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Article ; Online: Chemical targeting of G-quadruplexes in telomeres and beyond for molecular cancer therapeutics.

Seimiya, Hiroyuki / Nagasawa, Kazuo / Shin-Ya, Kazuo

2021 Volume 74, Issue 10, Page(s) 617–628

Abstract: G-quadruplexes (G4s) are higher-order structures formed by guanine-rich sequences of nucleic acids, such as the telomeric 5'-TTAGGG-3'/5'-UUAGGG-3' repeats and those in gene regulatory regions. G4s regulate various biological events, including ... ...

Abstract	G-quadruplexes (G4s) are higher-order structures formed by guanine-rich sequences of nucleic acids, such as the telomeric 5'-TTAGGG-3'/5'-UUAGGG-3' repeats and those in gene regulatory regions. G4s regulate various biological events, including replication, transcription, and translation. Imbalanced G4 dynamics is associated with diseases, such as cancer and neurodegenerative diseases. Telomestatin is a natural macrocyclic compound derived from Streptomyces anulatus 3533-SV4. It interacts with the guanine quartet via π-π stacking and potently stabilizes G4. Because G4 stabilization at the telomeric repeat inhibits the telomere-synthesizing enzyme telomerase, telomestatin was originally identified as a telomerase inhibitor. Whereas non-toxic doses of telomestatin induce gradual shortening of telomeres and eventual crisis in human cancer cells, higher doses trigger prompt replication stress and DNA damage responses, resulting in acute cell death. Suppression of the transcription and translation of G4-containing genes is also implicated in the anticancer effects of telomestatin. Because telomestatin is rare, labile, and insoluble, synthetic oxazole telomestatin derivatives have been developed and verified for their therapeutic efficacies in preclinical cancer models. Furthermore, a variety of G4-stabilizing compounds have been reported as promising seeds for molecular cancer therapeutics. To improve the design of future clinical studies, it will be important to identify predictive biomarkers of drug efficacy.
MeSH term(s)	Animals ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Drug Delivery Systems ; G-Quadruplexes ; Humans ; Neoplasms/drug therapy ; Telomere
Chemical Substances	Antineoplastic Agents
Language	English
Publishing date	2021-07-20
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	390800-8
ISSN	1881-1469 ; 0021-8820 ; 0368-3532
ISSN (online)	1881-1469
ISSN	0021-8820 ; 0368-3532
DOI	10.1038/s41429-021-00454-x
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Article ; Online: In Vitro Module Editing Of NRPS Enables Production Of Highly Potent G

Hashimoto, Takuya / Suenaga, Hikaru / Amagai, Keita / Hashimoto, Junko / Kozone, Ikuko / Takahashi, Shunji / Shin-Ya, Kazuo

Angewandte Chemie (International ed. in English)

2024 Volume 63, Issue 10, Page(s) e202317805

Abstract: Heterotrimeric G proteins are key mediators in the signaling of G protein-coupled receptors (GPCR) that are involved in a plethora of important physiological processes and thus major targets of pharmaceutical drugs. The cyclic depsipeptides YM-254890 and ...

Abstract	Heterotrimeric G proteins are key mediators in the signaling of G protein-coupled receptors (GPCR) that are involved in a plethora of important physiological processes and thus major targets of pharmaceutical drugs. The cyclic depsipeptides YM-254890 and FR900359 are strong and selective inhibitors of the G
MeSH term(s)	GTP-Binding Protein alpha Subunits, Gq-G11/metabolism ; Depsipeptides/chemistry ; Receptors, G-Protein-Coupled/metabolism ; Antineoplastic Agents
Chemical Substances	FR900359 ; GTP-Binding Protein alpha Subunits, Gq-G11 (EC 3.6.5.1) ; Depsipeptides ; Receptors, G-Protein-Coupled ; Antineoplastic Agents
Language	English
Publishing date	2024-02-02
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202317805
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Article ; Online: Carrier Protein Mediated Formation of the Dihydropyridazinone Ring in Actinopyridazinone Biosynthesis.

Arima, Kuga / Akiyama, Satoko / Shin-Ya, Kazuo / Matsuda, Kenichi / Wakimoto, Toshiyuki

Angewandte Chemie (International ed. in English)

2023 Volume 62, Issue 29, Page(s) e202305155

Abstract: Heterocycles with nitrogen-nitrogen (N-N) bonds are privileged building blocks of synthetic drugs. They are also found in natural products, although the biosynthetic logic behind them is poorly understood. Actinopyridazinones produced by Streptomyces sp. ...

Abstract	Heterocycles with nitrogen-nitrogen (N-N) bonds are privileged building blocks of synthetic drugs. They are also found in natural products, although the biosynthetic logic behind them is poorly understood. Actinopyridazinones produced by Streptomyces sp. MSD090630SC-05 possess unique dihydropyridazinone rings that have been studied as core nuclei in several approved synthetic therapeutics. Herein, we performed gene knockouts and in vitro biochemical experiments to elucidate the major steps in actinopyridazinone biosynthesis, including the unprecedented carrier protein mediated machinery for dihydropyridazinone formation.
MeSH term(s)	Carrier Proteins/metabolism ; Streptomyces/metabolism ; Biological Products/chemistry ; Nitrogen/metabolism ; Multigene Family
Chemical Substances	Carrier Proteins ; Biological Products ; Nitrogen (N762921K75)
Language	English
Publishing date	2023-06-06
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202305155
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Article ; Online: Identification of the Cirratiomycin Biosynthesis Gene Cluster in Streptomyces Cirratus: Elucidation of the Biosynthetic Pathways for 2,3-Diaminobutyric Acid and Hydroxymethylserine.

Sakata, Shunki / Li, Jiafeng / Yasuno, Yoko / Shinada, Tetsuro / Shin-Ya, Kazuo / Katsuyama, Yohei / Ohnishi, Yasuo

Chemistry (Weinheim an der Bergstrasse, Germany)

2024 , Page(s) e202400271

Abstract: Cirratiomycin, a heptapeptide with antibacterial activity, was isolated and characterized in 1981; however, its biosynthetic pathway has not been elucidated. It contains several interesting nonproteinogenic amino acids, such as (2S,3S)-2,3-diaminobutyric ...

Abstract	Cirratiomycin, a heptapeptide with antibacterial activity, was isolated and characterized in 1981; however, its biosynthetic pathway has not been elucidated. It contains several interesting nonproteinogenic amino acids, such as (2S,3S)-2,3-diaminobutyric acid ((2S,3S)-DABA) and α-(hydroxymethyl)serine, as building blocks. Here, we report the identification of a cirratiomycin biosynthetic gene cluster in Streptomyces cirratus. Bioinformatic analysis revealed that several Streptomyces viridifaciens and Kitasatospora aureofaciens strains also have this cluster. One S. viridifaciens strain was confirmed to produce cirratiomycin. The biosynthetic gene cluster was shown to be responsible for cirratiomycin biosynthesis in S. cirratus in a gene inactivation experiment using CRISPR-cBEST. Interestingly, this cluster encodes a nonribosomal peptide synthetase (NRPS) composed of 12 proteins, including those with an unusual domain organization: a stand-alone adenylation domain, two stand-alone condensation domains, two type II thioesterases, and two NRPS modules that have no adenylation domain. Using heterologous expression and in vitro analysis of recombinant enzymes, we revealed the biosynthetic pathway of (2S,3S)-DABA: (2S,3S)-DABA is synthesized from l-threonine by four enzymes, CirR, CirS, CirQ, and CirB. In addition, CirH, a glycine/serine hydroxymethyltransferase homolog, was shown to synthesize α-(hydroxymethyl)serine from d-serine in vitro. These findings broaden our knowledge of nonproteinogenic amino acid biosynthesis.
Language	English
Publishing date	2024-03-08
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202400271
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Article ; Online: $$\textrm{O}^+$$ O + density distribution in the nightside ionosphere reconstructed from ISS-IMAP/EUVI data

Shin’ya Nakano / Yuta Hozumi / Akinori Saito / Ichiro Yoshikawa / Atsushi Yamazaki / Kazuo Yoshioka / Go Murakami

Earth, Planets and Space, Vol 76, Iss 1, Pp 1-

2024 Volume 18

Abstract: Abstract The $$\textrm{O}^+$$ O + density distribution in the nightside ionosphere has been reconstructed from extreme ultraviolet (EUV) images taken by the EUVI-B imager of the International Space Station Ionosphere, Mesosphere, upper Atmosphere, and ... ...

Abstract	Abstract The $$\textrm{O}^+$$ O + density distribution in the nightside ionosphere has been reconstructed from extreme ultraviolet (EUV) images taken by the EUVI-B imager of the International Space Station Ionosphere, Mesosphere, upper Atmosphere, and Plasmasphere mapping (ISS-IMAP) cameras. The EUVI-B imager covers the wavelength range from about 70 nm to 110 nm and mainly observes the 91.1 nm emission from the recombination of $$\textrm{O}^+$$ O + ions and electrons. Assuming that the electron density is equal to the $$\textrm{O}^+$$ O + density in the F-region where the imager observes, the EUV intensity observed by EUVI-B is approximately proportional to the line-of-sight integral of the square of the $$\textrm{O}^+$$ O + density. This enables us to estimate the $$\textrm{O}^+$$ O + density distribution in the F-region from a sequence of EUVI-B data in each International Space Station (ISS) orbit with a Bayesian method. We demonstrate the reconstruction of the $$\textrm{O}^+$$ O + distribution. In particular, the $$\textrm{O}^+$$ O + density structure of the equatorial ionization anomaly (EIA) in the vicinity of an ISS orbit is obtained. Graphical Abstract
Keywords	$$\textrm{O}^+$$ O + ion distribution ; Ionosphere ; Extreme ultraviolet measurement ; Geography. Anthropology. Recreation ; G ; Geodesy ; QB275-343 ; Geology ; QE1-996.5
Subject code	541
Language	English
Publishing date	2024-01-01T00:00:00Z
Publisher	SpringerOpen
Document type	Article ; Online
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Article ; Online: Notch activator cyclopiazonic acid induces apoptosis in HL-60 cells through calcineurin activation.

Suzuki, Shiina / Saito, Shun / Narushima, Yuki / Kodani, Shunta / Kagaya, Noritaka / Suenaga, Hikaru / Shin-Ya, Kazuo / Arai, Midori A

The Journal of antibiotics

2023 Volume 77, Issue 1, Page(s) 30–38

Abstract: We screened a library of microbial extracts and compounds library using our constructed assay cells and found pulicatins F (1) and G (2), and cyclopiazonic acid (CPA) (3) as Notch activators. Pulicatin F (1) and (±)-pulicatin G were synthesized and their ...

Abstract	We screened a library of microbial extracts and compounds library using our constructed assay cells and found pulicatins F (1) and G (2), and cyclopiazonic acid (CPA) (3) as Notch activators. Pulicatin F (1) and (±)-pulicatin G were synthesized and their activities were evaluated. Notch activation of CPA (3) was investigated using Western blot and RT-PCR. CPA (3) increased protein level of HES1 and mRNA expression of HES1. Also, the expression of FMS-like tyrosine kinase 3 (FLT3), which was known to inhibit apoptosis, was also inhibited by CPA (3) addition. The Notch activation by CPA (3) and cytotoxicity against HL-60 were clearly canceled by addition of FK506, which is an inhibitor of calcineurin (CaN). In addition, it was revealed that CPA (3) induced apoptosis in HL-60 cells.
MeSH term(s)	Humans ; HL-60 Cells ; Calcineurin ; Apoptosis ; Indoles/pharmacology
Chemical Substances	Calcineurin (EC 3.1.3.16) ; cyclopiazonic acid (X9TLY4580Z) ; Indoles
Language	English
Publishing date	2023-11-08
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	390800-8
ISSN	1881-1469 ; 0021-8820 ; 0368-3532
ISSN (online)	1881-1469
ISSN	0021-8820 ; 0368-3532
DOI	10.1038/s41429-023-00673-4
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Article ; Online: Bacterial Avenalumic Acid Biosynthesis Includes Substitution of an Aromatic Amino Group for Hydride by Nitrous Acid Dependent Diazotization.

Kawai, Seiji / Hagihara, Ryota / Shin-Ya, Kazuo / Katsuyama, Yohei / Ohnishi, Yasuo

Angewandte Chemie (International ed. in English)

2022 Volume 61, Issue 45, Page(s) e202211728

Abstract: The diazo group is an important functional group that can confer biological activity to natural products owing to its high reactivity. Recent studies have revealed that diazo groups are synthesized from amino groups using nitrous acid in secondary ... ...

Abstract	The diazo group is an important functional group that can confer biological activity to natural products owing to its high reactivity. Recent studies have revealed that diazo groups are synthesized from amino groups using nitrous acid in secondary metabolites of actinomycetes. However, genome database analysis indicated that there are still many diazo group-biosynthesizing enzymes for unknown biosynthetic pathways. Here, we discovered an avenalumic acid biosynthesis gene cluster in Streptomyces sp. RI-77 by genome mining of enzymes involved in diazo group formation. Through heterologous expression, the gene cluster was revealed to direct avenalumic acid (AVA) biosynthesis via 3-aminoavenalumic acid (3-AAA). In vitro enzyme assays showed that AvaA6 and AvaA7 catalyzed the diazotization of 3-AAA using nitrous acid and substitution of the diazo group for hydride to synthesize AVA, respectively. This study revealed an unprecedented pathway for amino group removal via diazotization.
MeSH term(s)	Nitrous Acid/metabolism ; Streptomyces/metabolism ; Biosynthetic Pathways/genetics ; Multigene Family ; Biological Products/metabolism ; Bacterial Proteins/metabolism
Chemical Substances	Nitrous Acid (T2I5UM75DN) ; Biological Products ; Bacterial Proteins
Language	English
Publishing date	2022-10-07
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202211728
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Article ; Online: Acyltransferase Domain Exchange between Two Independent Type I Polyketide Synthases in the Same Producer Strain of Macrolide Antibiotics.

Kudo, Fumitaka / Kishikawa, Kosuke / Tsuboi, Kazuma / Kido, Takafusa / Usui, Takeo / Hashimoto, Junko / Shin-Ya, Kazuo / Miyanaga, Akimasa / Eguchi, Tadashi

Chembiochem : a European journal of chemical biology

2023 Volume 24, Issue 6, Page(s) e202200670

Abstract: Streptomyces graminofaciens A-8890 produces two macrolide antibiotics, FD-891 and virustomycin A, both of which show significant biological activity. In this study, we identified the virustomycin A biosynthetic gene cluster, which encodes type I ... ...

Abstract	Streptomyces graminofaciens A-8890 produces two macrolide antibiotics, FD-891 and virustomycin A, both of which show significant biological activity. In this study, we identified the virustomycin A biosynthetic gene cluster, which encodes type I polyketide synthases (PKSs), ethylmalonyl-CoA biosynthetic enzymes, methoxymalony-acyl carrier protein biosynthetic enzymes, and post-PKS modification enzymes. Next, we demonstrated that the acyltransferase domain can be exchanged between the Vsm PKSs and the PKSs involved in FD-891 biosynthesis (Gfs PKSs), without any supply problems of the unique extender units. We exchanged the malonyltransferase domain in the loading module of Gfs PKS with the ethylmalonyltransferase domain and the methoxymalonyltransferase domain of Vsm PKSs. Consequently, the expected two-carbon-elongated analog 26-ethyl-FD-891 was successfully produced with a titer comparable to FD-891 production by the wild type; however, exchange with the methoxymalonyltransferase domain did not produce any FD-891 analogs. Furthermore, 26-ethyl-FD-891 showed potent cytotoxic activity against HeLa cells, like natural FD-891.
MeSH term(s)	Humans ; Polyketide Synthases/genetics ; Polyketide Synthases/metabolism ; Acyltransferases/genetics ; Acyltransferases/metabolism ; HeLa Cells ; Macrolides/pharmacology ; Macrolides/metabolism ; Anti-Bacterial Agents/pharmacology
Chemical Substances	Polyketide Synthases (79956-01-7) ; virustomycin A (84777-85-5) ; FD 891 (142383-53-7) ; Acyltransferases (EC 2.3.-) ; Macrolides ; Anti-Bacterial Agents
Language	English
Publishing date	2023-02-09
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2020469-3
ISSN	1439-7633 ; 1439-4227
ISSN (online)	1439-7633
ISSN	1439-4227
DOI	10.1002/cbic.202200670
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Article ; Online: Collagen Lattice Model, Populated with Heterogeneous Cancer-Associated Fibroblasts, Facilitates Advanced Reconstruction of Pancreatic Cancer Microenvironment.

Song, Xiaoyu / Nihashi, Yuma / Imai, Yukiko / Mori, Nobuhito / Kagaya, Noritaka / Suenaga, Hikaru / Shin-Ya, Kazuo / Yamamoto, Masamichi / Setoyama, Daiki / Kunisaki, Yuya / Kida, Yasuyuki S

International journal of molecular sciences

2024 Volume 25, Issue 7

Abstract: Pancreatic ductal adenocarcinoma (PDAC) is a solid-tumor malignancy. To enhance the treatment landscape of PDAC, a 3D model optimized for rigorous drug screening is essential. Within the PDAC tumor microenvironment, a dense stroma comprising a large ... ...

Abstract	Pancreatic ductal adenocarcinoma (PDAC) is a solid-tumor malignancy. To enhance the treatment landscape of PDAC, a 3D model optimized for rigorous drug screening is essential. Within the PDAC tumor microenvironment, a dense stroma comprising a large extracellular matrix and cancer-associated fibroblasts (CAFs) is well-known for its vital role in modulating tumor growth, cellular heterogeneity, bidirectional paracrine signaling, and chemoresistance. In this study, we employed a fibroblast-populated collagen lattice (FPCL) modeling approach that has the ability to replicate fibroblast contractility in the collagenous matrix to build dense stroma. This FPCL model allows CAF differentiation by facilitating multifaceted cell-cell interactions between cancer cells and CAFs, with the differentiation further influenced by mechanical forces and hypoxia carried within the 3D structure. Our FPCL models displayed hallmark features, including ductal gland structures and differentiated CAFs with spindle shapes. Through morphological explorations alongside in-depth transcriptomic and metabolomic profiling, we identified substantial molecular shifts from the nascent to mature model stages and potential metabolic biomarkers, such as proline. The initial pharmacological assays highlighted the effectiveness of our FPCL model in screening for improved therapeutic strategies. In conclusion, our PDAC modeling platform mirrors complex tumor microenvironmental dynamics and offers an unparalleled perspective for therapeutic exploration.
MeSH term(s)	Humans ; Tumor Microenvironment ; Cancer-Associated Fibroblasts ; Pancreas ; Pancreatic Hormones ; Collagen ; Pancreatic Neoplasms ; Carcinoma, Pancreatic Ductal
Chemical Substances	Pancreatic Hormones ; Collagen (9007-34-5)
Language	English
Publishing date	2024-03-27
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms25073740
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Article ; Online: Capability of a large bacterial artificial chromosome clone harboring multiple biosynthetic gene clusters for the production of diverse compounds.

Kudo, Kei / Nishimura, Takehiro / Izumikawa, Miho / Kozone, Ikuko / Hashimoto, Junko / Fujie, Manabu / Suenaga, Hikaru / Ikeda, Haruo / Satoh, Nori / Shin-Ya, Kazuo

The Journal of antibiotics

2024 Volume 77, Issue 5, Page(s) 288–298

Abstract: The biosynthetic gene clusters (BGCs) for the macrocyclic lactone-based polyketide compounds are extremely large-sized because the polyketide synthases that generate the polyketide chains of the basic backbone are of very high molecular weight. In ... ...

Abstract	The biosynthetic gene clusters (BGCs) for the macrocyclic lactone-based polyketide compounds are extremely large-sized because the polyketide synthases that generate the polyketide chains of the basic backbone are of very high molecular weight. In developing a heterologous expression system for the large BGCs amenable to the production of such natural products, we selected concanamycin as an appropriate target. We obtained a bacterial artificial chromosome (BAC) clone with a 211-kb insert harboring the entire BGC responsible for the biosynthesis of concanamycin. Heterologous expression of this clone in a host strain, Streptomyces avermitilis SUKA32, permitted the production of concanamycin, as well as that of two additional aromatic polyketides. Structural elucidation identified these additional products as ent-gephyromycin and a novel compound that was designated JBIR-157. We describe herein sequencing and expression studies performed on these BGCs, demonstrating the utility of large BAC clones for the heterologous expression of cryptic or near-silent loci.
MeSH term(s)	Streptomyces/genetics ; Streptomyces/metabolism ; Multigene Family ; Chromosomes, Artificial, Bacterial/genetics ; Cloning, Molecular ; Polyketide Synthases/genetics ; Polyketide Synthases/metabolism ; Polyketides/metabolism ; Biological Products/metabolism
Chemical Substances	Polyketide Synthases (79956-01-7) ; Polyketides ; Biological Products
Language	English
Publishing date	2024-03-04
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	390800-8
ISSN	1881-1469 ; 0021-8820 ; 0368-3532
ISSN (online)	1881-1469
ISSN	0021-8820 ; 0368-3532
DOI	10.1038/s41429-024-00711-9
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