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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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General Review Article

Isolation, Synthesis and Medicinal Significance of Marine Pyridoacridine Alkaloids

Author(s): Saqlain Haider, Amar G. Chittiboyina * and Ikhlas A. Khan

Volume 23, Issue 13, 2019

Page: [1469 - 1495] Pages: 27

DOI: 10.2174/1385272823666190725093517

Price: $65

Abstract

Pyridoacridine alkaloids, distributed in marine organisms have emerged as an important class of compounds due to their uniqure chemical architecture, diversity and medicinal significance. These alkaloids are reported to exhibit a wide array of biological activities like anti-cancer, anti-bacterial, ant-viral, anti-fungal and anti-parasitic activities. The present review highlights the isolation, synthesis and medicinal significance of this important class of pyridoacridine alkaloids.

Keywords: Pyridoacridine, biosynthesis, annulation, Boekelheide rearrangement, isolation, synthesis, anti-parasitic.

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[1]
Sabrin, R.M.I.; Gamal, A.M. Marine pyridoacridine alkaloids: Biosynthesis and biological activities. Chem. Biodiversity (Nepean), 2016, 13, 37-47.
[2]
Tadeusz, F.M. Marine pyridoacridine alkaloids: Structure, synthesis, and biological chemistry. Chem. Rev., 1993, 93, 1825-1838.
[http://dx.doi.org/10.1021/cr00021a009]
[3]
Schmitz, F.J.; Agarwal, S.K.; Gunasekera, S.P.; Schmidt, P.G.; Shoolery, J.N. Amphimedine, new aromatic alkaloid from a pacific sponge, Amphimedon sp. Carbon connectivity determination from natural abundance 13C-13C coupling constants. J. Am. Chem. Soc., 1983, 105, 4835-4836.
[http://dx.doi.org/10.1021/ja00352a052]
[4]
Sabrin, R.M.I.; Gamal, A.M. Pyridoacridine alkaloids from deep-water marine organisms: Structural elucidation. Bull. Fac. Pharm. Cairo Univ., 2016, 54, 107-135.
[http://dx.doi.org/10.1016/j.bfopcu.2016.08.003]
[5]
Marshall, K.M.; Barrows, L.R. Biological activities of pyridoacridines. Nat. Prod. Rep., 2004, 21(6), 731-751.
[http://dx.doi.org/10.1039/b401662a] [PMID: 15565252]
[6]
Delphine, B.; Bernard, B.; Christophe, L.; Nataly, B. New pyridoacridine alkaloids from the purple morph of the ascidian Cystodytes dellechiajei. Tetrahedron Lett., 2011, 52, 3041-3044.
[http://dx.doi.org/10.1016/j.tetlet.2011.04.005]
[7]
Aoki, S.; Wei, H.; Matsui, K.; Rachmat, R.; Kobayashi, M. Pyridoacridine alkaloids inducing neuronal differentiation in a neuroblastoma cell line, from marine sponge Biemna fortis. Bioorg. Med. Chem., 2003, 11(9), 1969-1973.
[http://dx.doi.org/10.1016/S0968-0896(03)00086-5] [PMID: 12670647]
[8]
Clement, J.A.; Kitagaki, J.; Yang, Y.; Saucedo, C.J.; O’Keefe, B.R.; Weissman, A.M.; McKee, T.C.; McMahon, J.B. Discovery of new pyridoacridine alkaloids from Lissoclinum cf. badium that inhibit the ubiquitin ligase activity of Hdm2 and stabilize p53. Bioorg. Med. Chem., 2008, 16(23), 10022-10028.
[http://dx.doi.org/10.1016/j.bmc.2008.10.024] [PMID: 18977148]
[9]
Chu-min, Z.; Masami, I.; Keita, M.; Shiro, N.; Junichi, K. Two new polycyclic aromatic alkaloids from the Okinawan marine sponge Biemna sp. Tetrahedron, 1993, 49(37), 8337-8342.
[http://dx.doi.org/10.1016/S0040-4020(01)81917-7]
[10]
Jun’ichi, K. Jie-fei, C.; Markus, R.W.; Hideshi, N.; Yoshimasa, H.; Takuma, S.; Yasushi, O.; Cystodytins, A. B, and C, Novel tetracyclic aromatic alkaloids with potent antineoplastic activity from the okinawan tunicate Cystodytes dellechiajei. J. Org. Chem., 1988, 53(8), 1800-1804.
[http://dx.doi.org/10.1021/jo00243a038]
[11]
Kim, J.; Pordesimo, E.O.; Toth, S.I.; Schmitz, F.J.; Van Altena, I. Pantherinine, a cytotoxic aromatic alkaloid, and 7-deazainosine from the ascidian Aplidium pantherinum. J. Nat. Prod., 1993, 56(10), 1813-1816.
[http://dx.doi.org/10.1021/np50100a023] [PMID: 8277319]
[12]
Trong, D.T.; Ngoc, B.P.; Ronald, J.Q. Structure determination of pentacyclic pyridoacridine alkaloids from the australian marine organisms Ancorina geodides and Cnemidocarpa stolonifera. Eur. J. Org. Chem., 2014, 22, 4805-4816.
[13]
Anthony, R.C.; Niranjala, M.C.; Anthony, P.; Paul, J.S. A second shermilamine alkaloid from a tunicate Trididemnum sp. J. Org. Chem., 1989, 54(17), 4231-4232.
[http://dx.doi.org/10.1021/jo00278a048]
[14]
McDonald, L.A.; Eldredge, G.S.; Barrows, L.R.; Ireland, C.M. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: A mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem., 1994, 37(22), 3819-3827.
[http://dx.doi.org/10.1021/jm00048a017] [PMID: 7525959]
[15]
Bontemps, N.; Gattacceca, F.; Long, C.; Thomas, O.P.; Banaigs, B. Additional cytotoxic pyridoacridine alkaloids from the ascidian Cystodytes violatinctus and biogenetic considerations. J. Nat. Prod., 2013, 76(9), 1801-1805.
[http://dx.doi.org/10.1021/np400284z] [PMID: 23961991]
[16]
Koren-Goldshlager, G.; Aknin, M.; Kashman, Y. Cycloshermilamine D, a new pyridoacridine from the marine tunicate cystodytes violatinctus. J. Nat. Prod., 2000, 63(6), 830-831.
[http://dx.doi.org/10.1021/np990569h] [PMID: 10869211]
[17]
McDonald, L.A.; Eldredge, G.S.; Barrows, L.R.; Ireland, C.M. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: A mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem., 1994, 37(22), 3819-3827.
[http://dx.doi.org/10.1021/jm00048a017] [PMID: 7525959]
[18]
Nilar, N.; Sidebottom, P.J.; Carté, B.K.; Butler, M.S. Three new pyridoacridine type alkaloids from a singaporean ascidian. J. Nat. Prod., 2002, 65(8), 1198-1200.
[http://dx.doi.org/10.1021/np010629v] [PMID: 12193032]
[19]
Bontemps, N.; Bry, D.; López-Legentil, S.; Simon-Levert, A.; Long, C.; Banaigs, B. Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes dellechiajei. J. Nat. Prod., 2010, 73(6), 1044-1048.
[http://dx.doi.org/10.1021/np900751k] [PMID: 20491501]
[20]
Amira, R.; Yehuda, B.; Israel, G.; Yoel, K. Eilatin, a novel alkaloid from the marine tunicate eudistomasp. Tetrahedron Lett., 1988, 29(50), 6655-6656.
[http://dx.doi.org/10.1016/S0040-4039(00)82422-3]
[21]
Anuchit, P.; Bradley, S.D. Arnoamines A and B, New Cytotoxic Pentacyclic Pyridoacridine Alkaloids from the Ascidian Cystodytes sp. J. Org. Chem., 1998, 63, 1657-1659.
[http://dx.doi.org/10.1021/jo9719721]
[22]
Brent, R.C.; Jamaluddin, J.; Akbar, T.; Chris, M.I. Styelsamines A-D: New Tetracyclic Pyridoacridine Alkaloids from the Indonesian Ascidian Eusynstyela latericius. J. Org. Chem., 1998, 63, 8024-8026.
[http://dx.doi.org/10.1021/jo980905j]
[23]
Torres, Y.R.; Bugni, T.S.; Berlinck, R.G.; Ireland, C.M.; Magalhães, A.; Ferreira, A.G.; Moreira Da Rocha, R. Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei. J. Org. Chem., 2002, 67(15), 5429-5432.
[http://dx.doi.org/10.1021/jo011174h] [PMID: 12126446]
[24]
Florecita, S.G.; Brad, C.; Nelson, T.; John, F.; Mary, K.H.; Gisela, P.C.; Gina, C.M.; Sandra, S.M.; Louis, R.B.; Chris, M.I. Neoamphimedine: A new pyridoacridine topoisomerase II inhibitor which catenates DNA. J. Org. Chem., 1999, 64, 1400-1402.
[http://dx.doi.org/10.1021/jo982047x]
[25]
Marshall, K.M.; Andjelic, C.D.; Tasdemir, D.; Concepción, G.P.; Ireland, C.M.; Barrows, L.R. Deoxyamphimedine, a pyridoacridine alkaloid, damages DNA via the production of reactive oxygen species. Mar. Drugs, 2009, 7(2), 196-209.
[http://dx.doi.org/10.3390/md7020196] [PMID: 19597581]
[26]
Kijjoa, A.; Wattanadilok, R.; Campos, N.; Nascimento, M.S.; Pinto, M.; Herz, W. Anticancer activity evaluation of kuanoniamines A and C isolated from the marine sponge Oceanapia sagittaria, collected from the Gulf of Thailand. Mar. Drugs, 2007, 5(2), 6-22.
[http://dx.doi.org/10.3390/md502006] [PMID: 18463725]
[27]
Eder, C.; Schupp, P.; Proksch, P.; Wray, V.; Steube, K.; Müller, C.E.; Frobenius, W.; Herderich, M.; van Soest, R.W. Bioactive pyridoacridine alkaloids from the micronesian sponge Oceanapia sp. J. Nat. Prod., 1998, 61(2), 301-305.
[http://dx.doi.org/10.1021/np9702704] [PMID: 9514015]
[28]
McDonald, L.A.; Eldredge, G.S.; Barrows, L.R.; Ireland, C.M. Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: A mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem., 1994, 37(22), 3819-3827.
[http://dx.doi.org/10.1021/jm00048a017] [PMID: 7525959]
[29]
Xiaomei, W.; Tim, S.B.; Mary, K.H.; Imelda, T.S. Elizabeth, J.M.; Jennifer, S.; Ryan, M.V.W.; David A.J.; Chris. M.I. Evaluation of pyridoacridine Alkaloids in a Zebrafish Phenotypic Assay. Mar. Drugs, 2010, 8, 1769-1778.
[http://dx.doi.org/10.3390/md8061769]
[30]
Agrawal, M.S.; Bowden, B.F. Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp. Nat. Prod. Res., 2007, 21(9), 782-786.
[http://dx.doi.org/10.1080/14786410601132212] [PMID: 17763101]
[31]
David, R.A.; Norrie, A.P.; Gretchen, L.; Russell, C.B.; Brent, R.C. Isodiplamine, cystodytin K and lissoclinidine: Novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti. Tetrahedron, 2002, 58, 9779-9783.
[http://dx.doi.org/10.1016/S0040-4020(02)01296-6]
[32]
Emma, C.B.; Nur, A.B.M.S.; Elizabeth, D.W.; John, N.A.H.; Rohan, A.D. Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge, Ecionemia geodides. Tetrahedron, 2010, 66, 283-287.
[http://dx.doi.org/10.1016/j.tet.2009.10.109]
[33]
Yunjiang, F.; Rohan, A.D.; Melissa, L.S.; Vicky, M.A.; Anthony, R.C.; David, C.; Ronald, J.Q. Antitrypanosomal pyridoacridine alkaloids from the Australian ascidian Polysyncraton echinatum. Tetrahedron Lett., 2010, 51, 2477-2479.
[http://dx.doi.org/10.1016/j.tetlet.2010.02.161]
[34]
Francis, J.S.; Forecita, S.D.; Bilayet, M.H.; Dick, H. Cytotoxic aromatic alkaloids from the ascidian Amphicarpa meridiana and Leptoclinides sp.: Meridine and 11-Hydroxyascididemin. J. Org. Chem., 1991, 56(2), 804-808.
[http://dx.doi.org/10.1021/jo00002a055]
[35]
Ralifo, P.; Sanchez, L.; Gassner, N.C.; Tenney, K.; Lokey, R.S.; Holman, T.R.; Valeriote, F.A.; Crews, P. Pyrroloacridine alkaloids from Plakortis quasiamphiaster: Structures and bioactivity. J. Nat. Prod., 2007, 70(1), 95-99.
[http://dx.doi.org/10.1021/np060585w] [PMID: 17253856]
[36]
Ford, P.W.; Davidson, B.S. Plakinidine D, a new pyrroloacridine alkaloid from the ascidian Didemnum rubeum. J. Nat. Prod., 1997, 60(10), 1051-1053.
[http://dx.doi.org/10.1021/np970312o] [PMID: 9358649]
[37]
Carroll, A.R.; Ngo, A.; Quinn, R.J.; Redburn, J.; Hooper, J.N. Petrosamine B, an inhibitor of the Helicobacter pylori enzyme aspartyl semialdehyde dehydrogenase from the Australian sponge Oceanapia sp. J. Nat. Prod., 2005, 68(5), 804-806.
[http://dx.doi.org/10.1021/np049595s] [PMID: 15921437]
[38]
Hai-yin, H.; John, D.F. Eudistones A and B: Two Novel Octacyclic Alkaloids from a Seychelles Tunicate, Eudistoma sp. J. Org. Chem., 1991, 56, 5369-5371.
[http://dx.doi.org/10.1021/jo00018a031]
[39]
Geewananda, P.G.; Shigeo, K.; Sarath, P.G.; Oliver, J.M.; Frank, E.K. Dercitin, a new biologically active acridine alkaloid from a deep water marine sponge, Dercitus sp. J. Am. Chem. Soc., 1988, 110(14), 4856-4858.
[http://dx.doi.org/10.1021/ja00222a071]
[40]
Geewananda, P.G.; Shigeo, K.; Neal, S.B. New cytotoxic acridine alkaloids from two deep water marine sponges of the family Pachastrellidae. Tetrahedron Lett., 1989, 30, 4359-4362.
[http://dx.doi.org/10.1016/S0040-4039(00)99360-2]
[41]
Stephen, J.B.; Francis, J.S. A novel pentacyclic aromatic alkaloid from an ascidian. J. Am. Chem. Soc., 1987, 109(20), 6134-6136.
[http://dx.doi.org/10.1021/ja00254a037]
[42]
Tadeusz, F.M.; Chris, M.I. Varamines A and B, new cytotoxic thioalkaloids from Lissoclinum vareau. J. Org. Chem., 1989, 54(17), 4256-4259.
[http://dx.doi.org/10.1021/jo00278a058]
[43]
Gari, G.; Amira, R.; Yoel, K. Biomimetic synthesis of pyrido. Acridines. Tetrahedron Lett., 1993, 34(11), 1823-1826. [2,3,4-kl
[http://dx.doi.org/10.1016/S0040-4039(00)60789-X]
[44]
Riddick, D.A. A novel hetero Diels-Alder reaction as a route to annelated pyridines and bipyridines., 1995.
[45]
Bert, S.; Klaudia, B.; Winfried, P. Biosynthesis of Shermillamine B. Tetrahedron, 1993, 49(28), 6223-6228.
[http://dx.doi.org/10.1016/S0040-4020(01)87960-6]
[46]
Skyler, D.; Heathcock, C.H. The pyridoacridine family tree: A useful scheme for designing synthesis and predicting undiscovered natural products. J. Nat. Prod., 2002, 65(11), 1573-1581.
[http://dx.doi.org/10.1021/np020016y] [PMID: 12444679]
[47]
Melzer, B.; Plodek, A.; Bracher, F. Total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine. J. Org. Chem., 2014, 79(15), 7239-7242.
[http://dx.doi.org/10.1021/jo501312d] [PMID: 25081029]
[48]
Yin, H.; Shan, N.; Wang, S.; Yao, Z.J. Total synthesis of ascididemin-type alkaloids using alkyne building blocks. J. Org. Chem., 2014, 79(20), 9748-9753.
[http://dx.doi.org/10.1021/jo501927e] [PMID: 25238030]
[49]
Khalil, I.M.; Barker, D.; Copp, B.R. Bioinspired syntheses of the pyridoacridine marine alkaloids demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine. J. Org. Chem., 2016, 81(1), 282-289.
[http://dx.doi.org/10.1021/acs.joc.5b02312] [PMID: 26642369]
[50]
LaBarbera, D.V.; Bugni, T.S.; Ireland, C.M. The total synthesis of neoamphimedine. J. Org. Chem., 2007, 72(22), 8501-8505.
[http://dx.doi.org/10.1021/jo7017813] [PMID: 17900144]
[51]
Delfourne, E.; Roubin, C.; Bastide, J. The first synthesis of the pentacyclic pyridoacridine marine alkaloids: Arnoamines A and B. J. Org. Chem., 2000, 65(18), 5476-5479.
[http://dx.doi.org/10.1021/jo000011a] [PMID: 10970284]
[52]
Skyler, D.; Heathcock, C.H. A simple biomimetic synthesis of styelsamine B. Org. Lett., 2001, 3(26), 4323-4324.
[http://dx.doi.org/10.1021/ol010262l] [PMID: 11784208]
[53]
Yoshiyasu, K.; Shinsuke, N.; Takanobu, Y.; Masanori, N.; Akinori, K. Total synthesis of Kuanoniamine A, 11-hydroxyascididemin, and Neocalliactine Acetate. Heterocycles, 1993, 36, 943-946.
[http://dx.doi.org/10.3987/COM-92-6321]
[54]
Alois, P.; Franz, B. A divergent approach to the total synthesis of the marine pyridoacridine alkaloid eilatin and its synthetic isomer isoeilatin. Tetrahedron Lett., 2015, 56, 1445-1447.
[http://dx.doi.org/10.1016/j.tetlet.2015.01.176]
[55]
Nataly, B.; Evelyne, D.; Jean, B.; Christian, F.; Franz, B. Total synthesis of the marine pentacyclic alkaloid meridine. Tetrahedron, 1997, 53, 1743-1750.
[http://dx.doi.org/10.1016/S0040-4020(96)01096-4]
[56]
Proksch, P.; Edrada, R.A.; Ebel, R. Drugs from the seas - current status and microbiological implications. Appl. Microbiol. Biotechnol., 2002, 59(2-3), 125-134.
[http://dx.doi.org/10.1007/s00253-002-1006-8] [PMID: 12111137]
[57]
Burres, N.S.; Sazesh, S.; Gunawardana, G.P.; Clement, J.J. Antitumor activity and nucleic acid binding properties of dercitin, a new acridine alkaloid isolated from a marine Dercitus species sponge. Cancer Res., 1989, 49(19), 5267-5274.
[PMID: 2548717]
[58]
Bishop, M.J.; Ciufolini, M.A.; Michael, J.B.; Marco, A.C. Total synthesis of kuanoniamines and dercitins. J. Am. Chem. Soc., 1992, 114, 10081-10082.
[http://dx.doi.org/10.1021/ja00051a062]
[59]
Taraporewala, I.B.; Cessac, J.W.; Chanh, T.C.; Delgado, A.V.; Schinazi, R.F. HIV-1 neutralization and tumor cell proliferation inhibition in vitro by simplified analogues of pyrido[4,3,2-mn]thiazolo[5,4-b]acridine marine alkaloids. J. Med. Chem., 1992, 35(15), 2744-2752.
[http://dx.doi.org/10.1021/jm00093a005] [PMID: 1495008]
[60]
David, R.A.; Norrie, A.P.; Brent, R.C. Anti-Tuberculosis natural products: Synthesis and biological evaluation of pyridoacridine alkaloids related to ascididemin. Tetrahedron, 2010, 66, 4977-4986.
[http://dx.doi.org/10.1016/j.tet.2010.05.033]
[61]
Luedtke, N.W.; Hwang, J.S.; Glazer, E.C.; Gut, D.; Kol, M.; Tor, Y. Eilatin Ru(II) complexes display anti-HIV activity and enantiomeric diversity in the binding of RNA. ChemBioChem, 2002, 3(8), 766-771.
[http://dx.doi.org/10.1002/1439-7633(20020802)3:8<766:AID-CBIC766>3.0.CO;2-X] [PMID: 12203975]
[62]
Cortés, F.; Pastor, N.; Mateos, S.; Domínguez, I. Roles of DNA topoisomerases in chromosome segregation and mitosis. Mutat. Res., 2003, 543(1), 59-66.
[http://dx.doi.org/10.1016/S1383-5742(02)00070-4] [PMID: 12510017]
[63]
Deepak, K.; Diwan, S.R. Marine natural alkaloids as anticancer agents. Opportunity challenge and scope of natural products in medicinal chemistry, 2011, 213-268. ISBN: 978-81-308-0448-4.
[64]
Sørensen, B.S.; Sinding, J.; Andersen, A.H.; Alsner, J.; Jensen, P.B.; Westergaard, O. Mode of action of topoisomerase II-targeting agents at a specific DNA sequence. Uncoupling the DNA binding, cleavage and religation events. J. Mol. Biol., 1992, 228(3), 778-786.
[http://dx.doi.org/10.1016/0022-2836(92)90863-F] [PMID: 1335085]
[65]
Ashwani, K.; Sunil, K.; Sanddep, J.; Parvin, K.; Ruchika, G. Study of binding of pyridoacridine alkaloids on topoisomerase II using in silico tools. Med. Chem. Res., 2013, 22, 5431-5441.
[http://dx.doi.org/10.1007/s00044-013-0496-5]
[66]
Delfourne, E.; Darro, F.; Bontemps-Subielos, N.; Decaestecker, C.; Bastide, J.; Frydman, A.; Kiss, R. Synthesis and characterization of the antitumor activities of analogues of meridine, a marine pyridoacridine alkaloid. J. Med. Chem., 2001, 44(20), 3275-3282.
[http://dx.doi.org/10.1021/jm0108496] [PMID: 11563926]
[67]
Brent, S.L.; Louis, R.B.; Brent, R.C. Structural requirements for biological activity of the Marine Alkaloid Ascididemin. Bioorg. Med. Chem. Lett., 1995, 5, 739-742.
[http://dx.doi.org/10.1016/0960-894X(95)00106-4]
[68]
Peterson, J.R.; Zjawiony, J.K.; Liu, S.; Hufford, C.D.; Clark, A.M.; Rogers, R.D. Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines. J. Med. Chem., 1992, 35(22), 4069-4077.
[http://dx.doi.org/10.1021/jm00100a012] [PMID: 1433213]
[69]
Geera, A.C.; Tawnya, C.M.; Chris, M.I. Diplamine, A cytotoxic polyaromatic alkaloid from the Tunicate Diplosoma Sp. Tetrahedron Lett., 1989, 30, 4201-4202.
[http://dx.doi.org/10.1016/S0040-4039(01)80689-4]
[70]
McCarthy, P.J.; Pitts, T.P.; Gunawardana, G.P.; Kelly-Borges, M.; Pomponi, S.A. Antifungal activity of meridine, a natural product from the marine sponge Corticium sp. J. Nat. Prod., 1992, 55(11), 1664-1668.
[http://dx.doi.org/10.1021/np50089a016] [PMID: 1479383]
[71]
Copp, B.R.; Kayser, O.; Brun, R.; Kiderlen, A.F. Antiparasitic activity of marine pyridoacridone alkaloids related to the ascididemins. Planta Med., 2003, 69(6), 527-531.
[http://dx.doi.org/10.1055/s-2003-40640] [PMID: 12865971]
[72]
Alley, M.C.; Pacula-Cox, C.M.; Hursey, M.L.; Rubinstein, L.R.; Boyd, M.R. Morphometric and colorimetric analyses of human tumor cell line growth and drug sensitivity in soft agar culture. Cancer Res., 1991, 51(4), 1247-1256.
[PMID: 1705170]
[73]
Plowman, J.; Dykes, D.J.; Hollingshead, M.; Simpson-Herren, L.; Aleey, M.C. Anticancer Drug Development Guide: Preclinical Screening; Clinical Trials, and Approval: New Jersey, USA, 1997.
[http://dx.doi.org/10.1007/978-1-4615-8152-9_6]
[74]
Skipper, H.E.; Schabel, F.M., Jr; Wilcox, W.S.; Laster, W.R., Jr; Trader, M.W.; Thompson, S.A. Experimental evaluation of potential anticancer agents. 28. Effects of therapy on viability and rate of proliferation of leukemic cells in various anatomic sites. Cancer Chemother. Rep., 1965, 47, 41-64.
[PMID: 5829427]
[75]
Waud, W.R. Anticancer Drug Development Guide: Preclinical Screening; Clinical Trials, and Approval: New Jersey, USA, 1997.
[http://dx.doi.org/10.1007/978-1-4615-8152-9_4]
[76]
Bracher, F. Polycyclic aromatic alkaloids. XII: In vitro- and in vivo-investigations of the cytotoxic marine alkaloid 2-bromoleptoclinidinone. Pharmazie, 1997, 52(1), 57-60.
[PMID: 9035236]
[77]
Boyd, M.R. Status of the NCI preclinical antitumor drug discovery screen. Principles Practice Oncol., 1989, 3, 1-12.
[78]
Longley, R.E.; McConnell, O.J.; Essich, E.; Harmody, D. Evaluation of marine sponge metabolites for cytotoxicity and signal transduction activity. J. Nat. Prod., 1993, 56(6), 915-920.
[http://dx.doi.org/10.1021/np50096a015] [PMID: 8350092]
[79]
Lishner, M.; Shur, I.; Bleiberg, I.; Rudi, A.; Kashman, Y.; Fabian, I. Sensitivity of hematopoietic progenitors of acute myeloblastic leukemia to new compounds derived from marine organisms. Leukemia, 1995, 9(9), 1543-1548.
[PMID: 7658723]
[80]
Einat, M.; Lishner, M.; Amiel, A.; Nagler, A.; Yarkorli, S.; Rudi, A.; Kashman, Y.; Markel, D.; Fabian, I. Eilatin: A novel marine alkaloid inhibits in vitro proliferation of progenitor cells in chronic myeloid leukemia patients. Exp. Hematol., 1995, 23(14), 1439-1444.
[PMID: 8542929]
[81]
Bonnard, I.; Bontemps, N.; Lahmy, S.; Banaigs, B.; Combaut, G.; Francisco, C.; Colson, P.; Houssier, C.; Waring, M.J.; Bailly, C. Binding to DNA and cytotoxic evaluation of ascididemin, the major alkaloid from the mediterranean ascidian Cystodytes dellechiajei. Anticancer Drug Des., 1995, 10(4), 333-346.
[PMID: 7786398]
[82]
Matsumoto, S.S.; Sidford, M.H.; Holden, J.A.; Barrows, L.R.; Copp, B.R. Mechanism of action studies of cytotoxic marine alkaloids: Ascididemin exhibits thiol-dependent oxidative DNA cleavage. Tetrahedron Lett., 2000, 41, 1667-1670.
[http://dx.doi.org/10.1016/S0040-4039(00)00011-3]
[83]
Hecht, S.M.; Berry, D.E.; MacKenzie, L.J.; Busby, R.W.; Nasuti, C.A. A strategy for identifying novel, mechanistically unique inhibitors of topoisomerase I. J. Nat. Prod., 1992, 55(4), 401-413.
[http://dx.doi.org/10.1021/np50082a001] [PMID: 1324981]
[84]
Nitiss, J.L.; Liu, Y.X.; Harbury, P.; Jannatipour, M.; Wasserman, R.; Wang, J.C. Amsacrine and etoposide hypersensitivity of yeast cells overexpressing DNA topoisomerase II. Cancer Res., 1992, 52(16), 4467-4472.
[PMID: 1322791]
[85]
Nitiss, J.; Wang, J.C. DNA topoisomerase-targeting antitumor drugs can be studied in yeast. Proc. Natl. Acad. Sci. USA, 1988, 85(20), 7501-7505.
[http://dx.doi.org/10.1073/pnas.85.20.7501] [PMID: 2845409]
[86]
Geewananda, P.G.; Frank, E.K.; Angela, Y.L.; Jon, C.; Hai, Y.H.; Faulkner, D.J. Pyridoacridine alkaloids from deep-water marine sponges of the family Pachastrellidae: Structure revision of dercitin and related compounds and correlation with the kuanoniamines. J. Org. Chem., 1992, 57, 1523-1526.
[http://dx.doi.org/10.1021/jo00031a035]
[87]
Matsumoto, S.S.; Biggs, J.; Copp, B.R.; Holden, J.A.; Barrows, L.R. Mechanism of ascididemin-induced cytotoxicity. Chem. Res. Toxicol., 2003, 16(2), 113-122.
[http://dx.doi.org/10.1021/tx025618w] [PMID: 12588181]
[88]
Marshall, K.M.; Holden, J.A.; Koller, A.; Kashman, Y.; Copp, B.R.; Barrows, L.R. AK37: The first pyridoacridine described capable of stabilizing the topoisomerase I cleavable complex. Anticancer Drugs, 2004, 15(9), 907-913.
[http://dx.doi.org/10.1097/00001813-200410000-00012] [PMID: 15457132]
[89]
Holden, J.A.; Wall, M.E.; Wani, M.C.; Manikumar, G. Human DNA topoisomerase I: Quantitative analysis of the effects of camptothecin analogs and the benzophenanthridine alkaloids nitidine and 6-ethoxydihydronitidine on DNA topoisomerase I-induced DNA strand breakage. Arch. Biochem. Biophys., 1999, 370(1), 66-76.
[http://dx.doi.org/10.1006/abbi.1999.1355] [PMID: 10496978]
[90]
Marshall, K.M.; Matsumoto, S.S.; Holden, J.A.; Concepción, G.P.; Tasdemir, D.; Ireland, C.M.; Barrows, L.R. The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine. Biochem. Pharmacol., 2003, 66(3), 447-458.
[http://dx.doi.org/10.1016/S0006-2952(03)00209-0] [PMID: 12907244]
[91]
Tasdemir, D.; Marshall, K.M.; Mangalindan, G.C.; Concepción, G.P.; Barrows, L.R.; Harper, M.K.; Ireland, C.M. Deoxyamphimedine, a new pyridoacridine alkaloid from two tropical Xestospongia sponges. J. Org. Chem., 2001, 66(9), 3246-3248.
[http://dx.doi.org/10.1021/jo010153k] [PMID: 11325300]
[92]
Ciufolini, M.A.; Byrne, N.E. The total synthesis of cystodytins. J. Am. Chem. Soc., 1991, 113, 8016-8024.
[http://dx.doi.org/10.1021/ja00021a031]
[93]
Delfourne, E.; Darro, F.; Portefaix, P.; Galaup, C.; Bayssade, S.; Bouteillé, A.; Le Corre, L.; Bastide, J.; Collignon, F.; Lesur, B.; Frydman, A.; Kiss, R. Synthesis and in vitro antitumor activity of novel ring D analogues of the marine pyridoacridine ascididemin: Structure-activity relationship. J. Med. Chem., 2002, 45(17), 3765-3771.
[http://dx.doi.org/10.1021/jm0208774] [PMID: 12166949]
[94]
Debnath, B.; Gayen, S.; Bhattacharya, S.; Samanta, S.; Jha, T. QSAR study on some pyridoacridine ascididemin analogues as anti-tumor agents. Bioorg. Med. Chem., 2003, 11(24), 5493-5499.
[http://dx.doi.org/10.1016/j.bmc.2003.09.022] [PMID: 14642593]
[95]
Thale, Z.; Johnson, T.; Tenney, K.; Wenzel, P.J.; Lobkovsky, E.; Clardy, J.; Media, J.; Pietraszkiewicz, H.; Valeriote, F.A.; Crews, P. Structures and cytotoxic properties of sponge-derived bisannulated acridines. J. Org. Chem., 2002, 67(26), 9384-9391.
[http://dx.doi.org/10.1021/jo026459o] [PMID: 12492342]
[96]
Mucci-LoRusso, P.; Polin, L.; Bissery, M.C.; Valeriote, F.; Plowman, J.; Luk, G.D.; Corbett, T.H. Activity of batracylin (NSC-320846) against solid tumors of mice. Invest. New Drugs, 1989, 7(4), 295-306.
[http://dx.doi.org/10.1007/BF00173759] [PMID: 2557298]
[97]
Brahic, C.; Darro, F.; Belloir, M.; Bastide, J.; Kiss, R.; Delfourne, E. Synthesis and cytotoxic evaluation of analogues of the marine pyridoacridine amphimedine. Bioorg. Med. Chem., 2002, 10(9), 2845-2853.
[http://dx.doi.org/10.1016/S0968-0896(02)00148-7] [PMID: 12110304]
[98]
Delfourne, E.; Kiss, R.; Le Corre, L.; Dujols, F.; Bastide, J.; Collignon, F.; Lesur, B.; Frydman, A.; Darro, F. Synthesis and in vitro antitumor activity of phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine: Structure-activity relationship. J. Med. Chem., 2003, 46(16), 3536-3545.
[http://dx.doi.org/10.1021/jm0308702] [PMID: 12877592]
[99]
Delfourne, E.; Kiss, R.; Le Corre, L.; Merza, J.; Bastide, J.; Frydman, A.; Darro, F. Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds. Bioorg. Med. Chem., 2003, 11(20), 4351-4356.
[http://dx.doi.org/10.1016/S0968-0896(03)00483-8] [PMID: 13129571]
[100]
Shaikh, I.A.; Johnson, F.; Grollman, A.P. Streptonigrin. 1. Structure-activity relationships among simple bicyclic analogues. Rate dependence of DNA degradation on quinone reduction potential. J. Med. Chem., 1986, 29(8), 1329-1340.
[http://dx.doi.org/10.1021/jm00158a002] [PMID: 3525839]
[101]
Jaishankar, S.; Jayapal, B.B.; Ramadoss, G. Predicting Anti cancer activity of Marine Pyridoacridine alkaloids-computation approach using Topological indices. J. Comput. Methods Mol. Des., 2015, 5, 39-44.

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