cauteruccio, Anna I. Arkhypchuk, Arvind Kumar Gupta, Andreas Orthaber, Sascha Ott, Emanuela Licandro
Summary: This paper describes the first examples of a pi-conjugated benzo[b]phosphole P-oxide, in which two phosphole P-oxide units are connected by a carbon-carbon double bond. The molecules exist as stable cis and trans isomers (chiral and meso one respectively) with respect to the two stereogenic P atoms. The optical and electrochemical properties of both isomers have been investigated through experiments and computations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Jaru Taechalertpaisarn, Satoshi Ono, Okimasa Okada, Timothy C. Johnstone, R. Scott Lokey
Summary: Replacing hydrogen-bond donors in side chains can significantly improve the aqueous solubility and permeability of cyclic peptides.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi Zheng, Zuojie Wang, Zifen Li, Hang Liu, Jing Wei, Chuan Peng, Yeqiang Zhou, Jianshu Li, Qiang Fu, Hong Tan, Mingming Ding
Summary: Synthetic polypeptide vesicles can regulate their permeability through ordered transition of secondary conformations, similar to biological systems, showing potential for controlled drug delivery applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yukio Hitotsuyanagi, Taka-Aki Hinosawa, Yoshie Nakagawa, Ji-Ean Lee, Sho Ito, Tomoyo Hasuda
Summary: A bridged peptide analogue of RA-VII was synthesized and showed weaker cytotoxic activity towards human leukemia and colon cancer cells compared with RA-VII, possibly due to the difference in the orientation of the Tyr-6 phenyl ring plane.
Article
Chemistry, Organic
Qing Chen, Ming-hao Wu, Qi Chang, Xia Zhao
Summary: The new marine antibacterial cyclic hexapeptide Bacicyclin (1) and its 6 analogues were successfully synthesized to investigate the relationship between structure and activity. The study also revealed that unnatural amino acids with aryl fluorosulfate group have the potential to enhance the anti-tumor activity of cyclic peptides.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Takahiro Ono, Kazuhito V. Tabata, Hiroyuki Noji, Jumpei Morimoto, Shinsuke Sando
Summary: We compared the passive permeability of cyclosporin A (CsA) derivatives with side chain deletions across lipid bilayers. CsA maintained passive permeability after losing any one of the side chains, which suggests that the propensity of the backbone of CsA is an important component for high passive permeability.
Article
Biochemistry & Molecular Biology
Kaley M. Mientkiewicz, Leila Peraro, Joshua A. Kritzer
Summary: This study adapted the chloroalkane penetration assay to screen peptide libraries in a high-throughput, quantitative, and automation-ready manner, effectively exploring how the number, patterning, and stereochemistry of arginine residues affect the cytosolic penetration of a model 10-residue peptide.
ACS CHEMICAL BIOLOGY
(2021)
Review
Chemistry, Medicinal
Yang Li, Wang Li, Zhengshuang Xu
Summary: Peptides have a specific three-dimensional structure for binding to proteins, but low cell permeability is a challenge. Backbone N-methylation is used to manipulate the permeability of cyclic peptides/peptidomimetics. The importance of different N-methylations on total permeation may vary based on the intrinsic properties of the molecules.
Article
Chemistry, Multidisciplinary
Sopanant Datta, Taweetham Limpanuparb
Summary: This study investigated the stability of compounds with identical formulas consisting of C, N, P, O, and S atoms as core structures, with halogens H, F, Cl, Br, and I as substituents using quantum chemical methods. The prevalence of the most stable forms among different configurations and isomers was calculated and discussed, along with proposed quantitative and qualitative models to explain the stability of the 23 classes of halogenated compounds.
Article
Chemistry, Physical
Qingjun Zhang, Youguang Ma, Aiwu Zeng
Summary: This study investigates the mechanism of palladium-catalyzed carboxylation of thiophene and CO2 using density functional theory (DFT) calculations. The results show that the insertion of CO2 is the rate-determining step for this reaction.
Article
Chemistry, Analytical
Takayuki Kawai, Yasuhiro Mihara, Makiko Morita, Masahiko Ohkubo, Taiji Asami, Tomonobu M. Watanabe
Summary: Cyclic peptides (CPs) are considered next-generation drugs due to their cell-permeable potential and specific affinity, and single-cell cytoplasm mass spectrometry (SCC-MS) is a promising method for assessing their intracellular retention and transmembrane permeability.
ANALYTICAL CHEMISTRY
(2021)
Review
Chemistry, Medicinal
Yukio Hitotsuyanagi
Summary: An efficient method for synthesizing cycloisodityrosines from commercially available l-tyrosine derivatives was developed. The study explored the structure-activity relationships of the cycloisodityrosine moiety in RA-series peptides by designing and synthesizing several RA-VII analogues, and also established the structures of newly isolated natural peptides.
JOURNAL OF NATURAL MEDICINES
(2021)
Article
Materials Science, Multidisciplinary
Cheng Luo, Huang Yuan
Summary: In this study, the deformation-induced martensitic transformation in metastable austenitic steel was monitored in situ using the magnetic permeability method. The magnetic response and Villari effect under cyclic loading were systematically investigated. Phenomenological and stress partitioning models were proposed to describe the variation of martensitic phases and the distribution of macroscopic stress among constituent phases.
Article
Chemistry, Multidisciplinary
Akihiro Furukawa, Joshua Schwochert, Cameron R. Pye, Daigo Asano, Quinn D. Edmondson, Alexandra C. Turmon, Victoria G. Klein, Satoshi Ono, Okimasa Okada, R. Scott Lokey
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Medicinal
Koichiro Kato, Tomohide Masuda, Chiduru Watanabe, Naoki Miyagawa, Hideo Mizouchi, Shumpei Nagase, Kikuko Kamisaka, Kanji Oshima, Satoshi Ono, Hiroshi Ueda, Atsushi Tokuhisa, Ryo Kanada, Masateru Ohta, Mitsunori Ikeguchi, Yasushi Okuno, Kaori Fukuzawa, Teruki Honma
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2020)
Article
Chemistry, Medicinal
Takashi Goi, Tatsuo Nakajima, Yoshiyuki Komatsu, Atsushi Kawata, Shuhei Yamakoshi, Okimasa Okada, Masakatsu Sugahara, Asami Umeda, Yoko Takada, Jun Murakami, Rikiya Ohashi, Tomoko Watanabe, Koichi Fukase
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Multidisciplinary
Colin N. Kelly, Chad E. Townsend, Ajay N. Jain, Matthew R. Naylor, Cameron R. Pye, Joshua Schwochert, R. Scott Lokey
Summary: This study focused on investigating the structure-permeability relationships in lariat peptides, which are cyclized from one termini onto a side chain. A library of over 1000 novel lariat peptide scaffolds with molecular weights around 1000 was generated using stable isotopes to encode stereochemistry. The research found that passive permeability of lariat peptides was strongly dependent on N-methylation, stereochemistry, and ring topology, revealing various trends in structure-permeability relationships.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Victoria G. Klein, Walter M. Bray, Hao-Yuan Wang, Quinn Edmondson, Joshua Schwochert, Satoshi Ono, Matthew R. Naylor, Alexandra C. Turmon, Justin H. Faris, Okimasa Okada, Jack Taunton, R. Scott Lokey
Summary: Cordyheptapeptide A, a lipophilic cyclic peptide from Cordyceps fungal genus, has potent cytotoxicity in cancer cells by inhibiting protein synthesis. Further studies revealed its molecular target as eukaryotic translation elongation factor 1A (eEF1A), offering a strategy to study and improve cyclic peptide natural products.
ACS CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Medicinal
Satoshi Ono, Matthew R. Naylor, Chad E. Townsend, Chieko Okumura, Okimasa Okada, Hsiau-Wei Lee, R. Scott Lokey
Summary: The chameleonic behavior of cyclosporin A was studied using molecular dynamics simulations under various conditions, revealing its diverse conformational space and the influence of metal ions on its structures. The study showed that CsA can adopt multiple conformations, with metal ions potentially playing a key role in the cis/trans isomerization of N-methylated amino acids before binding to partner proteins.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2021)
Article
Chemistry, Medicinal
Jaru Taechalertpaisarn, Satoshi Ono, Okimasa Okada, Timothy C. Johnstone, R. Scott Lokey
Summary: Replacing hydrogen-bond donors in side chains can significantly improve the aqueous solubility and permeability of cyclic peptides.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Yuki Hosono, Satoshi Uchida, Moe Shinkai, Chad E. Townsend, Colin N. Kelly, Matthew R. Naylor, Hsiau-Wei Lee, Kayoko Kanamitsu, Mayumi Ishii, Ryosuke Ueki, Takumi Ueda, Koh Takeuchi, Masatake Sugita, Yutaka Akiyama, Scott R. Lokey, Jumpei Morimoto, Shinsuke Sando
Summary: Naturally occurring peptides with high membrane permeability usually have ester bonds on their backbones. This study evaluated the effect of amide-to-ester substitutions on the membrane permeability of cyclic peptides and found that this substitution is effective in improving membrane permeability. The findings provide insights into the development of membrane-permeable peptides through appropriate utilization of amide-to-ester substitutions.
NATURE COMMUNICATIONS
(2023)
Review
Genetics & Heredity
Ayaka Furukawa, Satoshi Ono, Katsuya Yamada, Nao Torimoto, Mahoko Asayama, Shigeharu Muto
Summary: This study developed a shareable QSAR tool based on nitrenium ion stability and evaluated its prediction accuracy using in-house aromatic amine intermediates. The results showed that the tool has comparable performance to commercial QSAR tools and can provide quantitative indicators to support expert review. This local QSAR tool is useful for explaining the substituent effects on the mutagenicity of primary aromatic amines.
GENES AND ENVIRONMENT
(2022)
