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Journal articles on the topic 'Papuamine'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

McDermott, Todd S., Andrew A. Mortlock, and Clayton H. Heathcock. "Total Syntheses of (−)-Papuamine and (−)-Haliclonadiamine." Journal of Organic Chemistry 61, no. 2 (January 1996): 700–709. http://dx.doi.org/10.1021/jo951647i.

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2

MCDERMOTT, T. S., A. A. MORTLOCK, and C. H. HEATHCOCK. "ChemInform Abstract: Total Syntheses of (-)-Papuamine (X) and (-)-Haliclonadiamine (XI)." ChemInform 27, no. 23 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199623263.

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3

Baker, Bill J., Paul J. Scheuer, and James N. Shoolery. "Papuamine, an antifungal pentacyclic alkaloid from a marine sponge, Haliclona sp." Journal of the American Chemical Society 110, no. 3 (February 3, 1988): 965–66. http://dx.doi.org/10.1021/ja00211a046.

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4

Adlington, Robert M., Jack E. Baldwin, Gregory L. Challis, Rhona J. Cox, and Gareth J. Pritchard. "Towards a Biomimetic Synthesis of the Marine Alkaloids Papuamine and Haliclonadiamine: Model Studies." Tetrahedron 56, no. 4 (January 2000): 623–28. http://dx.doi.org/10.1016/s0040-4020(99)01011-x.

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5

KANNO, SYU-ICHI, SHIN YOMOGIDA, AYAKO TOMIZAWA, HIROYUKI YAMAZAKI, KAZUYO UKAI, REMY E. P. MANGINDAAN, MICHIO NAMIKOSHI, and MASAAKI ISHIKAWA. "Combined effect of papuamine and doxorubicin in human breast cancer MCF-7 cells." Oncology Letters 8, no. 2 (June 3, 2014): 547–50. http://dx.doi.org/10.3892/ol.2014.2218.

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6

Barrett, Anthony G. M., Mark L. Boys, and Terri L. Boehm. "Total Synthesis of (+)-Papuamine: An Antifungal Pentacyclic Alkaloid from a Marine Sponge,Haliclonasp." Journal of Organic Chemistry 61, no. 2 (January 1996): 685–99. http://dx.doi.org/10.1021/jo951413z.

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7

Barrett, Anthony G. M., Mark L. Boys, and Terri L. Boehm. "Total synthesis of (+)-papuamine: determination of the absolute stereochemistry of the natural product." Journal of the Chemical Society, Chemical Communications, no. 16 (1994): 1881. http://dx.doi.org/10.1039/c39940001881.

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8

MIN, HYE-YOUNG, YUJIN JUNG, KWAN HEE PARK, and HO-YOUNG LEE. "Papuamine Inhibits Viability of Non-small Cell Lung Cancer Cells by Inducing Mitochondrial Dysfunction." Anticancer Research 40, no. 1 (December 31, 2019): 323–33. http://dx.doi.org/10.21873/anticanres.13956.

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9

Borzilleri, Robert M., Steven M. Weinreb, and Masood Parvez. "Total Synthesis of the Unusual Marine Alkaloid (-)-Papuamine Utilizing a Novel Imino Ene Reaction." Journal of the American Chemical Society 117, no. 44 (November 1995): 10905–13. http://dx.doi.org/10.1021/ja00149a013.

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10

Borzilleri, Robert M., Steven M. Weinreb, and Masood Parvez. "Total Synthesis of Papuamine via a Stereospecific Intramolecular Imino Ene Reaction of an Allenylsilane." Journal of the American Chemical Society 116, no. 21 (October 1994): 9789–90. http://dx.doi.org/10.1021/ja00100a070.

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11

BARRETT, A. G. M., M. L. BOYS, and T. L. BOEHM. "ChemInform Abstract: Total Synthesis of (+)-Papuamine: Determination of the Absolute Stereochemistry of the Natural Product." ChemInform 26, no. 3 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199503245.

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12

Adlington, Robert M., Jack E. Baldwin, Gregory L. Challis, Rhona J. Cox, and Gareth J. Pritchard. "ChemInform Abstract: Towards a Biomimetic Synthesis of the Marine Alkaloids Papuamine and Haliclonadiamine: Model Studies." ChemInform 31, no. 19 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200019200.

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13

BORZILLERI, R. M., S. M. WEINREB, and M. PARVEZ. "ChemInform Abstract: Total Synthesis of Papuamine via a Stereospecific Intramolecular Imino Ene Reaction of an Allenylsilane." ChemInform 26, no. 17 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199517211.

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14

BORZILLERI, R. M., S. M. WEINREB, and M. PARVEZ. "ChemInform Abstract: Total Synthesis of the Unusual Marine Alkaloid (-)-Papuamine Utilizing a Novel Imino Ene Reaction." ChemInform 27, no. 11 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199611267.

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15

Yamazaki, Hiroyuki, Defny S. Wewengkang, Syu-ichi Kanno, Masaaki Ishikawa, Henki Rotinsulu, Remy E. P. Mangindaan, and Michio Namikoshi. "Papuamine and haliclonadiamine, obtained from an Indonesian spongeHaliclonasp., inhibited cell proliferation of human cancer cell lines." Natural Product Research 27, no. 11 (June 2013): 1012–15. http://dx.doi.org/10.1080/14786419.2012.688050.

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16

Saha, Arabinda, and Anup Bhattacharjya. "Novel nitrile oxide cycloaddition approach towards papuamine: stereoselective synthesis of a potentially useful trans-hydrindane intermediate." Chemical Communications, no. 5 (1997): 495–96. http://dx.doi.org/10.1039/a700182g.

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17

Borzilleri, Robert M., Steven M. Weinreb, and Masood Parvez. "Total Synthesis of the Unusual Marine Alkaloid (−)-Papuamine Utilizing a Novel Imino Ene ReactionJ.Am.Chem.Soc.1995,117, 10905−10913." Journal of the American Chemical Society 118, no. 9 (January 1996): 2309. http://dx.doi.org/10.1021/ja965400u.

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18

BARRETT, A. G. M., M. L. BOYS, and T. L. BOEHM. "ChemInform Abstract: Total Synthesis of (+)-Papuamine (VII): An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp." ChemInform 27, no. 23 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199623262.

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19

SAHA, A., and A. BHATTACHARJYA. "ChemInform Abstract: Novel Nitrile Oxide Cycloaddition Approach Towards Papuamine: Stereoselective Synthesis of a Potentially Useful trans-Hydrindane Intermediate." ChemInform 28, no. 27 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199727235.

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20

Li, Qun, Chaoyu Chen, Amit Kapadia, Qiong Zhou, Mary Kay Harper, Jerome Schaack, and Daniel V. Labarbera. "3D Models of Epithelial-Mesenchymal Transition in Breast Cancer Metastasis." Journal of Biomolecular Screening 16, no. 2 (February 2011): 141–54. http://dx.doi.org/10.1177/1087057110392995.

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Despite advancements in therapies developed for the treatment of cancer, patient prognosis and mortality rates have improved minimally, and metastasis remains the primary cause of cancer mortality worldwide. An underlying mechanism promoting metastasis in many types of cancer is epithelial-mesenchymal transition (EMT). Here the authors report a novel 3D model of EMT and metastatic breast cancer suitable for high-throughput screening (HTS) drug discovery. The primary assay incorporates the expression of the prognostic biomarker vimentin, as a luciferase reporter of EMT, in basil-like/triple-negative MDA-MB-231 breast carcinoma spheroids. Using this model, the authors developed a number of known antitumor agents as control modulators of EMT. U0126, PKC412, PF2341066, dasatinib, and axitinib downregulated vimentin expression by 70% to 90% as compared to untreated spheroids. Counterassays were developed to measure spheroid viability and the invasive potential of MDA-MB-231 spheroids after small-molecule treatment and used to confirm hits from primary screening. Finally, the authors conducted a pilot screen to validate this model for HTS using a purified library of marine secondary metabolites. From 230 compounds screened, they obtained a Z′ score of 0.64, indicative of an excellent assay, and confirmed 4 hits, including isonaamidine B, papuamine, mycalolide E, and jaspamide. This HTS model demonstrates the potential to identify small-molecule modulators of EMT that could be used to discover novel antimetastatic agents for the treatment of cancer.

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21

KANNO, SYU-ICHI, SHIN YOMOGIDA, AYAKO TOMIZAWA, HIROYUKI YAMAZAKI, KAZUYO UKAI, REMY E. P. MANGINDAAN, MICHIO NAMIKOSHI, and MASAAKI ISHIKAWA. "Papuamine causes autophagy following the reduction of cell survival through mitochondrial damage and JNK activation in MCF-7 human breast cancer cells." International Journal of Oncology 43, no. 5 (September 10, 2013): 1413–19. http://dx.doi.org/10.3892/ijo.2013.2093.

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22

Flores-Holguín, Norma, Juan Frau, and Daniel Glossman-Mitnik. "Calculation of the Global and Local Conceptual DFT Indices for the Prediction of the Chemical Reactivity Properties of Papuamides A–F Marine Drugs." Molecules 24, no. 18 (September 11, 2019): 3312. http://dx.doi.org/10.3390/molecules24183312.

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Abstract:

A well-behaved model chemistry previously validated for the study of the chemical reactivity of peptides was considered for the calculation of the molecular properties and structures of the Papuamide family of marine peptides. A methodology based on Conceptual Density Functional Theory (CDFT) was chosen for the determination of the reactivity descriptors. The molecular active sites were associated with the active regions of the molecules related to the nucleophilic and electrophilic Parr functions. Finally, the drug-likenesses and the bioactivity scores for the Papuamide peptides were predicted through a homology methodology relating them with the calculated reactivity descriptors, while other properties such as the pKas were determined following a methodology developed by our group.

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23

Andjelic, Cynthia, Vicente Planelles, and Louis Barrows. "Characterizing the Anti-HIV Activity of Papuamide A." Marine Drugs 6, no. 4 (October 8, 2008): 528–49. http://dx.doi.org/10.3390/md20080027.

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24

Cassilly, Chelsi D., Marcus M. Maddox, Philip T. Cherian, John J. Bowling, Mark T. Hamann, Richard E. Lee, and Todd B. Reynolds. "SB-224289 Antagonizes the Antifungal Mechanism of the Marine Depsipeptide Papuamide A." PLOS ONE 11, no. 5 (May 16, 2016): e0154932. http://dx.doi.org/10.1371/journal.pone.0154932.

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25

Makino, Kazuishi, Eri Nagata, and Yasumasa Hamada. "Synthesis of tripeptide hydrolysate from papuamide A: determination of absolute stereostructure of β-methoxytyrosine." Tetrahedron Letters 46, no. 40 (October 2005): 6827–30. http://dx.doi.org/10.1016/j.tetlet.2005.08.023.

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26

Xie, Weiqing, Derong Ding, Weiwei Zi, Guangyu Li, and Dawei Ma. "Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties." Angewandte Chemie 120, no. 15 (March 31, 2008): 2886–90. http://dx.doi.org/10.1002/ange.200705557.

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27

Xie, Weiqing, Derong Ding, Weiwei Zi, Guangyu Li, and Dawei Ma. "Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties." Angewandte Chemie International Edition 47, no. 15 (March 31, 2008): 2844–48. http://dx.doi.org/10.1002/anie.200705557.

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28

Oku, Naoya, Ravi Krishnamoorthy, Alan G. Benson, Robert L. Ferguson, Mark A. Lipton, Lawrence R. Phillips, Kirk R. Gustafson, and James B. McMahon. "Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B." Journal of Organic Chemistry 70, no. 17 (August 2005): 6842–47. http://dx.doi.org/10.1021/jo0508853.

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29

Prasad, Pritesh, William Aalbersberg, Klaus-D. Feussner, and Ryan M. Van Wagoner. "Papuamides E and F, cytotoxic depsipeptides from the marine sponge Melophlus sp." Tetrahedron 67, no. 44 (November 2011): 8529–31. http://dx.doi.org/10.1016/j.tet.2011.08.100.

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30

Okamoto, Naoki, Osamu Hara, Kazuishi Makino, and Yasumasa Hamada. "Diastereoselective Synthesis of All Stereoisomers of β-Methoxytyrosine, a Component of Papuamides." Journal of Organic Chemistry 67, no. 26 (December 2002): 9210–15. http://dx.doi.org/10.1021/jo0258352.

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31

Ford, Paul W., Kirk R. Gustafson, Tawnya C. McKee, Nobuharu Shigematsu, Laura K. Maurizi, Lewis K. Pannell, David E. Williams, et al. "Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the SpongesTheonellamirabilisandTheonellaswinhoeiCollected in Papua New Guinea." Journal of the American Chemical Society 121, no. 25 (June 1999): 5899–909. http://dx.doi.org/10.1021/ja990582o.

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32

Makino, Kazuishi, Eri Nagata, and Yasumasa Hamada. "Practical synthesis of (2S,3R)-3-hydroxy-3-methylproline, a constituent of papuamides, using a diastereoselective tandem Michael-aldol reaction." Tetrahedron Letters 46, no. 47 (November 2005): 8159–62. http://dx.doi.org/10.1016/j.tetlet.2005.09.111.

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33

Okamoto, Naoki, Osamu Hara, Kazuishi Makino, and Yasumasa Hamada. "Stereoselective synthesis of (3S,4R)-3,4-dimethyl-(S)-glutamine and the absolute stereochemistry of the natural product from papuamides and callipeltin." Tetrahedron: Asymmetry 12, no. 9 (June 2001): 1353–58. http://dx.doi.org/10.1016/s0957-4166(01)00231-2.

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34

Andersen, Raymond J., and et al et al. "ChemInform Abstract: Papuamides A-D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea." ChemInform 30, no. 38 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199938195.

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35

Ramamoorthy, Gurusankar, Cristina M. Acevedo, Edgardo Alvira, and Mark A. Lipton. "Synthesis and spectroscopic correlation of the diastereoisomers of 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid: implications for the structures of papuamides A–D and mirabamides A–D." Tetrahedron: Asymmetry 19, no. 22 (November 2008): 2546–54. http://dx.doi.org/10.1016/j.tetasy.2008.09.031.

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36

BAKER, B. J., P. J. SCHEUER, and J. N. SHOOLERY. "ChemInform Abstract: Papuamine (I), an Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp." ChemInform 19, no. 22 (May 31, 1988). http://dx.doi.org/10.1002/chin.198822313.

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37

Fujimoto, Keiko, Ryo Tadakuma, Chiaki Tanaka, Yuko Hirota, Yuu Miyauchi, Yuji Ishii, and Yoshitaka Tanaka. "Papuamine prevents the fusion between autophagosomes and lysosomes by inhibiting the maturation of autophagosomes." FASEB Journal 33, S1 (April 2019). http://dx.doi.org/10.1096/fasebj.2019.33.1_supplement.661.1.

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38

Oku, Naoya, Ravi Krishnamoorthy, Alan G. Benson, Robert L. Ferguson, Mark A. Lipton, Lawrence R. Phillips, Kirk R. Gustafson, and James B. McMahon. "Complete Stereochemistry of Neamphamide A (I) and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B." ChemInform 37, no. 1 (January 3, 2006). http://dx.doi.org/10.1002/chin.200601190.

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