Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 2
688
Views
3
CrossRef citations to date
0
Altmetric
Articles

Synthesis and anticancer activities of proline-containing cyclic peptides and their linear analogs and congeners

, , , , &
Pages 221-236 | Received 12 Sep 2018, Accepted 15 Nov 2018, Published online: 13 Jan 2019

References

  • Kieber-Emmons, T.; Murali, R.; Greene, M. I. Therapeutic Peptides and Peptidomimetics. Curr. Opin. Biotechnol. 1997, 8, 435-441. DOI: 10.1016/S0958-1669(97)80065-1.
  • Albericio, F.; Kruger, H. G. Therapeutic Peptides. Future Med. Chem. 2012, 4, 1527-1531. DOI: 10.4155/fmc.12.94.
  • Roxin, Á.; Zheng, G. Flexible or Fixed: a Comparative Review of Linear and Cyclic Cancer-targeting Peptides. Future Med. Chem. 2012, 4, 1601-1618. DOI: 10.4155/fmc.12.75.
  • Zorzi, A.; Deyle, K.; Heinis, C. Cyclic Peptide Therapeutics: Past, Present and Future. Curr. Opin. Chem. Biol. 2017, 38, 24-29. DOI: 10.1016/j.cbpa.2017.02.006.
  • Bockus, A. T.; McEwen, C. M.; Lokey, R. S. Form and Function in Cyclic Peptide Natural Products: A Pharmacokinetic Perspective. CTMC. 2013, 13, 821-836. DOI: 10.2174/1568026611313070005.
  • Joo, S. H. Cyclic Peptides as Therapeutic Agents and Biochemical Tools. Biomol Ther. 2012, 20, 19-26. DOI: 10.4062/biomolther.2012.20.1.019.
  • Kritzer, J. A.; Hamamichi, S.; McCaffery, J. M.; Santagata, S.; Naumann, T. A.; Caldwell, K. A.; Caldwell, G. A.; Lindquist, S. Rapid Selection of Cyclic Peptides That Reduce α-Synuclein Toxicity in Yeast and Animal Models. Nat. Chem. Biol. 2009, 5, 655-663. DOI: 10.1038/nchembio.193.
  • Sun, L. Peptide-Based Drug Development. Mod. Chem. Appl. 2013, 1, e103. DOI: 10.4172/2329-6798.1000e103.
  • Kates, S. A.; Solé, N. A.; Albericio, F.; Barany, G. Solid-Phase Synthesis of Cyclic Peptides. In Peptides: Design, Synthesis and Biological Activity, Basava, C., Anantharamaiah G. M., Eds,; Birkhäuser: Basel, 1994, pp 39-58. DOI: 10.1007/978-1-4615-8176-5.
  • Davies, J. S. The Cyclization of Peptides and Depsipeptides. J. Pept. Sci. 2003, 9, 471-501. DOI: 10.1002/psc.491.
  • Blackburn, C.; Kates, S. A. Solid-phase Synthesis of Cyclic Homodetic Peptides. Methods Enzymol 1997, 289, 175-198. DOI: 10.1016/S0076-6879(97)89048-9.
  • Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. The Synthesis of Cyclic Peptides. J. Chem. Soc, Perkin Trans. 1 2001, 471-484. DOI: 10.1039/b001942i.
  • Wu, W.; Dai, H.; Bao, L.; Ren, B.; Lu, J.; Luo, Y.; Guo, L.; Zhang, L.; Liu, H. Isolation and Structural Elucidation of Proline-Containing Cyclopentapeptides from an Endolichenic Xylaria sp. J. Nat. Prod. 2011, 74, 1303-1308. DOI: 10.1021/np100909y.
  • Zhan, K. X.; Jiao, W. H.; Yang, F.; Li, J.; Wang, S. P.; Li, Y. S.; Han, B. N.; Lin, H. W. Reniochalistatins a − E, Cyclic Peptides from the Marine Sponge Reniochalina Stalagmitis. J. Nat. Prod. 2014, 77, 2678-2684. DOI: 10.1021/np5006778.
  • Feng, P.; Zhou, R.; Sun, Y.; Li, H.; Long, W.; Liao, X.; Xu, S. Synthesis and Biological Evaluation of Reniochalistatins a-E and a Reniochalistatin E analog. ChemMedChem. 2018, 13, 2202-2207. DOI:10.1002/cmdc.201800529.
  • Fatino, A.; Baca, G.; Weeramange, C.; Rafferty, R. J. Total Synthesis of Reniochalistatin E. J. Nat. Prod. 2017, 80, 3234-3240. DOI: 10.1021/acs.jnatprod.7b00656.
  • Luo, H.; Yin, H.; Tang, C.; Wang, P.; Liang, F. Synthesis of Cyclic Peptide Reniochalistatin E and Conformational Isomers. Chin. Chem. Lett. 2018, 29, 1143-1146. DOI: 10.1016/j.cclet.2018.05.033.
  • McKeever, B.; Pattenden, G. Total Synthesis of Trunkamide A, a Novel Thiazoline-based Prenylated Cyclopeptide Metabolite from Lissoclinum sp. Tetrahedron 2003, 59, 2713-2727. DOI: 10.1016/S0040-4020(03)00294-1.
  • Kelleman, A.; Mattern, R. H.; Pierschbacher, M. D.; Goodman, M. Incorporation of Thioether Building Blocks into an αvβ3-Specific RGD Peptide: Synthesis and Biological Activity. Biopolymers (Peptide Sci). 2003, 71, 686-695. DOI: 10.1002/bip.10586.
  • Duttagupta, I.; Misra, D.; Bhunya, S.; Paul, A.; Sinha, S. Cis-Trans Conformational Analysis of δ - Azaproline in Peptides. J. Org. Chem. 2015, 80, 10585-10604. DOI: 10.1021/acs.joc.5b01668.
  • Lécaillon, J.; Gilles, P.; Subra, G.; Martinez, J.; Amblard, M. Synthesis of Cyclic Peptides via O-N-acyl Migration. Tetrahedron Lett. 2008, 49, 4674-4676. DOI: 10.1016/j.tetlet.2008.05.049.
  • Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Fluorine in Medicinal Chemistry. Chem. Soc. Rev. 2008, 37, 320-330. DOI: 10.1039/b610213c.
  • Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. Applications of Fluorine in Medicinal Chemistry. J. Med. Chem. 2015, 58, 8315-8359. DOI: 10.1021/acs.jmedchem.5b00258.
  • Böhm, H. J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. Fluorine in Medicinal Chemistry. ChemBioChem. 2004, 5, 637-643. DOI: 10.1002/cbic.200301023.
  • Shah, P.; Westwell, A. D. The Role of Fluorine in Medicinal Chemistry. Enzyme Inhib. Med. Chem. 2007, 22, 527-540. DOI: 10.1080/14756360701425014. DOI: 10.1080/14756360701425014.
  • Cotarca, L.; Delogu, P.; Nardelli, A.; Šunjić, V. Bis(trichloromethyl) Carbonate in Organic Synthesis. Synthesis. 1996, 1996, 553-576. DOI: 10.1055/s-1996-4273. DOI: 10.1055/s-1996-4273.
  • Ghorbani-Choghamarani, A.; Azadi, G. Triphosgene and Its Application in Organic Synthesis. Coc. 2016, 20, 2881-2893. DOI: 10.2174/1385272820666160630124216
  • Barbie, P.; Kazmaier, U. Total Synthesis of Cyclomarin A, a Marine Cycloheptapeptide with anti-Tuberculosis and anti-Malaria Activity. Org. Lett. 2016, 18, 204-207. DOI: 10.1021/acs.orglett.5b03292.
  • Bladt, T. T.; Frisvad, J. C.; Knudsen, P. B.; Larsen, T. O. Anticancer and Antifungal Compounds from Aspergillus, Penicillium and Other Filamentous Fungi. Molecules 2013, 18, 11338-11376. DOI: 10.3390/molecules180911338.
  • Dolan, K.; Montgomery, S.; Buchheit, B.; DiDone, L.; Wellington, M.; Krysan, D. J. Antifungal Activity of Tamoxifen: In Vitro and in Vivo Activities and Mechanistic Characterization. Antimicrob. Agents Chemother. 2009, 53, 3337-3346. DOI: 10.1128/AAC.01564-08.
  • Huang, Y.; Wang, J.; Li, G.; Zheng, Z.; Su, W. Antitumor and Antifungal Activities in Endophytic Fungi Isolated from Pharmaceutical Plants Taxus Mairei, Cephalataxus Fortunei and Torreya Grandis. FEMS Immunol. Med. Microbiol. 2001, 31, 163-167. DOI: 10.1016/S0928-8244(01)00255-3.
  • Masłyk, M.; Janeczko, M.; Martyna, A.; Kubiński, K. CX-4945: The Protein Kinase CK2 Inhibitor and Anti-Cancer Drug Shows Anti-Fungal Activity. Mol. Cell. Biochem. 2017, 435, 193-196. DOI doi:10.1007/s11010-017-3068-z.
  • Crowley, L. C.; Christensen, M. E.; Waterhouse, N. J. Measuring Survival of Adherent Cells with the Colony-Forming Assay. Cold Spring Harb. Protoc. 2016, DOI: 10.1101/pdb.prot087171.
  • Rajkumar, V.; Anand Krishnan, V. I.; Vivek, K.; Neelam, A. A Novel Resveratrol-salinomycin Combination Sensitizes ER-positive Breast Cancer Cells to Apoptosis. Pharmacol. Rep. 2017, 69, 788-797. DOI: 10.1016/j.pharep.2017.03.024.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.