Anticancer Properties of Lamellarins

Power, 2002, The seasonality and role of the neurotoxin tetramine in the salivary glands of the red whelk Neptunea antiqua (L.), Toxicon, 40, 419, 10.1016/S0041-0101(01)00211-2

Li, 2013, A functional scaffold in marine alkaloid: An anticancer moiety for human, Curr. Med. Chem., 20, 3903, 10.2174/09298673113209990186

Burres, 1991, Antitumor activity and biochemical effects of topsentin, Biochem. Pharmacol., 42, 745, 10.1016/0006-2952(91)90031-Y

Carbone, 2013, A facile synthesis of deaza-analogues of the bisindole marine alkaloid topsentin, Molecules, 18, 2518, 10.3390/molecules18032518

Cavalcanti, 2008, Cytotoxic and genotoxic effects of tambjamine D, an alkaloid isolated from the nudibranch Tambja eliora, on Chinese hamster lung fibroblasts, Chem. Biol. Interact., 174, 155, 10.1016/j.cbi.2008.05.029

Yamaguchi, 2013, Spongiacidin C, a pyrrole alkaloid from the marine sponge Stylissa massa, functions as a USP7 inhibitor, Bioorg. Med. Chem. Lett., 23, 3884, 10.1016/j.bmcl.2013.04.066

Hu, 2011, Discorhabdins and pyrroloiminoquinone-related alkaloids, Chem. Rev., 111, 5465, 10.1021/cr100435g

Valeriote, 2012, Discovery and development of anticancer agents from marine sponges: Perspectives based on a chemistry-experimental therapeutics collaborative program, J. Exp. Ther. Oncol., 10, 119

Vollmar, 2013, Targeting apoptosis pathways by natural compounds in cancer: Marine compounds as lead structures and chemical tools for cancer therapy, Cancer Lett., 332, 295, 10.1016/j.canlet.2010.07.004

Ezell, 2010, Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent, Mar. Drugs, 8, 2129, 10.3390/md8072129

Wang, 2010, A novel synthetic iminoquinone, BA-TPQ, as an anti-breast cancer agent: In vitro and in vivo activity and mechanisms of action, Breast Cancer Res. Treat., 123, 321, 10.1007/s10549-009-0638-0

Zhang, 2012, Preclinical evaluation of anticancer efficacy and pharmacological properties of FBA-TPQ, a novel synthetic makaluvamine analog, Mar. Drugs, 10, 1138, 10.3390/md10051138

Chen, 2011, Experimental therapy of ovarian cancer with synthetic makaluvamine analog: In vitro and in vivo anticancer activity and molecular mechanisms of action, PLoS One, 6, e20729, 10.1371/journal.pone.0020729

Wang, 2009, In vitro and in vivo anticancer activity of novel synthetic makaluvamine analogues, Clin. Cancer Res., 15, 3511, 10.1158/1078-0432.CCR-08-2689

Barrows, 1993, Makaluvamines, marine natural products, are active anti-cancer agents and DNA topo II inhibitors, Anticancer Drug Des., 8, 333

Matsumoto, 1999, Makaluvamines vary in ability to induce dose-dependent DNA cleavage via topoisomerase II interaction, Anticancer Drugs, 10, 39, 10.1097/00001813-199901000-00006

Chen, 2013, Identification of the ZAK-MKK4-JNK-TGFβ signaling pathway as a molecular target for novel synthetic iminoquinone anticancer compound BA-TPQ, Curr. Cancer Drug Targets, 13, 651, 10.2174/15680096113139990040

Antunes, 2004, Cytotoxic pyrroloiminoquinones from four new species of South African latrunculid sponges, J. Nat. Prod., 67, 1268, 10.1021/np034084b

Legentil, 2006, Aza-analogues of the marine pyrroloquinoline alkaloids wakayin and tsitsikammamines: Synthesis and topoisomerase inhibition, Bioorg. Med. Chem. Lett., 16, 427, 10.1016/j.bmcl.2005.09.063

Larrieu, 2013, Indoleamine 2,3-dioxygenase inhibitory activity of derivatives of marine alkaloid tsitsikammamine A, Bioorg. Med. Chem. Lett., 23, 47, 10.1016/j.bmcl.2012.11.036

Vollmar, 2013, A new perspective on old drugs: Non-mitotic actions of tubulin-binding drugs play a major role in cancer treatment, Pharmazie, 68, 478

Wan, 2013, A new target for an old drug: Identifying mitoxantrone as a nanomolar inhibitor of PIM1 kinase via kinome-wide selectivity modeling, J. Med. Chem., 56, 2619, 10.1021/jm400045y

Sugumaran, 2010, Bioactive dehydrotyrosyl and dehydrodopyl compounds of marine origin, Mar. Drugs, 8, 2906, 10.3390/md8122906

Scott, 2014, Synthetic and biological studies of tubulin targeting c2-substituted 7-deazahypoxanthines derived from marine alkaloid rigidins, ChemMedChem, 9, 1428, 10.1002/cmdc.201300532

Frolova, 2013, Exploring natural product chemistry and biology with multicomponent reactions. 5. Discovery of a novel tubulin-targeting scaffold derived from the rigidin family of marine alkaloids, J. Med. Chem., 56, 6886, 10.1021/jm400711t

Cao, 2012, Total synthesis of a marine alkaloid—rigidin E, Mar. Drugs, 10, 1412, 10.3390/md10061412

Tsuda, 2003, Rigidins B-D, new pyrrolopyrimidine alkaloids from a tunicate Cystodytes species, J. Nat. Prod., 66, 292, 10.1021/np020393a

Loya, 1999, Polycitone A, a novel and potent general inhibitor of retroviral reverse transcriptases and cellular DNA polymerases, Biochem. J., 344, 85, 10.1042/bj3440085

Rudi, 2000, Polycitone B and prepolycitrin A: Two novel alkaloids from the marine ascidian Polycitor africanus, J. Nat. Prod., 63, 832, 10.1021/np9905158

Kang, 1997, Ningalins A–D: Novel Aromatic Alkaloids from a Western Australian Ascidian of the Genus Didemnum, J. Org. Chem., 62, 3254, 10.1021/jo962132+

Liu, 2008, Antioxidant alkaloid from the South China Sea marine sponge Iotrochota sp., Z Naturforsch. C, 63, 636, 10.1515/znc-2008-9-1003

Fan, 2010, Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera, Bioorg. Med. Chem., 18, 5466, 10.1016/j.bmc.2010.06.052

Andersen, 1985, Metabolites of the marine prosobranch mollusk Lamellaria sp., J. Am. Chem Soc., 107, 5492, 10.1021/ja00305a027

Davis, 1999, New lamellarin alkaloids from the Australian ascidian, Didemnum chartaceum, J. Nat. Prod., 62, 419, 10.1021/np9803530

Lindquist, 1988, New alkaloids of the lamellarin class from the marine ascidian Didemnum chartaceum (Sluiter, 1909), J. Org. Chem., 53, 4570, 10.1021/jo00254a029

Boger, 1999, Total syntheses of nigalin A, lamellarin O, lukaniol A, and permethyl storniamide utilizing heterocyclic azadiene Diels-Alder reactions, J. Am. Chem. Soc., 121, 54, 10.1021/ja982078+

Ishibashi, 1997, Total syntheses of lamellarin D and H. The first synthesis of lamellarin-class marine alkaloids, Tetrahedron, 53, 5951, 10.1016/S0040-4020(97)00287-1

Venkata, 1997, New lamellarin alkaloids from an unidentified ascidian from the Arabian Sea, Tetrahedron, 53, 3457, 10.1016/S0040-4020(97)00073-2

Urban, 1994, Lamellarins O and P: New aromatic metabolites for the Australian marine sponge Dendrilla cactos, Aust. J. Chem., 47, 1919, 10.1071/CH9941919

Liu, 2007, Molecular-targeted antitumor agents. 15. Neolamellarins from the marine sponge Dendrilla nigra inhibit hypoxia-inducible factor-1 activation and secreted vascular endothelial growth factor production in breast tumor cells, J. Nat. Prod., 70, 1741, 10.1021/np070206e

Arafeh, 2009, Synthesis of neolamellarin A, an inhibitor of hypoxia-inducible factor-1, Nat. Prod. Commun., 4, 925

Krishnaiah, 2004, New lamellarin alkaloids from the Indian ascidian Didemnum obscurum and their antioxidant properties, J. Nat. Prod., 67, 1168, 10.1021/np030503t

Reddy, 2005, New potent cytotoxic lamellarin alkaloids from Indian ascidian Didemnum obscurum, Tetrahedron, 61, 9242, 10.1016/j.tet.2005.07.067

Plisson, 2012, Kinase inhibitor scaffolds against neurodegenerative diseases from a Southern Australian ascidian, Didemnum sp., ChemMedChem, 7, 983, 10.1002/cmdc.201200169

Imbri, 2013, A high-yielding modular access to the lamellarins: Synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η, Chemistry, 19, 15080, 10.1002/chem.201303563

Fan, 2008, Lamellarins and related pyrrole-derived alkaloids from marine organisms, Chem. Rev., 108, 264, 10.1021/cr078199m

Bailly, 2004, Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids, Curr. Med. Chem. Anti-Cancer Agents, 4, 363, 10.2174/1568011043352939

Pla, 2008, Recent advances in lamellarin alkaloids: Isolation, synthesis and activity, Anticancer Agents Med. Chem., 8, 746, 10.2174/187152008785914789

Pla, 2011, Progress on lamellarins, Med. Chem. Commun., 2, 689, 10.1039/C1MD00003A

Korotaev, 2011, A simple synthesis of the pentacyclic lamellarin skeleton from 3-nitro-2- (trifluoromethyl)-2H-chromenes and 1-methyl(benzyl)-3,4-dihydroisoquinolines, Tetrahedron, 67, 8685, 10.1016/j.tet.2011.09.049

Liermann, 2008, Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated alpha-aminonitrile, J. Org. Chem., 73, 4526, 10.1021/jo800467e

Gupton, 2009, The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B, Tetrahedron, 65, 4283, 10.1016/j.tet.2009.03.085

Ploypradith, 2006, Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings, J. Org. Chem., 71, 9440, 10.1021/jo061810h

Ueda, 2014, β-Selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I, J. Am. Chem. Soc., 136, 13226, 10.1021/ja508449y

Fujikawa, 2006, Total synthesis of lamellarins D, L, and N, Tetrahedron, 62, 594, 10.1016/j.tet.2005.10.014

Korotaev, 2008, A facile route to pentacyclic lamellarin skeleton via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines, Tetrahedron Lett., 49, 5376, 10.1016/j.tetlet.2008.06.122

Korotaev, 2010, A simple synthesis of the lamellarin analogues from 3-nitro-2-trifluoromethyl-2H-chromenes and 1-benzyl-3,4-dihydroisoquinolines, Mendeleev Commun., 20, 321, 10.1016/j.mencom.2010.11.006

Li, 2011, Total synthesis of lamellarins D, H, and R and ningalin B, Org. Lett., 13, 312, 10.1021/ol1027877

Komatsubara, 2014, Modular synthesis of lamellarins via regioselective assembly of 3,4,5-differentially arylated pyrrole-2-carboxylates, J. Org. Chem., 79, 529, 10.1021/jo402181w

Ohta, 2009, Design and synthesis of lamellarin D analogues targeting topoisomerase I, J. Org. Chem., 74, 8143, 10.1021/jo901589e

Thasana, 2007, Copper(I)-mediated and microwave-assisted C(aryl)-O(carboxylic) coupling: Synthesis of benzopyranones and isolamellarin alkaloids, J. Org. Chem., 72, 9379, 10.1021/jo701599g

Gallego, 2008, Overcoming chemoresistance of non-small cell lung carcinoma through restoration of an AIF-dependent apoptotic pathway, Oncogene, 27, 1981, 10.1038/sj.onc.1210833

Cananzi, 2011, Synthesis and topoisomerase I inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D, Bioorg. Med. Chem., 19, 4971, 10.1016/j.bmc.2011.06.056

You, 2006, Pyrrolo[2,1-a]isoquinoline as a skeleton for the synthesis of bioactive lamellarin H, Biomed. Mater., 1, L7, 10.1088/1748-6041/1/3/L01

Liao, 2011, Novel 5, 6-Dihydropyrrolo[2,1-a]isoquinolines as scaffolds for synthesis of lamellarin analogues, Evid. Based Complement. Alternat. Med., 2011, 103425, 10.1155/2011/103425

Shen, 2010, Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents, Eur. J. Med. Chem., 45, 11, 10.1016/j.ejmech.2009.09.017

Neagoie, 2012, Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class, Eur. J. Med. Chem., 49, 379, 10.1016/j.ejmech.2012.01.040

Pla, 2009, Lamellarin D bioconjugates I: Synthesis and cellular internalization of PEG-derivatives, Bioconjug. Chem., 20, 1100, 10.1021/bc800503k

Pla, 2009, Lamellarin D bioconjugates II: Synthesis and cellular internalization of dendrimer and nuclear location signal derivatives, Bioconjug Chem., 20, 1112, 10.1021/bc800504t

Pungkham, 2011, PEG-b-PCL and PEG-b-PLA polymeric micelles as nanocarrieres for lamellarin N delivery, Conf. Proc. IEEE Eng. Med. Biol. Soc., 2011, 3245

Shen, 2014, Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents, Eur. J. Med. Chem., 85, 807, 10.1016/j.ejmech.2014.08.038

Ishibashi, 2002, Synthesis and structure-activity relationship study of lamellarin derivatives, J. Nat. Prod., 65, 500, 10.1021/np0104525

Yotapan, 2010, Synthesis and biological activities of azalamellarins, Chem. Asian J., 5, 2113, 10.1002/asia.201000237

Chittchang, 2010, Assessing the drug-likeness of lamellarins, a marine-derived natural product class with diverse oncological activities, Eur. J. Med. Chem., 45, 2165, 10.1016/j.ejmech.2010.01.053

Pla, 2006, Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D, J. Med. Chem., 49, 3257, 10.1021/jm0602458

Zhang, 2012, A search for BACE inhibitors reveals new biosynthetically related pyrrolidones, furanones and pyrroles from a southern Australian marine sponge, Ianthella sp., Org. Biomol. Chem., 10, 2656, 10.1039/c2ob06747a

Huang, 2014, Lamellarin O, a pyrrole alkaloid from an Australian marine sponge, Ianthella sp., reverses BCRP mediated drug resistance in cancer cells, Mar. Drugs, 12, 3818, 10.3390/md12073818

Breier, 2013, New insight into P-glycoprotein as a drug target, Anticancer Agents Med Chem., 13, 159, 10.2174/187152013804487380

Quesada, 1996, Polyaromatic alkaloids from marine invertebrates as cytotoxic compounds and inhibitors of multidrug resistance caused by P-glycoprotein, Br. J. Cancer., 74, 677, 10.1038/bjc.1996.421

Vanhuyse, 2005, Lamellarin D: A novel pro-apoptotic agent from marine origin insensitive to P-glycoprotein-mediated drug efflux, Cancer Lett., 221, 165, 10.1016/j.canlet.2004.09.022

Chittchang, 2009, Cytotoxicities and structure-activity relationships of natural and unnatural lamellarins toward cancer cell lines, ChemMedChem., 4, 457, 10.1002/cmdc.200800339

Tardy, 2003, Lamellarin D: A novel potent inhibitor of topoisomerase I, Cancer Res., 63, 7392

Tardy, 2004, Topoisomerase I-mediated DNA cleavage as a guide to the development of antitumor agents derived from the marine alkaloid lamellarin D: Triester derivatives incorporating amino acid residues, Bioorg. Med. Chem., 12, 1697, 10.1016/j.bmc.2004.01.020

Marco, 2005, Molecular determinants of topoisomerase I poisoning by lamellarins: Comparison with camptothecin and structure-activity relationships, J. Med. Chem., 48, 3796, 10.1021/jm049060w

Ballot, 2014, Another facet to the anticancer response to lamellarin D: Induction of cellular senescence through inhibition of topoisomerase I and intracellular Ros production, Mar. Drugs, 12, 779, 10.3390/md12020779

Khiati, 2014, Poisoning of mitochondrial topoisomerase I by lamellarin D, Mol. Pharmacol., 86, 193, 10.1124/mol.114.092833

Sobek, 2013, Negative regulation of mitochondrial transcription by mitochondrial topoisomerase I, Nucleic Acids Res., 41, 9848, 10.1093/nar/gkt768

Ridley, 2002, Total synthesis and evaluation of lamellarin alpha 20-Sulfate analogues, Bioorg. Med. Chem., 10, 3285, 10.1016/S0968-0896(02)00237-7

Hwang, 1999, Mechanism of inhibition of a poxvirus topoisomerase by the marine natural product sansalvamide A, Mol. Pharmacol., 55, 1049, 10.1124/mol.55.6.1049

Kluza, 2006, Cancer cell mitochondria are direct proapoptotic targets for the marine antitumor drug lamellarin D, Cancer Res., 66, 3177, 10.1158/0008-5472.CAN-05-1929

Skropeta, 2011, Kinase inhibitors from marine sponges, Mar. Drugs, 9, 2131, 10.3390/md9102131

Baunbaek, 1998, Anticancer alkaloid lamellarins inhibit protein kinases, Mar. Drugs, 6, 514, 10.3390/md20080026

Yoshida, 2013, Synthesis, resolution, and biological evaluation of atropisomeric (aR)- and (aS)-16-methyllamellarins N: Unique effects of the axial chirality on the selectivity of protein kinases inhibition, J. Med. Chem., 56, 7289, 10.1021/jm400719y

Ballot, 2009, Essential role of mitochondria in apoptosis of cancer cells induced by the marine alkaloid Lamellarin D, Mol. Cancer Ther., 8, 3307, 10.1158/1535-7163.MCT-09-0639

Dias, 2005, Drugs targeting mitochondrial functions to control tumor cell growth, Biochem Pharmacol., 70, 1, 10.1016/j.bcp.2005.03.021

Ballot, 2010, Inhibition of mitochondrial respiration mediates apoptosis induced by the anti-tumoral alkaloid lamellarin D, Apoptosis, 15, 769, 10.1007/s10495-010-0471-2

Lim, 2010, Biochemical disorders induced by cytotoxic marine natural products in breast cancer cells as revealed by proton NMR spectroscopy-based metabolomics, Biochem. Pharmacol., 80, 1170, 10.1016/j.bcp.2010.07.007

Lu, 2010, Marine compounds and their antiviral activities, Antiviral Res., 86, 231, 10.1016/j.antiviral.2010.03.009

Reddy, 1999, Lamellarin alpha 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture, J. Med. Chem., 42, 1901, 10.1021/jm9806650

Kamiyama, 2011, Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues, Bioorg. Med. Chem., 19, 7541, 10.1016/j.bmc.2011.10.030

Peters, 2013, Polypharmacology—Foe or friend?, J. Med. Chem., 56, 8955, 10.1021/jm400856t

Anighoro, 2014, Polypharmacology: Challenges and opportunities in drug discovery, J. Med. Chem., 57, 7874, 10.1021/jm5006463

Reddy, 2013, Polypharmacology: Drug discovery for the future, Expert Rev. Clin. Pharmacol., 6, 41, 10.1586/ecp.12.74

Urra, 2013, Mitochondria: A promising target for anticancer alkaloids, Curr. Top. Med. Chem., 13, 2171, 10.2174/15680266113139990150

Kaipparettu, 2013, Crosstalk from non-cancerous mitochondria can inhibit tumor properties of metastatic cells by suppressing oncogenic pathways, PLoS One, 8, e61747, 10.1371/journal.pone.0061747

Chen, 2014, Quantitative proteomics analysis identifies mitochondria as therapeutic targets of multidrug-resistance in ovarian cancer, Theranostics, 4, 1164, 10.7150/thno.8502

Edeas, 2013, Targeting mitochondria: Strategies, innovations and challenges: The future of medicine will come through mitochondria, Mitochondrion, 13, 389, 10.1016/j.mito.2013.03.009