메뉴 건너뛰기




Volumn 80, Issue , 2014, Pages 605-620

Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus

Author keywords

Aminoglycoside potentiation; Antibiotic; Small colony variants; Staphylococcus aureus; Steroid alkaloid; Structure activity relationship; Tomatidine

Indexed keywords

26 ACETYLAMINO 3BETA HYDROXY 5A FUROST 20(22) ENE; 26 ACETYLAMINO 3BETA HYDROXY 5A FUROSTANE; 26 ACETYLAMINO 3BETA,16BETA DIACETOXY 22 HYDROXY 5A CHOLESTANE; 26 ACETYLAMINO 3BETA,16BETA DIACETOXY 5A CHOLEST 22 ONE; 26 ACETYLAMINO 3BETA,16BETA,20 TRIHYDROXY 5A CHOLESTANE; 26 AMINO 3BETA ,16BETA DIHYDROXY 5A CHOLESTANO 22,26 PIPERIDINE; 26 AMINO 3BETA,16BETA ACETOXY N ACETYL 5A CHOLEST 22 ENO 22,26 PIPERIDINE; 3 (N AMINOBUTYL) AMINOTOMATIDINE HYDROCHLORIDE; 3 (N AMINOETHYL) AMINOTOMATIDINE HYDROCHLORIDE; 3 (N AMINOHEXYL) AMINOTOMATIDINE HYDROCHLORIDE; 3 ALPHA ACETOXY N FORMYL TOMATIDINE; 3 ALPHA HYDROXYTOMATIDINE HYDROCHLORIDE; 3 AMINOTOMATIDINE HYDROCHLORIDE; 3 BETA ALLYLOXY N FORMYLTOMATIDINE; 3 BETA ALLYLOXYTOMATIDINE HYDROCHLORIDE; 3 OXOTOMATIDINE HYDROCHLORIDE; 3ALPHA ACETOXY N ACETYLTOMATIDINE; 3BETA ACETOXY 27 ACETYLAMINO 5A FUROST 20(22) ENE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; GENTAMICIN; N FORMYL 3 (AMINOHEXYL)AMINOTOMATIDINE; N FORMYL 3 (N BOC AMINOBUTYL)AMINOTOMATIDINE; N FORMYL 3 (N BOC AMINOETHYL)AMINOTOMATIDINE; N FORMYL 3 AMINOTOMATIDINE; N FORMYL 3 OXOTOMATIDINE; N FORMYLTOMATIDINE; PIPERIDINE DERIVATIVE; PLANT EXTRACT; TOMATIDINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIINFECTIVE AGENT; TOMATINE;

EID: 84901917714     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.11.019     Document Type: Article
Times cited : (39)

References (51)
  • 1
    • 33144473431 scopus 로고    scopus 로고
    • Bad bugs need drugs: An update on the development pipeline from the Antimicrobial Availability Task Force of the Infectious Diseases Society of America
    • G.H. Talbot, J. Bradley, J.E. Edwards Jr., D. Gilbert, M. Scheld, and J.G. Bartlett Bad bugs need drugs: an update on the development pipeline from the Antimicrobial Availability Task Force of the Infectious Diseases Society of America Clin. Infect. Dis. 42 2006 657 668 (Pubitemid 43271379)
    • (2006) Clinical Infectious Diseases , vol.42 , Issue.5 , pp. 657-668
    • Talbot, G.H.1    Bradley, J.2    Edwards Jr., J.E.3    Gilbert, D.4    Scheid, M.5    Bartlett, J.G.6
  • 3
    • 79953710021 scopus 로고    scopus 로고
    • Novel classes of antibiotics or more of the same?
    • A.R. Coates, G. Halls, and Y. Hu Novel classes of antibiotics or more of the same? Br. J. Pharmacol. 163 2011 184 194
    • (2011) Br. J. Pharmacol. , vol.163 , pp. 184-194
    • Coates, A.R.1    Halls, G.2    Hu, Y.3
  • 4
    • 78751477224 scopus 로고    scopus 로고
    • Challenges of antibacterial discovery
    • L.L. Silver Challenges of antibacterial discovery Clin. Microbiol. Rev. 24 2011 71 109
    • (2011) Clin. Microbiol. Rev. , vol.24 , pp. 71-109
    • Silver, L.L.1
  • 5
    • 40449119374 scopus 로고    scopus 로고
    • New and emerging treatment of Staphylococcus aureus infections in the hospital setting
    • P. Moreillon New and emerging treatment of Staphylococcus aureus infections in the hospital setting Clin. Microbiol. Infect. 14 Suppl. 3 2008 32 41
    • (2008) Clin. Microbiol. Infect. , vol.14 , Issue.SUPPL. 3 , pp. 32-41
    • Moreillon, P.1
  • 6
    • 33845321413 scopus 로고    scopus 로고
    • The emergence of antibiotic resistance by mutation
    • DOI 10.1111/j.1469-0691.2006.01492.x
    • N. Woodford, and M.J. Ellington The emergence of antibiotic resistance by mutation Clin. Microbiol. Infect. 13 2007 5 18 (Pubitemid 44869202)
    • (2007) Clinical Microbiology and Infection , vol.13 , Issue.1 , pp. 5-18
    • Woodford, N.1    Ellington, M.J.2
  • 7
    • 0038665502 scopus 로고    scopus 로고
    • Antimicrobial resistance: The example of Staphylococcus aureus
    • DOI 10.1172/JCI200318535
    • F.D. Lowy Antimicrobial resistance: the example of Staphylococcus aureus J. Clin. Invest. 111 2003 1265 1273 (Pubitemid 36554694)
    • (2003) Journal of Clinical Investigation , vol.111 , Issue.9 , pp. 1265-1273
    • Lowy, F.D.1
  • 9
    • 0036834373 scopus 로고    scopus 로고
    • The future challenges facing the development of new antimicrobial drugs
    • DOI 10.1038/nrd940
    • A. Coates, Y. Hu, R. Bax, and C. Page The future challenges facing the development of new antimicrobial drugs Nat. Rev. Drug Discov. 1 2002 895 910 (Pubitemid 37361584)
    • (2002) Nature Reviews Drug Discovery , vol.1 , Issue.11 , pp. 895-910
    • Coates, A.1    Hu, Y.2    Bax, R.3    Page, C.4
  • 11
    • 70350292185 scopus 로고    scopus 로고
    • VanA-type vancomycin-resistant Staphylococcus aureus
    • B. Perichon, and P. Courvalin VanA-type vancomycin-resistant Staphylococcus aureus Antimicrob. Agents Chemother. 53 2009 4580 4587
    • (2009) Antimicrob. Agents Chemother. , vol.53 , pp. 4580-4587
    • Perichon, B.1    Courvalin, P.2
  • 14
    • 79955532603 scopus 로고    scopus 로고
    • Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells
    • G. Mitchell, M. Gattuso, G. Grondin, E. Marsault, K. Bouarab, and F. Malouin Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells Antimicrob. Agents Chemother. 55 2011 1937 1945
    • (2011) Antimicrob. Agents Chemother. , vol.55 , pp. 1937-1945
    • Mitchell, G.1    Gattuso, M.2    Grondin, G.3    Marsault, E.4    Bouarab, K.5    Malouin, F.6
  • 15
    • 84878098314 scopus 로고    scopus 로고
    • Persistent bacterial infections, antibiotic tolerance, and the oxidative stress response
    • S.S. Grant, and D.T. Hung Persistent bacterial infections, antibiotic tolerance, and the oxidative stress response Virulence 4 2013
    • (2013) Virulence , vol.4
    • Grant, S.S.1    Hung, D.T.2
  • 16
    • 77249165047 scopus 로고    scopus 로고
    • Staphylococcus aureus sigma B-dependent emergence of small-colony variants and biofilm production following exposure to Pseudomonas aeruginosa 4-hydroxy-2-heptylquinoline-N-oxide
    • G. Mitchell, D.L. Seguin, A.E. Asselin, E. Deziel, A.M. Cantin, E.H. Frost, S. Michaud, and F. Malouin Staphylococcus aureus sigma B-dependent emergence of small-colony variants and biofilm production following exposure to Pseudomonas aeruginosa 4-hydroxy-2-heptylquinoline-N-oxide BMC Microbiol. 10 2010 33
    • (2010) BMC Microbiol. , vol.10 , pp. 33
    • Mitchell, G.1    Seguin, D.L.2    Asselin, A.E.3    Deziel, E.4    Cantin, A.M.5    Frost, E.H.6    Michaud, S.7    Malouin, F.8
  • 17
    • 0034017033 scopus 로고    scopus 로고
    • Staphylococcus aureus small colony variants, electron transport and persistent infections
    • DOI 10.1016/S0924-8579(99)00170-3, PII S0924857999001703
    • P.J. McNamara, and R.A. Proctor Staphylococcus aureus small colony variants, electron transport and persistent infections Int. J. Antimicrob. Agents 14 2000 117 122 (Pubitemid 30138178)
    • (2000) International Journal of Antimicrobial Agents , vol.14 , Issue.2 , pp. 117-122
    • McNamara, P.J.1    Proctor, R.A.2
  • 18
    • 84877046974 scopus 로고    scopus 로고
    • Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression
    • K.H. Yan, L.M. Lee, S.H. Yan, H.C. Huang, C.C. Li, H.T. Lin, and P.S. Chen Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression Chem.-Biol. Interact. 203 2013 580 587
    • (2013) Chem.-Biol. Interact. , vol.203 , pp. 580-587
    • Yan, K.H.1    Lee, L.M.2    Yan, S.H.3    Huang, H.C.4    Li, C.C.5    Lin, H.T.6    Chen, P.S.7
  • 19
    • 84859902902 scopus 로고    scopus 로고
    • Structure-activity relationships of α-, β(1)-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells
    • S.H. Choi, J.B. Ahn, N. Kozukue, H.J. Kim, Y. Nishitani, L. Zhang, M. Mizuno, C.E. Levin, and M. Friedman Structure-activity relationships of α-, β(1)-, γ-, and δ-tomatine and tomatidine against human breast (MDA-MB-231), gastric (KATO-III), and prostate (PC3) cancer cells J. Agric. Food Chem. 60 2012 3891 3899
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 3891-3899
    • Choi, S.H.1    Ahn, J.B.2    Kozukue, N.3    Kim, H.J.4    Nishitani, Y.5    Zhang, L.6    Mizuno, M.7    Levin, C.E.8    Friedman, M.9
  • 20
    • 67649863290 scopus 로고    scopus 로고
    • Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells
    • M. Friedman, C.E. Levin, S.U. Lee, H.J. Kim, I.S. Lee, J.O. Byun, and N. Kozukue Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells J. Agric. Food Chem. 57 2009 5727 5733
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 5727-5733
    • Friedman, M.1    Levin, C.E.2    Lee, S.U.3    Kim, H.J.4    Lee, I.S.5    Byun, J.O.6    Kozukue, N.7
  • 22
    • 0035015140 scopus 로고    scopus 로고
    • Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells
    • Y. Lavie, T. Harel-Orbital, W. Gaffield, and M. Liscovitch Inhibitory effect of steroidal alkaloids on drug transport and multidrug resistance in human cancer cells Anticancer Res. 21 2001 1189 1194 (Pubitemid 32494229)
    • (2001) Anticancer Research , vol.21 , Issue.2 , pp. 1189-1194
    • Lavie, Y.1    Harel-Orbital, T.2    Gaffield, W.3    Liscovitch, M.4
  • 23
    • 84866072591 scopus 로고    scopus 로고
    • Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes
    • J.M. Medina, J.C.F. Rodrigues, W. De Souza, G.C. Atella, and H. Barrabin Tomatidine promotes the inhibition of 24-alkylated sterol biosynthesis and mitochondrial dysfunction in Leishmania amazonensis promastigotes Parasitology 139 2012 1253 1265
    • (2012) Parasitology , vol.139 , pp. 1253-1265
    • Medina, J.M.1    Rodrigues, J.C.F.2    De Souza, W.3    Atella, G.C.4    Barrabin, H.5
  • 24
    • 84858311207 scopus 로고    scopus 로고
    • Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT)
    • Y. Fujiwara, N. Kiyota, K. Tsurushima, M. Yoshitomi, H. Horlad, T. Ikeda, T. Nohara, M. Takeya, and R. Nagai Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT) J. Agric. Food Chem. 60 2012 2472 2479
    • (2012) J. Agric. Food Chem. , vol.60 , pp. 2472-2479
    • Fujiwara, Y.1    Kiyota, N.2    Tsurushima, K.3    Yoshitomi, M.4    Horlad, H.5    Ikeda, T.6    Nohara, T.7    Takeya, M.8    Nagai, R.9
  • 25
    • 45549098626 scopus 로고    scopus 로고
    • Tomatidine inhibits iNOS and COX-2 through suppression of NF-κB and JNK pathways in LPS-stimulated mouse macrophages
    • F.L. Chiu, and J.K. Lin Tomatidine inhibits iNOS and COX-2 through suppression of NF-κB and JNK pathways in LPS-stimulated mouse macrophages FEBS Lett. 582 2008 2407 2412
    • (2008) FEBS Lett. , vol.582 , pp. 2407-2412
    • Chiu, F.L.1    Lin, J.K.2
  • 27
    • 67650732735 scopus 로고    scopus 로고
    • Role of persisters and small-colony variants in antibiotic resistance of planktonic and biofilm-associated Staphylococcus aureus: An in vitro study
    • R. Singh, P. Ray, A. Das, and M. Sharma Role of persisters and small-colony variants in antibiotic resistance of planktonic and biofilm-associated Staphylococcus aureus: an in vitro study J. Med. Microbiol. 58 2009 1067 1073
    • (2009) J. Med. Microbiol. , vol.58 , pp. 1067-1073
    • Singh, R.1    Ray, P.2    Das, A.3    Sharma, M.4
  • 29
    • 84982060686 scopus 로고
    • Solanum-alkaloide, XXIII1). Synthese von Solanum-alkaloiden aus 16β-hydroxy-pregnan-derivaten
    • K. Schreiber, and G. Adam Solanum-alkaloide, XXIII1). Synthese von Solanum-alkaloiden aus 16β-hydroxy-pregnan-derivaten Justus Liebigs Ann. Chem. 666 1963 155 176
    • (1963) Justus Liebigs Ann. Chem. , vol.666 , pp. 155-176
    • Schreiber, K.1    Adam, G.2
  • 32
    • 0001106559 scopus 로고
    • The use of N-formylamino acids in peptide synthesis
    • J.C. Sheehan, and D.-D.H. Yang The use of N-formylamino acids in peptide synthesis J. Am. Chem. Soc. 80 1958 1154 1158
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 1154-1158
    • Sheehan, J.C.1    Yang, D.-D.H.2
  • 33
    • 0003060427 scopus 로고
    • Enantio-controlled synthesis of the AB ring moiety of ciguatoxin
    • H. Oguri, S. Hishiyama, T. Oishi, and M. Hirama Enantio-controlled synthesis of the AB ring moiety of ciguatoxin Synlett 1995 1995 1252 1254
    • (1995) Synlett , vol.1995 , pp. 1252-1254
    • Oguri, H.1    Hishiyama, S.2    Oishi, T.3    Hirama, M.4
  • 34
    • 33644528891 scopus 로고
    • Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • D.B. Dess, and J.C. Martin Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones J. Org. Chem. 48 1983 4155 4156
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
    • Dess, D.B.1    Martin, J.C.2
  • 35
    • 80052920611 scopus 로고    scopus 로고
    • Synthesis, characterization and biological evaluation of some 16β-azolyl-3β-amino-5α-androstane derivatives as potential anticancer agents
    • H. Guo, G. Zhang, T. Zhang, X. He, Z. Wu, Y. Xiao, Y. Pan, G. Qiu, P. Liu, and X. Hu Synthesis, characterization and biological evaluation of some 16β-azolyl-3β-amino-5α-androstane derivatives as potential anticancer agents Eur. J. Med. Chem. 46 2011 3662 3674
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 3662-3674
    • Guo, H.1    Zhang, G.2    Zhang, T.3    He, X.4    Wu, Z.5    Xiao, Y.6    Pan, Y.7    Qiu, G.8    Liu, P.9    Hu, X.10
  • 37
    • 33846675725 scopus 로고
    • The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. I. Improved preparation of 3β-acetoxy-5,16-pregnadien-20-one and 3β-acetoxy-5α-pregn-16-en-20-one from solasodine and tomatidine
    • Y. Sato, N. Ikekawa, and E. Mosettig The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. I. Improved preparation of 3β-acetoxy-5,16-pregnadien-20-one and 3β-acetoxy-5α-pregn-16-en- 20-one from solasodine and tomatidine J. Org. Chem. 25 1960 783 786
    • (1960) J. Org. Chem. , vol.25 , pp. 783-786
    • Sato, Y.1    Ikekawa, N.2    Mosettig, E.3
  • 38
    • 19944403642 scopus 로고
    • The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. II. Chemistry of 3β, 16β-diacetoxy-20-(2′-D2′- N-acetyl-5′-methyltetrahydropyridyl)-5-pregnene
    • Y. Sato, and N. Ikekawa The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. II. Chemistry of 3β, 16β-diacetoxy-20- (2′-D2′-N-acetyl-5′-methyltetrahydropyridyl)-5-pregnene J. Org. Chem. 25 1960 786 789
    • (1960) J. Org. Chem. , vol.25 , pp. 786-789
    • Sato, Y.1    Ikekawa, N.2
  • 39
    • 19944388652 scopus 로고
    • The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. III. The reaction of O,N-diacetylsolasodine in acidic media
    • Y. Sato, and N. Ikekawa The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. III. The reaction of O,N-diacetylsolasodine in acidic media J. Org. Chem. 25 1960 789 791
    • (1960) J. Org. Chem. , vol.25 , pp. 789-791
    • Sato, Y.1    Ikekawa, N.2
  • 40
    • 10244270117 scopus 로고
    • 17-Keto-17α-methyl-d-homosteroids from 17α-hydroxy-20-amino C21 steroids, stereochemistry of d-homoannulation
    • F. Ramirez, and S. Stafiej 17-Keto-17α-methyl-d-homosteroids from 17α-hydroxy-20-amino C21 steroids, stereochemistry of d-homoannulation J. Am. Chem. Soc. 77 1955 134 138
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 134-138
    • Ramirez, F.1    Stafiej, S.2
  • 42
    • 37049106008 scopus 로고
    • 18-Substituted steroids. Part 7. Synthesis and structure of 11β,18-epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one (3α,5β-tetrahydroaldosterone)
    • D.N. Kirk, and B.W. Miller 18-Substituted steroids. Part 7. Synthesis and structure of 11β,18-epoxy-3α,18,21-trihydroxy-5β-pregnan-20-one (3α,5β-tetrahydroaldosterone) J. Chem. Soc. Perkin Trans. 1 1980 2818
    • (1980) J. Chem. Soc. Perkin Trans. 1 , pp. 2818
    • Kirk, D.N.1    Miller, B.W.2
  • 44
    • 33747038108 scopus 로고    scopus 로고
    • An efficient and convenient method for synthesis of 1-substituted imidazoles
    • C. Min Lin, F. Fuh Wong, J.-J. Huang, and M.-Y. Yeh An efficient and convenient method for synthesis of 1-substituted imidazoles Heterocycles 68 2006 1359
    • (2006) Heterocycles , vol.68 , pp. 1359
    • Min Lin, C.1    Fuh Wong, F.2    Huang, J.-J.3    Yeh, M.-Y.4
  • 45
    • 37049165884 scopus 로고
    • Studies in the synthesis of cortisone. Part VII. The preparation of 3β: 17α-dihydroxyallopregnane-11: 20-dione
    • D.H.R. Barton, R.M. Evans, J.C. Hamlet, P.G. Jones, and T. Walker Studies in the synthesis of cortisone. Part VII. The preparation of 3β: 17α-dihydroxyallopregnane-11: 20-dione J. Chem. Soc. (Resumed) 1954 747
    • (1954) J. Chem. Soc. (Resumed) , pp. 747
    • Barton, D.H.R.1    Evans, R.M.2    Hamlet, J.C.3    Jones, P.G.4    Walker, T.5
  • 46
    • 33947456851 scopus 로고
    • The Wohl-Ziegler bromination of enol acetates of 20-keto steroids
    • C. Djerassi, and C.R. Scholz The Wohl-Ziegler bromination of enol acetates of 20-keto steroids J. Org. Chem. 14 1949 660 663
    • (1949) J. Org. Chem. , vol.14 , pp. 660-663
    • Djerassi, C.1    Scholz, C.R.2
  • 47
    • 79952126782 scopus 로고    scopus 로고
    • Synthesis of the antiproliferative agent hippuristanol and its analogues via Suarez cyclizations and Hg(II)-catalyzed spiroketalizations
    • K. Ravindar, M.S. Reddy, L. Lindqvist, J. Pelletier, and P. Deslongchamps Synthesis of the antiproliferative agent hippuristanol and its analogues via Suarez cyclizations and Hg(II)-catalyzed spiroketalizations J. Org. Chem. 76 2011 1269 1284
    • (2011) J. Org. Chem. , vol.76 , pp. 1269-1284
    • Ravindar, K.1    Reddy, M.S.2    Lindqvist, L.3    Pelletier, J.4    Deslongchamps, P.5
  • 48
    • 0038601510 scopus 로고    scopus 로고
    • Synergy, antagonism, and what the chequerboard puts between them
    • F.C. Odds Synergy, antagonism, and what the chequerboard puts between them J. Antimicrob. Chemother. 52 2003 1 (Pubitemid 36850074)
    • (2003) Journal of Antimicrobial Chemotherapy , vol.52 , Issue.1 , pp. 1
    • Odds, F.C.1
  • 49
    • 16544372671 scopus 로고    scopus 로고
    • Persistence of a Staphylococcus aureus small-colony variant under antibiotic pressure in vivo
    • DOI 10.1016/j.femsim.2003.12.007, PII S0928824404000215
    • E. Brouillette, A. Martinez, B.J. Boyll, N.E. Allen, and F. Malouin Persistence of a Staphylococcus aureus small-colony variant under antibiotic pressure in vivo FEMS Immunol. Med. Microbiol. 41 2004 35 41 (Pubitemid 38501580)
    • (2004) FEMS Immunology and Medical Microbiology , vol.41 , Issue.1 , pp. 35-41
    • Brouillette, E.1    Martinez, A.2    Boyll, B.J.3    Allen, N.E.4    Malouin, F.5
  • 50
    • 85047696497 scopus 로고    scopus 로고
    • Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water
    • DOI 10.1002/1521-3765(20020315)8: 6<1300::AID-CHEM1300>3.0.CO;2-W
    • K.B. Jensen, T.M. Braxmeier, M. Demarcus, J.G. Frey, and J.D. Kilburn Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water Chem. Eur. J. 8 2002 1300 1309 (Pubitemid 34259552)
    • (2002) Chemistry - A European Journal , vol.8 , Issue.6 , pp. 1300-1309
    • Jensen, K.B.1    Braxmeier, T.M.2    Demarcus, M.3    Frey, J.G.4    Kilburn, J.D.5
  • 51
    • 0034999411 scopus 로고    scopus 로고
    • Structure - Activity relationship of Aza-steroids as PI-PLC inhibitors
    • DOI 10.1016/S0968-0896(00)00302-3, PII S0968089600003023
    • W. Xie, H. Peng, D.-I. Kim, M. Kunkel, G. Powis, and L.H. Zalkow Structure-activity relationship of aza-steroids as PI-PLC inhibitors Bioorg. Med. Chem. 9 2001 1073 1083 (Pubitemid 32453267)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.5 , pp. 1073-1083
    • Xie, W.1    Peng, H.2    Kim, D.-I.3    Kunkel, M.4    Powis, G.5    Zalkow, L.H.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.