메뉴 건너뛰기




Volumn 93, Issue 3, 2015, Pages 251-265

Apoptolidins A and C activate AMPK in metabolically sensitive cell types and are mechanistically distinct from oligomycin A

Author keywords

Apoptolidin A; Coibamide A; Mitochondrial inhibitor; Oligomycin A; Warburg effect

Indexed keywords

ANTINEOPLASTIC AGENT; APOPTOLIDIN A; APOPTOLIDIN C; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE KINASE; MAMMALIAN TARGET OF RAPAMYCIN COMPLEX 1; OLIGOMYCIN; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATE SYNTHASE; UNCLASSIFIED DRUG; MACROLIDE; PYRONE DERIVATIVE;

EID: 84921712618     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2014.11.015     Document Type: Article
Times cited : (17)

References (48)
  • 1
    • 0030827941 scopus 로고    scopus 로고
    • Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp
    • J.W. Kim, H. Adachi, K. Shin-ya, Y. Hayakawa, and H. Seto Apoptolidin, a new apoptosis inducer in transformed cells from Nocardiopsis sp J Antibiot (Tokyo) 50 1997 628 630
    • (1997) J Antibiot (Tokyo) , vol.50 , pp. 628-630
    • Kim, J.W.1    Adachi, H.2    Shin-Ya, K.3    Hayakawa, Y.4    Seto, H.5
  • 2
    • 33644782577 scopus 로고    scopus 로고
    • Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues
    • P.A. Wender, O.D. Jankowski, K. Longcore, E.A. Tabet, H. Seto, and T. Tomikawa Correlation of F0F1-ATPase inhibition and antiproliferative activity of apoptolidin analogues Org Lett 8 2006 589 592
    • (2006) Org Lett , vol.8 , pp. 589-592
    • Wender, P.A.1    Jankowski, O.D.2    Longcore, K.3    Tabet, E.A.4    Seto, H.5    Tomikawa, T.6
  • 3
    • 0034687837 scopus 로고    scopus 로고
    • Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase
    • A.R. Salomon, D.W. Voehringer, L.A. Herzenberg, and C. Khosla Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F(0)F(1)-ATPase Proc Natl Acad Sci USA 97 2000 14766 14771
    • (2000) Proc Natl Acad Sci USA , vol.97 , pp. 14766-14771
    • Salomon, A.R.1    Voehringer, D.W.2    Herzenberg, L.A.3    Khosla, C.4
  • 4
    • 0035116589 scopus 로고    scopus 로고
    • Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase
    • A.R. Salomon, D.W. Voehringer, L.A. Herzenberg, and C. Khosla Apoptolidin, a selective cytotoxic agent, is an inhibitor of F0F1-ATPase Chem Biol 8 2001 71 80
    • (2001) Chem Biol , vol.8 , pp. 71-80
    • Salomon, A.R.1    Voehringer, D.W.2    Herzenberg, L.A.3    Khosla, C.4
  • 5
    • 0001221508 scopus 로고
    • On respiratory impairment in cancer cells
    • O. Warburg On respiratory impairment in cancer cells Science 124 1956 269 270
    • (1956) Science , vol.124 , pp. 269-270
    • Warburg, O.1
  • 6
    • 66249108601 scopus 로고    scopus 로고
    • Understanding the Warburg effect: The metabolic requirements of cell proliferation
    • M.G. Vander Heiden, L.C. Cantley, and C.B. Thompson Understanding the Warburg effect: the metabolic requirements of cell proliferation Science 324 2009 1029 1033
    • (2009) Science , vol.324 , pp. 1029-1033
    • Vander Heiden, M.G.1    Cantley, L.C.2    Thompson, C.B.3
  • 8
    • 0035887506 scopus 로고    scopus 로고
    • Total synthesis of apoptolidin: Part 2. Coupling of key building blocks and completion of the synthesis
    • K.C. Nicolaou, Y. Li, K.C. Fylaktakidou, H.J. Mitchell, and K. Sugita Total synthesis of apoptolidin: part 2. Coupling of key building blocks and completion of the synthesis Angew Chem Int Ed Engl 40 2001 3854 3857
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 3854-3857
    • Nicolaou, K.C.1    Li, Y.2    Fylaktakidou, K.C.3    Mitchell, H.J.4    Sugita, K.5
  • 11
    • 0013072405 scopus 로고    scopus 로고
    • Isoapoptolidin: Structure and activity of the ring-expanded isomer of apoptolidin
    • P.A. Wender, A.V. Gulledge, O.D. Jankowski, and H. Seto Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin Org Lett 4 2002 3819 3822
    • (2002) Org Lett , vol.4 , pp. 3819-3822
    • Wender, P.A.1    Gulledge, A.V.2    Jankowski, O.D.3    Seto, H.4
  • 12
    • 22244482218 scopus 로고    scopus 로고
    • Apoptolidins B and C: Isolation, structure determination, and biological activity
    • P.A. Wender, M. Sukopp, and K. Longcore Apoptolidins B and C: isolation, structure determination, and biological activity Org Lett 7 2005 3025 3028
    • (2005) Org Lett , vol.7 , pp. 3025-3028
    • Wender, P.A.1    Sukopp, M.2    Longcore, K.3
  • 13
    • 33847787613 scopus 로고    scopus 로고
    • Isolation, structure determination, and anti-cancer activity of apoptolidin D
    • P.A. Wender, and K.E. Longcore Isolation, structure determination, and anti-cancer activity of apoptolidin D Org Lett 9 2007 691 694
    • (2007) Org Lett , vol.9 , pp. 691-694
    • Wender, P.A.1    Longcore, K.E.2
  • 14
    • 72449208015 scopus 로고    scopus 로고
    • Apoptolidins e and F, new glycosylated macrolactones isolated from Nocardiopsis sp
    • P.A. Wender, and K.E. Longcore Apoptolidins E and F, new glycosylated macrolactones isolated from Nocardiopsis sp Org Lett 11 2009 5474 5477
    • (2009) Org Lett , vol.11 , pp. 5474-5477
    • Wender, P.A.1    Longcore, K.E.2
  • 15
    • 77954118920 scopus 로고    scopus 로고
    • Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry
    • B.O. Bachmann, R. McNees, B.J. Melancon, V.P. Ghidu, R. Clark, and B.C. Crews Light-induced isomerization of apoptolidin a leads to inversion of C2-C3 double bond geometry Org Lett 12 2010 2944 2947
    • (2010) Org Lett , vol.12 , pp. 2944-2947
    • Bachmann, B.O.1    McNees, R.2    Melancon, B.J.3    Ghidu, V.P.4    Clark, R.5    Crews, B.C.6
  • 16
    • 0141518527 scopus 로고    scopus 로고
    • Facile synthetic access to and biological evaluation of the macrocyclic core of apoptolidin
    • P.A. Wender, O.D. Jankowski, E.A. Tabet, and H. Seto Facile synthetic access to and biological evaluation of the macrocyclic core of apoptolidin Org Lett 5 2003 2299 2302
    • (2003) Org Lett , vol.5 , pp. 2299-2302
    • Wender, P.A.1    Jankowski, O.D.2    Tabet, E.A.3    Seto, H.4
  • 18
    • 33749263184 scopus 로고    scopus 로고
    • Apoptolidinone A: Synthesis of the apoptolidin A aglycone
    • J. Schuppan, H. Wehlan, S. Keiper, and U. Koert Apoptolidinone A: synthesis of the apoptolidin A aglycone Chemistry 12 2006 7364 7377
    • (2006) Chemistry , vol.12 , pp. 7364-7377
    • Schuppan, J.1    Wehlan, H.2    Keiper, S.3    Koert, U.4
  • 19
    • 34547201467 scopus 로고    scopus 로고
    • Lactol-directed osmylation. Stereodivergent synthesis of four C-19,20 apoptolidin diols from a single allylic hemiacetal
    • Y. Kim, and P.L. Fuchs Lactol-directed osmylation. Stereodivergent synthesis of four C-19,20 apoptolidin diols from a single allylic hemiacetal Org Lett 9 2007 2445 2448
    • (2007) Org Lett , vol.9 , pp. 2445-2448
    • Kim, Y.1    Fuchs, P.L.2
  • 20
    • 70350491037 scopus 로고    scopus 로고
    • An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts
    • C.A. Lewis, K.E. Longcore, S.J. Miller, and P.A. Wender An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts J Nat Prod 72 2009 1864 1869
    • (2009) J Nat Prod , vol.72 , pp. 1864-1869
    • Lewis, C.A.1    Longcore, K.E.2    Miller, S.J.3    Wender, P.A.4
  • 22
    • 0027551748 scopus 로고
    • Identification and localization of bacterial endosymbionts in hydrothermal vent taxa with symbiont-specific polymerase chain reaction amplification and in situ hybridization techniques
    • S.C. Cary, W. Warren, E. Anderson, and S.J. Giovannoni Identification and localization of bacterial endosymbionts in hydrothermal vent taxa with symbiont-specific polymerase chain reaction amplification and in situ hybridization techniques Mol Mar Biol Biotechnol 2 1993 51 62
    • (1993) Mol Mar Biol Biotechnol , vol.2 , pp. 51-62
    • Cary, S.C.1    Warren, W.2    Anderson, E.3    Giovannoni, S.J.4
  • 23
    • 0024444791 scopus 로고
    • Isolation and direct complete nucleotide determination of entire genes. Characterization of a gene coding for 16S ribosomal RNA
    • U. Edwards, T. Rogall, H. Blocker, M. Emde, and E.C. Bottger Isolation and direct complete nucleotide determination of entire genes. Characterization of a gene coding for 16S ribosomal RNA Nucleic Acids Res 17 1989 7843 7853
    • (1989) Nucleic Acids Res , vol.17 , pp. 7843-7853
    • Edwards, U.1    Rogall, T.2    Blocker, H.3    Emde, M.4    Bottger, E.C.5
  • 24
    • 44049107679 scopus 로고    scopus 로고
    • Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp
    • R.A. Medina, D.E. Goeger, P. Hills, S.L. Mooberry, N. Huang, and L.I. Romero Coibamide A, a potent antiproliferative cyclic depsipeptide from the Panamanian marine cyanobacterium Leptolyngbya sp J Am Chem Soc 130 2008 6324 6325
    • (2008) J Am Chem Soc , vol.130 , pp. 6324-6325
    • Medina, R.A.1    Goeger, D.E.2    Hills, P.3    Mooberry, S.L.4    Huang, N.5    Romero, L.I.6
  • 25
    • 33745840203 scopus 로고    scopus 로고
    • 5'-AMP-activated protein kinase (AMPK) is induced by low-oxygen and glucose deprivation conditions found in solid-tumor microenvironments
    • K.R. Laderoute, K. Amin, J.M. Calaoagan, M. Knapp, T. Le, and J. Orduna 5'-AMP-activated protein kinase (AMPK) is induced by low-oxygen and glucose deprivation conditions found in solid-tumor microenvironments Mol Cell Biol 26 2006 5336 5347
    • (2006) Mol Cell Biol , vol.26 , pp. 5336-5347
    • Laderoute, K.R.1    Amin, K.2    Calaoagan, J.M.3    Knapp, M.4    Le, T.5    Orduna, J.6
  • 26
    • 84878787575 scopus 로고    scopus 로고
    • Coibamide A induces mTOR-independent autophagy and cell death in human glioblastoma cells
    • A.M. Hau, J.A. Greenwood, C.V. Lohr, J.D. Serrill, P.J. Proteau, and I.G. Ganley Coibamide A induces mTOR-independent autophagy and cell death in human glioblastoma cells PLoS ONE 8 2013 e65250
    • (2013) PLoS ONE , vol.8 , pp. e65250
    • Hau, A.M.1    Greenwood, J.A.2    Lohr, C.V.3    Serrill, J.D.4    Proteau, P.J.5    Ganley, I.G.6
  • 27
    • 33846317064 scopus 로고    scopus 로고
    • Multiparameter metabolic analysis reveals a close link between attenuated mitochondrial bioenergetic function and enhanced glycolysis dependency in human tumor cells
    • M. Wu, A. Neilson, A.L. Swift, R. Moran, J. Tamagnine, and D. Parslow Multiparameter metabolic analysis reveals a close link between attenuated mitochondrial bioenergetic function and enhanced glycolysis dependency in human tumor cells Am J Physiol Cell Physiol 292 2007 C125 C136
    • (2007) Am J Physiol Cell Physiol , vol.292 , pp. C125-C136
    • Wu, M.1    Neilson, A.2    Swift, A.L.3    Moran, R.4    Tamagnine, J.5    Parslow, D.6
  • 28
    • 84893216650 scopus 로고    scopus 로고
    • AMPK: A cellular energy sensor primarily regulated by AMP
    • G.J. Gowans, and D.G. Hardie AMPK: a cellular energy sensor primarily regulated by AMP Biochem Soc Trans 42 2014 71 75
    • (2014) Biochem Soc Trans , vol.42 , pp. 71-75
    • Gowans, G.J.1    Hardie, D.G.2
  • 29
    • 84868005485 scopus 로고    scopus 로고
    • AMP-activated protein kinase: A target for drugs both ancient and modern
    • D.G. Hardie, F.A. Ross, and S.A. Hawley AMP-activated protein kinase: a target for drugs both ancient and modern Chem Biol 19 2012 1222 1236
    • (2012) Chem Biol , vol.19 , pp. 1222-1236
    • Hardie, D.G.1    Ross, F.A.2    Hawley, S.A.3
  • 30
    • 0034773404 scopus 로고    scopus 로고
    • Role of AMP-activated protein kinase in mechanism of metformin action
    • G. Zhou, R. Myers, Y. Li, Y. Chen, X. Shen, and J. Fenyk-Melody Role of AMP-activated protein kinase in mechanism of metformin action J Clin Invest 108 2001 1167 1174
    • (2001) J Clin Invest , vol.108 , pp. 1167-1174
    • Zhou, G.1    Myers, R.2    Li, Y.3    Chen, Y.4    Shen, X.5    Fenyk-Melody, J.6
  • 31
    • 84873675067 scopus 로고    scopus 로고
    • The ULK1 complex: Sensing nutrient signals for autophagy activation
    • P.M. Wong, C. Puente, I.G. Ganley, and X. Jiang The ULK1 complex: sensing nutrient signals for autophagy activation Autophagy 9 2013 124 137
    • (2013) Autophagy , vol.9 , pp. 124-137
    • Wong, P.M.1    Puente, C.2    Ganley, I.G.3    Jiang, X.4
  • 32
    • 79551598347 scopus 로고    scopus 로고
    • AMPK and mTOR regulate autophagy through direct phosphorylation of Ulk1
    • J. Kim, M. Kundu, B. Viollet, and K.L. Guan AMPK and mTOR regulate autophagy through direct phosphorylation of Ulk1 Nat Cell Biol 13 2011 132 141
    • (2011) Nat Cell Biol , vol.13 , pp. 132-141
    • Kim, J.1    Kundu, M.2    Viollet, B.3    Guan, K.L.4
  • 33
    • 79251587803 scopus 로고    scopus 로고
    • Phosphorylation of ULK1 (hATG1) by AMP-activated protein kinase connects energy sensing to mitophagy
    • D.F. Egan, D.B. Shackelford, M.M. Mihaylova, S. Gelino, R.A. Kohnz, and W. Mair Phosphorylation of ULK1 (hATG1) by AMP-activated protein kinase connects energy sensing to mitophagy Science 331 2011 456 461
    • (2011) Science , vol.331 , pp. 456-461
    • Egan, D.F.1    Shackelford, D.B.2    Mihaylova, M.M.3    Gelino, S.4    Kohnz, R.A.5    Mair, W.6
  • 34
    • 84866061320 scopus 로고    scopus 로고
    • AMPK-dependent phosphorylation of ULK1 regulates ATG9 localization
    • H.I. Mack, B. Zheng, J.M. Asara, and S.M. Thomas AMPK-dependent phosphorylation of ULK1 regulates ATG9 localization Autophagy 8 2012 1197 1214
    • (2012) Autophagy , vol.8 , pp. 1197-1214
    • Mack, H.I.1    Zheng, B.2    Asara, J.M.3    Thomas, S.M.4
  • 36
    • 77951250700 scopus 로고    scopus 로고
    • Oligomycin-induced bioenergetic adaptation in cancer cells with heterogeneous bioenergetic organization
    • W. Hao, C.P. Chang, C.C. Tsao, and J. Xu Oligomycin-induced bioenergetic adaptation in cancer cells with heterogeneous bioenergetic organization J Biol Chem 285 2010 12647 12654
    • (2010) J Biol Chem , vol.285 , pp. 12647-12654
    • Hao, W.1    Chang, C.P.2    Tsao, C.C.3    Xu, J.4
  • 37
    • 84884565721 scopus 로고    scopus 로고
    • AMP-activated protein kinase: A target for old drugs against diabetes and cancer
    • G.L. Russo, M. Russo, and P. Ungaro AMP-activated protein kinase: a target for old drugs against diabetes and cancer Biochem Pharmacol 86 2013 339 350
    • (2013) Biochem Pharmacol , vol.86 , pp. 339-350
    • Russo, G.L.1    Russo, M.2    Ungaro, P.3
  • 38
    • 0033922250 scopus 로고    scopus 로고
    • Inhibition of mitochondrial proton F0F1-ATPase/ATP synthase by polyphenolic phytochemicals
    • J. Zheng, and V.D. Ramirez Inhibition of mitochondrial proton F0F1-ATPase/ATP synthase by polyphenolic phytochemicals Br J Pharmacol 130 2000 1115 1123
    • (2000) Br J Pharmacol , vol.130 , pp. 1115-1123
    • Zheng, J.1    Ramirez, V.D.2
  • 39
    • 0034614420 scopus 로고    scopus 로고
    • Dimethylbiguanide inhibits cell respiration via an indirect effect targeted on the respiratory chain complex i
    • M.Y. El-Mir, V. Nogueira, E. Fontaine, N. Averet, M. Rigoulet, and X. Leverve Dimethylbiguanide inhibits cell respiration via an indirect effect targeted on the respiratory chain complex I J Biol Chem 275 2000 223 228
    • (2000) J Biol Chem , vol.275 , pp. 223-228
    • El-Mir, M.Y.1    Nogueira, V.2    Fontaine, E.3    Averet, N.4    Rigoulet, M.5    Leverve, X.6
  • 40
    • 0034659785 scopus 로고    scopus 로고
    • Evidence that metformin exerts its anti-diabetic effects through inhibition of complex 1 of the mitochondrial respiratory chain
    • M.R. Owen, E. Doran, and A.P. Halestrap Evidence that metformin exerts its anti-diabetic effects through inhibition of complex 1 of the mitochondrial respiratory chain Biochem J 348 Pt 3 2000 607 614
    • (2000) Biochem J , vol.348 , pp. 607-614
    • Owen, M.R.1    Doran, E.2    Halestrap, A.P.3
  • 41
    • 70349096755 scopus 로고    scopus 로고
    • Uncoupling of oxidative phosphorylation by curcumin: Implication of its cellular mechanism of action
    • H.W. Lim, H.Y. Lim, and K.P. Wong Uncoupling of oxidative phosphorylation by curcumin: implication of its cellular mechanism of action Biochem Biophys Res Commun 389 2009 187 192
    • (2009) Biochem Biophys Res Commun , vol.389 , pp. 187-192
    • Lim, H.W.1    Lim, H.Y.2    Wong, K.P.3
  • 42
    • 84876320551 scopus 로고    scopus 로고
    • LKB1 and AMPK and the cancer-metabolism link - Ten years after
    • D.G. Hardie, and D.R. Alessi LKB1 and AMPK and the cancer-metabolism link - ten years after BMC Biol 11 2013 36
    • (2013) BMC Biol , vol.11 , pp. 36
    • Hardie, D.G.1    Alessi, D.R.2
  • 43
    • 84871965497 scopus 로고    scopus 로고
    • MCT1-mediated transport of a toxic molecule is an effective strategy for targeting glycolytic tumors
    • K. Birsoy, T. Wang, R. Possemato, O.H. Yilmaz, C.E. Koch, and W.W. Chen MCT1-mediated transport of a toxic molecule is an effective strategy for targeting glycolytic tumors Nat Genet 45 2013 104 108
    • (2013) Nat Genet , vol.45 , pp. 104-108
    • Birsoy, K.1    Wang, T.2    Possemato, R.3    Yilmaz, O.H.4    Koch, C.E.5    Chen, W.W.6
  • 44
    • 77955287742 scopus 로고    scopus 로고
    • Metformin, independent of AMPK, inhibits mTORC1 in a rag GTPase-dependent manner
    • A. Kalender, A. Selvaraj, S.Y. Kim, P. Gulati, S. Brule, and B. Viollet Metformin, independent of AMPK, inhibits mTORC1 in a rag GTPase-dependent manner Cell Metab 11 2010 390 401
    • (2010) Cell Metab , vol.11 , pp. 390-401
    • Kalender, A.1    Selvaraj, A.2    Kim, S.Y.3    Gulati, P.4    Brule, S.5    Viollet, B.6
  • 45
    • 77449120994 scopus 로고    scopus 로고
    • High-throughput assay for modulators of mitochondrial membrane potential identifies a novel compound with beneficial effects on db/db mice
    • B.Y. Qiu, N. Turner, Y.Y. Li, M. Gu, M.W. Huang, and F. Wu High-throughput assay for modulators of mitochondrial membrane potential identifies a novel compound with beneficial effects on db/db mice Diabetes 59 2010 256 265
    • (2010) Diabetes , vol.59 , pp. 256-265
    • Qiu, B.Y.1    Turner, N.2    Li, Y.Y.3    Gu, M.4    Huang, M.W.5    Wu, F.6
  • 48
    • 78149452820 scopus 로고    scopus 로고
    • Catalytic asymmetric aldol equivalents in the enantioselective synthesis of the apoptolidin C aglycone
    • T.R. Vargo, J.S. Hale, and S.G. Nelson Catalytic asymmetric aldol equivalents in the enantioselective synthesis of the apoptolidin C aglycone Angew Chem Int Ed Engl 49 2010 8678 8681
    • (2010) Angew Chem Int Ed Engl , vol.49 , pp. 8678-8681
    • Vargo, T.R.1    Hale, J.S.2    Nelson, S.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.