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Journal articles on the topic 'N6-Isopentenyladenosine'

Author: Grafiati

Published: 10 March 2023

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1

Fiore, Donatella, Chiara Piscopo, Maria Proto, Michele Vasaturo, Fabrizio Dal Piaz, Bruno Fusco, Cristina Pagano, Chiara Laezza, Maurizio Bifulco, and Patrizia Gazzerro. "N6-Isopentenyladenosine Inhibits Colorectal Cancer and Improves Sensitivity to 5-Fluorouracil Targeting FBXW7 Tumor Suppressor." Cancers 11, no. 10 (September 28, 2019): 1456. http://dx.doi.org/10.3390/cancers11101456.

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N6-isopentenyladenosine has been shown to exert potent in vitro antitumor activity on different human cancers, including colorectal cancer. Although some potential biochemical targets have been identified, its precise mechanism of action remains unclear. We found that N6-isopentenyladenosine affects colorectal cancer proliferation in in vitro models carrying different mutational status of FBXW7 and TP53 genes, and in HCT116 xenografts in SCID mice, by increasing the expression of the well-established tumor suppressor FBXW7, a component of the SCF-E3 ubiquitin ligase complex that promotes degradation of various oncoproteins and transcription factors, such as c-Myc, SREBP and Mcl1. Corroborating our previous studies, we identified for the first time the FBXW7/SREBP/FDPS axis as a target of the compound. Pull down of ubiquitinated proteins, immunoprecipitation and luciferase assays, reveal that through the increase of FBXW7/c-Myc binding, N6-isopentenyladenosine induces the ubiquitination of c-Myc, inhibiting its transcriptional activity. Moreover, in FBXW7- and TP53-wild type cells, N6-isopentenyladenosine strongly synergizes with 5-Fluorouracil to inhibit colon cancer growth in vitro. Our results provide novel insights into the molecular mechanism of N6-isopentenyladenosine, revealing its multi-targeting antitumor action, in vitro and in vivo. Restoring of FBXW7 tumor-suppressor represents a valid therapeutic tool, enabling N6-isopentenyladenosine as optimizable compound for patient-personalized therapies in colorectal cancer.

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2

HASHIZUME, Takeshi, Wataru TANIGUCHI, and Tamiji SUGIYAMA. "Mass spectrometric determination of N6-isopentenyladenosine and N6-isopentenyladenine from human urine." Analytical Sciences 2, no. 2 (1986): 157–59. http://dx.doi.org/10.2116/analsci.2.157.

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3

Colombo, Francesca, F. Stefania Falvella, Loris De Cecco, Monica Tortoreto, Graziella Pratesi, Pierangela Ciuffreda, Roberta Ottria, et al. "Pharmacogenomics and analogues of the antitumour agent N6-isopentenyladenosine." International Journal of Cancer 124, no. 9 (May 1, 2009): 2179–85. http://dx.doi.org/10.1002/ijc.24168.

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4

Chmur, Magdalena, Andrzej Bajguz, and Alicja Piotrowska-Niczyporuk. "Effect of Cadmium on the Level of Isoprenoid-Derived Phytohormones in Duckweed Wolffia arrhiza." Journal of Plant Growth Regulation 39, no. 4 (May 28, 2020): 1518–30. http://dx.doi.org/10.1007/s00344-020-10154-9.

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AbstractWolffia arrhiza (L.) Horkel ex Wimm. is an aquatic plant belonging to the Lemnaceae family. It does not have leaves, stems, and roots, flowers rarely occur, while body size can reach 1 mm of width and 1.3 mm of length. The present study demonstrates the endogenous level of isoprenoid-derived phytohormones and their changes under the influence of different cadmium (Cd) concentrations (0.1, 1, 10, and 100 µM). A liquid chromatography quadrupole-time-of-flight mass spectrometry analysis indicated the presence of abscisic acid, eight brassinosteroids (6-deoxocastasterone, 6-deoxotyphasterol, cathasterone, typhasterol, castasterone, 24-epicastasterone, brassinolide, and 28-homobrassinolide), seven free bases of cytokinins [trans-zeatin (tZ), cis-zeatin (cZ), dihydrozeatin (DHZ), N6-isopentenyladenine, N6-isopentenyladenosine, ortho-topolin, and meta-topolin], eight conjugates of cytokinins (tZ riboside, tZ-9-glucoside, tZ-7-glucoside, tZ-O-glucoside riboside, cZ-9-glucoside, DHZ riboside, DHZ-O-glucoside, and N6-isopentenyladenosine-7-glucoside) and gibberellic acid (GA3) in this duckweed. The level of phytohormones in plants treated with Cd has changed, e.g., the ABA level increased while GA3 decreased. Whereas the amount of BRs and CKs was different in Cd dose-dependent manner. Besides, it is worth noting that the distribution of 25 various phytohormones in the Wolffia arrhiza is reported for the first time.

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5

Dassano, Alice, Mariateresa Mancuso, Paola Giardullo, Loris De Cecco, Pierangela Ciuffreda, Enzo Santaniello, Anna Saran, Tommaso A. Dragani, and Francesca Colombo. "N6-isopentenyladenosine and analogs activate the NRF2-mediated antioxidant response." Redox Biology 2 (2014): 580–89. http://dx.doi.org/10.1016/j.redox.2014.03.001.

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6

Bifulco, Maurizio, Anna Malfitano, Maria Proto, Antonietta Santoro, Maria Caruso, and Chiara Laezza. "Biological and Pharmacological Roles of N6-Isopentenyladenosine: An Emerging Anticancer Drug." Anti-Cancer Agents in Medicinal Chemistry 8, no. 2 (February 1, 2008): 200–204. http://dx.doi.org/10.2174/187152008783497028.

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7

Kierzek, Elżbieta, and Ryszard Kierzek. "Influence of N6-isopentenyladenosine (i6A) on thermal stability of RNA duplexes." Biophysical Chemistry 91, no. 2 (July 2001): 135–40. http://dx.doi.org/10.1016/s0301-4622(01)00165-x.

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8

Rajabi, Mehdi, Jamshid Mehrzad, Elena Gorincioi, and Enzo Santaniello. "Antiproliferative Activity of N6-Isopentenyladenosine on HCT-15 Colon Carcinoma Cell Line." Nucleic Acid Therapeutics 21, no. 5 (October 2011): 355–58. http://dx.doi.org/10.1089/nat.2011.0314.

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9

Spinola, Monica, Francesca Colombo, F. Stefania Falvella, and Tommaso A. Dragani. "N6-isopentenyladenosine: A potential therapeutic agent for a variety of epithelial cancers." International Journal of Cancer 120, no. 12 (2007): 2744–48. http://dx.doi.org/10.1002/ijc.22601.

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10

Laezza, Chiara, Angelo Migliaro, Rosalba Cerbone, Idolo Tedesco, Mariarosaria Santillo, Corrado Garbi, and Maurizio Bifulco. "N6-Isopentenyladenosine Affects cAMP-Dependent Microfilament Organization in FRTL-5 Thyroid Cells." Experimental Cell Research 234, no. 1 (July 1997): 178–82. http://dx.doi.org/10.1006/excr.1997.3610.

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11

Covelli, Verdiana, Manuela Grimaldi, Rosario Randino, Mohammad Firoznezhad, Maria Chiara Proto, Veronica De Simone, Gianluca Matteoli, et al. "Towards an Improvement of Anticancer Activity of Benzyl Adenosine Analogs." Molecules 26, no. 23 (November 25, 2021): 7146. http://dx.doi.org/10.3390/molecules26237146.

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N6-Isopentenyladenosine (i6A) is a naturally occurring modified nucleoside displaying in vitro and in vivo antiproliferative and pro-apoptotic properties. In our previous studies, including an in silico inverse virtual screening, NMR experiments and in vitro enzymatic assays, we demonstrated that i6A targeted farnesyl pyrophosphate synthase (FPPS), a key enzyme involved in the mevalonate (MVA) pathway and prenylation of downstream proteins, which are aberrant in several cancers. Following our interest in the anticancer effects of FPPS inhibition, we developed a panel of i6A derivatives bearing bulky aromatic moieties in the N6 position of adenosine. With the aim of clarifying molecular action of N6-benzyladenosine analogs on the FPPS enzyme inhibition and cellular toxicity and proliferation, herein we report the evaluation of the N6-benzyladenosine derivatives’ (compounds 2a–m) effects on cell viability and proliferation on HCT116, DLD-1 (human) and MC38 (murine) colorectal cancer cells (CRC). We found that compounds 2, 2a and 2c showed a persistent antiproliferative effect on human CRC lines and compound 2f exerted a significant effect in impairing the prenylation of RAS and Rap-1A proteins, confirming that the antitumor activity of 2f was related to the ability to inhibit FPPS activity.

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12

Castiglioni, Sara, Silvana Casati, Roberta Ottria, Pierangela Ciuffreda, and Jeanette A.M. Maier. "N6-Isopentenyladenosine and its Analogue N6-Benzyladenosine Induce Cell Cycle Arrest and Apoptosis in Bladder Carcinoma T24 Cells." Anti-Cancer Agents in Medicinal Chemistry 13, no. 4 (March 1, 2013): 672–78. http://dx.doi.org/10.2174/1871520611313040016.

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13

Gillman, E. C., L. B. Slusher, N. C. Martin, and A. K. Hopper. "MOD5 translation initiation sites determine N6-isopentenyladenosine modification of mitochondrial and cytoplasmic tRNA." Molecular and Cellular Biology 11, no. 5 (May 1991): 2382–90. http://dx.doi.org/10.1128/mcb.11.5.2382-2390.1991.

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MOD5 is one of several genes that code for enzymes found in mitochondria and another cellular compartment. Like other such genes, it contains two in-frame ATGs that could be used to produce two proteins, differing from each other by an amino-terminal extension. Certain other genes produce heterogeneous mRNAs with some 5' ends falling upstream of the longest open reading frame and some 5' ends falling between the first and second ATGs. In these cases, selection of transcription start sites appears to play a significant role in translation start site selection. MOD5, in contrast, produces mRNAs with 5' ends that all fall upstream of both ATGs. To determine how MOD5 encodes isozymes that are located in different cellular compartments and to determine whether they differ in structure, we constructed MOD5 and MOD5-COXIV fusions with mutations of the first, second, or both ATGs. The effect of these alterations on protein production, tRNA modification, and cellular location was assessed. Both the first and second ATGs are used to produce MOD5 protein in vivo, but only the long form of the protein is imported into mitochondria. Thus, the first 11 amino acids present on the amino-terminal extended protein are necessary for mitochondrial import. Surprisingly, this extension does not promote complete import of the long form of the protein, but rather a functional pool of the extended protein remains in the cytoplasm. The amino-terminal extension is also unusual because it is probably not proteolytically removed upon import and therefore does not constitute part of a mitochondrial presequence.

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14

Gillman, E. C., L. B. Slusher, N. C. Martin, and A. K. Hopper. "MOD5 translation initiation sites determine N6-isopentenyladenosine modification of mitochondrial and cytoplasmic tRNA." Molecular and Cellular Biology 11, no. 5 (May 1991): 2382–90. http://dx.doi.org/10.1128/mcb.11.5.2382.

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MOD5 is one of several genes that code for enzymes found in mitochondria and another cellular compartment. Like other such genes, it contains two in-frame ATGs that could be used to produce two proteins, differing from each other by an amino-terminal extension. Certain other genes produce heterogeneous mRNAs with some 5' ends falling upstream of the longest open reading frame and some 5' ends falling between the first and second ATGs. In these cases, selection of transcription start sites appears to play a significant role in translation start site selection. MOD5, in contrast, produces mRNAs with 5' ends that all fall upstream of both ATGs. To determine how MOD5 encodes isozymes that are located in different cellular compartments and to determine whether they differ in structure, we constructed MOD5 and MOD5-COXIV fusions with mutations of the first, second, or both ATGs. The effect of these alterations on protein production, tRNA modification, and cellular location was assessed. Both the first and second ATGs are used to produce MOD5 protein in vivo, but only the long form of the protein is imported into mitochondria. Thus, the first 11 amino acids present on the amino-terminal extended protein are necessary for mitochondrial import. Surprisingly, this extension does not promote complete import of the long form of the protein, but rather a functional pool of the extended protein remains in the cytoplasm. The amino-terminal extension is also unusual because it is probably not proteolytically removed upon import and therefore does not constitute part of a mitochondrial presequence.

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15

Scrima, Mario, Gianluigi Lauro, Manuela Grimaldi, Sara Di Marino, Alessandra Tosco, Paola Picardi, Patrizia Gazzerro, et al. "Structural Evidence of N6-Isopentenyladenosine As a New Ligand of Farnesyl Pyrophosphate Synthase." Journal of Medicinal Chemistry 57, no. 18 (September 15, 2014): 7798–803. http://dx.doi.org/10.1021/jm500869x.

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16

Ciaglia, Elena, Chiara Laezza, Mario Abate, Simona Pisanti, Roberta Ranieri, Alba D'alessandro, Paola Picardi, Patrizia Gazzerro, and Maurizio Bifulco. "Recognition by natural killer cells of N6-isopentenyladenosine-treated human glioma cell lines." International Journal of Cancer 142, no. 1 (September 21, 2017): 176–90. http://dx.doi.org/10.1002/ijc.31036.

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17

Li, Miao, Yonghao Qi, Jing Wei, Lulu Lu, Xuan Zhao, and Lijun Zhou. "N6-Isopentenyladenosine promoted HeLa cell apoptosis through inhibitions of AKT and transforming growth factor β–activated kinase 1 activation." Tumor Biology 39, no. 3 (March 2017): 101042831769596. http://dx.doi.org/10.1177/1010428317695966.

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N6-Isopentenyladenosine, a member of the family of plant hormones, possesses anti-cancer activities on a number of cancer cell lines. However, its mode of action in cervical cancer cell remains poorly understood. Our computational docking studies showed that N6-Isopentenyladenosine could bind with the really interesting new gene domain of tumor necrosis factor receptor–associated factor 6, which is an ubiquitination E3 ligase. Tumor necrosis factor receptor–associated factor 6–mediated ubiquitination is known to activate both protein kinase B (also known as AKT) and transforming growth factor β–activated kinase 1, and the really interesting new gene domain comprises the core of the ubiquitin ligase catalytic domain. First, we evaluated the effects of iPA on cervical cancer cell line HeLa using MTT and flow cytometry. Second, we examined the effects of iPA on activation of tumor necrosis factor receptor–associated factor 6–mediated downstream targets using western blot or immunoprecipitation. iPA could reduce HeLa cell proliferation through apoptosis, and such anti-cancer activity is associated with inhibitions of both AKT and transforming growth factor β–activated kinase 1 signaling pathways. In addition, suppression of the anti-apoptotic protein Bcl-2 and elevation of the pro-apoptotic protein Bax were also observed. Anti-proliferation properties of iPA are likely due to its binding at the really interesting new gene domain of tumor necrosis factor receptor–associated factor 6 and loss of AKT and transforming growth factor β–activated kinase 1 activities as a result of functional modulations of tumor necrosis factor receptor–associated factor 6. These results support the emerging notion that tumor necrosis factor receptor–associated factor 6 could serve as a viable target for developing new cancer therapeutics.

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18

Fakruddin, Md, Fan Yan Wei, Shohei Emura, Shigeru Matsuda, Takehiro Yasukawa, Dongchon Kang, and Kazuhito Tomizawa. "Cdk5rap1-mediated 2-methylthio-N6-isopentenyladenosine modification is absent from nuclear-derived RNA species." Nucleic Acids Research 45, no. 20 (September 14, 2017): 11954–61. http://dx.doi.org/10.1093/nar/gkx819.

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19

Pisanti, Simona, Paola Picardi, Elena Ciaglia, Luigi Margarucci, Roberto Ronca, Arianna Giacomini, Anna Maria Malfitano, et al. "Antiangiogenic effects of N6‐isopentenyladenosine, an endogenous isoprenoid end product, mediated by AMPK activation." FASEB Journal 28, no. 3 (November 21, 2013): 1132–44. http://dx.doi.org/10.1096/fj.13-238238.

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20

Laezza, Chiara, Maria Notarnicola, Maria Gabriella Caruso, Caterina Messa, Marco Macchia, Simone Bertini, Filippo Minutolo, et al. "N6‐isopentenyladenosine arrests tumor cell proliferation by inhibiting farnesyl diphosphate synthase and protein prenylation." FASEB Journal 20, no. 3 (March 2006): 412–18. http://dx.doi.org/10.1096/fj.05-4044lsf.

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21

Petrullo, L. A., and D. Elseviers. "Effect of a 2-methylthio-N6-isopentenyladenosine deficiency on peptidyl-tRNA release in Escherichia coli." Journal of Bacteriology 165, no. 2 (1986): 608–11. http://dx.doi.org/10.1128/jb.165.2.608-611.1986.

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22

Pagano, Cristina, Laura Coppola, Giovanna Navarra, Giorgio Avilia, Sara Bruzzaniti, Erica Piemonte, Mario Galgani, et al. "N6-Isopentenyladenosine Impairs Mitochondrial Metabolism through Inhibition of EGFR Translocation on Mitochondria in Glioblastoma Cells." Cancers 14, no. 24 (December 8, 2022): 6044. http://dx.doi.org/10.3390/cancers14246044.

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Glioblastoma multiforme (GBM) is the most aggressive malignant brain tumor and is poorly susceptible to cytotoxic therapies. Amplification of the epidermal growth factor receptor (EGFR) and deletion of exons 2 to 7, which generates EGFR variant III (vIII), are the most common molecular alterations of GBMs that contribute to the aggressiveness of the disease. Recently, it has been shown that EGFR/EGFRvIII-targeted inhibitors enhance mitochondrial translocation by causing mitochondrial accumulation of these receptors, promoting the tumor drug resistance; moreover, they negatively modulate intrinsic mitochondria-mediated apoptosis by sequestering PUMA, leading to impaired apoptotic response in GBM cells. N6-isopentenyladenosine (i6A or iPA), a cytokinin consisting of an adenosine linked to an isopentenyl group deriving from the mevalonate pathway, has antiproliferative effects on numerous tumor cells, including GBM cells, by inducing cell death in vitro and in vivo. Here, we observed that iPA inhibits the mitochondrial respiration in GBM cells by preventing the translocation of EGFR/EGFRvIII to the mitochondria and allowing PUMA to interact with them by promoting changes in mitochondrial activity, thus playing a critical role in cell death. Our findings clearly demonstrate that iPA interferes with mitochondrial bioenergetic capacity, providing a rationale for an effective strategy for treating GBM.

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23

Yamamoto, Takahiro, Atsushi Fujimura, Wei Fan-Yan, Keitarou Kai, Tatsuya Takezaki, Kazutaka Ohta, Jun-Ichirou Kuroda, Naoki Shinojima, Kazuhito Tomizawa, and Akitake Mukasa. "BOT-02 2-METHYLTHIO MODIFICATION OF N6-ISOPENTENYLADENOSINE IN MITOCHONDRIAL TRNAS BY CDK5RAP1 PROMOTES THE MAINTENANCE OF GLIOMA-INITIATING CELLS." Neuro-Oncology Advances 1, Supplement_2 (December 2019): ii12. http://dx.doi.org/10.1093/noajnl/vdz039.054.

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Abstract 2-Methylthio-N6-isopentenyl modification of adenosine (ms2i6A) is an evolutionally conserved modification that is found in mitochondrial (mt)-tRNAs. Cdk5 regulatory subunit-associated protein 1 (CDK5RAP1) specifically converts N6-isopentenyladenosine (i6A) to ms2i6A at position A37 of four mt-DNA-encoded tRNAs, and the modification regulates efficient mitochondrial translation and energy metabolism in mammals. Here, we report that the ms2 conversion mediated by CDK5RAP1 in mt-tRNAs is required to sustain glioma-initiating cell (GIC)-related traits. CDK5RAP1 maintained the self-renewal capacity, undifferentiated state, and tumorigenic potential of GICs. This regulation was not related to the translational control of mt-proteins. CDK5RAP1 abrogated the antitumor effect of i6A by converting i6A to ms2i6A and protected GICs from excessive autophagy triggered by i6A. The elevated activity of CDK5RAP1 contributed to the amelioration of the cytotoxic effect of i6A and promoted GIC maintenance. The hypoxic microenvironment in the tumor core activated CDK5RAP1, whose activity was inversely correlated with the oxygen concentration because of two [4Fe-4S] clusters in the enzyme. This work demonstrates that CDK5RAP1 is crucial for the detoxification of endogenous i6A and that GICs readily utilize this mechanism for survival.

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24

Castiglioni, Sara, Valentina Romeo, Silvana Casati, Roberta Ottria, Cristiana Perrotta, Pierangela Ciuffreda, and Jeanette A. M. Maier. "N6-isopentenyladenosine a new potential anti-angiogenic compound that targets human microvascular endothelial cells in vitro." Nucleosides, Nucleotides & Nucleic Acids 37, no. 10 (October 3, 2018): 533–45. http://dx.doi.org/10.1080/15257770.2018.1503673.

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25

Laezza, Chiara, Maria Gabriella Caruso, Teresa Gentile, Maria Notarnicola, Anna Maria Malfitano, Tiziana Di Matola, Caterina Messa, Patrizia Gazzerro, and Maurizio Bifulco. "N6-isopentenyladenosine inhibits cell proliferation and induces apoptosis in a human colon cancer cell line DLD1." International Journal of Cancer 124, no. 6 (March 15, 2009): 1322–29. http://dx.doi.org/10.1002/ijc.24056.

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26

Laezza, Chiara, Anna M. Malfitano, Tiziana Di Matola, Paolo Ricchi, and Maurizio Bifulco. "Involvement of Akt/NF-κB pathway in N6-isopentenyladenosine-induced apoptosis in human breast cancer cells." Molecular Carcinogenesis 49, no. 10 (July 29, 2010): 892–901. http://dx.doi.org/10.1002/mc.20666.

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27

Wang, Xin, Junhong Bai, Wei Wang, and Guangliang Zhang. "Leaf metabolites profiling between red and green phenotypes of Suaeda salsa by widely targeted metabolomics." Functional Plant Biology 46, no. 9 (2019): 845. http://dx.doi.org/10.1071/fp18182.

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The Chenopodiaceae Suaeda salsa (L.) Pall. is a traditional Chinese medicine and food with green and red phenotypes in the Yellow River Delta. We identified 521 metabolites using widely targeted metabolomics, of which 165 were selected as significantly differential metabolites which could be related to the leaf traits of different phenotypes of S. salsa. Two anthocyanins (i.e. cyanidin O-acetylhexoside and delphinidin-3-O-(6ʹ-O-α-rhamnopyranosy l-β-glucopyranoside)) were responsible for red colour in red leaves of S. salsa. Gallic acid, which existed only in red one, was the main reason for leaf succulence. D-arabitol and ribitol were two significantly upregulated carbohydrates in red phenotype. Four alkaloids (i.e. harmaline, aminophylline, pipecolate and trigonelline) were upregulated in red leaves. Hormonal changed involved a decrease in indoleacetic acid-valine (IAA-Val), N6-isopentenyladenosine-5ʹ-monophosphate (iPRMP), isopentenyladenineriboside (iPR), trans-abscisic acid (S-ABA), salicylic acid O-hexoside, methyl jasmonate, N6-isopentenyladenine (iP), trans-zeatin riboside-O-glucoside iso2, trans-zeatin riboside-O-glucoside, and a tendency for dihydrozeatin 9-O-glucoside (DZ9G) down accumulation. In addition, the regulation of amino acids and lipids also contributed to the adaptation of red phenotype to harsh environment. Generally, our findings provide a comprehensive comparison of the metabolites between two phenotypes of S. salsa and an interpretation of phenotypic differences from the point of metabolomics.

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Ranieri, Roberta, Elena Ciaglia, Giuseppina Amodio, Paola Picardi, Maria Chiara Proto, Patrizia Gazzerro, Chiara Laezza, Paolo Remondelli, Maurizio Bifulco, and Simona Pisanti. "N6-isopentenyladenosine dual targeting of AMPK and Rab7 prenylation inhibits melanoma growth through the impairment of autophagic flux." Cell Death & Differentiation 25, no. 2 (October 13, 2017): 353–67. http://dx.doi.org/10.1038/cdd.2017.165.

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Rajabi, Mehdi, Paola Signorelli, Elena Gorincioi, Riccardo Ghidoni, and Enzo Santaniello. "Antiproliferative Activity of N6-Isopentenyladenosine on MCF-7 Breast Cancer Cells: Cell Cycle Analysis and DNA-Binding Study." DNA and Cell Biology 29, no. 11 (November 2010): 687–91. http://dx.doi.org/10.1089/dna.2010.1073.

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30

Tararov, Vitali I., Aloys Tijsma, Svetlana V. Kolyachkina, Vladimir E. Oslovsky, Johan Neyts, Mikhail S. Drenichev, Pieter Leyssen, and Sergey N. Mikhailov. "Chemical modification of the plant isoprenoid cytokinin N6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication." European Journal of Medicinal Chemistry 90 (January 2015): 406–13. http://dx.doi.org/10.1016/j.ejmech.2014.11.048.

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31

Yamamoto, Takahiro, Atsushi Fujimura, Fan-Yan Wei, Naoki Shinojima, Jun-ichiro Kuroda, Akitake Mukasa, and Kazuhito Tomizawa. "2-Methylthio Conversion of N6-Isopentenyladenosine in Mitochondrial tRNAs by CDK5RAP1 Promotes the Maintenance of Glioma-Initiating Cells." iScience 21 (November 2019): 42–56. http://dx.doi.org/10.1016/j.isci.2019.10.012.

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32

Ciaglia, Elena, Mario Abate, Chiara Laezza, Simona Pisanti, Mario Vitale, Vincenzo Seneca, Giovanni Torelli, et al. "Antiglioma effects of N6-isopentenyladenosine, an endogenous isoprenoid end product, through the downregulation of epidermal growth factor receptor." International Journal of Cancer 140, no. 4 (November 16, 2016): 959–72. http://dx.doi.org/10.1002/ijc.30505.

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33

Bifulco, Maurizio, Alba D'Alessandro, Simona Paladino, Anna M. Malfitano, Maria Notarnicola, Maria G. Caruso, and Chiara Laezza. "N6-isopentenyladenosine improves nuclear shape in fibroblasts from humans with progeroid syndromes by inhibiting the farnesylation of prelamin A." FEBS Journal 280, no. 23 (November 18, 2013): 6223–32. http://dx.doi.org/10.1111/febs.12544.

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34

Durand, J. M., G. R. Björk, A. Kuwae, M. Yoshikawa, and C. Sasakawa. "The modified nucleoside 2-methylthio-N6-isopentenyladenosine in tRNA of Shigella flexneri is required for expression of virulence genes." Journal of bacteriology 179, no. 18 (1997): 5777–82. http://dx.doi.org/10.1128/jb.179.18.5777-5782.1997.

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35

Pagano, Cristina, Giovanna Navarra, Olga Pastorino, Giorgio Avilia, Laura Coppola, Rosa Della Monica, Lorenzo Chiariotti, et al. "N6-Isopentenyladenosine Hinders the Vasculogenic Mimicry in Human Glioblastoma Cells through Src-120 Catenin Pathway Modulation and RhoA Activity Inhibition." International Journal of Molecular Sciences 22, no. 19 (September 29, 2021): 10530. http://dx.doi.org/10.3390/ijms221910530.

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Background: Vasculogenic mimicry (VM) is a functional microcirculation pattern formed by aggressive tumor cells. Thus far, no effective drugs have been developed to target VM. Glioblastoma (GBM) is the most malignant form of brain cancer and is a highly vascularized tumor. Vasculogenic mimicry represents a means whereby GBM can escape anti-angiogenic therapies. Methods: Here, using an in vitro tube formation assay on Matrigel, we evaluated the ability of N6-isopentenyladenosine (iPA) to interfere with vasculogenic mimicry (VM). RhoA activity was assessed using a pull-down assay, while the modulation of the adherens junctions proteins was analyzed by Western blot analysis. Results: We found that iPA at sublethal doses inhibited the formation of capillary-like structures suppressing cell migration and invasion of U87MG, U343MG, and U251MG cells, of patient-derived human GBM cells and GBM stem cells. iPA reduces the vascular endothelial cadherin (VE-cadherin) expression levels in a dose-dependent manner, impairs the vasculogenic mimicry network by modulation of the Src/p120-catenin pathway and inhibition of RhoA-GTPase activity. Conclusions: Taken together, our results revealed iPA as a promising novel anti-VM drug in GBM clinical therapeutics.

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Ciaglia, Elena, Simona Pisanti, Paola Picardi, Chiara Laezza, Anna Maria Malfitano, Alba DˈAlessandro, Patrizia Gazzerro, Mario Vitale, Ennio Carbone, and Maurizio Bifulco. "N6-isopentenyladenosine, an endogenous isoprenoid end product, directly affects cytotoxic and regulatory functions of human NK cells through FDPS modulation." Journal of Leukocyte Biology 94, no. 6 (July 11, 2013): 1207–19. http://dx.doi.org/10.1189/jlb.0413190.

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Gonzalez, Gabriel, Jiří Grúz, Cosimo Walter D’Acunto, Petr Kaňovský, and Miroslav Strnad. "Cytokinin Plant Hormones Have Neuroprotective Activity in In Vitro Models of Parkinson’s Disease." Molecules 26, no. 2 (January 12, 2021): 361. http://dx.doi.org/10.3390/molecules26020361.

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Cytokinins are adenine-based phytohormones that regulate key processes in plants, such as cell division and differentiation, root and shoot growth, apical dominance, branching, and seed germination. In preliminary studies, they have also shown protective activities against human neurodegenerative diseases. To extend knowledge of the protection (protective activity) they offer, we investigated activities of natural cytokinins against salsolinol (SAL)-induced toxicity (a Parkinson’s disease model) and glutamate (Glu)-induced death of neuron-like dopaminergic SH-SY5Y cells. We found that kinetin-3-glucoside, cis-zeatin riboside, and N6-isopentenyladenosine were active in the SAL-induced PD model. In addition, trans-, cis-zeatin, and kinetin along with the iron chelator deferoxamine (DFO) and the necroptosis inhibitor necrostatin 1 (NEC-1) significantly reduced cell death rates in the Glu-induced model. Lactate dehydrogenase assays revealed that the cytokinins provided lower neuroprotective activity than DFO and NEC-1. Moreover, they reduced apoptotic caspase-3/7 activities less strongly than DFO. However, the cytokinins had very similar effects to DFO and NEC-1 on superoxide radical production. Overall, they showed protective activity in the SAL-induced model of parkinsonian neuronal cell death and Glu-induced model of oxidative damage mainly by reduction of oxidative stress.

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Ciaglia, Elena, Simona Pisanti, Paola Picardi, Chiara Laezza, Silvio Sosa, Aurelia Tubaro, Mario Vitale, Patrizia Gazzerro, Anna Maria Malfitano, and Maurizio Bifulco. "N6-isopentenyladenosine affects cytotoxic activity and cytokines production by IL-2 activated NK cells and exerts topical anti-inflammatory activity in mice." Pharmacological Research 89 (November 2014): 1–10. http://dx.doi.org/10.1016/j.phrs.2014.07.003.

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39

Santoro, Antonietta, Elena Ciaglia, Vanessa Nicolin, Alessandra Pescatore, Lucia Prota, Mario Capunzo, Matilde V. Ursini, Stefania L. Nori, and Maurizio Bifulco. "The isoprenoid end product N6-isopentenyladenosine reduces inflammatory response through the inhibition of the NFκB and STAT3 pathways in cystic fibrosis cells." Inflammation Research 67, no. 4 (December 11, 2017): 315–26. http://dx.doi.org/10.1007/s00011-017-1123-6.

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Nguyen, Thien Q., Anna B. Kisiala, Nguyen Ngoc Hai, Suresh Narine, and R. J. Neil Emery. "Phytohormone dynamics impact fatty acid and oil accumulation during soybean seed maturation." Seed Science Research 31, no. 4 (November 9, 2021): 278–91. http://dx.doi.org/10.1017/s0960258521000192.

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AbstractFatty acid (FA) levels and profiles are vital for soybean oil quality, while cytokinins (CKs) and abscisic acid (ABA) are potent regulators of plant growth and development. Previous research suggested associations between FA biosynthesis and hormonal signalling networks; however, hormonal regulation of FA accumulation during soybean (Glycine max) seed maturation has never been measured. We analysed hormone and FA profiles obtained from HPLC-(ESI)-MS/MS and GC-FID screening during soybean seed maturation. A multilayered data processing approach, involving heat-maps, principal component analysis (PCA), correlation and multiregression models, suggested a strong relationship between hormone metabolism and FA/oil accumulation during seed maturation. Most strikingly, positive correlations were found between the levels of CK ribosides [transZeatin riboside (tZR), N6-isopentenyladenosine (iPR)] at the early stages of SM (R5-R6) and C18:0, C18:2 and oil content at the R8 stage. Moreover, multiple regression models revealed functional linkages between several CK derivatives and FA and oil content in mature seeds. To further test the significance of hormone regulation in FA metabolism, plants of two soybean accessions with contrasting hormone and FA profiles were sprayed with exogenous ABA and transZeatin (tZ) during the seed-filling period (R5-R6). Depending on the hormone type and concentration, these treatments distinctly modified biosynthesis of all tested FAs, except for C18:0. Most remarkably, tZ (50 nM) promoted production of C16:0, C18:1, C18:2, C18:3, and oil accumulation in maturing seeds. Overall, the results indicate impactful roles for ABA and CKs in FA accumulation during SM and represent a further step towards understanding FA biosynthesis, and potential improvements of soybean oil profiles.

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Pagano, Cristina, Giovanna Navarra, Laura Coppola, Giorgio Avilia, Olga Pastorino, Rosa Della Monica, Michela Buonaiuto, et al. "N6-isopentenyladenosine induces cell death through necroptosis in human glioblastoma cells." Cell Death Discovery 8, no. 1 (April 7, 2022). http://dx.doi.org/10.1038/s41420-022-00974-x.

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AbstractTargeting necroptosis is considered a promising therapeutic strategy in cancer, including Glioblastoma Multiforme (GBM), one of the most lethal brain tumors. Necroptosis is a mechanism of programmed cell death overcoming the apoptosis resistance mechanism underlying GBM tumorigenesis and malignant progression. N6-isopentenyladenosine (iPA), adenosine modified with isoprenoid derivative, displays antitumor activity in different cancer models. In previous studies, we demonstrated that iPA interferes with EGFR signaling reducing glioma cell viability. Here, we show that iPA induces necroptosis in glioblastoma cell lines and in primary cells established from tumor explants, without affecting the viability of non-cancerous brain cell lines, (Normal Human Astrocyte). The activation of RIP1, RIP3, and MLKL and the upregulation of necrosome formation were increased upon iPA treatment while caspase-3, caspase-8, and PARP were not activated in GBM cells. Co-treatment with specific necroptosis inhibitor necrostatin-1 (Nec-1) or Necrosulfonamide (NSA) prevented cell death caused by iPA treatment while the general caspase inhibitor Z-VAD-fluoromethylketone (z-VAD-fmk) did not elicit any effect, suggesting that this molecule induces caspase-independent necroptosis. These results suggest that iPA treatment can be able to bypass the apoptosis resistance mechanism in glioblastoma thereby offering higher therapeutic efficacy.

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Yakita, Maya, Takeshi Chujo, Fan-Yan Wei, Mayumi Hirayama, Koji Kato, Nozomu Takahashi, Kenta Naganuma, et al. "Extracellular N6-isopentenyladenosine (i6A) addition induces co-transcriptional i6A incorporation into ribosomal RNAs." RNA, April 12, 2022, rna.079176.122. http://dx.doi.org/10.1261/rna.079176.122.

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N6-isopentenyladenosine (i6A), a modified adenosine monomer, is known to induce cell death upon its addition to the culture medium. However, the molecular fate of extracellularly added i6A has yet to be identified. Here we show that i6A addition to cell culture medium results in i6A incorporation into cellular RNA in several cell lines, including the 5-fluorouracil (5-FU)-resistant human oral squamous cell carcinoma cell line FR2-SAS and its parental 5-FU-sensitive cell line SAS. i6A was predominantly incorporated into 18S and 28S rRNAs, and i6A incorporation into total RNA was mostly suppressed by treating these cell lines with an RNA Polymerase I (Pol I) inhibitor. i6A was incorporated into RNA even upon inactivation of TRIT1, the only cellular i6A-modifying enzyme. These results indicate that upon cellular uptake of i6A, it is anabolized to be used for Pol I transcription. Interestingly, at lower i6A concentrations, the cytotoxic effect of i6A was substantially more pronounced in FR2-SAS cells than in SAS cells. Moreover, in FR2-SAS cells, i6A treatment decreased the rate of cellular protein synthesis and increased intracellular protein aggregation, and these effects were more pronounced than in SAS cells. Our work provides insights into the molecular fate of extracellularly-applied i6A in the context of intracellular nucleic acid anabolism and suggests investigation of i6A as a candidate for chemotherapy agent against 5-FU-resistant cancer cells.

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Proto, Maria Chiara, Donatella Fiore, Chiara Piscopo, Chiara Laezza, Maurizio Bifulco, and Patrizia Gazzerro. "Modified Adenosines Sensitize Glioblastoma Cells to Temozolomide by Affecting DNA Methyltransferases." Frontiers in Pharmacology 13 (April 26, 2022). http://dx.doi.org/10.3389/fphar.2022.815646.

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Glioblastoma (GBM) is the most common and lethal primary malignant brain tumor, and due to its unique features, its management is certainly one of the most challenging ones among all cancers. N6-isopentenyladenosine (IPA) and its analog N6-benzyladenosine (N6-BA) are modified nucleosides endowed with potent antitumor activity on different types of human cancers, including GBM. Corroborating our previous finding, we demonstrated that IPA and N6-BA affect GBM cell line proliferation by modulating the expression of the F-box WD repeat domain-containing-7 (FBXW7), a tumor suppressor with a crucial role in the turnover of many proteins, such as SREBPs and Mcl1, involved in malignant progression and chemoresistance. Luciferase assay revealed that IPA-mediated upregulation of FBXW7 translates in transcriptional inactivation of its oncogenic substrates (Myc, NFkB, or HIF-1α). Moreover, downregulating MGMT expression, IPA strongly enhances the killing effect of temozolomide (TMZ), producing a favorable sensitizing effect starting from a concentration range much lower than TMZ EC50. Through DNA methyltransferase (DNMT) activity assay, analysis of the global DNA methylation, and the histone modification profiles, we demonstrated that the modified adenosines behave similar to 5-AZA-dC, known DNMT inhibitor. Overall, our results provide new perspectives for the first time, suggesting the modified adenosines as epigenetic tools able to improve chemo- and radiotherapy efficacy in glioblastoma and potentially other cancers.

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44

Proto, Maria Chiara, Donatella Fiore, Chiara Piscopo, Chiara Laezza, Maurizio Bifulco, and Patrizia Gazzerro. "Modified Adenosines Sensitize Glioblastoma Cells to Temozolomide by Affecting DNA Methyltransferases." Frontiers in Pharmacology 13 (April 26, 2022). http://dx.doi.org/10.3389/fphar.2022.815646.

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Glioblastoma (GBM) is the most common and lethal primary malignant brain tumor, and due to its unique features, its management is certainly one of the most challenging ones among all cancers. N6-isopentenyladenosine (IPA) and its analog N6-benzyladenosine (N6-BA) are modified nucleosides endowed with potent antitumor activity on different types of human cancers, including GBM. Corroborating our previous finding, we demonstrated that IPA and N6-BA affect GBM cell line proliferation by modulating the expression of the F-box WD repeat domain-containing-7 (FBXW7), a tumor suppressor with a crucial role in the turnover of many proteins, such as SREBPs and Mcl1, involved in malignant progression and chemoresistance. Luciferase assay revealed that IPA-mediated upregulation of FBXW7 translates in transcriptional inactivation of its oncogenic substrates (Myc, NFkB, or HIF-1α). Moreover, downregulating MGMT expression, IPA strongly enhances the killing effect of temozolomide (TMZ), producing a favorable sensitizing effect starting from a concentration range much lower than TMZ EC50. Through DNA methyltransferase (DNMT) activity assay, analysis of the global DNA methylation, and the histone modification profiles, we demonstrated that the modified adenosines behave similar to 5-AZA-dC, known DNMT inhibitor. Overall, our results provide new perspectives for the first time, suggesting the modified adenosines as epigenetic tools able to improve chemo- and radiotherapy efficacy in glioblastoma and potentially other cancers.

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45

Proto, Maria Chiara, Donatella Fiore, Chiara Piscopo, Chiara Laezza, Maurizio Bifulco, and Patrizia Gazzerro. "Modified Adenosines Sensitize Glioblastoma Cells to Temozolomide by Affecting DNA Methyltransferases." Frontiers in Pharmacology 13 (April 26, 2022). http://dx.doi.org/10.3389/fphar.2022.815646.

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Abstract:

Glioblastoma (GBM) is the most common and lethal primary malignant brain tumor, and due to its unique features, its management is certainly one of the most challenging ones among all cancers. N6-isopentenyladenosine (IPA) and its analog N6-benzyladenosine (N6-BA) are modified nucleosides endowed with potent antitumor activity on different types of human cancers, including GBM. Corroborating our previous finding, we demonstrated that IPA and N6-BA affect GBM cell line proliferation by modulating the expression of the F-box WD repeat domain-containing-7 (FBXW7), a tumor suppressor with a crucial role in the turnover of many proteins, such as SREBPs and Mcl1, involved in malignant progression and chemoresistance. Luciferase assay revealed that IPA-mediated upregulation of FBXW7 translates in transcriptional inactivation of its oncogenic substrates (Myc, NFkB, or HIF-1α). Moreover, downregulating MGMT expression, IPA strongly enhances the killing effect of temozolomide (TMZ), producing a favorable sensitizing effect starting from a concentration range much lower than TMZ EC50. Through DNA methyltransferase (DNMT) activity assay, analysis of the global DNA methylation, and the histone modification profiles, we demonstrated that the modified adenosines behave similar to 5-AZA-dC, known DNMT inhibitor. Overall, our results provide new perspectives for the first time, suggesting the modified adenosines as epigenetic tools able to improve chemo- and radiotherapy efficacy in glioblastoma and potentially other cancers.

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46

Navarra, Giovanna, Cristina Pagano, Roberto Pacelli, Elvira Crescenzi, Elena Longobardi, Patrizia Gazzerro, Donatella Fiore, et al. "N6-Isopentenyladenosine Enhances the Radiosensitivity of Glioblastoma Cells by Inhibiting the Homologous Recombination Repair Protein RAD51 Expression." Frontiers in Oncology 9 (January 14, 2020). http://dx.doi.org/10.3389/fonc.2019.01498.

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47

Elena, Ciaglia, Pisanti Simona, Picardi Paola, Laezza Chiara, Malfitano Anna Maria, D'Alessandro Alba, Gazzerro Patrizia, Carbone Ennio, and Bifulco Maurizio. "N6-isopentenyladenosine, an endogenous isoprenoid end product, directly affects cytotoxic and regulatory functions of human NK cells through FDPS modulation." Frontiers in Immunology 4 (2013). http://dx.doi.org/10.3389/conf.fimmu.2013.02.00150.

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48

Tian, Jieyun, Yao Ma, Yabing Chen, Xue Chen, and Anzhi Wei. "Plant Hormone Response to Low-Temperature Stress in Cold-Tolerant and Cold-Sensitive Varieties of Zanthoxylum bungeanum Maxim." Frontiers in Plant Science 13 (April 29, 2022). http://dx.doi.org/10.3389/fpls.2022.847202.

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Plant growth and survival in nature, its growth process, will be affected by various factors from the environment, among which temperature has a greater impact. In recent years, extreme weather has frequently appeared, and the growth of crops has been increasingly affected by the environment. As an important flavoring and Chinese herbal medicine crop, Zanthoxylum bungeanum is also facing the harm of low-temperature stress. Plant hormones play a vital role in the response of plants to low temperatures. In this study, ultra-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) was used to determine the hormone components of cold-tolerant and cold-sensitive varieties of Z. bungeanum. Combined with chemometric analysis and weighted gene co-expression network analysis (WGCNA), the hormone component differences and hormone response strategies of Z. bungeanum under low-temperature stress were comprehensively studied. The results showed that 45 hormones were detected in Z. bungeanum. Among them, there were 7 kinds of components with high content and were detected in both two varieties. At the late stage of low-temperature stress, the contents of abscisic acid (ABA) and ABA-glucosyl ester (ABA-GE) in Fuguhuajiao (FG) were significantly increased, and the latter served as the storage of the former to supplement the active ABA. Orthogonal partial least squares discriminant analysis (OPLS-DA) found that indole-3-carboxylic acid (ICA), indole-3-carboxaldehyde (ICAld), meta-Topolin riboside (mTR), cis-Zeatin-O-glucoside riboside (cZROG), and N6-isopentenyladenosine (IPR) in FG were the upregulated important difference components, and IPR and 2-methylthio-cis-zeatin riboside (2MeScZR) in Fengxiandahongpao (FX) were the upregulated important difference components. There were common crossing points and independent response pathways in response to low temperature in two varieties. WGCNA analysis found that the main hormone components were associated with multiple metabolic pathways including carbon, fatty acid, amino acid, and sugar metabolism, indicating that hormone regulation plays an important role in the response of Z. bungeanum to low temperature. This study clarified the hormone response mechanism of Z. bungeanum under low-temperature stress and provided a reference and basis for further improving the cold resistance of Z. bungeanum and cultivating new varieties.

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