論文発表 (2017)

Rational design and synthesis of post-functionalizable peptide foldamers as helical templates

T. Misawa,* Y. Kanda, Y. Demizu*

Bioconj. Chem., in press.

Right-handed and left-handed helical structures with fourteen (R)-chiral centers

R. Eto, M. Oba, A. Ueda, T. Uku, M. Doi, Y. Demizu, M. Kurihara, M. Tanaka*

Chem. Eur. J., in press.

Development of a small hybrid molecule that mediates degradation of His tag-fused proteins

K. Okitsu, T. Hattori, T. Misawa, T. Shoda, M. Kurihara, M. Naito,* Y. Demizu*

J. Med. Chem., in press.

Development of a peptide-based inducer of protein degradation targeting NOTCH1

N. Ohoka, T. Misawa, M. Kurihara, Y. Demizu,* M. Naito*

Bioorg. Med. Chem. Lett., 27, 4985-4988 (2017).

Preorganized and side-chain functionalized cyclic a,a-disubstituted a-amino acids that function as peptide-helix inducers

H. Kobayashi, T. Misawa, K. Matsuno, Y. Demizu*

J. Org. Chem., 82, 10722-10726 (2017).

Helical L-Leu-based peptides having chiral five-membered carbocyclic ring amino acids with an ethylene acetal moiety

Y. Koba, A. Ueda, M. Oba, M. Doi, Y. Demizu, M. Kurihara, M. Tanaka*

ChemistrySelect, 2, 8108-8114 (2017).

Simple and efficient knockdown of His-tagged proteins by ternary molecules consist of His-tag ligand, ubiquitin ligase ligand and cell penetrating peptide

T. Hattori, K. Okitsu, N. Yamazaki, N. Ohoka, N. Shibata, T. Misawa, M. Kurihara, Y. Demizu,* M. Naito*

Bioorg. Med. Chem. Lett., 27, 4478-4481 (2017).

Development of helix-stabilized antimicrobial peptides composed of lysine and hydrophobic a,a-disubstituted a-amino acid residues

T. Misawa, M. Imamura, Y. Ozawa, K. Haishima, M. Kurihara, Y. Kikuchi,* Y. Demizu*

Bioorg. Med. Chem. Lett., 27, 3950-3953 (2017).

Low pH-responsive change in side chain structure of an amino acid from cyclic acetal to acyclic diol leads to conformational change in a peptide from a helical to random structure

K. Furukawa, M. Oba,* K. Toyama, G. O. Opiyo, Y. Demizu, M. Kurihara, M. Doi, M. Tanaka*

Org. Biomol. Chem., 15, 6302-6305 (2017). <Selected as Cover Picture>

PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

T. Sugiyama,* G. Hasegawa, C. Niikura, K. Kuwata, Y. Imamura, Y. Demizu, M. Kurihara, M. Takano, A. Kittaka*

Bioorg. Med. Chem. Lett., 27, 3337-3341 (2017).

Development of an ON/OFF switchable fluorescent probe targeting His tag fused proteins in living cells

K. Okitsu, T. Misawa,* T. Shoda, M. Kurihara, Y. Demizu*

Bioorg. Med. Chem. Lett., 27, 3417-3422 (2017).

Efficient synthesis of a multi-substituted diphenylmethane skeleton as a steroid mimetic

T. Misawa,* K. Tanaka, Y. Demizu, M. Kurihara*

Bioorg. Med. Chem. Lett., 27, 2590-2593 (2017).

Tamoxifen and fulvestrant hybrid showed potency as a selective estrogen receptor down-regulator

T. Shoda,* M. Kato, T. Fujisato, Y. Demizu, H. Inoue, M. Naito, M. Kurihara*

Med. Chem. (Bentham), 13, 206-213 (2017).

Development of non-secosteroidal vitamin D receptor (VDR) ligands bearing a long alkyl chain

T. Misawa,* Y. Demizu, T. Yachide, N. Ohoka, H. Nojiri, A. Kittaka, M. Makishima, M. Naito, M. Kurihara*

Bitamin, 91, 113-120 (2017).

Development of helix-stabilized cell-penetrating peptides containing cationic a,a-disubstituted amino acids as helical promoters

H. Yamashita, T. Misawa, M. Oba, M. Tanaka, M. Naito, M. Kurihara,* Y. Demizu*

Bioorg. Med. Chem., 25, 1846-1851 (2017).

Targeted degradation of proteins localized in subcellular compartments by hybrid small molecules

K. Okuhira, T. Shoda, R. Omura, N. Ohoka, T. Hattori, N. Shibata, Y. Demizu, R. Sugihara, A. Ichino, H. Kawahara, Y. Ito, M. Ishikawa, Y. Hashimoto, M. Kurihara, H. Saito, M. Naito*

Mol. Pharmacol., 91, 159-166 (2017).

Design and synthesis of novel selective estrogen receptor degradation inducers based on diphenylheptane skeleton

T. Misawa,* T. Fujisato, Y. Kanda, N. Ohoka, T. Shoda, M. Yorioka, M. Makishima, Y. Sekino, M. Naito, Y. Demizu, M. Kurihara*

MedChemComm, 8, 239-246 (2017).

論文発表 (2016)

Influence of L-Leu to D-Leu replacement on the helical secondary structures of L-Leu-Aib-based dodecapeptides

Y. Demizu,* K. Okitsu, M. Doi, T. Misawa, M. Oba, M. Tanaka, M. Kurihara*

ChemistrySelect, 1, 5805-5811 (2016).

Development of BCR-ABL degradation inducers via the conjugation of an imatinib derivative and a cIAP1 ligand

Y. Demizu,* N. Shibata, T. Hattori, N. Ohoka, H. Motoi, T. Misawa, T. Shoda, M. Naito,* M. Kurihara*

Bioorg. Med. Chem. Lett., 26, 4865-4869 (2016).

Helical structures of homo-chiral isotope-labeled a-aminoisobutyric acid peptides

A. Ueda, M. Oba, Y. Izumi, Y. Sueyoshi, M. Doi, Y. Demizu, M. Kurihara, M. Tanaka*

Tetrahedron, 39, 5864-5871 (2016).

Development of a cell-penetrating peptide that exhibits responsive changes in its secondary structure in the cellular environment

H. Yamashita, T. Kato, M. Oba, T. Misawa, T. Hattori, N. Ohoka, M. Tanaka, M. Naito, M. Kurihara,* Y. Demizu*

Sci. Rep., 6, 33003, DOI:10.1038/srep33003 (2016).

The side-chain hydroxy groups of a cyclic a,a-disubstituted a-amino acid promote oligopeptide helix packing in the crystalline state

Y. Demizu,* M. Doi, H. Yamashita, T. Misawa, M. Oba, M. Kurihara, H. Suemune, M. Tanaka

Biopolymers (Pept. Sci.), 106, 757-768 (2016).

Identification of embryonic precursor cells that differentiate into thymic epithelial cells expressing autoimmune regulator

N. Akiyama, N. Takizawa, M. Miyauchi, H. Yanai, R. Tateishi, M. Shinzawa, R. Yoshinaga, M. Kurihara, Y. Demizu, H. Yasuda, S. Yagi, G. Wu, M. Matsumoto, R. Sakamoto, N. Yoshida, J. M. Penninger, Y. Kobayashi, J. Inoue, T. Akiyama*

J. Exp. Med., 213, 1441-1458 (2016).

Syntheses of chiral five-membered ring amino acids with an acetal moiety and helical conformations of its homo-chiral homopepitdes

Y. Koba, Y. Hirata, A. Ueda, M. Oba, M. Doi, Y. Demizu, M. Kurihara, M. Tanaka*

Biopolymers (Pept. Sci.), 106, 555-562 (2016).

Peptide nucleic acid with a lysine side chain at the b-position: synthesis and application for DNA cleavage

T. Sugiyama,* K. Kuwata, Y. Imamura, Y. Demizu, M. Kurihara, M. Takano, A. Kittaka

Chem. Pharm. Bull., 64, 817-823 (2016).

Synthesis and evaluation of raloxifene derivatives as a selective estrogen receptor down-regulator

T. Shoda,* M. Kato, T. Fujisato, T. Misawa, Y. Demizu, H. Inoue, M. Naito, M. Kurihara*

Bioorg. Med. Chem., 24, 2914-2919 (2016).

a-Helical structures of oligopeptides with alternating L-Leu-Aib segment

Y. Demizu,* K. Okitsu, H. Yamashita, M. Doi, T. Misawa, M. Oba, M. Tanaka, M. Kurihara*

Eur. J. Org. Chem., 2815-2820 (2016).

Plasmid DNA delivery using arginine-rich cell-penetrating peptides containing unnatural amino acids

T. Kato, H. Yamashita, T. Misawa, K. Nishida, M. Kurihara, M. Tanaka, Y. Demizu,* M. Oba*

Bioorg. Med. Chem., 24, 2681-2687 (2016).

Development of peptide-based nuclear receptors degradation inducer

Y. Demizu,* N. Ohoka, T. Nagakubo, H. Yamashita, T. Misawa, K. Okuhira, M. Naito, M. Kurihara*

Bioorg. Med. Chem. Lett., 26, 2655-2658 (2016).

1,4-Bis[(N-acetyl-L-phenylalanyl-glycyl-L-alanyl)aminomethyl]benzene

Y. Demizu,* K. Tsutsui, T. Misawa, M. Kurihara*

Molbank, doi:10.3390/M893 (2016).

Handedness preferences of heterochiral helical peptides containing homochiral peptide segments

Y. Demizu,* H. Yamashita, T. Misawa, M. Doi, M. Oba, M. Tanaka, M. Kurihara*

Eur. J. Org. Chem., 840-846 (2016).

A helix-stabilized cell-penetrating peptide as an intracellular-delivery tool

H. Yamashita, M. Oba, T. Misawa, M. Tanaka, T. Hattori, M. Naito, M. Kurihara,* Y. Demizu*

ChemBioChem, 17, 137-140 (2016). <Selected as Cover Picture>

Induction of proteasomal degradation of ERa and subsequent cell death in breast cancer cells

K. Okuhira, Y. Demizu, T. Hattori, N. Ohoka, N. Shibata, T. Nishimaki-Mogami, H. Okuda, M. Kurihara, M. Naito*

Methods Mol. Biol., 1366, 549-560 (2016).

論文発表 (2015)

Effects of alkyl side chains and terminal hydrophilicity on vitamin D receptor (VDR) agonistic activity based on the diphenylpentane skeleton

T. Misawa, M. Yorioka, Y. Demizu, T. Noguchi-Yachide, N. Ohoka, M. Kurashima-Kinoshita, H. Motoyoshi, H. Nojiri, A. Kittaka, M. Makishima, M. Naito, M. Kurihara*

Bioorg. Med. Chem. Lett., 25, 5362-5366 (2015).

Topological study of the structures of heterochiral peptides with equal amounts of L-Leu and D-Leu

Y. Demizu,* H. Yamashita, M. Doi, T. Misawa, M. Oba, M. Tanaka, M. Kurihara*

J. Org. Chem., 80, 8597-8603 (2015).

A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N-OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products

N. Uchiyama,* Y. Shimokawa, R. Kikura-Hanajiri, Y. Demizu, Y. Goda, T. Hakamatsuka

Forensic Toxicol., 33, 244-259 (2015).

Synthesis, evaluation, and molecular docking studies of novel carbocyclic oxetanocin A (COA-Cl) derivatives as potential tube formation agents

N. Sakakibara,* J. Igarashi, M. Takata, Y. Demizu, T. Misawa, M. Kurihara, R. Konishi, Y. Kato, T. Maruyama, I. Tsukamoto

Chem. Pharm. Bull., 63, 701-709 (2015).

Design, synthesis, and anti-HIV-1 activity of 1-substituted 3-(3,5-dimethylbenzyl)triazine derivatives

N. Sakakibara,* G. Balboni, C. Congiu, V. Onnis, Y. Demizu, T. Misawa, M. Kurihara, Y. Kato, T. Maruyama, M. Toyama, M. Okamoto, M. Baba

Antiviral Chem. Chemother., 24, 62-71 (2015).

Plasmid DNA delivery using fluorescein-labeled arginine-rich peptides

M. Oba,* Y. Demizu, H. Yamashita, M. Kurihara, M. Tanaka

Bioorg. Med. Chem., 23, 4911-4918 (2015).

Structural development of stabilized helical peptides as inhibitors of estrogen receptor (ER)-mediated transcription

Y. Demizu*, T. Misawa, T. Nagakubo, Y. Kanda, K. Okuhira, Y. Sekino, M. Naito, M. Kurihara*

Bioorg. Med. Chem., 23, 4132-4138 (2015).

Synthesis and resolution of substituted [5]carbohelicenes

K. Usui,* K. Yamamoto, T. Shimizu, M. Biao, M. Okazumi, Y. Demizu, M. Kurihara, H. Suemune*

J. Org. Chem., 80, 6502-6508 (2015).

Synthesis and evaluation of tamoxifen derivatives with a long alkyl side chain as selective estrogen receptor down-regulators

T. Shoda,* M. Kato, T. Fujisato, K. Okuhira, Y. Demizu, H. Inoue, M. Naito, M. Kurihara*

Bioorg. Med. Chem., 23, 3091-3096 (2015).

A preorganized b-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

Y. Demizu,* M. Oba, K. Okitsu, H. Yamashita, T. Misawa, M. Tanaka, M. Kurihara, S. H. Gellman

Org. Biomol. Chem., 13, 5617-5620 (2015).

Methyl 2-[(2-aminophenyl)ethynyl]benzoate and 2-[(2-acetamidophenyl)ethynyl]benzoic acid

Y. Demizu,* T. Misawa, N. Yamagata, M. Doi, M. Kurihara*

Molbank, M854, doi:10.3390/M854 (2015).

Peptide foldamers composed of six-membered ring a,a-disubstituted a-amino acid with two changeable chiral acetal moieties

K. Tanda, R. Eto, K. Kato, M. Oba, A. Ueda, H. Suemune, M. Doi, Y. Demizu, M. Kurihara, M. Tanaka*

Tetrahedron, 71, 3909-3914 (2015).

Amino equatorial effect of a six-membered ring amino acid on its peptide 310- and a-helices

T. Hirata, A. Ueda, M. Oba, M. Doi, Y. Demizu, M. Kurihara, M. Nagano, H. Suemune, M. Tanaka*

Tetrahedron, 71, 2409-2420 (2015).

Synthesis of a bis-cationic a,a-disubstituted amino acid (9-amino-bispidine-9-carboxylic acid) and its effects on the conformational properties of peptides

H. Yamashita, Y. Demizu,* T. Misawa, T. Shoda, M. Kurihara*

Tetrahedron, 71, 2241-2245 (2015).

Structural development of stapled short helical peptides as vitamin D receptor (VDR)-coactivator interaction inhibitors

T. Misawa, Y. Demizu,* M. Kawamura, N. Yamagata, M. Kurihara*

Bioorg. Med. Chem., 23, 1055-1061 (2015).

Effects of D-Leu residues on the helical secondary structures of L-Leu-based nonapeptides

Y. Demizu,* H. Yamashita, T. Misawa, M. Doi, M. Tanaka, M. Kurihara*

Chem. Pharm. Bull., 63, 218-224 (2015).

Design, synthesis and anti-HIV-1 activity of 1-aromatic methyl-substituted 3-(3,5-dimethylbenzyl)uracil and N-3,5-dimethylbenzyl-substituted urea derivatives

N. Sakakibara,* M. Baba, M. Okamoto, M. Toyama, Y. Demizu, T. Misawa, M. Kurihara, K. Irie, Y. Kato, T. Maruyama

Antiviral Chem. Chemother., 24, 3-18 (2015).

論文発表 (2014)

Development of cell-penetrating R7 fragment-conjugated helical peptides as inhibitors of estrogen receptor-mediated transcription

T. Nagakubo, Y. Demizu*, Y. Kanda, T. Misawa, T. Shoda, K. Okuhira, Y. Sekino, M. Naito, M. Kurihara*

Bioconj. Chem., 25, 1921-1924 (2014).

短鎖ペプチドのヘリカル構造制御と機能化

出水庸介*,三澤隆史,栗原正明*

有機合成化学協会誌72, 1336-1347 (2014).

N. Hirata, S. Yamada, T. Shoda, M. Kurihara, Y. Sekino, Y. Kanda, Sphingosine-1-phosphate promotes expansion of cancer stem cells via S1PR3 by a ligand-independent Notch activation
Nat. Commun., 5, Article number: 4806

Conformational studies on peptides having chiral five-membered ring amino acid with two azido or triazole functional groups within the sequence of Aib residues

M. Oba,* N. Kawabe, H. Takazaki, Y. Demizu, M. Doi, M. Kurihara, H. Suemune, M. Tanaka*

Tetrahedron, 70, 8900-8907 (2014).

Helical peptide-foldamers having chiral five-membered ring amino acid with two azido functional groups

M. Oba, H. Takazaki, N. Kawabe, M. Doi, Y. Demizu, M. Kurihara, H. Kawakubo, M. Nagano, H. Suemune, M. Tanaka*

J. Org. Chem., 79, 9125-9140 (2014).

NAD-dependent isocitrate dehydrogenase as a novel target of tributyltin in human embryonic carcinoma cells

S. Yamada, Y. Kotake, Y. Demizu, M. Kurihara, Y. Sekino, Y. Kanda*

Sci. Rep., 4, 5952, DOI:10.1038/srep05952 (2014).

Amphipathic short helix-stabilized peptides with cell-membrane penetration

H. Yamashita, Y. Demizu,* T. Shoda, Y. Sato, M. Oba, M. Tanaka, M. Kurihara*

Bioorg. Med. Chem., 22, 2403-2408 (2014).

Design and synthesis of a tamoxifen derivative of selective estrogen receptor down-regulator

T. Shoda,* K. Okuhira, M. Kato, Y. Demizu, H. Inoue, M. Naito, M. Kurihara*

Bioorg. Med. Chem. Lett., 24, 87-89 (2014).

論文発表 (2013)

Oligopeptides with equal amounts of L- and D-amino acids may prefer a helix screw sense

Y. Demizu,* H. Yamashita, N. Yamazaki, Y. Sato, M. Doi, M. Tanaka, M. Kurihara*

J. Org. Chem., 78, 12106-12113 (2013).

Helical oligomer with changeable chiral acetal moiety

M. Oba, N. Ishikawa, Y. Demizu, M. Kurihara, H. Suemune, M. Tanaka*

Eur. J. Org. Chem., 7679-7682 (2013).

Development of hybrid small molecules that induce degradation of estrogen receptor-alpha and necrotic cell death in breast cancer cells

K. Okuhira, Y. Demizu, T. Hattori, N. Ohoka, N. Shibata, T. Nishimaki-Mogami, H. Okuda, M. Kurihara, M. Naito*

Cancer Science, 104, 1492-1498 (2013).

Helical foldamer containing a combination of cyclopentane-1,2-diamine and 2,2-dimethylmalonic acid

N. Yamazaki, Y. Demizu,* Y. Sato, M. Doi, M. Kurihara*

J. Org. Chem., 78, 9991-9994 (2013).

Development of stapled short helical peptides capable of inhibiting vitamin D receptor (VDR)-coactivator interactions

Y. Demizu,* S. Nagoya, M. Shirakawa, M. Kawamura, N. Yamagata, Y. Sato, M. Doi, M. Kurihara*

Bioorg. Med. Chem. Lett., 23, 4292-4296 (2013).

Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents

N. Sakakibara,* T. Hamasaki, M. Baba, Y. Demizu, M. Kurihara, K. Irie, M. Iwai, R. Asada, Y. Kato, T. Maruyama

Bioorg. Med. Chem., 21, 5900-5906 (2013).