Masaki Kita

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Organization: University of Tsukuba , Japan

Department: Graduate School of Pure and Applied Sciences

Title: Associate Professor(PhD)

TOPICS

Organic Chemistry

Polymer

Olefin Metathesis

Chemicals
References

Analysis of the aplyronine A-induced protein–protein interaction between actin and tubulin by surface plasmon resonance

Co-reporter:Yuichiro Hirayama, Kota Yamagishi, Tomohiro Suzuki, Hirokazu Kawagishi, Masaki Kita, Hideo Kigoshi

Bioorganic & Medicinal Chemistry 2016 Volume 24(Issue 12) pp:2809-2814

Publication Date(Web):15 June 2016

DOI:10.1016/j.bmc.2016.04.049

The antitumor macrolide aplyronine A induces protein–protein interaction (PPI) between actin and tubulin to exert highly potent biological activities. The interactions and binding kinetics of these molecules were analyzed by the surface plasmon resonance with biotinylated aplyronines or tubulin as ligands. Strong binding was observed for tubulin and actin with immobilized aplyronine A. These PPIs were almost completely inhibited by one equivalent of either aplyronine A or C, or mycalolide B. In contrast, a non-competitive actin-depolymerizing agent, latrunculin A, highly accelerated their association. Significant binding was also observed for immobilized tubulin with an actin–aplyronine A complex, and the dissociation constant KD was 1.84 μM. Our method could be used for the quantitative analysis of the PPIs between two polymerizing proteins stabilized with small agents.

Aplysiasecosterols B and C: two new 9,11-secosteroids with a cis-fused 1,4-quinone structure from the sea hare Aplysia kurodai

Co-reporter:Masaki Kita, Atsushi Kawamura, Hideo Kigoshi

Tetrahedron Letters 2016 Volume 57(Issue 8) pp:858-860

Publication Date(Web):24 February 2016

DOI:10.1016/j.tetlet.2016.01.028

Two new 9,11-secosteroids with a cis-fused 3β,5β-dihydroxy-1,4-quinone structure, aplysiasecosterols B and C, were isolated from the sea hare Aplysia kurodai. Their structures were determined by 1D- and 2D-NMR spectroscopic analysis, molecular modeling studies, and a modified Mosher’s method. Aplysiasecosterol B might be the biosynthetic precursor of aplysiasecosterol A, another 9,11-secosteroid with a tricyclic γ-diketone structure from A. kurodai, via two α-ketol rearrangements and intramolecular acetalization.

Marine natural products that interfere with multiple cytoskeletal protein interactions

Co-reporter:Masaki Kita and Hideo Kigoshi

Natural Product Reports 2015 vol. 32(Issue 4) pp:534-542

Publication Date(Web):16 Dec 2014

DOI:10.1039/C4NP00129J

Covering: up to 2014 Various marine natural products that target cytoskeletal proteins have been discovered. A few of these compounds have recently been shown to induce or inhibit protein–protein interactions. Lobophorolide, an actin filament-disrupting macrolide, binds to actin with a unique 2:2 stoichiometry in which two lobophorolide molecules cooperate to stabilize an actin dimer. Adociasulfates, merotriterpenoid derivatives, inhibit microtubule-stimulated ATPase activity of a motor protein kinesin by blocking both the binding of microtubules and the processive motion of kinesin along microtubules. The antitumor macrolide aplyronine A synergistically binds to tubulin in association with actin, and prevents spindle formation and mitosis. In this highlight, we address recent chemical biology studies on these mechanistically-attractive marine natural products. These findings may be useful for the design and development of new pharmacological tools and therapeutic agents.

Total Synthesis of Mycalolides A and B through Olefin Metathesis

Co-reporter:Dr. Masaki Kita;Hirotaka Oka;Akihiro Usui;Tomoya Ishitsuka;Dr. Yuzo Mogi;Hidekazu Watanabe;Masaki Tsunoda ;Dr. Hideo Kigoshi

Angewandte Chemie 2015 Volume 127( Issue 47) pp:14380-14384

Publication Date(Web):

DOI:10.1002/ange.201507795

Abstract

An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side-chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps.

AplysiasecosterolA: A 9,11-Secosteroid with an Unprecedented Tricyclic -Diketone Structure from the Sea Hare Aplysia kurodai

Co-reporter:Atsushi Kawamura;Dr. Masaki Kita;Dr. Hideo Kigoshi

Angewandte Chemie 2015 Volume 127( Issue 24) pp:7179-7182

Publication Date(Web):

DOI:10.1002/ange.201501749

Abstract

A new 9,11-secosteroid having an unprecedented tricyclic γ-diketone structure, aplysiasecosterol A (1), was isolated from the sea hare Aplysia kurodai. The structure was determined by one- and two-dimensional NMR spectroscopic analysis, molecular modeling studies, a comparison of experimental and calculated ECD spectra, and a modified Mosher′s method. Aplysiasecosterol A (1) exhibited cytotoxicity against human myelocytic leukemia HL-60 cells. A biosynthetic pathway for 1 from a known cholesterol was proposed and includes twice α-ketol rearrangements and an intramolecular acetalization.

Total Synthesis of Mycalolides A and B through Olefin Metathesis

Co-reporter:Dr. Masaki Kita;Hirotaka Oka;Akihiro Usui;Tomoya Ishitsuka;Dr. Yuzo Mogi;Hidekazu Watanabe;Masaki Tsunoda ;Dr. Hideo Kigoshi

Angewandte Chemie International Edition 2015 Volume 54( Issue 47) pp:14174-14178

Publication Date(Web):

DOI:10.1002/anie.201507795

Abstract

AplysiasecosterolA: A 9,11-Secosteroid with an Unprecedented Tricyclic -Diketone Structure from the Sea Hare Aplysia kurodai

Co-reporter:Atsushi Kawamura;Dr. Masaki Kita;Dr. Hideo Kigoshi

Angewandte Chemie International Edition 2015 Volume 54( Issue 24) pp:7073-7076

Publication Date(Web):

DOI:10.1002/anie.201501749

Abstract

Inhibition of Microtubule Assembly by a Complex of Actin and Antitumor Macrolide Aplyronine A

Co-reporter:Masaki Kita ; Yuichiro Hirayama ; Kozo Yoneda ; Kota Yamagishi ; Takumi Chinen ; Takeo Usui ; Eriko Sumiya ; Motonari Uesugi ;Hideo Kigoshi

Journal of the American Chemical Society 2013 Volume 135(Issue 48) pp:18089-18095

Publication Date(Web):November 14, 2013

DOI:10.1021/ja406580w

Aplyronine A (ApA) is a marine natural product that shows potent antitumor activity. While both ApA and ApC, a derivative of ApA that lacks a trimethylserine ester moiety, inhibit actin polymerization in vitro to the same extent, only ApA shows potent cytotoxicity. Therefore, the molecular targets and mechanisms of action of ApA in cells have remained unclear. We report that ApA inhibits tubulin polymerization in a hitherto unprecedented way. ApA forms a 1:1:1 heterotrimeric complex with actin and tubulin, in association with actin synergistically binding to tubulin, and inhibits tubulin polymerization. Tubulin-targeting agents have been widely used in cancer chemotherapy, but there are no previous descriptions of microtubule inhibitors that also bind to actin and affect microtubule assembly. ApA inhibits spindle formation and mitosis in HeLa S3 cells at 100 pM, a much lower concentration than is needed for the disassembly of the actin cytoskeleton. The results of the present study indicate that ApA represents a rare type of natural product, which binds to two different cytoplasmic proteins to exert highly potent biological activities.

Stylissatin A, a cyclic peptide that inhibits nitric oxide production from the marine sponge Stylissa massa

Co-reporter:Masaki Kita, Baro Gise, Atsushi Kawamura, Hideo Kigoshi

Tetrahedron Letters 2013 Volume 54(Issue 50) pp:6826-6828

Publication Date(Web):11 December 2013

DOI:10.1016/j.tetlet.2013.10.003

•A new cyclic heptapeptide, stylissatin A, was isolated from the marine sponge.•The structure of stylissatin A is cyclo-[Tyr1–Ile2–Phe3–Pro4–Ile5–Pro6–Phe7].•Stylissatin A inhibited NO production in LPS-stimulated macrophage RAW264.7 cells.A new cyclic heptapeptide, stylissatin A (1), was isolated from the Papua New Guinean marine sponge Stylissa massa. Through the use of 1D and 2D NMR spectroscopic analysis, Marfey’s method, and MS/MS analysis, its structure was determined to be cyclo-[Tyr1–Ile2–Phe3–Pro4–Ile5–Pro6–Phe7]. Stylissatin A inhibited nitric oxide production in LPS-stimulated murine macrophage RAW264.7 cells with an IC50 value of 87 μM.

Interactions of the Antitumor Macrolide Aplyronine A with Actin and Actin-Related Proteins Established by Its Versatile Photoaffinity Derivatives

Co-reporter:Masaki Kita ; Yuichiro Hirayama ; Kota Yamagishi ; Kozo Yoneda ; Ryosuke Fujisawa ;Hideo Kigoshi

Journal of the American Chemical Society 2012 Volume 134(Issue 50) pp:20314-20317

Publication Date(Web):November 30, 2012

DOI:10.1021/ja310495p

The antitumor and apoptogenic macrolide aplyronine A (ApA) is a potent actin-depolymerizing agent. We developed an ApA acetylene analog that bears the aryldiazirine group at the C34 terminus, which formed a covalent bond with actin. With the use of the photoaffinity biotin derivatives of aplyronines A and C, Arp2 and Arp3 (actin-related proteins) were specifically purified as binding proteins along with actin from tumor cell lysate. However, Arp2 and Arp3 did not covalently bind to aplyronine photoaffinity derivatives. Thus, actin-related proteins might indirectly bind to ApA as the ternary adducts of the actin/ApA complex or through the oligomeric actin.

Synthesis and biological activities of the tris-oxazole macrolactone analogs of mycalolides

Co-reporter:Masaki Kita, Hirotaka Oka, Akihiro Usui, Tomoya Ishitsuka, Yuzo Mogi, Hidekazu Watanabe, Hideo Kigoshi

Tetrahedron 2012 68(42) pp: 8753-8760

Publication Date(Web):

DOI:10.1016/j.tet.2012.08.012

Inside Cover: Fluorescent Aplyronine A: Intracellular Accumulation and Disassembly of Actin Cytoskeleton in Tumor Cells ChemBioChem 12/2012)

Co-reporter: Dr. Masaki Kita;Kozo Yoneda;Yuichiro Hirayama;Kota Yamagishi;Yuki Saito;Yuka Sugiyama;Dr. Yoshihiro Miwa;Dr. Osamu Ohno;Maho Morita; Dr. Kiyotake Suenaga; Dr. Hideo Kigoshi

ChemBioChem 2012 Volume 13( Issue 12) pp:

Publication Date(Web):

DOI:10.1002/cbic.201290049

Fluorescent Aplyronine A: Intracellular Accumulation and Disassembly of Actin Cytoskeleton in Tumor Cells

Co-reporter: Dr. Masaki Kita;Kozo Yoneda;Yuichiro Hirayama;Kota Yamagishi;Yuki Saito;Yuka Sugiyama;Dr. Yoshihiro Miwa;Dr. Osamu Ohno;Maho Morita; Dr. Kiyotake Suenaga; Dr. Hideo Kigoshi

ChemBioChem 2012 Volume 13( Issue 12) pp:1754-1758

Publication Date(Web):

DOI:10.1002/cbic.201200385

Rcktitelbild: Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of AplyronineA (Angew. Chem. 42/2011)

Co-reporter:Dr. Masaki Kita;Yuichiro Hirayama;Miyuki Sugiyama ;Dr. Hideo Kigoshi

Angewandte Chemie 2011 Volume 123( Issue 42) pp:

Publication Date(Web):

DOI:10.1002/ange.201106017

Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of AplyronineA

Co-reporter:Dr. Masaki Kita;Yuichiro Hirayama;Miyuki Sugiyama ;Dr. Hideo Kigoshi

Angewandte Chemie 2011 Volume 123( Issue 42) pp:10045-10048

Publication Date(Web):

DOI:10.1002/ange.201103802

Back Cover: Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of AplyronineA (Angew. Chem. Int. Ed. 42/2011)

Co-reporter:Dr. Masaki Kita;Yuichiro Hirayama;Miyuki Sugiyama ;Dr. Hideo Kigoshi

Angewandte Chemie International Edition 2011 Volume 50( Issue 42) pp:

Publication Date(Web):

DOI:10.1002/anie.201106017

Development of Highly Cytotoxic and Actin-Depolymerizing Biotin Derivatives of AplyronineA

Co-reporter:Dr. Masaki Kita;Yuichiro Hirayama;Miyuki Sugiyama ;Dr. Hideo Kigoshi

Angewandte Chemie International Edition 2011 Volume 50( Issue 42) pp:9871-9874

Publication Date(Web):

DOI:10.1002/anie.201103802

Bioactive secondary metabolites from symbiotic marine dinoflagellates: symbiodinolide and durinskiols

Co-reporter:Masaki Kita;Osamu Ohno;Chunguang Han;Daisuke Uemura

The Chemical Record 2010 Volume 10( Issue 2) pp:57-69

Publication Date(Web):

DOI:10.1002/tcr.200900007

Abstract

Symbiotic relationships play critical roles in marine ecosystems. Among symbionts, marine dinoflagellates have attracted the attention of natural products chemists, biologists, and ecologists, since they are rich sources of unique bioactive secondary metabolites. The polyol compound symbiodinolide, which was isolated from the symbiotic dinoflagellate Symbiodinium sp., exhibits significant voltage-dependent N-type Ca²⁺ channel-opening activity and may serve as a defense substance to prevent digestion of the host animals. Durinskiols are also unique long carbon-chain polyol compounds that were isolated from the dinoflagellate Durinskia sp. We found a selective cleavage reaction of allylic 1,2-diol using an olefin metathesis catalyst, and developed a fluorescent-labeling method for MS/MS analysis to achieve the structural elucidation of huge polyol compounds. This review highlights recent advances in structural and biological studies on symbiodinolide, durinskiols, and related polyol compounds. © 2010 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 10: 57–69; 2010: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.200900007

Marine huge molecules: the longest carbon chains in natural products

Co-reporter:Masaki Kita;Daisuke Uemura

The Chemical Record 2010 Volume 10( Issue 1) pp:48-52

Publication Date(Web):

DOI:10.1002/tcr.200900030

Abstract

Marine huge polyol and polyether compounds are remarkable molecules owing to their extraordinary structures and significant biological activities. Currently, palytoxin and maitotoxin are believed to have the longest carbon chains in nature (more than 100 Å in length), except for biopolymers. The structural properties of such marine huge molecules are highlighted, especially with regard to the length and shape of their carbon chains. © 2010 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 10: 000–000; 2010: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.200900030