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Volumn 46, Issue 15, 2003, Pages 3185-3188

Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; ANTINEOPLASTIC AGENT; MOLVIZARIN; UNCLASSIFIED DRUG;

EID: 0037480025     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020548b     Document Type: Article
Times cited : (55)

References (30)
  • 1
    • 0038017364 scopus 로고    scopus 로고
    • Progress in the recent discovery and development of promising anticancer and anti-HIV agents from natural products in the United States
    • Antitumor Agents 224. For the previous paper in the series, see Wu, J. H.; Morris-Natschke, S. L.; Lee, K. H. Progress in the recent discovery and development of promising anticancer and anti-HIV agents from natural products in the United States. J. Chin. Chem. Soc. 2003, 50, 11-22.
    • (2003) J. Chin. Chem. Soc. , vol.50 , pp. 11-22
    • Wu, J.H.1    Morris-Natschke, S.L.2    Lee, K.H.3
  • 2
    • 0032891112 scopus 로고    scopus 로고
    • Annonaceous acetogenins: Recent progress
    • Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. Annonaceous acetogenins: Recent progress. J. Nat. Prod. 1999, 62, 504-540.
    • (1999) J. Nat. Prod. , vol.62 , pp. 504-540
    • Alali, F.Q.1    Liu, X.X.2    McLaughlin, J.L.3
  • 3
    • 0030942665 scopus 로고    scopus 로고
    • Structure-activity relationships of diverse annonaceous actogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells
    • Oberlies, N. H.; Chang, C. J.; McLaughlin, J. L. Structure-activity relationships of diverse Annonaceous actogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. J. Med. Chem. 1997, 40, 2102-2106.
    • (1997) J. Med. Chem. , vol.40 , pp. 2102-2106
    • Oberlies, N.H.1    Chang, C.J.2    McLaughlin, J.L.3
  • 4
    • 0032551770 scopus 로고    scopus 로고
    • Essential structural features of Annonaceous actogenins as potent inhibitors of mitochodrial complex I
    • Miyoshi, H.; Ohshima, M. Shimada, H.; Akagi T.; Iwamura, H. McLaughlin, J. L. Essential structural features of Annonaceous actogenins as potent inhibitors of mitochodrial complex I. Biochim. Biophys. Acta 1998, 1365, 443-452.
    • (1998) Biochim. Biophys. Acta , vol.1365 , pp. 443-452
    • Miyoshi, H.1    Ohshima, M.2    Shimada, H.3    Akagi, T.4    Iwamura, H.5    McLaughlin, J.L.6
  • 6
    • 0027182618 scopus 로고
    • Mode of action of bullatacin: A potent antitumor and pesticidal Annonaceous acetogenin
    • Ahammadsahib, K. I.; Hollingworth, R. M.; McGovern, J. P.; Hui, Y. H.; McLaughlin, J. L. Mode of action of bullatacin: a potent antitumor and pesticidal Annonaceous acetogenin. Life Sci. 1993, 53, 1113-1120.
    • (1993) Life Sci. , vol.53 , pp. 1113-1120
    • Ahammadsahib, K.I.1    Hollingworth, R.M.2    McGovern, J.P.3    Hui, Y.H.4    McLaughlin, J.L.5
  • 7
    • 0028326253 scopus 로고
    • New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides
    • Hollingworth, R. M.; Ahammadsahib, K. I.; Gadelhak, G.; McLaughlin, J. L. New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Biochem. Soc. Trans. 1994, 22, 230-233.
    • (1994) Biochem. Soc. Trans. , vol.22 , pp. 230-233
    • Hollingworth, R.M.1    Ahammadsahib, K.I.2    Gadelhak, G.3    McLaughlin, J.L.4
  • 8
    • 0028896375 scopus 로고
    • New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides
    • Morre, D. J.; de Cabo, R.; Farley, C.; Oberlies, N. H.; McLaughlin, J. L. New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Life Sci. 1995, 56, 343-348.
    • (1995) Life Sci. , vol.56 , pp. 343-348
    • Morre, D.J.1    De Cabo, R.2    Farley, C.3    Oberlies, N.H.4    McLaughlin, J.L.5
  • 9
    • 0031149817 scopus 로고    scopus 로고
    • The Annnonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells
    • Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. The Annnonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett. 1997, 115, 73-79.
    • (1997) Cancer Lett. , vol.115 , pp. 73-79
    • Oberlies, N.H.1    Croy, V.L.2    Harrison, M.L.3    McLaughlin, J.L.4
  • 11
    • 0032548446 scopus 로고    scopus 로고
    • Membrane conformations and their relation to cytotoxicity of asimicin and its analogues
    • Shimada, H.; Grutzner, J. Bl; Kozlowski, J. F.; McLaughlin, J. L. Membrane conformations and their relation to cytotoxicity of asimicin and its analogues. Biochemistry 1998, 37, 854-866.
    • (1998) Biochemistry , vol.37 , pp. 854-866
    • Shimada, H.1    Grutzner, J.B.L.2    Kozlowski, J.F.3    McLaughlin, J.L.4
  • 12
    • 0035800417 scopus 로고    scopus 로고
    • Bullatacin, a potent antitumor Annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction
    • Chih, H. W.; Chiu, H. F.; Tang, K. S.; Chang, F. R.; Wu, Y. C. Bullatacin, a potent antitumor Annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. Life Sci. 2001, 69, 1321-1331.
    • (2001) Life Sci. , vol.69 , pp. 1321-1331
    • Chih, H.W.1    Chiu, H.F.2    Tang, K.S.3    Chang, F.R.4    Wu, Y.C.5
  • 14
    • 0034910949 scopus 로고    scopus 로고
    • A. muricata I
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (2001) J. Nat. Prod. , vol.64 , pp. 925-931
  • 15
    • 0036239550 scopus 로고    scopus 로고
    • A. muricata II
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (2002) Nat J. Prod. , vol.65 , pp. 470-475
  • 16
    • 0038017365 scopus 로고    scopus 로고
    • A. muricata III
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (2003) Planta Med. , vol.69 , pp. 241-246
  • 17
    • 85045828797 scopus 로고
    • A. montana
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (1994) Heterocycles , vol.38 , pp. 1475-1478
  • 18
    • 85045826517 scopus 로고
    • A. reticulata I
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (1992) Heterocycles , vol.34 , pp. 667-674
  • 19
    • 0027484450 scopus 로고
    • A. reticulata II
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (1993) J. Nat Prod. , vol.56 , pp. 1688-1694
  • 20
    • 0033031798 scopus 로고    scopus 로고
    • A. atemoya
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (1999) Phytochemistry , vol.51 , pp. 883-889
  • 21
    • 0033427188 scopus 로고    scopus 로고
    • R. mucosa
    • Annonaceous acetogenins were isolated from Formosan Annonaceous plants in Dr. Yang-Chang Wu's laboratory in Taiwan, including Annona muricata, A. montana, A. atemoya, A. reticulata, and Rollinia mucosa. Compounds 1-18, 22, 23, and 24 were isolated from A. muricata. Compounds 14, 15, 18, 20, and 25 were isolated from A. montana. Compounds 19, 22, 26, 27, and 28 were isolated from A. reticulata. Compounds 19 and 21 were isolated from A. atemoya. Compounds 19 and 27 were isolated from R. mucosa. Among them, 1-7, 9, 10, 20, 23, and 24 were published as new compounds. All of the Annonaceous acetogenins were repurified by reversed-phase HPLC before bioevaluation. (A. muricata I: J. Nat. Prod. 2001, 64, 925-931. A. muricata II: J. Nat. Prod. 2002, 65, 470-475. A. muricata III: Planta Med. 2003, 69, 241-246; A. montana: Heterocycles 1994, 38, 1475-1478; A. reticulata I: Heterocycles 1992, 34, 667-674. A. reticulata II: J. Nat. Prod. 1993, 56, 1688-1694; A. atemoya: Phytochemistry 1999, 51, 883-889; R. mucosa: J. Nat. Prod. 1999, 62, 1613-1617.)
    • (1999) J. Nat. Prod. , vol.62 , pp. 1613-1617
  • 22
    • 0025367455 scopus 로고
    • Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines
    • Rubinstein, L. V.; Shoemaker, R. H.; Paull, K. D.; Simon, R. M.; Tosini, S.; Skehan, P.; Scudiero, D. A.; Monks, A.; Boyd, M. R. Comparison of in vitro anticancer-drug-screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Natl. Cancer. Inst. 1990, 82, 1113-1118.
    • (1990) J. Natl. Cancer. Inst. , vol.82 , pp. 1113-1118
    • Rubinstein, L.V.1    Shoemaker, R.H.2    Paull, K.D.3    Simon, R.M.4    Tosini, S.5    Skehan, P.6    Scudiero, D.A.7    Monks, A.8    Boyd, M.R.9
  • 23
    • 0038017342 scopus 로고    scopus 로고
    • note
    • 50 is the concentration of agent that reduced cell growth by 50% under the experimental conditions. Human tumor cell lines [KB (nasopharyngeal), HCT-8 (ileocecal), A549 (lung), MCF-7 (breast), PC-3 (prostate), HOS (bone), SK-MEL-2 (melanoma), CAKI (kidney)] were obtained from ATCC (Rockville, MD). KB-VIN (vincristine resistant KB subline) cell line was a generous gift of Dr. Y.-C Cheng (Yale University). 1A9 (ovarian) and PTX10 (subline of 1A9, which has a mutated β-tubulin gene) cell lines were generous gifts of Dr. P. Ginnakakou (NCI, Bethesda, MD). All cell lines were cultured in RPMI-1640 medium supplemented with 25 mM HEPES, 0.25% sodium bicarbonate, 10% fetal bovine serum, and 100 μg/mL kanamycin.
  • 25
    • 0030758777 scopus 로고    scopus 로고
    • Paclitaxel-resistant human ovarian cancer cells have mutant beta-tubulins that exhibit impaired paclitaxel-driven polymerization
    • Giannakakou, P.; Sackett, D. L.; Kang Y. K.; Zhan, Z.; Buters, J. T.; Fojo, T.; Poruchynsky, M. S. Paclitaxel-resistant human ovarian cancer cells have mutant beta-tubulins that exhibit impaired paclitaxel-driven polymerization. J. Biol. Chem. 1997, 272, 17118-17125.
    • (1997) J. Biol. Chem. , vol.272 , pp. 17118-17125
    • Giannakakou, P.1    Sackett, D.L.2    Kang, Y.K.3    Zhan, Z.4    Buters, J.T.5    Fojo, T.6    Poruchynsky, M.S.7
  • 26
    • 5844221874 scopus 로고    scopus 로고
    • Squamotacin: An annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3)
    • Hopp, D. C.; Zeng, L.; Gu, Z. M.; McLaughlin, J. L. Squamotacin: an annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3). J. Nat. Prod. 1996, 59, 97-99.
    • (1996) J. Nat. Prod. , vol.59 , pp. 97-99
    • Hopp, D.C.1    Zeng, L.2    Gu, Z.M.3    McLaughlin, J.L.4
  • 27
    • 0038017348 scopus 로고    scopus 로고
    • United States Patent 5,955,497, 1999
    • McLaughlin, J. L.; Hopp, D. C. United States Patent 5,955,497, 1999.
    • McLaughlin, J.L.1    Hopp, D.C.2
  • 28
    • 0032909482 scopus 로고    scopus 로고
    • Goniotriocin and (2,4-cis- and -trans)-xylomaticinones, bioactive Annonaceous acetogenins from Goniothalamus giganteus
    • Alali, F. Q.; Rogers, L.; Zhang, Y.; McLaughlin J. L. Goniotriocin and (2,4-cis- and -trans)-xylomaticinones, bioactive Annonaceous acetogenins from Goniothalamus giganteus. J. Nat. Prod. 1999, 62, 31-34.
    • (1999) J. Nat. Prod. , vol.62 , pp. 31-34
    • Alali, F.Q.1    Rogers, L.2    Zhang, Y.3    McLaughlin, J.L.4
  • 29
    • 0024539601 scopus 로고
    • A preparative suspension culture system permitting quantitation of anchorageindependent growth by direct radiolabeling of cellular DNA
    • Assoian, R. K.; Boardman, L. A.; Drosinos, S. A preparative suspension culture system permitting quantitation of anchorageindependent growth by direct radiolabeling of cellular DNA. Anal. Biochem. 1989, 177, 95-99.
    • (1989) Anal. Biochem. , vol.177 , pp. 95-99
    • Assoian, R.K.1    Boardman, L.A.2    Drosinos, S.3
  • 30
    • 0034073521 scopus 로고    scopus 로고
    • Characterization of human lung cancer cells resistant to 4′-O-demethyl-4β-(2″-nitro-4″-fluoroanilino)-4- desoxypodophyllo-toxin, a unique compound in the epipodophyllotoxin antitumor class
    • Tachibana, Y.; Zhu, X. K.; Krishnan, P.; Lee, K. H.; Bastow, K. F. Characterization of human lung cancer cells resistant to 4′-O-demethyl-4β-(2″-nitro-4″-fluoroanilino)-4- desoxypodophyllo-toxin, a unique compound in the epipodophyllotoxin antitumor class. Anticancer Drugs 2000, 19-28.
    • (2000) Anticancer Drugs , pp. 19-28
    • Tachibana, Y.1    Zhu, X.K.2    Krishnan, P.3    Lee, K.H.4    Bastow, K.F.5


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