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Review

Enhancement of drug absorption by noncharged detergents through membrane and P-glycoprotein binding

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Pages 733-752 | Published online: 03 Oct 2006

Bibliography

  • RIEHM H, BIEDLER JL: Potentiation of drug effect by Tween 80 in Chinese hamster cells resistant to actinomycin D and daunomycin. Cancer Res. (1972) 32(6):1195-1200.
  • FRICHE E, JENSEN PB, SEHESTED M, DEMANT EJ, NISSEN NN: The solvents Cremophor EL and Tween 80 modulate daunorubicin resistance in the multidrug resistant Ehrlich ascites tumor. Cancer Commun. (1990) 2(9):297-303.
  • COON JS, KNUDSON W, CLODFELTER K, LU B, WEINSTEIN RS: Solutol HS 15, nontoxic polyoxyethylene esters of 12-hydroxystearic acid, reverses multidrug resistance. Cancer Res. (1991) 51(3):897-902.
  • SPOELSTRA EC, DEKKER H, SCHUURHUIS GJ, BROXTERMAN HJ, LANKELMA J: P-glycoprotein drug efflux pump involved in the mechanisms of intrinsic drug resistance in various colon cancer cell lines. Evidence for a saturation of active daunorubicin transport. Biochem. Pharmacol. (1991) 41(3):349-359.
  • WOODCOCK DM, LINSENMEYER ME, CHOJNOWSKI G et al.: Reversal of multidrug resistance by surfactants. Br. J. Cancer (1992) 66(1):62-68.
  • LOE DW, SHAROM FJ: Interaction of multidrug-resistant Chinese hamster ovary cells with amphiphiles. Br. J. Cancer (1993) 68(2):342-351.
  • ZORDAN-NUDO T, LING V, LIU Z, GEORGES E: Effects of nonionic detergents on P-glycoprotein drug binding and reversal of multidrug resistance. Cancer Res. (1993) 53(24):5994-6000.
  • DRORI S, EYTAN GD, ASSARAF YG: Potentiation of anticancer-drug cytotoxicity by multidrug-resistance chemosensitizers involves alterations in membrane fluidity leading to increased membrane permeability. Eur. J. Biochem. (1995) 228(3):1020-1029.
  • BORREL MN, FIALLO M, VERESS I, GARNIER-SUILLEROT A: The effect of crown ethers, tetraalkylammonium salts, and polyoxyethylene amphiphiles on pirarubicin incorporation in K562 resistant cells. Biochem. Pharmacol. (1995) 50(12):2069-2076.
  • LITMAN T, DRULEY TE, STEIN WD, BATES SE: From MDR to MXR: new understanding of multidrug resistance systems, their properties and clinical significance. Cell. Mol. Life Sci. (2001) 58(7):931-959.
  • STOUCH TR, GUDMUNDSSON O: Progress in understanding the structure–activity relationships of P-glycoprotein. Adv. Drug Deliv. Rev. (2002) 54(3):315-328.
  • CORDON-CARDO C, O’BRIEN JP, CASALS D et al.: Multidrug-resistance gene (P-glycoprotein) is expressed by endothelial cells at blood–brain barrier sites. Proc. Natl. Acad. Sci. USA (1989) 86(2):695-698.
  • THIEBAUT F, TSURUO T, HAMADA H, GOTTESMAN MM, PASTAN I, WILLINGHAM MC: Cellular localization of the multidrug-resistance gene product P-glycoprotein in normal human tissues. Proc. Natl. Acad. Sci. USA (1987) 84(21):7735-7738.
  • TANIGAWARA Y: Role of P-glycoprotein in drug disposition. Ther. Drug Monit. (2000) 22(1):137-140.
  • SEELIG A, GATLIK-LANDWOJTOWICZ E: Inhibitors of multidrug efflux transporters: their membrane and protein interactions. Mini Rev. Med. Chem. (2005) 5(2):135-151.
  • DEAN M, HAMON Y, CHIMINI G: The human ATP-binding cassette (ABC) transporter superfamily. J. Lipid Res. (2001) 42(7):1007-1017.
  • ZAMEK-GLISZCZYNSKI MJ, HOFFMASTER KA, NEZASA K, TALLMAN MN, BROUWER KL: Integration of hepatic drug transporters and phase II metabolizing enzymes: mechanisms of hepatic excretion of sulfate, glucuronide, and glutathione metabolites. Eur. J. Pharm. Sci. (2006) 27(5):447-486.
  • SEELIG A, BLATTER XL, WOHNSLAND F: Substrate recognition by P-glycoprotein and the multidrug resistance-associated protein MRP1: a comparison. Int. J. Clin. Pharmacol. Ther. (2000) 38(3):111-121.
  • ZHANG Y, BENET LZ: The gut as a barrier to drug absorption: combined role of cytochrome P450 3A and P-glycoprotein. Clin. Pharmacokinet. (2001) 40(3):159-168.
  • HIGGINS CF, GOTTESMAN MM: Is the multidrug transporter a flippase? Trends Biochem. Sci. (1992) 17(1):18-21.
  • GATLIK-LANDWOJTOWICZ E, AANISMAA P, SEELIG A: Quantification and characterization of P-glycoprotein-substrate interactions. Biochemistry (2006) 45(9):3020-3032.
  • ORLOWSKI S, SELOSSE MA, BOUDON C et al.: Effects of detergents on P-glycoprotein atpase activity: differences in perturbations of basal and verapamil-dependent activities. Cancer Biochem. Biophys. (1998) 16(1-2):85-110.
  • REGEV R, ASSARAF YG, EYTAN GD: Membrane fluidization by ether, other anesthetics, and certain agents abolishes P-glycoprotein ATPase activity and modulates efflux from multidrug-resistant cells. Eur. J. Biochem. (1999) 259(1-2):18-24.
  • MEIER M, LI-BLATTER X, SEELIG A, SEELIG J: Interaction of verapamil with lipid membranes and P-glycoprotein. Connecting thermodynamics and membrane structure with functional activity. Biophysical J. (In Press).
  • WAKITA M, KURODA Y, NAKAGAWA T: Interactions between local anesthetic dibucaine and pig erythrocyte membranes as studied by proton and phosphorus-31 nuclear magnetic resonance spectroscopy. Chem. Pharm. Bull. (Tokyo) (1992) 40(6):1361-1365.
  • REGE BD, KAO JP, POLLI JE: Effects of nonionic surfactants on membrane transporters in Caco-2 cell monolayers. Eur. J. Pharm. Sci. (2002) 16(4-5):237-246.
  • NERVI P: Peptide and drug interactions in murine models in vitro and in vivo studies with microphysiometry, confocal microscopy and functional magnetic resonance imaging. PhD Thesis, University of Basel, Switzerland (2004).
  • KABANOV AV, BATRAKOVA EV, MILLER DW: Pluronic block copolymers as modulators of drug efflux transporter activity in the blood–brain barrier. Adv. Drug Deliv. Rev. (2003) 55(1):151-164.
  • SEELIG J, SEELIG A: Lipid conformation in model membranes and biological membranes. Q. Rev. Biophys. (1980) 13(1):19-61.
  • SEELIG A, SEELIG J: Membrane Structure. In: Encyclopedia of Physical Science and Technology, 3rd edn. Academic Press, NY, USA (2002):355-367.
  • LITMAN T, NIELSEN D, SKOVSGAARD T, BUKHAVE K: Lipid composition of sensitive and multidrug resistant Ehrlich ascites tumour cells. Cell. Pharmacol. (1995) 2:9-14.
  • FISCHER H, GOTTSCHLICH R, SEELIG A: Blood–brain barrier permeation: molecular parameters governing passive diffusion. J. Membr. Biol. (1998) 165(3):201-211.
  • FISCHER H, SEELIG A, CHOU RC, VAN DE WATERBEEMD J: The difference between the diffusion through the blood–brain barrier and the gastro-intestinal membrane. 4th International Conference on Drug Absorption. Edinburgh, UK (1997).
  • SEELIG A: Local anesthetics and pressure: a comparison of dibucaine binding to lipid monolayers and bilayers. Biochim. Biophys. Acta (1987) 899(2):196-204.
  • BOGUSLAVSKY V, REBECCHI M, MORRIS AJ, JHON DY, RHEE SG, MCLAUGHLIN S: Effect of monolayer surface pressure on the activities of phosphoinositide-specific phospholipase C-β1, -γ1, and -δ1. Biochemistry (1994) 33(10):3032-3037.
  • GEREBTZOFF G, LI-BLATTER X, FISCHER H, FRENTZEL A, SEELIG A: Halogenation of drugs enhances membrane binding and permeation. Chembiochem (2004) 5(5):676-684.
  • GOBAS FA, LAHITTETE JM, GAROFALO G, SHIU WY, MACKAY D: A novel method for measuring membrane-water partition coefficients of hydrophobic organic chemicals: comparison with 1-octanol–water partitioning. J. Pharm. Sci. (1988) 77(3):265-272.
  • HEERKLOTZ H, SEELIG J: Correlation of membrane/water partition coefficients of detergents with the critical micelle concentration. Biophys. J. (2000) 78(5):2435-2440.
  • WU G, MAJEWSKI J, EGE C, KJAER K, WEYGAND MJ, LEE KY: Lipid corralling and poloxamer squeeze-out in membranes. Phys. Rev. Lett. (2004) 93(2):028101.
  • MASKARINEC SA, HANNIG J, LEE RC, LEE KY: Direct observation of poloxamer 188 insertion into lipid monolayers. Biophys. J. (2002) 82(3):1453-1459.
  • WU G, MAJEWSKI J, EGE C, KJAER K, WEYGAND MJ, LEE KY: Interaction between lipid monolayers and poloxamer 188: an X-ray reflectivity and diffraction study. Biophys. J. (2005) 89(5):3159-3173.
  • CHANG LC, LIN CY, KUO MW, GAU CS: Interactions of Pluronics with phospholipid monolayers at the air–water interface. J. Colloid Interface Sci. (2005) 285(2):640-652.
  • KRYLOVA OO, POHL P: Ionophoric activity of pluronic block copolymers. Biochemistry (2004) 43(12):3696-3703.
  • DEMINA T, GROZDOVA I, KRYLOVA O et al.: Relationship between the structure of amphiphilic copolymers and their ability to disturb lipid bilayers. Biochemistry (2005) 44(10):4042-4054.
  • BATRAKOVA EV, MILLER DW, LI S, ALAKHOV VY, KABANOV AV, ELMQUIST WF: Pluronic P85 enhances the delivery of digoxin to the brain: in vitro and in vivo studies. J. Pharmacol. Exp. Ther. (2001) 296(2):551-557.
  • OTTEN D, BROWN MF, BEYER K: Softening of membrane bilayers by detergents elucidated by deuterium NMR spectroscopy. J. Phys. Chem. B (2000) 104:12119-12129.
  • THEWALT JL, TULLOCH AP, CUSHLEY RJ: A deuterium NMR study of labelled n-alkanol anesthetics in a model membrane. Chem. Phys. Lipids (1986) 39(1-2):93-107.
  • WENK MR, ALT T, SEELIG A, SEELIG J: Octyl-β-d-glucopyranoside partitioning into lipid bilayers: thermodynamics of binding and structural changes of the bilayer. Biophys. J. (1997) 72(4):1719-1731.
  • HEERKLOTZ H: Triton promotes domain formation in lipid raft mixtures. Biophys. J. (2002) 83(5):2693-2701.
  • WASSALL SR, THEWALT JL, WONG L, GORRISSEN H, CUSHLEY RJ: Deuterium NMR study of the interaction of α-tocopherol with a phospholipid model membrane. Biochemistry (1986) 25(2):319-326.
  • HUGGER ED, NOVAK BL, BURTON PS, AUDUS KL, BORCHARDT RT: A comparison of commonly used polyethoxylated pharmaceutical excipients on their ability to inhibit P-glycoprotein activity in vitro. J. Pharm. Sci. (2002) 91(9):1991-2002.
  • LIANG X, MAO G, NG KY: Effect of chain lengths of PEO-PPO-PEO on small unilamellar liposome morphology and stability: an AFM investigation. J. Colloid Interface Sci. (2005) 285(1):360-372.
  • OMOTE H, AL-SHAWI MK: Interaction of transported drugs with the lipid bilayer and P-glycoprotein through a solvation exchange mechanism. Biophys. J. (2006) 90(11):4046-4059.
  • SEELIG A, LANDWOJTOWICZ E, FISCHER H, BLATTER XL: Towards P-glycoprotein structure–activity relationships. In: Drug bioavailability/Estimation of solubility, permeability, absorption and bioavailability. Van der Waterbeemd H, Lennernas H, Arthurson P (Eds), Wiley-VCH Verlag GmbH, Weinheim, Germany (2003).
  • SEELIG A: A general pattern for substrate recognition by P-glycoprotein. Eur. J. Biochem. (1998) 251(1-2):252-261.
  • ECKER G, HUBER M, SCHMID D, CHIBA P: The importance of a nitrogen atom in modulators of multidrug resistance. Mol. Pharmacol. (1999) 56(4):791-796.
  • SEELIG A, LANDWOJTOWICZ E: Structure–activity relationship of P-glycoprotein substrates and modifiers. Eur. J. Pharm. Sci. (2000) 12(1):31-40.
  • CHIBA P, ERKER T, GALANSKI M, HITZLER M, ECKER GF: Synthesis and multidrug-resistance modulating activity of a series of thienothiazines. Arch. Pharm. (Weinheim) (2002) 335(5):223-228.
  • SEELIG A: Unraveling membrane-mediated substrate–transporter interactions. Biophys. J. (2006) 90(11):3825-3826.
  • LANDWOJTOWICZ E, NERVI P, SEELIG A: Real-time monitoring of P-glycoprotein activation in living cells. Biochemistry (2002) 41(25):8050-8057.
  • AL-SHAWI MK, POLAR MK, OMOTE H, FIGLER RA: Transition state analysis of the coupling of drug transport to ATP hydrolysis by P-glycoprotein. J. Biol. Chem. (2003) 278(52):52629-52640.
  • RAGGERS RJ, POMORSKI T, HOLTHUIS JC, KALIN N, VAN MEER G: Lipid traffic: the ABC of transbilayer movement. Traffic (2000) 1(3):226-234.
  • ROMSICKI Y, SHAROM FJ: Phospholipid flippase activity of the reconstituted P-glycoprotein multidrug transporter. Biochemistry (2001) 40(23):6937-6947.
  • LITMAN T, ZEUTHEN T, SKOVSGAARD T, STEIN WD: Structure-activity relationships of P-glycoprotein interacting drugs: kinetic characterization of their effects on ATPase activity. Biochim. Biophys. Acta (1997) 1361(2):159-168.
  • GATLIK-LANDWOJTOWICZ E, AANISMAA P, SEELIG A: The rate of P-glycoprotein activation depends on the metabolic state of the cell. Biochemistry (2004) 43(46):14840-14851.
  • URBATSCH IL, AL-SHAWI MK, SENIOR AE: Characterization of the ATPase activity of purified Chinese hamster P-glycoprotein. Biochemistry (1994) 33(23):7069-7076.
  • SHAPIRO AB, LING V: Stoichiometry of coupling of rhodamine 123 transport to ATP hydrolysis by P-glycoprotein. Eur. J. Biochem. (1998) 254(1):189-193.
  • SAUNA ZE, AMBUDKAR SV: Characterization of the catalytic cycle of ATP hydrolysis by human P-glycoprotein. The two ATP hydrolysis events in a single catalytic cycle are kinetically similar but affect different functional outcomes. J. Biol. Chem. (2001) 276(15):11653-11661.
  • NERURKAR MM, HO NF, BURTON PS, VIDMAR TJ, BORCHARDT RT: Mechanistic roles of neutral surfactants on concurrent polarized and passive membrane transport of a model peptide in Caco-2 cells. J. Pharm. Sci. (1997) 86(7):813-821.
  • BRAVO GONZALEZ RC, HUWYLER J, BOESS F, WALTER I, BITTNER B: In vitro investigation on the impact of the surface-active excipients Cremophor EL, Tween 80 and Solutol HS-15 on the metabolism of midazolam. Biopharm. Drug Dispos. (2004) 25(1):37-49.
  • BITTNER B, GONZALEZ RC, WALTER I, KAPPS M, HUWYLER J: Impact of Solutol HS 15 on the pharmacokinetic behaviour of colchicine upon intravenous administration to male Wistar rats. Biopharm. Drug Dispos. (2003) 24(4):173-181.
  • BRAVO GONZALEZ RC, HUWYLER J, WALTER I, MOUNTFIELD R, BITTNER B: Improved oral bioavailability of cyclosporin A in male Wistar rats. Comparison of a Solutol HS 15 containing self-dispersing formulation and a microsuspension. Int. J. Pharm. (2002) 245(1-2):143-151.
  • BITTNER B, GONZALEZ RCB, WALTER I, HUWYLER J: Impact of oral administration of the surface-active excipient solutol HS-15 on the pharmacokinetics of intravenously administered colchicine. Lett. Drug Des. Disc. (2005) 2(3):193-195.
  • WANG SW, MONAGLE J, MCNULTY C, PUTNAM D, CHEN H: Determination of P-glycoprotein inhibition by excipients and their combinations using an integrated high-throughput process. J. Pharm. Sci. (2004) 93(11):2755-2767.
  • DUDEJA PK, ANDERSON KM, HARRIS JS, BUCKINGHAM L, COON JS: Reversal of multidrug resistance phenotype by surfactants: relationship to membrane lipid fluidity. Arch. Biochem. Biophys. (1995) 319(1):309-315.
  • LITMAN T, SKOVSGAARD T, STEIN WD: Pumping of drugs by P-glycoprotein: a two-step process? J. Pharmacol. Exp. Ther. (2003) 307(3):846-853.
  • ATTWOOD D, FLORENCE AT: Surfactant systems: their chemistry, pharmacy and biology. Chapman and Hall, London (UK) and New York (USA) (1983).
  • BOGMAN K, ZYSSET Y, DEGEN L et al.: P-glycoprotein and surfactants: effect on intestinal talinolol absorption. Clin. Pharmacol. Ther. (2005) 77(1):24-32.
  • JAGANNATH C, WELLS A, MSHVILDADZE M et al.: Significantly improved oral uptake of amikacin in FVB mice in the presence of CRL-1605 copolymer. Life Sci. (1999) 64(19):1733-1738.
  • BANERJEE SK, JAGANNATH C, HUNTER RL, DASGUPTA A: Bioavailability of tobramycin after oral delivery in FVB mice using CRL-1605 copolymer, an inhibitor of P-glycoprotein. Life Sci. (2000) 67(16):2011-2016.
  • GAUCHER G, DUFRESNE MH, SANT VP, KANG N, MAYSINGER D, LEROUX JC: Block copolymer micelles: preparation, characterization and application in drug delivery. J. Control. Release (2005) 109(1-3):169-188.
  • GELDERBLOM H, VERWEIJ J, NOOTER K, SPARREBOOM A: Cremophor EL: the drawbacks and advantages of vehicle selection for drug formulation. Eur. J. Cancer (2001) 37(13):1590-1598.
  • COORS EA, SEYBOLD H, MERK HF, MAHLER V: Polysorbate 80 in medical products and nonimmunologic anaphylactoid reactions. Ann. Allergy Asthma Immunol. (2005) 95(6):593-599.
  • HAVEL M, MULLER M, GRANINGER W, KURZ R, LINDEMAYR H: Tolerability of a new vitamin K1 preparation for parenteral administration to adults: one case of anaphylactoid reaction. Clin. Ther. (1987) 9(4):373-379.
  • THEIS JG, LIAU-CHU M, CHAN HS, DOYLE J, GREENBERG ML, KOREN G: Anaphylactoid reactions in children receiving high-dose intravenous cyclosporine for reversal of tumor resistance: the causative role of improper dissolution of Cremophor EL. J. Clin. Oncol. (1995) 13(10):2508-2516.
  • PENDSE S, SAYEGH MH, FRANK MH: P-glycoprotein-a novel therapeutic target for immunomodulation in clinical transplantation and autoimmunity? Curr. Drug Targets (2003) 4(6):469-476.
  • BEGLEY GS, HORVATH AR, TAYLOR JC, HIGGINS CF: Cytoplasmic domains of the transporter associated with antigen processing and P-glycoprotein interact with subunits of the proteasome. Mol. Immunol. (2005) 42(1):137-141.
  • COGGER VC, HILMER SN, SULLIVAN D, MULLER M, FRASER R, LE COUTEUR DG: Hyperlipidemia and surfactants: the liver sieve is a link. Atherosclerosis (2006) (In Press).
  • SEEBALLUCK F, ASHFORD MB, O’DRISCOLL CM: The effects of pluronics block copolymers and Cremophor EL on intestinal lipoprotein processing and the potential link with P-glycoprotein in Caco-2 cells. Pharm. Res. (2003) 20(7):1085-1092.
  • JOHNSON BM, CHARMAN WN, PORTER CJ: An in vitro examination of the impact of polyethylene glycol 400, Pluronic P85, and vitamin E d-α-tocopheryl polyethylene glycol 1000 succinate on P-glycoprotein efflux and enterocyte-based metabolism in excised rat intestine. AAPS PharmSci (2002) 4(4):40.
  • BATRAKOVA EV, LI S, MILLER DW, KABANOV AV: Pluronic P85 increases permeability of a broad spectrum of drugs in polarized BBMEC and Caco-2 cell monolayers. Pharm. Res. (1999) 16(9):1366-1372.
  • MILLER DW, BATRAKOVA EV, KABANOV AV: Inhibition of multidrug resistance-associated protein (MRP) functional activity with pluronic block copolymers. Pharm. Res. (1999) 16(3):396-401.
  • BOGMAN K, ERNE-BRAND F, ALSENZ J, DREWE J: The role of surfactants in the reversal of active transport mediated by multidrug resistance proteins. J. Pharm. Sci. (2003) 92(6):1250-1261.
  • DEMEL RA, GEURTS VAN KESSEL WS, ZWAAL RF, ROELOFSEN B, VAN DEENEN LL: Relation between various phospholipase actions on human red cell membranes and the interfacial phospholipid pressure in monolayers. Biochim. Biophys. Acta (1975) 406(1):97-107.
  • BLUME A: A comparative study of the phase transitions of phospholipid bilayers and monolayers. Biochim. Biophys. Acta (1979) 557(1):32-44.
  • NERVI P, LI BLATTER X, SEELIG A: Surfactants as P-glycoprotein substrates and inhibitors. (In preparation).
  • BRAVO GONZALEZ RC, BOESS F, DURR E, SCHAUB N, BITTNER B: In vitro investigation on the impact of Solutol HS 15 on the uptake of colchicine into rat hepatocytes. Int. J. Pharm. (2004) 279(1-2):27-31.
  • BITTNER B, GUENZI A, FULLHARDT P, ZUERCHER G, GONZALEZ RC, MOUNTFIELD RJ: Improvement of the bioavailability of colchicine in rats by co-administration of d-α-tocopherol polyethylene glycol 1000 succinate and a polyethoxylated derivative of 12-hydroxy-stearic acid. Arzneimittelforschung (2002) 52(9):684-688.
  • DINTAMAN JM, SILVERMAN JA: Inhibition of P-glycoprotein by d-α-tocopheryl polyethylene glycol 1000 succinate (TPGS). Pharm. Res. (1999) 16(10):1550-1556.
  • REBBEOR JF, SENIOR AE: Effects of cardiovascular drugs on ATPase activity of P-glycoprotein in plasma membranes and in purified reconstituted form. Biochim. Biophys. Acta (1998) 1369(1):85-93.
  • LO YL: Relationships between the hydrophilic-lipophilic balance values of pharmaceutical excipients and their multidrug resistance modulating effect in Caco-2 cells and rat intestines. J. Control. Release (2003) 90(1):37-48.
  • HIRSCH-ERNST KI, ZIEMANN C, RUSTENBECK I, KAHL GF: Inhibitors of mdr1-dependent transport activity delay accumulation of the mdr1 substrate rhodamine 123 in primary rat hepatocyte cultures. Toxicology (2001) 167(1):47-57.

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