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Volumn 113, Issue 11, 2016, Pages 2851-2856

Structural basis for DNA cleavage by the potent antiproliferative agent (-)-lomaiviticin A

Author keywords

DNA; Double strand break; Natural product; NMR

Indexed keywords

ANTINEOPLASTIC AGENT; DOUBLE STRANDED DNA; HYDROGEN; KINAMYCIN; LOMAIVITICIN A; LOMAIVITICIN B; LOMAIVITICIN C; UNCLASSIFIED DRUG; ANTINEOPLASTIC ANTIBIOTIC; CALF THYMUS DNA; DNA; FLUORENE DERIVATIVE; HETERODUPLEX;

EID: 84962584081     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1519846113     Document Type: Article
Times cited : (27)

References (48)
  • 1
    • 0034812241 scopus 로고    scopus 로고
    • Lomaiviticins A and B, potent antitumor antibiotics from Micromonospora lomaivitiensis
    • He H, et al. (2001) Lomaiviticins A and B, potent antitumor antibiotics from Micromonospora lomaivitiensis. J Am Chem Soc 123(22):5362-5363.
    • (2001) J Am Chem Soc , vol.123 , Issue.22 , pp. 5362-5363
    • He, H.1
  • 2
    • 84866517248 scopus 로고    scopus 로고
    • Isolation of lomaiviticins C-E, transformation of lomaiviticin C to lomaiviticin A, complete structure elucidation of lomaiviticin A, and structure-activity analyses
    • Woo CM, Beizer NE, Janso JE, Herzon SB (2012) Isolation of lomaiviticins C-E, transformation of lomaiviticin C to lomaiviticin A, complete structure elucidation of lomaiviticin A, and structure-activity analyses. J Am Chem Soc 134(37):15285-15288.
    • (2012) J Am Chem Soc , vol.134 , Issue.37 , pp. 15285-15288
    • Woo, C.M.1    Beizer, N.E.2    Janso, J.E.3    Herzon, S.B.4
  • 3
    • 84878015616 scopus 로고    scopus 로고
    • Bioactivity-guided genome mining reveals the lomaiviticin biosynthetic gene cluster in Salinispora tropica
    • Kersten RD, et al. (2013) Bioactivity-guided genome mining reveals the lomaiviticin biosynthetic gene cluster in Salinispora tropica. ChemBioChem 14(8):955-962.
    • (2013) ChemBioChem , vol.14 , Issue.8 , pp. 955-962
    • Kersten, R.D.1
  • 5
    • 0015081375 scopus 로고
    • A new antibiotic, kinamycin: Fermentation, isolation, purification and properties
    • Hata T, Omura S, Iwai Y, Nakagawa A, Otani M (1971) A new antibiotic, kinamycin: Fermentation, isolation, purification and properties. J Antibiot (Tokyo) 24(6):353-359.
    • (1971) J Antibiot (Tokyo) , vol.24 , Issue.6 , pp. 353-359
    • Hata, T.1    Omura, S.2    Iwai, Y.3    Nakagawa, A.4    Otani, M.5
  • 6
    • 85008135775 scopus 로고
    • Structure of kinamycin C, and the structural relation among kinamycin A, B, C, and D
    • Omura S, et al. (1971) Structure of kinamycin C, and the structural relation among kinamycin A, B, C, and D. Chem Pharm Bull (Tokyo) 19(11):2428-2430.
    • (1971) Chem Pharm Bull (Tokyo) , vol.19 , Issue.11 , pp. 2428-2430
    • Omura, S.1
  • 7
    • 84987335907 scopus 로고
    • Crystal and molecular structure of kinamycin C p-bromobenzoate
    • Furusaki A, et al. (1972) Crystal and molecular structure of kinamycin C p-bromobenzoate. Isr J Chem 10(2):173-187.
    • (1972) Isr J Chem , vol.10 , Issue.2 , pp. 173-187
    • Furusaki, A.1
  • 10
    • 0024503717 scopus 로고
    • New products related to kinamycin from Streptomyces murayamaensis. II. Structures of pre-kinamycin, keto-anhydrokinamycin, and kinamycins e and F
    • Seaton PJ, Gould SJ (1989) New products related to kinamycin from Streptomyces murayamaensis. II. Structures of pre-kinamycin, keto-anhydrokinamycin, and kinamycins E and F. J Antibiot (Tokyo) 42(2):189-197.
    • (1989) J Antibiot (Tokyo) , vol.42 , Issue.2 , pp. 189-197
    • Seaton, P.J.1    Gould, S.J.2
  • 11
    • 0031952729 scopus 로고    scopus 로고
    • Cloning and heterologous expression of genes from the kinamycin biosynthetic pathway of Streptomyces murayamaensis
    • Gould SJ, Hong ST, Carney JR (1998) Cloning and heterologous expression of genes from the kinamycin biosynthetic pathway of Streptomyces murayamaensis. J Antibiot (Tokyo) 51(1):50-57.
    • (1998) J Antibiot (Tokyo) , vol.51 , Issue.1 , pp. 50-57
    • Gould, S.J.1    Hong, S.T.2    Carney, J.R.3
  • 12
    • 0001017011 scopus 로고    scopus 로고
    • Biosynthesis of the kinamycins
    • Gould SJ (1997) Biosynthesis of the Kinamycins. Chem Rev 97(7):2499-2510.
    • (1997) Chem Rev , vol.97 , Issue.7 , pp. 2499-2510
    • Gould, S.J.1
  • 13
    • 0043195579 scopus 로고    scopus 로고
    • Naturally occurring diazo compounds: The kinamycins
    • Marco-Contelles J, Molina MT (2003) Naturally occurring diazo compounds: The kinamycins. Curr Org Chem 7(14):1433-1442.
    • (2003) Curr Org Chem , vol.7 , Issue.14 , pp. 1433-1442
    • Marco-Contelles, J.1    Molina, M.T.2
  • 14
    • 43749099869 scopus 로고    scopus 로고
    • Diazo and diazonium DNA cleavage agents: Studies on model systems and natural product mechanisms of action
    • ed Lee M (Springer, Berlin, Heidelberg)
    • Arya DP (2006) Diazo and diazonium DNA cleavage agents: Studies on model systems and natural product mechanisms of action. Heterocyclic Antitumor Antiobiotics, Topics in Heterocyclic Chemistry, ed Lee M (Springer, Berlin, Heidelberg), Vol 2 , pp 129-152.
    • (2006) Heterocyclic Antitumor Antiobiotics, Topics in Heterocyclic Chemistry , vol.2 , pp. 129-152
    • Arya, D.P.1
  • 15
    • 79960814345 scopus 로고    scopus 로고
    • Natural products containing a diazo group
    • Nawrat CC, Moody CJ (2011) Natural products containing a diazo group. Nat Prod Rep 28(8):1426-1444.
    • (2011) Nat Prod Rep , vol.28 , Issue.8 , pp. 1426-1444
    • Nawrat, C.C.1    Moody, C.J.2
  • 17
    • 83455196242 scopus 로고    scopus 로고
    • The diazofluorene antitumor antibiotics: Structural elucidation, biosynthetic, synthetic, and chemical biological studies
    • Herzon SB, Woo CM (2012) The diazofluorene antitumor antibiotics: Structural elucidation, biosynthetic, synthetic, and chemical biological studies. Nat Prod Rep 29(1): 87-118.
    • (2012) Nat Prod Rep , vol.29 , Issue.1 , pp. 87-118
    • Herzon, S.B.1    Woo, C.M.2
  • 18
    • 84901347004 scopus 로고    scopus 로고
    • The cytotoxicity of (-)-lomaiviticin A arises from induction of double-strand breaks in DNA
    • Colis LC, et al. (2014) The cytotoxicity of (-)-lomaiviticin A arises from induction of double-strand breaks in DNA. Nat Chem 6(6):504-510.
    • (2014) Nat Chem , vol.6 , Issue.6 , pp. 504-510
    • Colis, L.C.1
  • 19
    • 84928962994 scopus 로고    scopus 로고
    • Mechanism of action studies of lomaiviticin A and the monomeric lomaiviticin aglycon. Selective and potent activity toward DNA double-strand break repair-deficient cell lines
    • Colis LC, Hegan DC, Kaneko M, Glazer PM, Herzon SB (2015) Mechanism of action studies of lomaiviticin A and the monomeric lomaiviticin aglycon. Selective and potent activity toward DNA double-strand break repair-deficient cell lines. J Am Chem Soc 137(17):5741-5747.
    • (2015) J Am Chem Soc , vol.137 , Issue.17 , pp. 5741-5747
    • Colis, L.C.1    Hegan, D.C.2    Kaneko, M.3    Glazer, P.M.4    Herzon, S.B.5
  • 20
    • 84891622264 scopus 로고    scopus 로고
    • Targeting DNA double-strand break signalling and repair: Recent advances in cancer therapy
    • Hühn D, Bolck HA, Sartori AA (2013) Targeting DNA double-strand break signalling and repair: Recent advances in cancer therapy. Swiss Med Wkly 143:w13837.
    • (2013) Swiss Med Wkly , vol.143 , pp. w13837
    • Hühn, D.1    Bolck, H.A.2    Sartori, A.A.3
  • 21
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • Burrows CJ, Muller JG (1998) Oxidative nucleobase modifications leading to strand scission. Chem Rev 98(3):1109-1152.
    • (1998) Chem Rev , vol.98 , Issue.3 , pp. 1109-1152
    • Burrows, C.J.1    Muller, J.G.2
  • 22
    • 84906789106 scopus 로고    scopus 로고
    • Analysis of diazofluorene DNA binding and damaging activity: DNA cleavage by a synthetic monomeric diazofluorene
    • Woo CM, Ranjan N, Arya DP, Herzon SB (2014) Analysis of diazofluorene DNA binding and damaging activity: DNA cleavage by a synthetic monomeric diazofluorene. Angew Chem Int Ed Engl 53(35):9325-9328.
    • (2014) Angew Chem Int Ed Engl , vol.53 , Issue.35 , pp. 9325-9328
    • Woo, C.M.1    Ranjan, N.2    Arya, D.P.3    Herzon, S.B.4
  • 23
    • 0034641332 scopus 로고    scopus 로고
    • Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity
    • Boger DL, Fink BE, Hedrick MP (2000) Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity. J Am Chem Soc 122(27):6382-6394.
    • (2000) J Am Chem Soc , vol.122 , Issue.27 , pp. 6382-6394
    • Boger, D.L.1    Fink, B.E.2    Hedrick, M.P.3
  • 24
    • 0034833710 scopus 로고    scopus 로고
    • A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity
    • Boger DL, Fink BE, Brunette SR, Tse WC, Hedrick MP (2001) A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J Am Chem Soc 123(25):5878-5891.
    • (2001) J Am Chem Soc , vol.123 , Issue.25 , pp. 5878-5891
    • Boger, D.L.1    Fink, B.E.2    Brunette, S.R.3    Tse, W.C.4    Hedrick, M.P.5
  • 25
    • 1642576322 scopus 로고    scopus 로고
    • A fluorescent intercalator displacement assay for establishing DNA binding selectivity and affinity
    • Tse WC, Boger DL (2004) A fluorescent intercalator displacement assay for establishing DNA binding selectivity and affinity. Acc Chem Res 37(1):61-69.
    • (2004) Acc Chem Res , vol.37 , Issue.1 , pp. 61-69
    • Tse, W.C.1    Boger, D.L.2
  • 26
    • 0022819747 scopus 로고
    • Thiazole orange: A new dye for reticulocyte analysis
    • Lee LG, Chen C-H, Chiu LA (1986) Thiazole orange: A new dye for reticulocyte analysis. Cytometry 7(6):508-517.
    • (1986) Cytometry , vol.7 , Issue.6 , pp. 508-517
    • Lee, L.G.1    Chen, C.-H.2    Chiu, L.A.3
  • 27
    • 34447310304 scopus 로고    scopus 로고
    • DNA binding of tilorone: 1H NMR and calorimetric studies of the intercalation
    • Nishimura T, et al. (2007) DNA binding of tilorone: 1H NMR and calorimetric studies of the intercalation. Biochemistry 46(27):8156-8163.
    • (2007) Biochemistry , vol.46 , Issue.27 , pp. 8156-8163
    • Nishimura, T.1
  • 29
    • 0026696172 scopus 로고
    • Determination of nucleic acid backbone conformation by 1H NMR
    • Kim S-G, Lin L-J, Reid BR (1992) Determination of nucleic acid backbone conformation by 1H NMR. Biochemistry 31(14):3564-3574.
    • (1992) Biochemistry , vol.31 , Issue.14 , pp. 3564-3574
    • Kim, S.-G.1    Lin, L.-J.2    Reid, B.R.3
  • 30
    • 35048819920 scopus 로고    scopus 로고
    • Insertion of a bulky rhodium complex into a DNA cytosine-cytosine mismatch: An NMR solution study
    • Cordier C, Pierre VC, Barton JK (2007) Insertion of a bulky rhodium complex into a DNA cytosine-cytosine mismatch: An NMR solution study. J Am Chem Soc 129(40): 12287-12295.
    • (2007) J Am Chem Soc , vol.129 , Issue.40 , pp. 12287-12295
    • Cordier, C.1    Pierre, V.C.2    Barton, J.K.3
  • 31
    • 27244458221 scopus 로고    scopus 로고
    • Characterization of the bisintercalative DNA binding mode of a bifunctional platinum-acridine agent
    • Choudhury JR, Bierbach U (2005) Characterization of the bisintercalative DNA binding mode of a bifunctional platinum-acridine agent. Nucleic Acids Res 33(17):5622-5632.
    • (2005) Nucleic Acids Res , vol.33 , Issue.17 , pp. 5622-5632
    • Choudhury, J.R.1    Bierbach, U.2
  • 32
    • 84962593154 scopus 로고    scopus 로고
    • Spartan 10 for PC Wavefunction, Inc., Irvine, CA
    • Spartan 10 for PC (2010) (Wavefunction, Inc., Irvine, CA).
    • (2010)
  • 34
    • 23444454552 scopus 로고    scopus 로고
    • The Amber biomolecular simulation programs
    • Case DA, et al. (2005) The Amber biomolecular simulation programs. J Comput Chem 26(16):1668-1688.
    • (2005) J Comput Chem , vol.26 , Issue.16 , pp. 1668-1688
    • Case, D.A.1
  • 35
    • 84884931806 scopus 로고    scopus 로고
    • Twenty-five years of nucleic acid simulations
    • Cheatham TE, 3rd, Case DA (2013) Twenty-five years of nucleic acid simulations. Biopolymers 99(12):969-977.
    • (2013) Biopolymers , vol.99 , Issue.12 , pp. 969-977
    • Cheatham, T.E.1    Case, D.A.2
  • 36
    • 84872547120 scopus 로고    scopus 로고
    • Drugging topoisomerases: Lessons and challenges
    • Pommier Y (2013) Drugging topoisomerases: Lessons and challenges. ACS Chem Biol 8(1):82-95.
    • (2013) ACS Chem Biol , vol.8 , Issue.1 , pp. 82-95
    • Pommier, Y.1
  • 39
    • 0037076390 scopus 로고    scopus 로고
    • Looped out and perpendicular: Deformation of Watson-Crick base pair associated with actinomycin D binding
    • Chou S-H, Chin K-H, Chen F-M (2002) Looped out and perpendicular: Deformation of Watson-Crick base pair associated with actinomycin D binding. Proc Natl Acad Sci USA 99(10):6625-6630.
    • (2002) Proc Natl Acad Sci USA , vol.99 , Issue.10 , pp. 6625-6630
    • Chou, S.-H.1    Chin, K.-H.2    Chen, F.-M.3
  • 40
    • 45549101686 scopus 로고    scopus 로고
    • Crystal structure of trioxacarcin A covalently bound to DNA
    • Pfoh R, Laatsch H, Sheldrick GM (2008) Crystal structure of trioxacarcin A covalently bound to DNA. Nucleic Acids Res 36(10):3508-3514.
    • (2008) Nucleic Acids Res , vol.36 , Issue.10 , pp. 3508-3514
    • Pfoh, R.1    Laatsch, H.2    Sheldrick, G.M.3
  • 41
    • 32644434270 scopus 로고    scopus 로고
    • Base-stacking and basepairing contributions into thermal stability of the DNA double helix
    • Yakovchuk P, Protozanova E, Frank-Kamenetskii MD (2006) Base-stacking and basepairing contributions into thermal stability of the DNA double helix. Nucleic Acids Res 34(2):564-574.
    • (2006) Nucleic Acids Res , vol.34 , Issue.2 , pp. 564-574
    • Yakovchuk, P.1    Protozanova, E.2    Frank-Kamenetskii, M.D.3
  • 42
    • 0002746148 scopus 로고    scopus 로고
    • Bleomycins: A structural model for specificity, binding, and double strand cleavage
    • Stubbe J, Kozarich JW, Wu W, Vanderwall DE (1996) Bleomycins: A structural model for specificity, binding, and double strand cleavage. Acc Chem Res 29(7): 322-330.
    • (1996) Acc Chem Res , vol.29 , Issue.7 , pp. 322-330
    • Stubbe, J.1    Kozarich, J.W.2    Wu, W.3    Vanderwall, D.E.4
  • 43
    • 0017548298 scopus 로고
    • DNA double-strand breaks and alkali-labile bonds produced by bleomycin
    • Povirk LF, Wübter W, Köhnlein W, Hutchinson F (1977) DNA double-strand breaks and alkali-labile bonds produced by bleomycin. Nucleic Acids Res 4(10): 3573-3580.
    • (1977) Nucleic Acids Res , vol.4 , Issue.10 , pp. 3573-3580
    • Povirk, L.F.1    Wübter, W.2    Köhnlein, W.3    Hutchinson, F.4
  • 44
    • 0028925819 scopus 로고
    • Sequence-specific double-strand cleavage of DNA by Fe-bleomycin. 1. The detection of sequence-specific double-strand breaks using hairpin oligonucleotides
    • Absalon MJ, Kozarich JW, Stubbe J (1995) Sequence-specific double-strand cleavage of DNA by Fe-bleomycin. 1. The detection of sequence-specific double-strand breaks using hairpin oligonucleotides. Biochemistry 34(6):2065-2075.
    • (1995) Biochemistry , vol.34 , Issue.6 , pp. 2065-2075
    • Absalon, M.J.1    Kozarich, J.W.2    Stubbe, J.3
  • 45
    • 0031081549 scopus 로고    scopus 로고
    • Catalysis of the CC-1065 and duocarmycin DNA alkylation reaction: DNA binding induced conformational change in the agent results in activation
    • Boger DL, Garbaccio RM (1997) Catalysis of the CC-1065 and duocarmycin DNA alkylation reaction: DNA binding induced conformational change in the agent results in activation. Bioorg Med Chem 5(2):263-276.
    • (1997) Bioorg Med Chem , vol.5 , Issue.2 , pp. 263-276
    • Boger, D.L.1    Garbaccio, R.M.2
  • 46
    • 0033377095 scopus 로고    scopus 로고
    • Shape-dependent catalysis: Insights into the source of catalysis for the CC-1065 and duocarmycin DNA alkylation reaction
    • Boger DL, Garbaccio RM (1999) Shape-dependent catalysis: Insights into the source of catalysis for the CC-1065 and duocarmycin DNA alkylation reaction. Acc Chem Res 32(12):1043-1052.
    • (1999) Acc Chem Res , vol.32 , Issue.12 , pp. 1043-1052
    • Boger, D.L.1    Garbaccio, R.M.2
  • 47
    • 0036628558 scopus 로고    scopus 로고
    • Mechanisms of in situ activation for DNA-targeting antitumor agents
    • Wolkenberg SE, Boger DL (2002) Mechanisms of in situ activation for DNA-targeting antitumor agents. Chem Rev 102(7):2477-2495.
    • (2002) Chem Rev , vol.102 , Issue.7 , pp. 2477-2495
    • Wolkenberg, S.E.1    Boger, D.L.2
  • 48
    • 10644249279 scopus 로고    scopus 로고
    • Sequence-selective DNA recognition: Natural products and nature's lessons
    • Tse WC, Boger DL (2004) Sequence-selective DNA recognition: Natural products and nature's lessons. Chem Biol 11(12):1607-1617.
    • (2004) Chem Biol , vol.11 , Issue.12 , pp. 1607-1617
    • Tse, W.C.1    Boger, D.L.2


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