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Volumn 10, Issue 5, 2012, Pages 1126-1137

Biochemical studies of the lagunamides, potent cytotoxic cyclic depsipeptides from the marine cyanobacterium Lyngbya majuscula

Author keywords

Apoptosis; Cyclic depsipeptides; Cytotoxicity; Lagunamides; Marine cyanobacterium

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLODEPSIPEPTIDE; LAGUNAMIDE A; LAGUNAMIDE B; UNCLASSIFIED DRUG;

EID: 84862899581     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md10051126     Document Type: Article
Times cited : (49)

References (31)
  • 1
    • 33947104489 scopus 로고    scopus 로고
    • Bioactive natural products from marine cyanobacteria for drug discovery
    • DOI 10.1016/j.phytochem.2007.01.012, PII S0031942207000519
    • Tan, L.T. Bioactive natural products from marine cyanobacteria for drug discovery. Phytochemistry 2007, 68, 954-979. (Pubitemid 46413338)
    • (2007) Phytochemistry , vol.68 , Issue.7 , pp. 954-979
    • Tan, L.T.1
  • 2
    • 0032475992 scopus 로고    scopus 로고
    • Harnessing the biosynthetic code: Combinations, permutations, and mutations
    • DOI 10.1126/science.282.5386.63
    • Cane, D.E.; Walsh, C.T.; Khosla, C. Harnessing the biosynthetic code: Combinations, permutations, and mutations. Science 1998, 282, 63-68. (Pubitemid 28471127)
    • (1998) Science , vol.282 , Issue.5386 , pp. 63-68
    • Cane, D.E.1    Walsh, C.T.2    Khosla, C.3
  • 3
    • 78650214297 scopus 로고    scopus 로고
    • Filamentous tropical marine cyanobacteria: A rich source of natural products for anticancer drug discovery
    • Tan, L.T. Filamentous tropical marine cyanobacteria: A rich source of natural products for anticancer drug discovery. J. Appl. Phycol. 2010, 22, 659-676.
    • (2010) J. Appl. Phycol. , vol.22 , pp. 659-676
    • Tan, L.T.1
  • 4
    • 84858032909 scopus 로고    scopus 로고
    • Brentuximab vedotin: A new age in the treatment of Hodgkin lymphoma and anaplastic large cell lymphoma
    • Minich, S.S. Brentuximab vedotin: A new age in the treatment of Hodgkin lymphoma and anaplastic large cell lymphoma. Ann. Pharmacother. 2012, 46, 377-383.
    • (2012) Ann. Pharmacother. , vol.46 , pp. 377-383
    • Minich, S.S.1
  • 5
    • 84856406381 scopus 로고    scopus 로고
    • Lessons from the past and charting the future of marine natural products drug discovery and chemical biology
    • Gerwick, W.H.; Moore, B.S. Lessons from the past and charting the future of marine natural products drug discovery and chemical biology. Chem. Biol. 2012, 19, 85-98.
    • (2012) Chem. Biol. , vol.19 , pp. 85-98
    • Gerwick, W.H.1    Moore, B.S.2
  • 6
    • 45649084241 scopus 로고    scopus 로고
    • Besarhanamides A and B from the marine cyanobacterium Lyngbya majuscula
    • Tan, L.T.; Chang, Y.Y.; Tripathi, A. Besarhanamides A and B from the marine cyanobacterium Lyngbya majuscula. Phytochemistry 2008, 69, 2067-2069.
    • (2008) Phytochemistry , vol.69 , pp. 2067-2069
    • Tan, L.T.1    Chang, Y.Y.2    Tripathi, A.3
  • 7
    • 60549092554 scopus 로고    scopus 로고
    • Hantupeptin A, a cytotoxic cyclic depsipeptide from a Singapore collection of Lyngbya majuscula
    • Tripathi, A.; Puddick, J.; Prinsep, M.R.; Lee, P.P.; Tan, L.T. Hantupeptin A, a cytotoxic cyclic depsipeptide from a Singapore collection of Lyngbya majuscula. J. Nat. Prod. 2009, 72, 29-32.
    • (2009) J. Nat. Prod. , vol.72 , pp. 29-32
    • Tripathi, A.1    Puddick, J.2    Prinsep, M.R.3    Lee, P.P.4    Tan, L.T.5
  • 8
    • 73649113803 scopus 로고    scopus 로고
    • Hantupeptins B and C, cytotoxic cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula
    • Tripathi, A.; Puddick, J.; Prinsep, M.R.; Lee, P.P.; Tan, L.T. Hantupeptins B and C, cytotoxic cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. Phytochemistry 2010, 71, 307-311.
    • (2010) Phytochemistry , vol.71 , pp. 307-311
    • Tripathi, A.1    Puddick, J.2    Prinsep, M.R.3    Lee, P.P.4    Tan, L.T.5
  • 9
    • 78650205958 scopus 로고    scopus 로고
    • Lagunamides A and B: Cytotoxic and antimalarial cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula
    • Tripathi, A.; Puddick, J.; Prinsep, M.R.; Rottmann, M.; Tan, L.T. Lagunamides A and B: cytotoxic and antimalarial cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2010, 73, 1810-1814.
    • (2010) J. Nat. Prod. , vol.73 , pp. 1810-1814
    • Tripathi, A.1    Puddick, J.2    Prinsep, M.R.3    Rottmann, M.4    Tan, L.T.5
  • 10
    • 0012285509 scopus 로고    scopus 로고
    • Natural products as inducers of apoptosis: Implication for cancer therapy and prevention
    • Taraphdar, A.K.; Roy, M.; Bhattacharya, R.K. Natural products as inducers of apoptosis: Implication for cancer therapy and prevention. Curr. Sci. 2001, 80, 1387-1396. (Pubitemid 33620231)
    • (2001) Current Science , vol.80 , Issue.11 , pp. 1387-1396
    • Taraphdar, A.K.1    Roy, M.2    Bhattacharya, R.K.3
  • 11
    • 68149100711 scopus 로고    scopus 로고
    • The changing shape of mitochondrial apoptosis
    • Wasilewski, M.; Scorrano, L. The changing shape of mitochondrial apoptosis. Trends Endocrinol. Metab. 2009, 20, 287-294.
    • (2009) Trends Endocrinol. Metab. , vol.20 , pp. 287-294
    • Wasilewski, M.1    Scorrano, L.2
  • 12
    • 0034614637 scopus 로고    scopus 로고
    • The hallmarks of cancer
    • Hanahan, D.; Weinberg, R.A. The hallmarks of cancer. Cell 2000, 100, 57-70. (Pubitemid 30046295)
    • (2000) Cell , vol.100 , Issue.1 , pp. 57-70
    • Hanahan, D.1    Weinberg, R.A.2
  • 13
    • 4344694626 scopus 로고    scopus 로고
    • Kulokekahilide-2, a cytotoxic depsipeptide from a cephalaspidean mollusk Philinopsis Speciosa
    • DOI 10.1021/np049949f
    • Nakao, Y.; Yoshida, W.Y.; Takada, Y.; Kimura, J.; Yang, L.; Mooberry, S.L.; Scheuer, P.J. Kulokekahilide-2, a cytotoxic depsipeptide from a cephalaspidean mollusk Philinopsis speciosa. J. Nat. Prod. 2004, 67, 1332-1340. (Pubitemid 39145639)
    • (2004) Journal of Natural Products , vol.67 , Issue.8 , pp. 1332-1340
    • Nakao, Y.1    Yoshida, W.Y.2    Takada, Y.3    Kimura, J.4    Yang, L.5    Mooberry, S.L.6    Scheuer, P.J.7
  • 14
    • 33744460793 scopus 로고    scopus 로고
    • Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula
    • DOI 10.1021/np0503911
    • Han, B.; Gross, H.; Goeger, D.E.; Mooberry, S.L.; Gerwick, W.H. Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J. Nat. Prod. 2006, 69, 572-575. (Pubitemid 43798104)
    • (2006) Journal of Natural Products , vol.69 , Issue.4 , pp. 572-575
    • Han, B.1    Gross, H.2    Goeger, D.E.3    Mooberry, S.L.4    Gerwick, W.H.5
  • 15
    • 38349141838 scopus 로고    scopus 로고
    • Revised absolute stereochemistry of natural kulokekahilide-2
    • Takada, Y.; Umehara, M.; Nakao, Y.; Kimura, J. Revised absolute stereochemistry of natural kulokekahilide-2. Tetrahedron Lett. 2008, 49, 1163-1165.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1163-1165
    • Takada, Y.1    Umehara, M.2    Nakao, Y.3    Kimura, J.4
  • 16
    • 0030576999 scopus 로고    scopus 로고
    • Isolation and stereostructure of aurilide, a novel cyclodepsipeptide from the Japanese sea hare Dolabella auricularia
    • DOI 10.1016/S0040-4039(96)01464-5
    • Suenaga, K.; Mutou, T.; Shibata, T.; Itoh, T.; Kigoshi, H.; Yamada, K. Isolation and stereostructure of aurilide, a novel cyclodepsipeptide from the Japanese sea hare Dolabella auricularia. Tetrahedron Lett. 1996, 37, 6771-6774. (Pubitemid 26287976)
    • (1996) Tetrahedron Letters , vol.37 , Issue.37 , pp. 6771-6774
    • Suenaga, K.1    Mutou, T.2    Shibata, T.3    Itoh, T.4    Kigoshi, H.5    Yamada, K.6
  • 17
    • 4444219509 scopus 로고    scopus 로고
    • Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity
    • Suenaga, K.; Mutou, T.; Shibata, T.; Itoh, T.; Fujita, T.; Takada, N.; Hayamizu, K.; Takagi, M.; Irifune, T.; Kigoshi, H.; et al. Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity. Tetrahedron 2004, 60, 8509-8527.
    • (2004) Tetrahedron , vol.60 , pp. 8509-8527
    • Suenaga, K.1    Mutou, T.2    Shibata, T.3    Itoh, T.4    Fujita, T.5    Takada, N.6    Hayamizu, K.7    Takagi, M.8    Irifune, T.9    Kigoshi, H.10
  • 18
    • 0141675075 scopus 로고    scopus 로고
    • Solid phase library synthesis of cyclic depsipeptides: Aurilide and aurilide analogues
    • DOI 10.1021/cc020091r
    • Takashi, T.; Nagamiya, H.; Doi, T.; Griffiths, P.G.; Bray, A.M. Solid phase library synthesis of cyclic depsipeptides: aurilide and aurilide analogues. J. Comb. Chem. 2003, 5, 414-428. (Pubitemid 37140553)
    • (2003) Journal of Combinatorial Chemistry , vol.5 , Issue.4 , pp. 414-428
    • Takahashi, T.1    Nagamiya, H.2    Doi, T.3    Griffiths, P.G.4    Bray, A.M.5
  • 20
    • 34548833003 scopus 로고    scopus 로고
    • Reinvestigation of the stereochemistry of kulokekahilide-2
    • DOI 10.1016/j.tetlet.2007.08.093, PII S0040403907017121
    • Takada, Y.; Mori, E.; Umehara, M.; Nakao, Y.; Kimura, J. Reinvestigation of the stereochemistry of kulokekahilide-2. Tetrahedron Lett. 2007, 48, 7653-7656. (Pubitemid 47451484)
    • (2007) Tetrahedron Letters , vol.48 , Issue.43 , pp. 7653-7656
    • Takada, Y.1    Mori, E.2    Umehara, M.3    Nakao, Y.4    Kimura, J.5
  • 21
    • 82955235549 scopus 로고    scopus 로고
    • The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs
    • Takada, Y.; Umehara, M.; Katsumata, R.; Nakao, Y.; Kimura, J. The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs. Tetrahedron 2012, 68, 659-669.
    • (2012) Tetrahedron , vol.68 , pp. 659-669
    • Takada, Y.1    Umehara, M.2    Katsumata, R.3    Nakao, Y.4    Kimura, J.5
  • 22
    • 0024382760 scopus 로고
    • The p53 proto-oncogene can act as a suppressor of transformation
    • DOI 10.1016/0092-8674(89)90045-7
    • Finlay, C.A.; Hinds, P.W.; Levine, A.J. The p53 proto-oncogene can act as a suppressor of transformation. Cell 1989, 57, 1083-1093. (Pubitemid 19169804)
    • (1989) Cell , vol.57 , Issue.7 , pp. 1083-1093
    • Finlay, C.A.1    Hinds, P.W.2    Levine, A.J.3
  • 23
    • 9244224723 scopus 로고    scopus 로고
    • Intrinsic tumour suppression
    • DOI 10.1038/nature03098
    • Lowe, S.W.; Cepero, E.; Evan, G. Intrinsic tumour suppression. Nature 2004, 432, 307-315. (Pubitemid 39551658)
    • (2004) Nature , vol.432 , Issue.7015 , pp. 307-315
    • Lowe, S.W.1    Cepero, E.2    Evan, G.3
  • 24
    • 33746886979 scopus 로고    scopus 로고
    • Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy
    • DOI 10.1038/sj.onc.1209608, PII 1209608
    • Fulda, S.; Debatin, K.-M. Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy. Oncogene 2006, 25, 4798-4811. (Pubitemid 44187627)
    • (2006) Oncogene , vol.25 , Issue.34 , pp. 4798-4811
    • Fulda, S.1    Debatin, K.-M.2
  • 25
    • 26444489119 scopus 로고    scopus 로고
    • Connected to death: The (unexpurgated) mitochondrial pathway of apoptosis
    • DOI 10.1126/science.1117105
    • Spierings, D.; McStay, G.; Saleh, M.; Bender, C.; Chipuk, J.; Maurer, U.; Green, D.R. Connected to death: The (unexpurgated) mitochondrial pathway of apoptosis. Science 2005, 310, 66-67. (Pubitemid 41434533)
    • (2005) Science , vol.310 , Issue.5745 , pp. 66-67
    • Spierings, D.1    McStay, G.2    Saleh, M.3    Bender, C.4    Chipuk, J.5    Maurer, U.6    Green, D.R.7
  • 26
    • 80955122677 scopus 로고    scopus 로고
    • Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity
    • Chen, Q.Y.; Liu, Y.; Luesch, H. Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity. ACS Med. Chem. Lett. 2011, 2, 861-865.
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 861-865
    • Chen, Q.Y.1    Liu, Y.2    Luesch, H.3
  • 27
    • 0033602576 scopus 로고    scopus 로고
    • Induction of CD95 (Fas) and apoptosis in respiratory epithelial cell cultures following respiratory syncytial virus infection
    • DOI 10.1006/viro.1999.9650
    • O'Donnell, D.R.; Milligan, L.; Stark, J.M. Induction of CD95 (Fas) and apoptosis in respiratory epithelial cell cultures following respiratory syncytial virus infection. Virology 1999, 257, 198-207. (Pubitemid 29391813)
    • (1999) Virology , vol.257 , Issue.1 , pp. 198-207
    • O'Donnell, D.R.1    Milligan, L.2    Stark, J.M.3
  • 29
    • 79251577725 scopus 로고    scopus 로고
    • Marine natural product aurilide activates the OPA1-mediated apoptosis by binding to prohibitin
    • Sato, S.; Murata, A.; Orihara, T.; Shirakawa, T.; Suenaga, K.; Kigoshi, H.; Uesugi, M. Marine natural product aurilide activates the OPA1-mediated apoptosis by binding to prohibitin. Chem. Biol. 2011, 18, 131-138.
    • (2011) Chem. Biol. , vol.18 , pp. 131-138
    • Sato, S.1    Murata, A.2    Orihara, T.3    Shirakawa, T.4    Suenaga, K.5    Kigoshi, H.6    Uesugi, M.7


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