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Volumn 53, Issue 4, 1999, Pages 393-402

Synthesis and evaluation of the physicochemical properties of esterase- sensitive cyclic prodrugs of opioid peptides using an (acyloxy)alkoxy linker

Author keywords

Leu5 enkephalin; Cyclic prodrug (acyloxy)alkoxy; DADLE; Peptide delivery

Indexed keywords

ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; ESTERASE; GLYCOPROTEIN P; LEUCINE ENKEPHALIN; OPIATE PEPTIDE; PRODRUG;

EID: 0033040559     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00070.x     Document Type: Article
Times cited : (31)

References (17)
  • 1
    • 0342567858 scopus 로고    scopus 로고
    • Synthesis and evaluation of the physicochemical properties of esterase-sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers
    • 1. Wang, B., Nimkar, K., Wang, W., Zhang, H., Shan, D., Gudmundsson, O., Gangwar, S., Siahaan, T. & Borchardt, R.T. (1999) Synthesis and evaluation of the physicochemical properties of esterase-sensitive cyclic prodrugs of opioid peptides using coumarinic acid and phenylpropionic acid linkers. J. Peptide Res. 53, 370-382.
    • (1999) J. Peptide Res. , vol.53 , pp. 370-382
    • Wang, B.1    Nimkar, K.2    Wang, W.3    Zhang, H.4    Shan, D.5    Gudmundsson, O.6    Gangwar, S.7    Siahaan, T.8    Borchardt, R.T.9
  • 2
    • 0032937786 scopus 로고    scopus 로고
    • Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability
    • 2. Gudmundsson, O.S., Pauletti, G.M., Wang, W., Shan, D., Zhang, H., Wang, B. & Borchardt, R.T. (1999) Coumarinic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability. Pharm. Res. 16, 7-15.
    • (1999) Pharm. Res. , vol.16 , pp. 7-15
    • Gudmundsson, O.S.1    Pauletti, G.M.2    Wang, W.3    Shan, D.4    Zhang, H.5    Wang, B.6    Borchardt, R.T.7
  • 3
    • 0032930316 scopus 로고    scopus 로고
    • Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability
    • 3. Gudmundsson, O.S., Nimkar, K., Gangwar, S., Siahaan, T.J. & Borchardt, R.T. (1999) Phenylpropionic acid-based cyclic prodrugs of opioid peptides that exhibit metabolic stability to peptidases and excellent cellular permeability. Pharm. Res. 16, 16-23.
    • (1999) Pharm. Res. , vol.16 , pp. 16-23
    • Gudmundsson, O.S.1    Nimkar, K.2    Gangwar, S.3    Siahaan, T.J.4    Borchardt, R.T.5
  • 4
    • 0030934663 scopus 로고    scopus 로고
    • Synthesis of a novel esterase-sensitive cyclic prodrug of a hexapeptide using an (acyloxy) alkoxy promoiety
    • 4. Gangwar, S., Pauletti, G.M., Siahaan, T.J., Stella, V.J. & Borchardt, R.T. (1997) Synthesis of a novel esterase-sensitive cyclic prodrug of a hexapeptide using an (acyloxy) alkoxy promoiety. J. Org. Chem. 62, 1356-1362.
    • (1997) J. Org. Chem. , vol.62 , pp. 1356-1362
    • Gangwar, S.1    Pauletti, G.M.2    Siahaan, T.J.3    Stella, V.J.4    Borchardt, R.T.5
  • 5
    • 0030470532 scopus 로고    scopus 로고
    • Esterase-sensitive cyclic prudrugs of peptides: Evaluation of an acyloxyalkoxy promoiety in a model hexapeptide
    • 5. Pauletti, G.M., Gangwar, S., Okumu, F.W., Siahaan, T.J., Stella, V.J. & Borchardt, R.T. (1996) Esterase-sensitive cyclic prudrugs of peptides: evaluation of an acyloxyalkoxy promoiety in a model hexapeptide. Pharm. Res. 13, 1613-1621.
    • (1996) Pharm. Res. , vol.13 , pp. 1613-1621
    • Pauletti, G.M.1    Gangwar, S.2    Okumu, F.W.3    Siahaan, T.J.4    Stella, V.J.5    Borchardt, R.T.6
  • 6
    • 0030480443 scopus 로고    scopus 로고
    • The effect of conformation on membrane permeability of an acyloxyalkoxy-linked cyclic prodrug of a model hexapeptide
    • 6. Gangwar, S., Jois, S.D.S., Siahaan, T.J., Vander Velde, D., Stella, V.J. & Borchardt, R.T. (1996) The effect of conformation on membrane permeability of an acyloxyalkoxy-linked cyclic prodrug of a model hexapeptide. Pharm. Res. 13, 1655-1660.
    • (1996) Pharm. Res. , vol.13 , pp. 1655-1660
    • Gangwar, S.1    Jois, S.D.S.2    Siahaan, T.J.3    Vander Velde, D.4    Stella, V.J.5    Borchardt, R.T.6
  • 7
    • 0000637656 scopus 로고
    • Lipophilicity measurements of protonated basic compounds by reverse-phase high-performance liquid chromatography. I. Relationship between capacity factors and the methanol concentration in methanol-water eluents
    • 7. Tayar, N.E., Waterbeemd, H.V. & d. & Testa, B. (1985) Lipophilicity measurements of protonated basic compounds by reverse-phase high-performance liquid chromatography. I. Relationship between capacity factors and the methanol concentration in methanol-water eluents. J. Chromatogr. 320, 293-304.
    • (1985) J. Chromatogr. , vol.320 , pp. 293-304
    • Tayar, N.E.1    Waterbeemd, H.V.D.2    Testa, B.3
  • 8
    • 5644303902 scopus 로고
    • Lipophilicity measurements of protonated basic compounds by reverse-phase high-performance liquid chromatography. II. Procedure for the determination of a lipophilic index measured by reverse-phase high performance liquid chromatography
    • 8. Tayar, N.E., Waterbeemd, H.V. & d. & Testa, B. (1985) Lipophilicity measurements of protonated basic compounds by reverse-phase high-performance liquid chromatography. II. Procedure for the determination of a lipophilic index measured by reverse-phase high performance liquid chromatography. J. Chromatogr. 320, 305-312.
    • (1985) J. Chromatogr. , vol.320 , pp. 305-312
    • Tayar, N.E.1    Waterbeemd, H.V.D.2    Testa, B.3
  • 9
    • 33646376290 scopus 로고
    • Spin diffusion measurements: Spin echoes in the presence of a time-dependent field gradient
    • 9. Setjskal, E.O. & Tanner, J.E. (1965) Spin diffusion measurements: spin echoes in the presence of a time-dependent field gradient. J. Chem. Phys. 42, 288-292.
    • (1965) J. Chem. Phys. , vol.42 , pp. 288-292
    • Setjskal, E.O.1    Tanner, J.E.2
  • 10
    • 34047191652 scopus 로고
    • Fourier transform pulsed-gradient spin-echo studies of molecular diffusion
    • 10. Stilbs, P. (1987) Fourier transform pulsed-gradient spin-echo studies of molecular diffusion. Prog. Nucl. Magn. Reson. Spectros. 19, 1-45.
    • (1987) Prog. Nucl. Magn. Reson. Spectros. , vol.19 , pp. 1-45
    • Stilbs, P.1
  • 11
    • 0001402032 scopus 로고    scopus 로고
    • Experimental study of dynamic isotope effects in molecular liquids: Detection of translation-rotation coupling
    • 11. Holz, M., Mao, X., Seiferling, D. & Sacco, A. (1996) Experimental study of dynamic isotope effects in molecular liquids: detection of translation-rotation coupling. J. Chem. Phys. 104, 669.
    • (1996) J. Chem. Phys. , vol.104 , pp. 669
    • Holz, M.1    Mao, X.2    Seiferling, D.3    Sacco, A.4
  • 12
    • 0030932221 scopus 로고    scopus 로고
    • Synthesis of a novel esterase-sensitive cyclic prodrug system for peptides that utilizes a 'trimethyl lock'-facilitated lactonization reaction
    • 12. Wang, B., Gangwar, S., Pauletti, G.M., Siahaan, T.J. & Borchardt, R.T. (1997) Synthesis of a novel esterase-sensitive cyclic prodrug system for peptides that utilizes a 'trimethyl lock'-facilitated lactonization reaction. J. Org. Chem. 62, 1363-1367.
    • (1997) J. Org. Chem. , vol.62 , pp. 1363-1367
    • Wang, B.1    Gangwar, S.2    Pauletti, G.M.3    Siahaan, T.J.4    Borchardt, R.T.5
  • 13
    • 0342437513 scopus 로고    scopus 로고
    • Improvement of oral peptide bioavailability: Peptide mimetics and prodrug strategies
    • 13. Pauletti, G.M., Gangwar, S., Siahaan, T.J., Aube, J. & Borchardt, R.T. (1997) Improvement of oral peptide bioavailability: peptide mimetics and prodrug strategies. Adv. Drug Del. Rev. 27, 235-256.
    • (1997) Adv. Drug Del. Rev. , vol.27 , pp. 235-256
    • Pauletti, G.M.1    Gangwar, S.2    Siahaan, T.J.3    Aube, J.4    Borchardt, R.T.5
  • 14
    • 0030903756 scopus 로고    scopus 로고
    • Effect of size and charge on the passive diffusion of peptides across caco-2 cell munolayers via the paracellular pathway
    • 14. Pauletti, G.M., Okumu, F.W. & Borchardt, R.T. (1997) Effect of size and charge on the passive diffusion of peptides across caco-2 cell munolayers via the paracellular pathway. Pharm. Res. 14, 164-168.
    • (1997) Pharm. Res. , vol.14 , pp. 164-168
    • Pauletti, G.M.1    Okumu, F.W.2    Borchardt, R.T.3
  • 15
    • 0032908281 scopus 로고    scopus 로고
    • Acyloxyalkoxy-based cyclic prodrugs of opioid peptides: Evaluation of the chemical and enzymatic stability as well as their transport properties across caco-2 cell monolayers
    • 15. Bak, A., Gudmundsson, O.S., Friis, G.J., Siahaan, T.J. & Borchardt, R.T. (1999) Acyloxyalkoxy-based cyclic prodrugs of opioid peptides: evaluation of the chemical and enzymatic stability as well as their transport properties across caco-2 cell monolayers. Pharm. Res. 16, 24-29.
    • (1999) Pharm. Res. , vol.16 , pp. 24-29
    • Bak, A.1    Gudmundsson, O.S.2    Friis, G.J.3    Siahaan, T.J.4    Borchardt, R.T.5
  • 16
    • 0031023675 scopus 로고    scopus 로고
    • In vitro permeability of peptidomimetics: The role of polarized efflux pathways as additional barriers to absorption
    • 16. Burton, P.S., Goodwin, J.T., Conradi, R.A., Ho, N.F.H. & Holgers, A.R. (1997) In vitro permeability of peptidomimetics: the role of polarized efflux pathways as additional barriers to absorption. Adv. Drug. Deliv. Rev. 23, 143-156.
    • (1997) Adv. Drug. Deliv. Rev. , vol.23 , pp. 143-156
    • Burton, P.S.1    Goodwin, J.T.2    Conradi, R.A.3    Ho, N.F.H.4    Holgers, A.R.5
  • 17
    • 0033067843 scopus 로고    scopus 로고
    • The effect of conformation on the membrane permeability of coumarinic acid-and phenylpropionic acid-based cyclic prodrugs of opioid peptides
    • 17. Gudmundsson, O.S., Jois, S.D.S., Vander Velde, D.G., Siahaan, T.J., Wang, B. & Borchardt, R.T. (1999) The effect of conformation on the membrane permeability of coumarinic acid-and phenylpropionic acid-based cyclic prodrugs of opioid peptides. J. Peptide Res. 53, 383-392.
    • (1999) J. Peptide Res. , vol.53 , pp. 383-392
    • Gudmundsson, O.S.1    Jois, S.D.S.2    Vander Velde, D.G.3    Siahaan, T.J.4    Wang, B.5    Borchardt, R.T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.