메뉴 건너뛰기




Volumn 12, Issue 10, 2014, Pages 5209-5221

Modification of marine natural product ningalin B and SAR study lead to potent P-glycoprotein inhibitors

Author keywords

Multidrug resistance (MDR); Ningalin B analogues; P glycoprotein; P gp modulators; Pyrrole

Indexed keywords

ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; FUSED HETEROCYCLIC RINGS; MULTIDRUG RESISTANCE PROTEIN; NINGALIN B; PIPERAZINE; PIPERAZINE DERIVATIVE;

EID: 84908199216     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12105209     Document Type: Article
Times cited : (12)

References (29)
  • 1
    • 84882696152 scopus 로고    scopus 로고
    • P-glycoprotein inhibition for optimal drug delivery
    • Amin, M.L. P-glycoprotein inhibition for optimal drug delivery. Drug Target Insights 2013, 7, 27-34.
    • (2013) Drug Target Insights , vol.7 , pp. 27-34
    • Amin, M.L.1
  • 2
    • 67649786798 scopus 로고    scopus 로고
    • Recent advances in the development of P-gp inhibitors
    • Baumert, C.; Hilgeroth, A. Recent advances in the development of P-gp inhibitors. Anticancer. Agents Med. Chem. 2009, 9, 415-436.
    • (2009) Anticancer. Agents Med. Chem. , vol.9 , pp. 415-436
    • Baumert, C.1    Hilgeroth, A.2
  • 3
    • 67650685020 scopus 로고    scopus 로고
    • ABC efflux pump-based resistance to chemotherapy drugs
    • Eckford, P.D.; Sharom, F.J. ABC efflux pump-based resistance to chemotherapy drugs. Chem. Rev. 2009, 109, 2989-3011.
    • (2009) Chem. Rev. , vol.109 , pp. 2989-3011
    • Eckford, P.D.1    Sharom, F.J.2
  • 4
    • 0037242335 scopus 로고    scopus 로고
    • New multidrug resistance reversal agents
    • Kawase, M.; Motohashi, N. New multidrug resistance reversal agents. Curr. Drug Targets 2003, 4, 31-43.
    • (2003) Curr. Drug Targets , vol.4 , pp. 31-43
    • Kawase, M.1    Motohashi, N.2
  • 6
    • 0032891198 scopus 로고    scopus 로고
    • New lamellarin alkaloids from the australian ascidian, didemnum chartaceum
    • Davis, R.A.; Carroll, A.R.; Pierens, G.K.; Quinn, R.J. New lamellarin alkaloids from the australian ascidian, didemnum chartaceum. J. Nat. Prod. 1999, 62, 419-424.
    • (1999) J. Nat. Prod. , vol.62 , pp. 419-424
    • Davis, R.A.1    Carroll, A.R.2    Pierens, G.K.3    Quinn, R.J.4
  • 7
    • 38749120651 scopus 로고    scopus 로고
    • Lamellarins and related pyrrole-derived alkaloids from marine organisms
    • Fan, H.; Peng, J.; Hamann, M.T.; Hu, J.F. Lamellarins and related pyrrole-derived alkaloids from marine organisms. Chem. Rev. 2008, 108, 264-287.
    • (2008) Chem. Rev. , vol.108 , pp. 264-287
    • Fan, H.1    Peng, J.2    Hamann, M.T.3    Hu, J.F.4
  • 9
    • 0034697265 scopus 로고    scopus 로고
    • Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents
    • Boger, D.L.; Soenen, D.R.; Boyce, C.W.; Hedrick, M.P.; Jin, Q. Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents. J. Org. Chem. 2000, 65, 2479-2483.
    • (2000) J. Org. Chem. , vol.65 , pp. 2479-2483
    • Boger, D.L.1    Soenen, D.R.2    Boyce, C.W.3    Hedrick, M.P.4    Jin, Q.5
  • 10
    • 0037184774 scopus 로고    scopus 로고
    • Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: A concise total synthesis of ningalin B
    • Bullington, J.L.; Wolff, R.R.; Jackson, P.F. Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: A concise total synthesis of ningalin B. J. Org. Chem. 2002, 67, 9439-9442.
    • (2002) J. Org. Chem. , vol.67 , pp. 9439-9442
    • Bullington, J.L.1    Wolff, R.R.2    Jackson, P.F.3
  • 11
    • 1542524871 scopus 로고    scopus 로고
    • Ningalins A-D: Novel aromatic alkaloids from a western australian ascidian of the genus didemnum
    • Kang, H.; Fenical, W. Ningalins A-D: Novel aromatic alkaloids from a western australian ascidian of the genus didemnum. J. Org. Chem. 1997, 62, 3254-3262.
    • (1997) J. Org. Chem. , vol.62 , pp. 3254-3262
    • Kang, H.1    Fenical, W.2
  • 12
    • 77955418722 scopus 로고    scopus 로고
    • Baculiferins A-O O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera
    • Fan, G.; Li, Z.; Shen, S.; Zeng, Y.; Yang, Y.; Xu, M.; Bruhn, T.; Bruhn, H.; Morschhauser, J.; Bringmann, G.; Lin, W. Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera. Bioorg. Med. Chem. 2010, 18, 5466-5474.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 5466-5474
    • Fan, G.1    Li, Z.2    Shen, S.3    Zeng, Y.4    Yang, Y.5    Xu, M.6    Bruhn, T.7    Bruhn, H.8    Morschhauser, J.9    Bringmann, G.10    Lin, W.11
  • 13
    • 0033935999 scopus 로고    scopus 로고
    • Polycitone B and prepolycitrin A: Two novel alkaloids from the marine ascidian Polycitor africanus
    • Rudi, A.; Evan, T.; Aknin, M.; Kashma, Y.N. Polycitone B and prepolycitrin A: Two novel alkaloids from the marine ascidian Polycitor africanus. J. Nat. Prod. 2000, 63, 832-833.
    • (2000) J. Nat. Prod. , vol.63 , pp. 832-833
    • Rudi, A.1    Evan, T.2    Aknin, M.3    Kashma, Y.N.4
  • 14
    • 0037136502 scopus 로고    scopus 로고
    • Total syntheses of the marine pyrrole alkaloids polycitone A and B
    • Kreipl, A.T.; Reid, C.; Steglich, W. Total syntheses of the marine pyrrole alkaloids polycitone A and B. Org. Lett. 2002, 4, 3287-3288.
    • (2002) Org. Lett. , vol.4 , pp. 3287-3288
    • Kreipl, A.T.1    Reid, C.2    Steglich, W.3
  • 15
    • 3142764930 scopus 로고    scopus 로고
    • Lamellarins from A to Z: A family of anticancer marine pyrrole alkaloids
    • Bailly, C. Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids. Curr. Med. Chem. Anticancer Agents 2004, 4, 363-378.
    • (2004) Curr. Med. Chem. Anticancer Agents , vol.4 , pp. 363-378
    • Bailly, C.1
  • 16
    • 0032985884 scopus 로고    scopus 로고
    • A cyclized didemnimide alkaloid from the caribbean ascidian didemnumconchyliatum
    • Vervoort, H.C.; Fenical, W.; Keifer, P.A. A cyclized didemnimide alkaloid from the caribbean ascidian didemnumconchyliatum. J. Nat. Prod. 1999, 62, 389-391.
    • (1999) J. Nat. Prod. , vol.62 , pp. 389-391
    • Vervoort, H.C.1    Fenical, W.2    Keifer, P.A.3
  • 17
    • 84870055324 scopus 로고    scopus 로고
    • Purpuroines A-J halogenated alkaloids from the sponge Iotrochota purpurea with antibiotic activity and regulation of tyrosine kinases
    • Shen, S.; Liu, D.; Wei, C.; Proksch, P.; Lin, W. Purpuroines A-J, halogenated alkaloids from the sponge Iotrochota purpurea with antibiotic activity and regulation of tyrosine kinases. Bioorg. Med. Chem. 2012, 20, 6924-6928.
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 6924-6928
    • Shen, S.1    Liu, D.2    Wei, C.3    Proksch, P.4    Lin, W.5
  • 20
    • 62749137447 scopus 로고    scopus 로고
    • Cytotoxicities and structure-activity relationships of natural and unnatural lamellarins toward cancer cell lines
    • Chittchang, M.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Cytotoxicities and structure-activity relationships of natural and unnatural lamellarins toward cancer cell lines. ChemMedChem 2009, 4, 457-465.
    • (2009) ChemMedChem , vol.4 , pp. 457-465
    • Chittchang, M.1    Batsomboon, P.2    Ruchirawat, S.3    Ploypradith, P.4
  • 21
    • 23244448041 scopus 로고    scopus 로고
    • Potent reversal of multidrug resistance by ningalins and its use in drug combinations against human colon carcinoma xenograft in nude mice
    • Chou, T.C.; Guan, Y.; Soenen, D.R.; Danishefsky, S.J.; Boger, D.L. Potent reversal of multidrug resistance by ningalins and its use in drug combinations against human colon carcinoma xenograft in nude mice. Cancer Chemother. Pharmacol. 2005, 56, 379-390.
    • (2005) Cancer Chemother. Pharmacol. , vol.56 , pp. 379-390
    • Chou, T.C.1    Guan, Y.2    Soenen, D.R.3    Danishefsky, S.J.4    Boger, D.L.5
  • 23
    • 84889250368 scopus 로고    scopus 로고
    • Structure-activity relationship study of permethyl ningalin B analogues as P-glycoprotein chemosensitizers
    • Bin, J.W.; Wong, I.L.; Hu, X.; Yu, Z.X.; Xing, L.F.; Jiang, T.; Chow, L.M.; Biao, W.S. Structure-activity relationship study of permethyl ningalin B analogues as P-glycoprotein chemosensitizers. J. Med. Chem. 2013, 56, 9057-9070.
    • (2013) J. Med. Chem. , vol.56 , pp. 9057-9070
    • Bin, J.W.1    Wong, I.L.2    Hu, X.3    Yu, Z.X.4    Xing, L.F.5    Jiang, T.6    Chow, L.M.7    Biao, W.S.8
  • 24
    • 77954709180 scopus 로고    scopus 로고
    • Design and syntheses of permethyl ningalin B analogues: Potent multidrug resistance (MDR) reversal agents of cancer cells
    • Zhang, P.Y.; Wong, I.L.; Yan, C.S.; Zhang, X.Y.; Jiang, T.; Chow, L.M.; Wan, S.B. Design and syntheses of permethyl ningalin B analogues: Potent multidrug resistance (MDR) reversal agents of cancer cells. J. Med. Chem. 2010, 53, 5108-5120.
    • (2010) J. Med. Chem. , vol.53 , pp. 5108-5120
    • Zhang, P.Y.1    Wong, I.L.2    Yan, C.S.3    Zhang, X.Y.4    Jiang, T.5    Chow, L.M.6    Wan, S.B.7
  • 25
    • 0031562375 scopus 로고    scopus 로고
    • New Lamellarin alkaloids from an unidentified ascidian from the Arabian Sea
    • Venkata, M.; Reddy, M.V.R.; Faulkner, D.J.; Venkateswarlu, Y.; Rao, M.R. New Lamellarin alkaloids from an unidentified ascidian from the Arabian Sea. Tetrhedron 1997, 53, 3457-3466.
    • (1997) Tetrhedron , vol.53 , pp. 3457-3466
    • Venkata, M.1    Reddy, M.V.R.2    Faulkner, D.J.3    Venkateswarlu, Y.4    Rao, M.R.5
  • 26
    • 84858039954 scopus 로고    scopus 로고
    • Amine linked flavonoid dimers as modulators for P-glycoprotein-based multidrug resistance: Structure-activity relationship and mechanism of modulation
    • Chan, K.F.; Wong, I.L.; Kan, J.W.; Yan, C.S.; Chow, L.M.; Chan, T.H. Amine linked flavonoid dimers as modulators for P-glycoprotein-based multidrug resistance: Structure-activity relationship and mechanism of modulation. J. Med. Chem. 2012, 55, 1999-2014.
    • (2012) J. Med. Chem. , vol.55 , pp. 1999-2014
    • Chan, K.F.1    Wong, I.L.2    Kan, J.W.3    Yan, C.S.4    Chow, L.M.5    Chan, T.H.6
  • 27
    • 33751020848 scopus 로고    scopus 로고
    • Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Synthetic apigenin homodimers linked with defined-length poly(ethylene glycol) spacers increase drug retention and enhance chemosensitivity in resistant cancer cells
    • Chan, K.F.; Zhao, Y.; Burkett, B.A.; Wong, I.L.; Chow, L.M.; Chan, T.H. Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Synthetic apigenin homodimers linked with defined-length poly(ethylene glycol) spacers increase drug retention and enhance chemosensitivity in resistant cancer cells. J. Med. Chem. 2006, 49, 6742-6759.
    • (2006) J. Med. Chem. , vol.49 , pp. 6742-6759
    • Chan, K.F.1    Zhao, Y.2    Burkett, B.A.3    Wong, I.L.4    Chow, L.M.5    Chan, T.H.6
  • 28
    • 65549092069 scopus 로고    scopus 로고
    • Flavonoid dimers as bivalent modulators for p-glycoprotein-based multidrug resistance: Structure-activity relationships
    • Chan, K.F.; Zhao, Y.; Chow, T.W.; Yan, C.S.; Ma, D.L.; Burkett, B.A.; Wong, I.L.; Chow, L.M.; Chan, T.H. Flavonoid dimers as bivalent modulators for p-glycoprotein-based multidrug resistance: Structure-activity relationships. ChemMedChem 2009, 4, 594-614.
    • (2009) ChemMedChem , vol.4 , pp. 594-614
    • Chan, K.F.1    Zhao, Y.2    Chow, T.W.3    Yan, C.S.4    Ma, D.L.5    Burkett, B.A.6    Wong, I.L.7    Chow, L.M.8    Chan, T.H.9
  • 29
    • 69949099322 scopus 로고    scopus 로고
    • Modulation of multidrug resistance protein 1 (MRP1/ABCC1)-mediated multidrug resistance by bivalent apigenin homodimers and their derivatives
    • Wong, I.L.; Chan, K.F.; Tsang, K.H.; Lam, C.Y.; Zhao, Y.; Chan, T.H.; Chow, L.M. Modulation of multidrug resistance protein 1 (MRP1/ABCC1)-mediated multidrug resistance by bivalent apigenin homodimers and their derivatives. J. Med. Chem. 2009, 52, 5311-5322.
    • (2009) J. Med. Chem. , vol.52 , pp. 5311-5322
    • Wong, I.L.1    Chan, K.F.2    Tsang, K.H.3    Lam, C.Y.4    Zhao, Y.5    Chan, T.H.6    Chow, L.M.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.