메뉴 건너뛰기




Volumn 12, Issue 3, 2014, Pages 1335-1348

Cyclic marinopyrrole derivatives as disruptors of Mcl-1 and Bcl-xl binding to Bim

Author keywords

Apoptosis; Cyclic marinopyrroles; Protein protein interaction disruptors; SAR

Indexed keywords

3 HYDROXY 4 (2,3,7 TRICHLORO 13 OXO 10 (DIETHYLPHOSPHONYL) 1,13 DIHYDROBENZO[G]DIPYRROLO[2,1 B: 3',2' D][1,3]OXAZOCINE 5 CARBONYL)DIETHYL PHOSPHONATE; 3 HYDROXY 4 (2,3,7 TRICHLORO 13 OXO 10 PHOSPHORYL 1,13 DIHYDROBENZO[G]DIPYRROLO[2,1 B:3',2' D] [1,3]OXAZOCINE 5 CARBONYL)PHOSPHONIC ACID; 3 HYDROXY 4 [2,3,7 TRICHLORO 13 OXO 10 [[(TRIFLUOROMETHYL)SULFONYL]OXY] 1,13 DIHYDROBENZO[G]DIPYRROLO[2,1 B:3',2' D][1,3]OXAZOCINE 5 CARBONYL]PHENYL TRIFLUOROMETHANESULFONATE; 5 (4 CARBOXY 2 HYDROXYBENZOYL) 2,3,7 TRICHLORO 13 OXO 1,13 DIHYDROBENZO[G]DIPYRROLO[2,1 B:3',2' D] [1,3]OXAZOCINE 10 CARBOXYLIC ACID; BIM PROTEIN; CASPASE 3; CYCLIC MARINOPYRROLE DERIVATIVE; DIMETHYL 4,4' (4,4',5,5' TETRACHLORO 1' H [1,3' BIPYRROLE] 2,2' DICARBONYL)BIS(3 HYDROXYBENZOATE); MARINOPYRROLE A; METHYL 2,3,7 TRICHLORO 5 [2 HYDROXY 4 (METHOXYCARBONYL)BENZOYL] 13 OXO 1,13 DIHYDROBENZO[G]DIPYRROLO[2,1 B:3',2' D][1,3]OXAZOCINE 10 CARBOXYLATE; PROTEIN BCL XL; PROTEIN MCL 1; PYRROLE DERIVATIVE; TETRAETHYL[(4,4',5,5' TETRACHLORO 1' H [1,3' BIPYRROLE] 2,2' DICARBONYL)BIS(3 HYDROXY 4,1 PHENYLENE)]BIS(PHOSPHONATE); UNCLASSIFIED DRUG; [(4,4',5,5' TETRACHLORO 1' H [1,3' BIPYRROLE] 2,2' DICARBONYL)BIS(3 HYDROXY 4,1 PHENYLENE)]DIPHOSPHONIC ACID;

EID: 84897047031     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12031335     Document Type: Article
Times cited : (17)

References (22)
  • 1
    • 39749179651 scopus 로고    scopus 로고
    • The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp
    • Hughes, C.C.; Prieto-Davo, A.; Jensen, P.R.; Fenical, W. The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp. Org. Lett. 2008, 10, 629-631.
    • (2008) Org. Lett. , vol.10 , pp. 629-631
    • Hughes, C.C.1    Prieto-Davo, A.2    Jensen, P.R.3    Fenical, W.4
  • 2
    • 77952515063 scopus 로고    scopus 로고
    • Structures, reactivities, and antibiotic properties of the marinopyrroles A-F
    • Hughes, C.C.; Kauffman, C.A.; Jensen, P.R.; Fenical, W. Structures, reactivities, and antibiotic properties of the marinopyrroles A-F. J. Org. Chem. 2010, 75, 3240-3250.
    • (2010) J. Org. Chem. , vol.75 , pp. 3240-3250
    • Hughes, C.C.1    Kauffman, C.A.2    Jensen, P.R.3    Fenical, W.4
  • 3
    • 77954556076 scopus 로고    scopus 로고
    • Total synthesis of (±)-marinopyrrole A and its library as potential antibiotic and anticancer agents
    • Cheng, C.; Pan, L.; Chen, Y.; Song, H.; Qin, Y.; Li, R. Total synthesis of (±)-marinopyrrole A and its library as potential antibiotic and anticancer agents. J. Comb. Chem. 2010, 12, 541-547.
    • (2010) J. Comb. Chem. , vol.12 , pp. 541-547
    • Cheng, C.1    Pan, L.2    Chen, Y.3    Song, H.4    Qin, Y.5    Li, R.6
  • 4
    • 78049519082 scopus 로고    scopus 로고
    • Total synthesis of (±)-marinopyrrole A via copper-mediated N-arylation
    • Kanakis, A.A.; Sarli, V. Total synthesis of (±)-marinopyrrole A via copper-mediated N-arylation. Org. Lett. 2010, 12, 4872-4875.
    • (2010) Org. Lett. , vol.12 , pp. 4872-4875
    • Kanakis, A.A.1    Sarli, V.2
  • 5
    • 79953208943 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of marinopyrrole A and analogues
    • Nicolaou, K.C.; Simmons, N.L.; Chen, J.S.; Haste, N.M.; Nizet, V. Total synthesis and biological evaluation of marinopyrrole A and analogues. Tetrahedron Lett. 2011, 52, 2041-2043.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 2041-2043
    • Nicolaou, K.C.1    Simmons, N.L.2    Chen, J.S.3    Haste, N.M.4    Nizet, V.5
  • 6
    • 84860604664 scopus 로고    scopus 로고
    • Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus
    • I
    • Liu, Y.; Haste, N.M.; Thienphrapa, W.; Nizet, V.; Hensler, M.; Li, R. Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus (I). Mar. Drugs 2012, 10, 953-962.
    • (2012) Mar. Drugs , vol.10 , pp. 953-962
    • Liu, Y.1    Haste, N.M.2    Thienphrapa, W.3    Nizet, V.4    Hensler, M.5    Li, R.6
  • 7
    • 84865642446 scopus 로고    scopus 로고
    • Optimization of synthetic method of marinopyrrole A derivatives
    • Pan, L.; Cheng, C.; Song, H. Optimization of synthetic method of marinopyrrole A derivatives. Chem. J. Chin. Univ. 2012, 33, 1476-1480.
    • (2012) Chem. J. Chin. Univ. , vol.33 , pp. 1476-1480
    • Pan, L.1    Cheng, C.2    Song, H.3
  • 8
    • 84864454017 scopus 로고    scopus 로고
    • Flavoenzyme-catalyzed atropo-selective N,C-bipyrrole homocoupling in marinopyrrole biosynthesis
    • Yamanaka, K.; Ryan, K.S.; Gulder, T.A.; Hughes, C.C.; Moore, B.S. Flavoenzyme-catalyzed atropo-selective N,C-bipyrrole homocoupling in marinopyrrole biosynthesis. J. Am. Chem. Soc. 2012, 134, 12434-12437.
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 12434-12437
    • Yamanaka, K.1    Ryan, K.S.2    Gulder, T.A.3    Hughes, C.C.4    Moore, B.S.5
  • 10
    • 84877761799 scopus 로고    scopus 로고
    • The marinopyrroles
    • Clive, D.L.J.; Cheng, P. The marinopyrroles. Tetrahedron 2013, 69, 5067-5078.
    • (2013) Tetrahedron , vol.69 , pp. 5067-5078
    • Clive, D.L.J.1    Cheng, P.2
  • 11
    • 84883802768 scopus 로고    scopus 로고
    • Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus
    • II
    • Cheng, C.; Liu, Y.; Song, H.; Pan, L.; Li, J.; Qin, Y.; Li, R. Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus (II). Mar. Drugs 2013, 11, 2927-2948.
    • (2013) Mar. Drugs , vol.11 , pp. 2927-2948
    • Cheng, C.1    Liu, Y.2    Song, H.3    Pan, L.4    Li, J.5    Qin, Y.6    Li, R.7
  • 12
    • 84858957737 scopus 로고    scopus 로고
    • Discovery of marinopyrrole A (Maritoclax) as a selective Mcl-1 antagonist that overcomes ABT-737 resistance by binding to and targeting Mcl-1 for proteasomal degradation
    • Doi, K.; Li, R.; Sung, S.S.; Wu, H.; Liu, Y.; Manieri, W.; Krishnegowda, G.; Awwad, A.; Dewey, A.; Liu, X.; et al. Discovery of marinopyrrole A (Maritoclax) as a selective Mcl-1 antagonist that overcomes ABT-737 resistance by binding to and targeting Mcl-1 for proteasomal degradation. J. Biol. Chem. 2012, 287, 10224-10235.
    • (2012) J. Biol. Chem. , vol.287 , pp. 10224-10235
    • Doi, K.1    Li, R.2    Sung, S.S.3    Wu, H.4    Liu, Y.5    Manieri, W.6    Krishnegowda, G.7    Awwad, A.8    Dewey, A.9    Liu, X.10
  • 14
    • 33845984909 scopus 로고    scopus 로고
    • Catalytic diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups
    • Uyanik, M.; Ishihara, K.; Yamamoto, H. Catalytic diastereoselective polycyclization of homo(polyprenyl)arene analogues bearing terminal siloxyvinyl groups. Org. Lett. 2006, 8, 5649-5652.
    • (2006) Org. Lett. , vol.8 , pp. 5649-5652
    • Uyanik, M.1    Ishihara, K.2    Yamamoto, H.3
  • 16
    • 0001761056 scopus 로고
    • Palladium-catalyzed substituions of triflates derivaed from tyrosine-containing peptides and simpler hydroxyarenens forming 4-(diethoxyphosphinyl) phenylalanines and diethyl aryphosphonates
    • Petrakis, K.S.; Nagabhushan, T.L. Palladium-catalyzed substituions of triflates derivaed from tyrosine-containing peptides and simpler hydroxyarenens forming 4-(diethoxyphosphinyl) phenylalanines and diethyl aryphosphonates. J. Am. Chem. Soc. 1987, 109, 2831-2833.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2831-2833
    • Petrakis, K.S.1    Nagabhushan, T.L.2
  • 17
    • 11744331329 scopus 로고
    • Estimation of pKa for organic oxyacids using calculated atomic charge
    • Dixon, S.L.; Jurs, P.C. Estimation of pKa for organic oxyacids using calculated atomic charge. J. Comp. Chem. 1993, 14, 1460-1467.
    • (1993) J. Comp. Chem. , vol.14 , pp. 1460-1467
    • Dixon, S.L.1    Jurs, P.C.2
  • 20
    • 77949799227 scopus 로고    scopus 로고
    • Intramolecular hydrogen bonding in medicinal chemistry
    • Kuhn, B.; Mohr, P.; Stahl, M. Intramolecular hydrogen bonding in medicinal chemistry. J. Med. Chem. 2010, 53, 2601-2611.
    • (2010) J. Med. Chem. , vol.53 , pp. 2601-2611
    • Kuhn, B.1    Mohr, P.2    Stahl, M.3
  • 21
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(00)00129-0, PII S0169409X00001290
    • Lipinski, C.A.; Lombardo, F.; Dominy, B.W.; Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Rev. 2001, 46, 3-26. (Pubitemid 33653411)
    • (2000) Advanced Drug Delivery Reviews , vol.46 , Issue.1-3 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 22
    • 79955504184 scopus 로고    scopus 로고
    • Combination of farnesyltransferase and Akt inhibitors is synergistic in breast cancer cells and causes significant breast tumor regression in ErbB2 transgenic mice
    • Balasis, M.E.; Forinash, K.D.; Chen, Y.A.; Fulp, W.J.; Coppola, D.; Hamilton, A.D.; Cheng, J.Q.; Sebti, S.M. Combination of farnesyltransferase and Akt inhibitors is synergistic in breast cancer cells and causes significant breast tumor regression in ErbB2 transgenic mice. Clin. Cancer Res. 2011, 17, 2852-2862.
    • (2011) Clin. Cancer Res. , vol.17 , pp. 2852-2862
    • Balasis, M.E.1    Forinash, K.D.2    Chen, Y.A.3    Fulp, W.J.4    Coppola, D.5    Hamilton, A.D.6    Cheng, J.Q.7    Sebti, S.M.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.