메뉴 건너뛰기




Volumn 8, Issue 4, 2011, Pages 1073-1082

Effect of structural modification of α-aminoxy peptides on their intestinal absorption and transport mechanism

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATASE; ALPHA AMINOXY PEPTIDE; BREAST CANCER RESISTANCE PROTEIN; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN; PEPTIDOMIMETIC AGENT; PROPIONIC ACID; UNCLASSIFIED DRUG;

EID: 79961056417     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp1003866     Document Type: Article
Times cited : (10)

References (39)
  • 1
    • 34247362490 scopus 로고    scopus 로고
    • Foldamers as versatile frameworks for the design and evolution of function
    • DOI 10.1038/nchembio876, PII NCHEMBIO876
    • Goodman, C. M.; Choi, S.; Shandler, S.; DeGrado, W. F. Foldamers as versatile frameworks for the design and evolution of function Nat. Chem. Biol. 2007, 3, 252-262 (Pubitemid 46628637)
    • (2007) Nature Chemical Biology , vol.3 , Issue.5 , pp. 252-262
    • Goodman, C.M.1    Choi, S.2    Shandler, S.3    DeGrado, W.F.4
  • 3
    • 57349199922 scopus 로고    scopus 로고
    • Alpha-aminoxy acids: New possibilities from foldamers to anion receptors and channels
    • Li, X.; Wu, Y. D.; Yang, D. Alpha-aminoxy acids: new possibilities from foldamers to anion receptors and channels Acc. Chem. Res. 2008, 41, 1428-1438
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1428-1438
    • Li, X.1    Wu, Y.D.2    Yang, D.3
  • 5
    • 0035382627 scopus 로고    scopus 로고
    • The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: An in vitro investigation with fifteen peptidases
    • Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. The outstanding biological stability of beta- and gamma-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases ChemBioChem 2001, 2, 445-455 (Pubitemid 33723576)
    • (2001) ChemBioChem , vol.2 , Issue.6 , pp. 445-455
    • Frackenpohl, J.1    Arvidsson, P.I.2    Schreiber, J.V.3    Seebach, D.4
  • 6
    • 33746888291 scopus 로고    scopus 로고
    • Peptides of aminoxy acids as foldamers
    • DOI 10.1039/b602230h
    • Li, X.; Yang, D. Peptides of aminoxy acids as foldamers Chem. Commun. (Cambridge) 2006, 28, 3367-3379 (Pubitemid 44200344)
    • (2006) Chemical Communications , Issue.32 , pp. 3367-3379
    • Li, X.1    Yang, D.2
  • 7
    • 34250837547 scopus 로고    scopus 로고
    • A small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes
    • DOI 10.1021/ja071961h
    • Li, X.; Shen, B.; Yao, X. Q.; Yang, D. A Small synthetic molecule forms chloride channels to mediate chloride transport across cell membranes J. Am. Chem. Soc. 2007, 129, 7264-7265 (Pubitemid 46980799)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.23 , pp. 7264-7265
    • Li, X.1    Shen, B.2    Yao, X.-Q.3    Yang, D.4
  • 8
    • 18744373064 scopus 로고    scopus 로고
    • A cyclic hexapeptide comprising alternating α-aminoxy and α-amino acids is a selective chloride ion receptor
    • DOI 10.1002/chem.200500098
    • Yang, D.; Li, X.; Sha, Y.; Wu, Y. D. A cyclic hexapeptide comprising alternating alpha-aminoxy and alpha-amino acids is a selective chloride ion receptor Chemistry 2005, 11, 3005-3009 (Pubitemid 40672457)
    • (2005) Chemistry - A European Journal , vol.11 , Issue.10 , pp. 3005-3009
    • Yang, D.1    Li, X.2    Sha, Y.3    Wu, Y.-D.4
  • 10
    • 8444230840 scopus 로고    scopus 로고
    • Investigation of intestinal absorption and disposition of green tea catechins by Caco-2 monolayer model
    • DOI 10.1016/j.ijpharm.2004.08.020, PII S0378517304005071
    • Zhang, L.; Zheng, Y.; Chow, M. S.; Zuo, Z. Investigation of intestinal absorption and disposition of green tea catechins by Caco-2 monolayer model Int. J. Pharm. 2004, 287, 1-12 (Pubitemid 39487237)
    • (2004) International Journal of Pharmaceutics , vol.287 , Issue.1-2 , pp. 1-12
    • Zhang, L.1    Zheng, Y.2    Chow, M.S.S.3    Zuo, Z.4
  • 11
    • 0025311288 scopus 로고
    • Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells
    • DOI 10.1002/jps.2600790604
    • Artursson, P. Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells J. Pharm. Sci. 1990, 79, 476-482 (Pubitemid 20221389)
    • (1990) Journal of Pharmaceutical Sciences , vol.79 , Issue.6 , pp. 476-482
    • Artursson, P.1
  • 12
    • 0242552334 scopus 로고    scopus 로고
    • Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogenated metabolite of liquiritigenin, using human intestinal cell line Caco-2
    • DOI 10.1016/j.jep.2003.09.009
    • Asano, T.; Ishihara, K.; Morota, T.; Takeda, S.; Aburada, M. Permeability of the flavonoids liquiritigenin and its glycosides in licorice roots and davidigenin, a hydrogenated metabolite of liquiritigenin, using human intestinal cell line Caco-2 J. Ethnopharmacol. 2003, 89, 285-289 (Pubitemid 37378204)
    • (2003) Journal of Ethnopharmacology , vol.89 , Issue.2-3 , pp. 285-289
    • Asano, T.1    Ishihara, K.2    Morota, T.3    Takeda, S.4    Aburada, M.5
  • 13
    • 0025804183 scopus 로고
    • Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells
    • Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. Commun. 1991, 175, 880-885
    • (1991) Biochem. Biophys. Res. Commun. , vol.175 , pp. 880-885
    • Artursson, P.1    Karlsson, J.2
  • 14
    • 44349185775 scopus 로고    scopus 로고
    • A catenary model to study transport and conjugation of baicalein, a bioactive flavonoid, in the caco-2 cell monolayer: Demonstration of substrate inhibition
    • DOI 10.1124/jpet.108.137463
    • Sun, H.; Zhang, L.; Chow, E. C.; Lin, G.; Zuo, Z.; Pang, K. S. A catenary model to study transport and conjugation of baicalein, a bioactive flavonoid, in the Caco-2 cell monolayer: demonstration of substrate inhibition J Pharmacol Exp Ther. 2008, 326, 117-126 (Pubitemid 351872137)
    • (2008) Journal of Pharmacology and Experimental Therapeutics , vol.326 , Issue.1 , pp. 117-126
    • Sun, H.1    Zhang, L.2    Chow, E.C.Y.3    Lin, G.4    Zuo, Z.5    Pang, K.S.6
  • 15
    • 0033943453 scopus 로고    scopus 로고
    • A study of the intestinal absorption of an ester-type prodrug, ME3229, in rats: Active efflux transport as a cause of poor bioavailability of the active drug
    • Okudaira, N.; Tatebayashi, T.; Speirs, G. C.; Komiya, I.; Sugiyama, Y. A study of the intestinal absorption of an ester-type prodrug, ME3229, in rats: active efflux transport as a cause of poor bioavailability of the active drug J. Pharmacol. Exp. Ther. 2000, 294, 580-587 (Pubitemid 30490832)
    • (2000) Journal of Pharmacology and Experimental Therapeutics , vol.294 , Issue.2 , pp. 580-587
    • Okudaira, N.1    Tatebayashi, T.2    Speirs, G.C.3    Komiya, I.4    Sugiyama, Y.5
  • 16
    • 0037382316 scopus 로고    scopus 로고
    • In vivo modulation of intestinal CYP3A metabolism by P-glycoprotein: Studies using the rat single-pass intestinal perfusion model
    • DOI 10.1124/jpet.102.044719
    • Cummins, C. L.; Salphati, L.; Reid, M. J.; Benet, L. Z. In vivo modulation of intestinal CYP3A metabolism by P-glycoprotein: studies using the rat single-pass intestinal perfusion model J. Pharmacol. Exp. Ther. 2003, 305, 306-314 (Pubitemid 36373865)
    • (2003) Journal of Pharmacology and Experimental Therapeutics , vol.305 , Issue.1 , pp. 306-314
    • Cummins, C.L.1    Salphati, L.2    Reid, M.J.3    Benet, L.Z.4
  • 17
    • 23744497186 scopus 로고    scopus 로고
    • Role of intestinal first-pass metabolism of baicalein in its absorption process
    • DOI 10.1007/s11095-005-5303-7
    • Zhang, L.; Lin, G.; Chang, Q.; Zuo, Z. Role of intestinal first-pass metabolism of baicalein in its absorption process Pharm. Res. 2005, 22, 1050-1058 (Pubitemid 41127062)
    • (2005) Pharmaceutical Research , vol.22 , Issue.7 , pp. 1050-1058
    • Zhang, L.1    Lin, G.2    Chang, Q.3    Zuo, Z.4
  • 18
    • 0037416093 scopus 로고    scopus 로고
    • Intestinal permeability of chlorpyrifos using the single-pass intestinal perfusion method in the rat
    • DOI 10.1016/S0300-483X(02)00555-3, PII S0300483X02005553
    • Cook, T. J.; Shenoy, S. S. Intestinal permeability of chlorpyrifos using the single-pass intestinal perfusion method in the rat Toxicology 2003, 184, 125-133 (Pubitemid 36009294)
    • (2003) Toxicology , vol.184 , Issue.2-3 , pp. 125-133
    • Cook, T.J.1    Shenoy, S.S.2
  • 19
    • 0030990079 scopus 로고    scopus 로고
    • In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man - Fact or myth
    • DOI 10.1023/A:1012102522787
    • Yee, S. In vitro permeability across Caco-2 cells (colonic) can predict in vivo (small intestinal) absorption in man - fact or myth Pharm. Res. 1997, 14, 763-766 (Pubitemid 27281671)
    • (1997) Pharmaceutical Research , vol.14 , Issue.6 , pp. 763-766
    • Yee, S.1
  • 20
    • 34249297623 scopus 로고    scopus 로고
    • Mechanistic study on the intestinal absorption and disposition of baicalein
    • DOI 10.1016/j.ejps.2007.04.001, PII S0928098707000814
    • Zhang, L.; Lin, G.; Kovacs, B.; Jani, M.; Krajcsi, P.; Zuo, Z. Mechanistic study on the intestinal absorption and disposition of baicalein Eur. J. Pharm. Sci. 2007, 31, 221-231 (Pubitemid 46818982)
    • (2007) European Journal of Pharmaceutical Sciences , vol.31 , Issue.3-4 , pp. 221-231
    • Zhang, L.1    Lin, G.2    Kovacs, B.3    Jani, M.4    Krajcsi, P.5    Zuo, Z.6
  • 21
    • 19944393579 scopus 로고    scopus 로고
    • Enzyme kinetics for clinically relevant CYP inhibition
    • DOI 10.2174/1389200054021834
    • Zhang, Z. Y.; Wong, Y. N. Enzyme kinetics for clinically relevant CYP inhibition Curr. Drug Metab. 2005, 6, 241-257 (Pubitemid 40753855)
    • (2005) Current Drug Metabolism , vol.6 , Issue.3 , pp. 241-257
    • Zhang, Z.-Y.1    Wong, Y.N.2
  • 23
  • 24
    • 33847341135 scopus 로고    scopus 로고
    • Lipid formulation strategies for enhancing intestinal transport and absorption of P-glycoprotein (P-gp) substrate drugs: In vitro/in vivo case studies
    • DOI 10.1002/jps.20780
    • Constantinides, P. P.; Wasan, K. M. Lipid formulation strategies for enhancing intestinal transport and absorption of P-glycoprotein (P-gp) substrate drugs: in vitro/in vivo case studies J. Pharm. Sci. 2007, 96, 235-248 (Pubitemid 46363554)
    • (2007) Journal of Pharmaceutical Sciences , vol.96 , Issue.2 , pp. 235-248
    • Constantinides, P.P.1    Wasan, K.M.2
  • 25
    • 46449138901 scopus 로고    scopus 로고
    • Closing the gaps: A full scan of the intestinal expression of P-glycoprotein, breast cancer resistance protein, and multidrug resistance-associated protein 2 in male and female rats
    • DOI 10.1124/dmd.108.020859
    • MacLean, C.; Moenning, U.; Reichel, A.; Fricker, G. Closing the gaps: a full scan of the intestinal expression of p-glycoprotein, breast cancer resistance protein, and multidrug resistance-associated protein 2 in male and female rats Drug Metab. Pharmacokinet. 2008, 36, 1249-1254 (Pubitemid 351929307)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.7 , pp. 1249-1254
    • MacLean, C.1    Moenning, U.2    Reichel, A.3    Fricker, G.4
  • 26
    • 0037081788 scopus 로고    scopus 로고
    • Influence of t-butylhydroquinone and β-naphthoflavone on formation and transport of 4-methylumbelliferone glucuronide in Caco-2/TC-7 cell monolayers
    • DOI 10.1016/S0006-2952(01)00833-4, PII S0006295201008334
    • Bock-Hennig, B. S.; Kohle, C.; Nill, K.; Bock, K. W. Influence of t-butylhydroquinone and beta-naphthoflavone on formation and transport of 4-methylumbelliferone glucuronide in Caco-2/TC-7 cell monolayers Biochem. Pharmacol. 2002, 63, 123-128 (Pubitemid 34158811)
    • (2002) Biochemical Pharmacology , vol.63 , Issue.2 , pp. 123-128
    • Bock-Hennig, B.S.1    Kohle, C.2    Nill, K.3    Bock, K.W.4
  • 27
    • 6344242987 scopus 로고    scopus 로고
    • Differential multidrug resistance-associated protein 1 through 6 isoform expression and function in human intestinal epithelial Caco-2 cells
    • DOI 10.1124/jpet.104.068775
    • Prime-Chapman, H. M.; Fearn, R. A.; Cooper, A. E.; Moore, V.; Hirst, B. H. Differential multidrug resistance-associated protein 1 through 6 isoform expression and function in human intestinal epithelial Caco-2 cells J. Pharmacol. Exp. Ther. 2004, 311, 476-484 (Pubitemid 39391531)
    • (2004) Journal of Pharmacology and Experimental Therapeutics , vol.311 , Issue.2 , pp. 476-484
    • Prime-Chapman, H.M.1    Fearn, R.A.2    Cooper, A.E.3    Moore, V.4    Hirst, B.H.5
  • 28
    • 0037432669 scopus 로고    scopus 로고
    • Interaction of ochratoxin A with human intestinal Caco-2 cells: Possible implication of a multidrug resistance-associated protein (MRP2)
    • DOI 10.1016/S0378-4274(03)00043-2
    • Berger, V.; Gabriel, A. F.; Sergent, T.; Trouet, A.; Larondelle, Y.; Schneider, Y. J. Interaction of ochratoxin A with human intestinal Caco-2 cells: possible implication of a multidrug resistance-associated protein (MRP2) Toxicol. Lett. 2003, 140-141, 465-476 (Pubitemid 36378966)
    • (2003) Toxicology Letters , vol.140-141 , pp. 465-476
    • Berger, V.1    Gabriel, A.-F.2    Sergent, T.3    Trouet, A.4    Larondelle, Y.5    Schneider, Y.-J.6
  • 29
    • 33645885302 scopus 로고    scopus 로고
    • Ochratoxin A secretion by ATP-dependent membrane transporters in Caco-2 cells
    • Schrickx, J.; Lektarau, Y.; Fink-Gremmels, J. Ochratoxin A secretion by ATP-dependent membrane transporters in Caco-2 cells Arch. Toxicol. 2006, 80, 243-249
    • (2006) Arch. Toxicol. , vol.80 , pp. 243-249
    • Schrickx, J.1    Lektarau, Y.2    Fink-Gremmels, J.3
  • 30
    • 0025329248 scopus 로고
    • Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs on different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells
    • DOI 10.1002/jps.2600790710
    • Artursson, P.; Magnusson, C. Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells J. Pharm. Sci. 1990, 79, 595-600 (Pubitemid 20222724)
    • (1990) Journal of Pharmaceutical Sciences , vol.79 , Issue.7 , pp. 595-600
    • Artursson, P.1    Magnusson, C.2
  • 31
    • 17644382927 scopus 로고    scopus 로고
    • S-adenosyl-L-methionine: Transcellular transport and uptake by Caco-2 cells and hepatocytes
    • DOI 10.1211/0022357056082
    • McMillan, J. M.; Walle, U. K.; Walle, T. S-adenosyl-L-methionine: transcellular transport and uptake by Caco-2 cells and hepatocytes J. Pharm. Pharmacol. 2005, 57, 599-605 (Pubitemid 40562399)
    • (2005) Journal of Pharmacy and Pharmacology , vol.57 , Issue.5 , pp. 599-605
    • McMillan, J.M.1    Walle, U.K.2    Walle, T.3
  • 32
    • 72949102068 scopus 로고    scopus 로고
    • Transepithelial transport of ambroxol hydrochloride across human intestinal Caco-2 cell monolayers
    • Stetinova, V.; Smetanova, L.; Kholova, D.; Svoboda, Z.; Kvetina, J. Transepithelial transport of ambroxol hydrochloride across human intestinal Caco-2 cell monolayers Gen. Physiol. Biophys. 2009, 28, 309-315
    • (2009) Gen. Physiol. Biophys. , vol.28 , pp. 309-315
    • Stetinova, V.1    Smetanova, L.2    Kholova, D.3    Svoboda, Z.4    Kvetina, J.5
  • 33
    • 1542619707 scopus 로고    scopus 로고
    • Transport of Octreotide and Evaluation of Mechanism of Opening the Paracellular Tight Junctions using Superporous Hydrogel Polymers in Caco-2 Cell Monolayers
    • DOI 10.1002/jps.10570
    • Dorkoosh, F. A.; Broekhuizen, C. A.; Borchard, G.; Rafiee-Tehrani, M.; Verhoef, J. C.; Junginger, H. E. Transport of octreotide and evaluation of mechanism of opening the paracellular tight junctions using superporous hydrogel polymers in Caco-2 cell monolayers J. Pharm. Sci. 2004, 93, 743-752 (Pubitemid 38332306)
    • (2004) Journal of Pharmaceutical Sciences , vol.93 , Issue.3 , pp. 743-752
    • Dorkoosh, F.A.1    Broekhuizen, C.A.N.2    Borchard, G.3    Rafiee-Tehrani, M.4    Verhoef, J.C.5    Junginger, H.E.6
  • 34
    • 34547169521 scopus 로고    scopus 로고
    • Expression of thirty-six drug transporter genes in human intestine, liver, kidney, and organotypic cell lines
    • DOI 10.1124/dmd.107.014902
    • Hilgendorf, C.; Ahlin, G.; Seithel, A.; Artursson, P.; Ungell, A. L.; Karlsson, J. Expression of thirty-six drug transporter genes in human intestine, liver, kidney, and organotypic cell lines Drug Metab. Dispos. 2007, 35, 1333-1340 (Pubitemid 47121774)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.8 , pp. 1333-1340
    • Hilgendorf, C.1    Ahlin, G.2    Seithel, A.3    Artursson, P.4    Ungell, A.-L.5    Karlsson, J.6
  • 35
    • 0034739238 scopus 로고    scopus 로고
    • Oral delivery of salmon calcitonin
    • DOI 10.1016/S0169-409X(00)00063-6, PII S0169409X00000636
    • Lee, Y. H.; Sinko, P. J. Oral delivery of salmon calcitonin Adv. Drug Delivery Rev. 2000, 42, 225-238 (Pubitemid 30645779)
    • (2000) Advanced Drug Delivery Reviews , vol.42 , Issue.3 , pp. 225-238
    • Lee, Y.-H.1    Sinko, P.J.2
  • 36
    • 33644692007 scopus 로고    scopus 로고
    • P-glycoprotein recognition of substrates and circumvention through rational drug design
    • DOI 10.1021/mp0500871
    • Raub, T. J. P-glycoprotein recognition of substrates and circumvention through rational drug design Mol. Pharmaceutics 2006, 3, 3-25 (Pubitemid 43331747)
    • (2006) Molecular Pharmaceutics , vol.3 , Issue.1 , pp. 3-25
    • Raub, T.J.1
  • 38
    • 77949398878 scopus 로고    scopus 로고
    • Xenobiotic, bile acid, and cholesterol transporters: Function and regulation
    • Klaassen, C. D.; Aleksunes, L. M. Xenobiotic, bile acid, and cholesterol transporters: function and regulation Pharmacol. Rev. 2010, 62, 1-96
    • (2010) Pharmacol. Rev. , vol.62 , pp. 1-96
    • Klaassen, C.D.1    Aleksunes, L.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.