메뉴 건너뛰기




Volumn 13, Issue 3, 2008, Pages 519-547

Prodrugs for amines

Author keywords

Amines; Chemical activation; Enzymatic activation; Prodrugs

Indexed keywords

AMINE; PRODRUG;

EID: 41649091174     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13030519     Document Type: Review
Times cited : (111)

References (120)
  • 1
    • 0019493180 scopus 로고
    • Prodrugs as drug delivery systems. XIX. Bioreversible derivatisation of aromatic amines by formation of N-Mannich bases with succinimide
    • Bundgaard, H.; Johansen, M. Prodrugs as drug delivery systems. XIX. Bioreversible derivatisation of aromatic amines by formation of N-Mannich bases with succinimide. Int. J. Pharm. 1981, 8, 183-192.
    • (1981) Int. J. Pharm , vol.8 , pp. 183-192
    • Bundgaard, H.1    Johansen, M.2
  • 2
    • 0026500650 scopus 로고
    • Prodrugs as a means to improve the delivery of peptide drugs. 1
    • Bundgaard, H. Prodrugs as a means to improve the delivery of peptide drugs. 1. Adv. Drug Deliv. Rev. 1992, 8, 1-38.
    • (1992) Adv. Drug Deliv. Rev , vol.8 , pp. 1-38
    • Bundgaard, H.1
  • 3
    • 0033006069 scopus 로고    scopus 로고
    • Prodrug approaches to the improved delivery of peptide drugs
    • Wang, W.; Jiang, J.; Ballard, C.; Wang, B. Prodrug approaches to the improved delivery of peptide drugs. Curr. Pharm. Des. 1999, 5, 265-287.
    • (1999) Curr. Pharm. Des , vol.5 , pp. 265-287
    • Wang, W.1    Jiang, J.2    Ballard, C.3    Wang, B.4
  • 6
    • 0023589169 scopus 로고
    • N,N-dipropargyl-2- phenylethylamine, a potential prodrug of 2-phenylethylamine: Neurochemical and neuropharmacological studies in rat
    • Rao, T.S.; Baker, G.B.; Coutts, R.T. N,N-dipropargyl-2- phenylethylamine, a potential prodrug of 2-phenylethylamine: neurochemical and neuropharmacological studies in rat. Brain Res. Bull. 1987, 19, 47-55.
    • (1987) Brain Res. Bull , vol.19 , pp. 47-55
    • Rao, T.S.1    Baker, G.B.2    Coutts, R.T.3
  • 7
    • 0023240730 scopus 로고
    • Pharmacokinetic and neurochemical studies on N-propargyl-2-phenylethylamine, a prodrug of 2-phenylethylamine
    • Rao, T.S.; Baker, G.B.; Coutts, R.T. Pharmacokinetic and neurochemical studies on N-propargyl-2-phenylethylamine, a prodrug of 2-phenylethylamine. N.-S. Arch. Pharmacol. 1987, 336, 25-32
    • (1987) N.-S. Arch. Pharmacol , vol.336 , pp. 25-32
    • Rao, T.S.1    Baker, G.B.2    Coutts, R.T.3
  • 8
    • 0023427368 scopus 로고
    • Neuropharmacological and neurochemical properties of N-(2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine
    • Baker, G.B.; Coutts, R.T.; Rao, T.S. Neuropharmacological and neurochemical properties of N-(2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine. Br. J. Pharmacol. 1987, 92, 243-255.
    • (1987) Br. J. Pharmacol , vol.92 , pp. 243-255
    • Baker, G.B.1    Coutts, R.T.2    Rao, T.S.3
  • 9
    • 0023265497 scopus 로고
    • N-(3-chloropropyl) phenylethylamine as a possible prodrug of beta-phenylethylamine: Studies in the rat brain
    • Rao, T.S.; Baker, G.B.; Coutts, R.T. N-(3-chloropropyl) phenylethylamine as a possible prodrug of beta-phenylethylamine: studies in the rat brain. Prog. Neuropsychopharmacol. Biol. Psychiatry 1987, 11, 301-308.
    • (1987) Prog. Neuropsychopharmacol. Biol. Psychiatry , vol.11 , pp. 301-308
    • Rao, T.S.1    Baker, G.B.2    Coutts, R.T.3
  • 10
    • 0004255131 scopus 로고
    • Bundgaard, H, Ed, Elsevier: Amsterdam, Chapter 1
    • Bundgaard, H. In Design of prodrugs; Bundgaard, H., Ed.; Elsevier: Amsterdam, 1985; Chapter 1.
    • (1985) Design of prodrugs
    • Bundgaard, H.1
  • 11
    • 0026664664 scopus 로고
    • An orally effective peripheral dopamine prodrug - Docarpamine TA-870
    • Nishiyama, S.; Yoshikawa, M.; Yamaguchi, I. An orally effective peripheral dopamine prodrug - Docarpamine TA-870. Cardiovasc. Drug Rev. 1992, 10, 101-116.
    • (1992) Cardiovasc. Drug Rev , vol.10 , pp. 101-116
    • Nishiyama, S.1    Yoshikawa, M.2    Yamaguchi, I.3
  • 13
    • 0343462226 scopus 로고    scopus 로고
    • Prodrugs and targeted drug delivery
    • Kearney, A.S. Prodrugs and targeted drug delivery. Adv. Drug Deliv. Rev. 1996, 19, 225-239.
    • (1996) Adv. Drug Deliv. Rev , vol.19 , pp. 225-239
    • Kearney, A.S.1
  • 14
    • 0026015884 scopus 로고
    • Five years experience with γ-L-glutamyl- L-dopa- a relatively renally specific dopaminergic prodrug in man
    • Lee, M. Five years experience with γ-L-glutamyl- L-dopa- a relatively renally specific dopaminergic prodrug in man. J. Auton. Pharmacol. 1990, 10, S103-S108.
    • (1990) J. Auton. Pharmacol , vol.10
    • Lee, M.1
  • 15
    • 0033373993 scopus 로고    scopus 로고
    • Oral administration of the dopamine prodrug docarpamine shortens need for drip infusion of dopamine in patients with low cardiac output syndrome after cardiac surgery
    • Matsubayashi, K.; Ueda, Y.; Ogino, H.; Sugita, T.; Sakakibara, Y.; Matsuyama, K.; Nomoto, T. Oral administration of the dopamine prodrug docarpamine shortens need for drip infusion of dopamine in patients with low cardiac output syndrome after cardiac surgery. Thorac. Cardiovasc. Surg. 1999, 47, 352-356.
    • (1999) Thorac. Cardiovasc. Surg , vol.47 , pp. 352-356
    • Matsubayashi, K.1    Ueda, Y.2    Ogino, H.3    Sugita, T.4    Sakakibara, Y.5    Matsuyama, K.6    Nomoto, T.7
  • 16
    • 0030961047 scopus 로고    scopus 로고
    • Effect of docarpamine, a novel orally active dopamine prodrug, on the formation of free and sulfoconjugated dopamine in patients who underwent cardiac surgery
    • Tano, K.; Yoshizumi, M.; Kitagawa, T.; Hori, T.; Kitaichi, T.; Itoh, K.; Katoh, I. Effect of docarpamine, a novel orally active dopamine prodrug, on the formation of free and sulfoconjugated dopamine in patients who underwent cardiac surgery. Life Sci. 1997, 61, 1469-1478.
    • (1997) Life Sci , vol.61 , pp. 1469-1478
    • Tano, K.1    Yoshizumi, M.2    Kitagawa, T.3    Hori, T.4    Kitaichi, T.5    Itoh, K.6    Katoh, I.7
  • 17
    • 0024390614 scopus 로고
    • A novel orally active dopamine prodrug TA-870 II. Evidence that TA-870 is a dopamine prodrug
    • Nishiyama, S.; Yamaguchi, I.; Akimoto, Y.; Yoshikawa, M.; Nakajima, H. A novel orally active dopamine prodrug TA-870 II. Evidence that TA-870 is a dopamine prodrug. J. Cardiovasc. Pharmacol. 1989, 14, 175-183.
    • (1989) J. Cardiovasc. Pharmacol , vol.14 , pp. 175-183
    • Nishiyama, S.1    Yamaguchi, I.2    Akimoto, Y.3    Yoshikawa, M.4    Nakajima, H.5
  • 19
    • 0027982230 scopus 로고
    • Pharmacokinetics of Dapsone and Amino Acid Prodrugs of Dapsone
    • Pochopin, N.L.; Charman, W.N.; Stella, V.J. Pharmacokinetics of Dapsone and Amino Acid Prodrugs of Dapsone. Drug Metab. Dispos. 1994, 22, 770-775.
    • (1994) Drug Metab. Dispos , vol.22 , pp. 770-775
    • Pochopin, N.L.1    Charman, W.N.2    Stella, V.J.3
  • 20
    • 0029054737 scopus 로고
    • Amino Acid Derivatives of Dapsone as Water-Soluble Prodrugs
    • Pochopin, N.L.; Charman, W.N.; Stella, V.J. Amino Acid Derivatives of Dapsone as Water-Soluble Prodrugs. Int. J. Pharm. 1995, 121, 157-167.
    • (1995) Int. J. Pharm , vol.121 , pp. 157-167
    • Pochopin, N.L.1    Charman, W.N.2    Stella, V.J.3
  • 22
    • 0032744429 scopus 로고    scopus 로고
    • Prodrugs of neuron-selective monoamine oxidase inhibitors: Amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes
    • Florvall, L.; Fagervall, I.; Larson, L.; Ross, S.B. Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes. Eur. J. Med. Chem. 1999, 34, 137-151.
    • (1999) Eur. J. Med. Chem , vol.34 , pp. 137-151
    • Florvall, L.1    Fagervall, I.2    Larson, L.3    Ross, S.B.4
  • 23
    • 33745254504 scopus 로고    scopus 로고
    • Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives
    • Tsuda M.; Terada T.; Irie M.; Katsura T.; Niida A.; Tomita K.; Fujii N.; Inui K.J. Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. Pharmaco.l Exp. Ther. 2006, 318, 455-460.
    • (2006) Pharmaco.l Exp. Ther , vol.318 , pp. 455-460
    • Tsuda, M.1    Terada, T.2    Irie, M.3    Katsura, T.4    Niida, A.5    Tomita, K.6    Fujii, N.7    Inui, K.J.8
  • 24
    • 0021992244 scopus 로고    scopus 로고
    • Bundgaard, H.; Falch, E. Allopurinol prodrugs. I. Synthesis, stability and physicochemical properties of various N1-acyl allopurinol derivatives. Int. J. Pharm. 1985, 23, 223-237.
    • Bundgaard, H.; Falch, E. Allopurinol prodrugs. I. Synthesis, stability and physicochemical properties of various N1-acyl allopurinol derivatives. Int. J. Pharm. 1985, 23, 223-237.
  • 25
    • 0033213530 scopus 로고    scopus 로고
    • Kinetics of hydrolysis of acetyl, valeroyl and nicotinoyl acyl derivatives of stobadine
    • Stankoviov, M. Kinetics of hydrolysis of acetyl, valeroyl and nicotinoyl acyl derivatives of stobadine. Life Sci. 1999, 65, 2007-2010.
    • (1999) Life Sci , vol.65 , pp. 2007-2010
    • Stankoviov, M.1
  • 26
    • 0034729742 scopus 로고    scopus 로고
    • A novel approach for a water-soluble long acting insulin prodrug: Design, preparation, and analysis of [(2-sulfo)-9-fluorenylmethoxycarbonyl]3-insulin
    • Gershonov, E.; Goldwaser, I.; Fridkin, M.; Shechter, Y. A novel approach for a water-soluble long acting insulin prodrug: design, preparation, and analysis of [(2-sulfo)-9-fluorenylmethoxycarbonyl]3-insulin. J. Med. Chem. 2000, 43, 2530-2537.
    • (2000) J. Med. Chem , vol.43 , pp. 2530-2537
    • Gershonov, E.1    Goldwaser, I.2    Fridkin, M.3    Shechter, Y.4
  • 27
    • 0038029374 scopus 로고    scopus 로고
    • (2-sulfo)-9- fluorenylmethoxycarbonyl]3-exendin-4 a long acting glucose-lowering prodrug
    • Shechter, Y.; Tsubery, H.; Fridkin, M. [(2-sulfo)-9- fluorenylmethoxycarbonyl]3-exendin-4 a long acting glucose-lowering prodrug. Biochem. Biophys. Res. Commun. 2003, 305, 386-391.
    • (2003) Biochem. Biophys. Res. Commun , vol.305 , pp. 386-391
    • Shechter, Y.1    Tsubery, H.2    Fridkin, M.3
  • 28
    • 0036286708 scopus 로고    scopus 로고
    • Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT)
    • Jordan, A.; Khan, T.; Malkin, H.; Osborn, H. Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg. Med. Chem. 2002, 10, 2625-2633.
    • (2002) Bioorg. Med. Chem , vol.10 , pp. 2625-2633
    • Jordan, A.1    Khan, T.2    Malkin, H.3    Osborn, H.4
  • 30
    • 0030048830 scopus 로고    scopus 로고
    • Identification of human liver cytochrome P450 enzymes that metabolize the nonsedating antihistamine loratadine. Formation of descarboethoxyloratadine by CYP3A4 and CYP2D6
    • Yumibe, N.; Huie, K.; Chen, K.J.; Snow, M.; Clement, R.P.; Cayen, M.N. Identification of human liver cytochrome P450 enzymes that metabolize the nonsedating antihistamine loratadine. Formation of descarboethoxyloratadine by CYP3A4 and CYP2D6. Biochem Pharmacol. 1996, 51, 165-172.
    • (1996) Biochem Pharmacol , vol.51 , pp. 165-172
    • Yumibe, N.1    Huie, K.2    Chen, K.J.3    Snow, M.4    Clement, R.P.5    Cayen, M.N.6
  • 31
    • 18544394511 scopus 로고    scopus 로고
    • Desloratadine for the treatment of chronic urticaria
    • Monroe, E. Desloratadine for the treatment of chronic urticaria, Skin Therapy Lett. 2002, 7, 1-2,5.
    • (2002) Skin Therapy Lett , vol.7 , Issue.1-2 , pp. 5
    • Monroe, E.1
  • 33
    • 33745929348 scopus 로고    scopus 로고
    • Review of capecitabine as oral treatment of gastric, gastroesophageal, and esophageal cancers
    • Ajani, J. Review of capecitabine as oral treatment of gastric, gastroesophageal, and esophageal cancers. Cancer 2006, 107, 221-231.
    • (2006) Cancer , vol.107 , pp. 221-231
    • Ajani, J.1
  • 34
    • 38349105297 scopus 로고    scopus 로고
    • Identification of human intestinal carboxylesterase as the primary enzyme for activation of a doxazolidine carbamate prodrug
    • Barthel, B.L.; Torres, R.C.; Hyatt, J.L.; Edwards, C.C.; Hatfield, M.J.; Potter, P.M.; Koch, T.H. Identification of human intestinal carboxylesterase as the primary enzyme for activation of a doxazolidine carbamate prodrug. J. Med. Chem. 2008, 51, 298-304.
    • (2008) J. Med. Chem , vol.51 , pp. 298-304
    • Barthel, B.L.1    Torres, R.C.2    Hyatt, J.L.3    Edwards, C.C.4    Hatfield, M.J.5    Potter, P.M.6    Koch, T.H.7
  • 35
    • 0343026463 scopus 로고    scopus 로고
    • Prodrugs for improved ocular drug delivery
    • Järvinen, T.; Järvinen, K. Prodrugs for improved ocular drug delivery. Adv. Drug Deliv. Rev. 1996, 19, 203-224.
    • (1996) Adv. Drug Deliv. Rev , vol.19 , pp. 203-224
    • Järvinen, T.1    Järvinen, K.2
  • 36
    • 0032104465 scopus 로고    scopus 로고
    • Alkylcarbonyloxymethyl prodrugs of theophylline: Topical delivery of theophylline
    • Kerr, D.; Roberts, W.; Tebbett, I.; Sloan, K. /-Alkylcarbonyloxymethyl prodrugs of theophylline: topical delivery of theophylline. Int. J. Pharm. 1998, 167, 37-48.
    • (1998) Int. J. Pharm , vol.167 , pp. 37-48
    • Kerr, D.1    Roberts, W.2    Tebbett, I.3    Sloan, K.4
  • 37
    • 0033549849 scopus 로고    scopus 로고
    • Novel prodrug approach for tertiary amines: Synthesis and preliminary evaluation of N-phosphonooxymethyl prodrugs
    • Krise, J.P.; Zygmunt, J.; Georg, G.I; Stella, V.J. Novel prodrug approach for tertiary amines: synthesis and preliminary evaluation of N-phosphonooxymethyl prodrugs. J. Med. Chem. 1999, 42, 3094-3100.
    • (1999) J. Med. Chem , vol.42 , pp. 3094-3100
    • Krise, J.P.1    Zygmunt, J.2    Georg, G.I.3    Stella, V.J.4
  • 38
    • 0032820005 scopus 로고    scopus 로고
    • A novel prodrug approach for tertiary amines. 2. Physicochemical and in vitro enzymatic evaluation of N-phosphonooxymethyl prodrugs
    • Krise, J.P.; Narisawa, S.; Stella, V.J. A novel prodrug approach for tertiary amines. 2. Physicochemical and in vitro enzymatic evaluation of N-phosphonooxymethyl prodrugs. J. Pharm. Sci. 1999, 88, 922-927.
    • (1999) J. Pharm. Sci , vol.88 , pp. 922-927
    • Krise, J.P.1    Narisawa, S.2    Stella, V.J.3
  • 39
    • 0032840753 scopus 로고    scopus 로고
    • A novel prodrug approach for tertiary amines. 3. In vivo evaluation of two N-phosphonooxymethyl prodrugs in rats and dogs
    • Krise, J.P.; Charman, W.N.; Charman, S.A.; Stella, V.J. A novel prodrug approach for tertiary amines. 3. In vivo evaluation of two N-phosphonooxymethyl prodrugs in rats and dogs. J. Pharm. Sci. 1999, 88, 928-932.
    • (1999) J. Pharm. Sci , vol.88 , pp. 928-932
    • Krise, J.P.1    Charman, W.N.2    Charman, S.A.3    Stella, V.J.4
  • 40
    • 0342833001 scopus 로고    scopus 로고
    • A Case for Prodrugs: Fosphenytoin
    • Stella, V.J. A Case for Prodrugs: Fosphenytoin. Adv. Drug Del. Rev. 1996; 19, 311-330.
    • (1996) Adv. Drug Del. Rev , vol.19 , pp. 311-330
    • Stella, V.J.1
  • 41
    • 0023605117 scopus 로고
    • N-(acyloxyalkoxycarbonyl) derivatives as potential prodrugs for amines. I. Kinetics and mechanism of degradation in aqueous solutions
    • Gogate, U.S.; Repta, A.J.; Alexander, J. N-(acyloxyalkoxycarbonyl) derivatives as potential prodrugs for amines. I. Kinetics and mechanism of degradation in aqueous solutions. Int. J. Pharm. 1987, 40, 235-248.
    • (1987) Int. J. Pharm , vol.40 , pp. 235-248
    • Gogate, U.S.1    Repta, A.J.2    Alexander, J.3
  • 42
    • 0023605394 scopus 로고
    • N-(acyloxyalkoxycarbonyl) derivatives as potential prodrugs for amines. II. Esterase-catalysed release of parent amines from model prodrugs
    • Gogate, U.S.; Repta, A.J. N-(acyloxyalkoxycarbonyl) derivatives as potential prodrugs for amines. II. Esterase-catalysed release of parent amines from model prodrugs. Int. J. Pharm. 1987, 40, 249-255.
    • (1987) Int. J. Pharm , vol.40 , pp. 249-255
    • Gogate, U.S.1    Repta, A.J.2
  • 43
    • 0030670763 scopus 로고    scopus 로고
    • Synthesis of (alkoxycarbonyloxy) methyl, (acyloxy)methyl and (oxodioxolenyl)methyl carbamates as bioreversible prodrug moieties for amines
    • Li, Z.; Bitha, P.; Lang, S.; Lin, Y. Synthesis of (alkoxycarbonyloxy) methyl, (acyloxy)methyl and (oxodioxolenyl)methyl carbamates as bioreversible prodrug moieties for amines. Bioorg. Med. Chem. Lett. 1997, 22, 2909-2912.
    • (1997) Bioorg. Med. Chem. Lett , vol.22 , pp. 2909-2912
    • Li, Z.1    Bitha, P.2    Lang, S.3    Lin, Y.4
  • 44
    • 0004255131 scopus 로고
    • Bundgaard, H, Ed, Elsevier: Amsterdam, Chapter 11
    • Bodor, N. in Design of prodrugs; Bundgaard, H., Ed.; Elsevier: Amsterdam, 1985; Chapter 11.
    • (1985) Design of prodrugs
    • Bodor, N.1
  • 46
    • 0000658454 scopus 로고
    • (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: Increased permeation through biological membranes
    • Alexander, J.; Cargyl, R.; Michelson, S.; Schwam, H. (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: increased permeation through biological membranes. J. Med. Chem. 1988, 31, 318-322.
    • (1988) J. Med. Chem , vol.31 , pp. 318-322
    • Alexander, J.1    Cargyl, R.2    Michelson, S.3    Schwam, H.4
  • 48
    • 4644328982 scopus 로고    scopus 로고
    • Cundy, K.C.; Branch, R.; Chernov-Rogan, T.; Dias, T.; Estrada, T.; Hold, K.; Koller, K.; Liu, X.; Mann, A.; Panuwat, M.; Raillard, S.P.; Upadhyay, S.; Wu, Q.Q.; Xiang, J.N.; Yan, H.; Zerangue, N.; Zhou, C.X.; Barrett, R.W.; Gallop, M.A. XP13512 [(+/-)-1-([(α-isobutanoyloxyethoxy) carbonyl]aminomethyl)-1- cyclohexane acetic acid], a Novel Gabapentin Prodrug: I. Design, Synthesis, Enzymatic Conversion to Gabapentin, and Transport by Intestinal Solute Transporters. J. Pharmacol. Exp. Ther. 2004, 311, 315-323.
    • Cundy, K.C.; Branch, R.; Chernov-Rogan, T.; Dias, T.; Estrada, T.; Hold, K.; Koller, K.; Liu, X.; Mann, A.; Panuwat, M.; Raillard, S.P.; Upadhyay, S.; Wu, Q.Q.; Xiang, J.N.; Yan, H.; Zerangue, N.; Zhou, C.X.; Barrett, R.W.; Gallop, M.A. XP13512 [(+/-)-1-([(α-isobutanoyloxyethoxy) carbonyl]aminomethyl)-1- cyclohexane acetic acid], a Novel Gabapentin Prodrug: I. Design, Synthesis, Enzymatic Conversion to Gabapentin, and Transport by Intestinal Solute Transporters. J. Pharmacol. Exp. Ther. 2004, 311, 315-323.
  • 49
    • 4644251930 scopus 로고    scopus 로고
    • XP13512 [(+/-)-1-([(α-isobutanoyloxyethoxy) carbonyl] aminomethyl)-1-cyclohexane acetic acid], a Novel Gabapentin Prodrug: II. Improved Oral Bioavailability, Dose Proportionality, and Colonic Absorption Compared with Gabapentin in Rats and Monkeys
    • Cundy, K.C.; Annamalai, T.; Bu, L.; De Vera, J.; Estrela, J.; Luo, W.; Shirsat, P.; Torneros, A.; Yao, F.; Zou, J.; Barrett, R.W.; Gallop, M.A. XP13512 [(+/-)-1-([(α-isobutanoyloxyethoxy) carbonyl] aminomethyl)-1-cyclohexane acetic acid], a Novel Gabapentin Prodrug: II. Improved Oral Bioavailability, Dose Proportionality, and Colonic Absorption Compared with Gabapentin in Rats and Monkeys. J. Pharmacol. Exp. Ther. 2004, 311, 324-333.
    • (2004) J. Pharmacol. Exp. Ther , vol.311 , pp. 324-333
    • Cundy, K.C.1    Annamalai, T.2    Bu, L.3    De Vera, J.4    Estrela, J.5    Luo, W.6    Shirsat, P.7    Torneros, A.8    Yao, F.9    Zou, J.10    Barrett, R.W.11    Gallop, M.A.12
  • 51
    • 0027282618 scopus 로고
    • Phosphoryloxymethyl carbamates and carbonates - novel water soluble prodrugs for amines and hindered alcohols
    • Safadi, M.; Oliyai, R.; Stella, V.J. Phosphoryloxymethyl carbamates and carbonates - novel water soluble prodrugs for amines and hindered alcohols. Pharm. Res. 1993, 10, 1350-1355.
    • (1993) Pharm. Res , vol.10 , pp. 1350-1355
    • Safadi, M.1    Oliyai, R.2    Stella, V.J.3
  • 52
    • 0032460731 scopus 로고    scopus 로고
    • The origin of 20th century discoveries transforming clinical gastroenterology
    • Kirshner, J. The origin of 20th century discoveries transforming clinical gastroenterology. Am. J. Gastroenterol. 1998, 93, 862-871.
    • (1998) Am. J. Gastroenterol , vol.93 , pp. 862-871
    • Kirshner, J.1
  • 53
    • 0036897124 scopus 로고    scopus 로고
    • Rational selection of oral 5-aminosalicylate formulations and prodrugs for the treatment of ulcerative colitis
    • Sandborn, W. Rational selection of oral 5-aminosalicylate formulations and prodrugs for the treatment of ulcerative colitis. Am. J. Gastroenterol. 2002, 97, 2939-2941.
    • (2002) Am. J. Gastroenterol , vol.97 , pp. 2939-2941
    • Sandborn, W.1
  • 54
    • 0035155157 scopus 로고    scopus 로고
    • Colon-specific prodrug of 5-aminosalicylic acid: Synthesis and in vitro/in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid
    • Jung, Y.; Lee, J.; Kim, Y. Colon-specific prodrug of 5-aminosalicylic acid: synthesis and in vitro/in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid. J. Pharm. Sci. 2001, 90, 1767-1775.
    • (2001) J. Pharm. Sci , vol.90 , pp. 1767-1775
    • Jung, Y.1    Lee, J.2    Kim, Y.3
  • 55
    • 0031742631 scopus 로고    scopus 로고
    • Bioreductive therapies: An overview of drugs and their mechanism of action
    • Rauth, A.; Melo, T.; Misra, V. Bioreductive therapies: an overview of drugs and their mechanism of action. Int. J. Radiat. Oncol. Biol. Phys. 1998, 42, 755-762.
    • (1998) Int. J. Radiat. Oncol. Biol. Phys , vol.42 , pp. 755-762
    • Rauth, A.1    Melo, T.2    Misra, V.3
  • 56
    • 0036569920 scopus 로고    scopus 로고
    • Modifying rates of reductive elimination of leaving groups from indolequinone prodrugs: A key factor in controlling hypoxia-selective drug release
    • Everett, S.; Swann, E.; Naylor, M.; Stratford, M.; Patel, K.; Tian, N.; Newman, R.; Vojnovic, B.; Moody, C.; Wardman, P. Modifying rates of reductive elimination of leaving groups from indolequinone prodrugs: a key factor in controlling hypoxia-selective drug release. Biochem. Pharmacol. 2002, 63, 1629-1639.
    • (2002) Biochem. Pharmacol , vol.63 , pp. 1629-1639
    • Everett, S.1    Swann, E.2    Naylor, M.3    Stratford, M.4    Patel, K.5    Tian, N.6    Newman, R.7    Vojnovic, B.8    Moody, C.9    Wardman, P.10
  • 57
    • 0028292905 scopus 로고
    • Relationships between structure and kinetics of cyclization-activated aromatic mustards
    • Atwell, G.; Sykes, B.; O'Connor, C.; Denny, W. Relationships between structure and kinetics of cyclization-activated aromatic mustards. J. Med. Chem. 1994, 37, 371-380.
    • (1994) J. Med. Chem , vol.37 , pp. 371-380
    • Atwell, G.1    Sykes, B.2    O'Connor, C.3    Denny, W.4
  • 58
    • 34547653834 scopus 로고    scopus 로고
    • Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: A role for NADPH:cytochrome P450 oxidoreductase under hypoxia
    • Guise, C.P.; Wang, A.T.; Theil, A.; Bridewell, D.J.; Wilson, W.R.; Patterson, A.V. Identification of human reductases that activate the dinitrobenzamide mustard prodrug PR-104A: a role for NADPH:cytochrome P450 oxidoreductase under hypoxia. Biochem. Pharmacol. 2007, 74, 810-820.
    • (2007) Biochem. Pharmacol , vol.74 , pp. 810-820
    • Guise, C.P.1    Wang, A.T.2    Theil, A.3    Bridewell, D.J.4    Wilson, W.R.5    Patterson, A.V.6
  • 59
    • 0032972169 scopus 로고    scopus 로고
    • N-substituted 2-(2,6-dinitrophenylamino)propanamides: Novel prodrugs that release a primary amine via nitroreduction and intramolecular cyclization
    • Sykes, B.; Atwell, G.; Hogg, A.; Wilson, W.; O'Connor C.; Denny W. N-substituted 2-(2,6-dinitrophenylamino)propanamides: novel prodrugs that release a primary amine via nitroreduction and intramolecular cyclization. J. Med. Chem. 1999, 42, 346-355.
    • J. Med. Chem , vol.1999 , Issue.42 , pp. 346-355
    • Sykes, B.1    Atwell, G.2    Hogg, A.3    Wilson, W.4    O'Connor, C.5    Denny, W.6
  • 60
    • 0002934074 scopus 로고    scopus 로고
    • The 4-azidoberazyloxycarbonyl function: Application as a novel protecting group and potential prodrug modification for amines
    • Griffin, R.; Evers, E.; Davison, R.; Gibson, A.; Layton, D.; Irwin, W. The 4-azidoberazyloxycarbonyl function: application as a novel protecting group and potential prodrug modification for amines. J. Chem. Soc. Perkin Trans. 1 1996, 11, 1205-1211.
    • (1996) J. Chem. Soc. Perkin Trans. 1 , vol.11 , pp. 1205-1211
    • Griffin, R.1    Evers, E.2    Davison, R.3    Gibson, A.4    Layton, D.5    Irwin, W.6
  • 61
    • 0029935930 scopus 로고    scopus 로고
    • Tertiary amines N-oxides as bioreductive drugs: DACA N-oxide, nitracarine N-oxide and AQ4N
    • Wilson, W.; Denny, W.; Pullen, S.; Thompson, K.; Li, A.; Patterson, L.; Lee, H. Tertiary amines N-oxides as bioreductive drugs: DACA N-oxide, nitracarine N-oxide and AQ4N. Br. J. Cancer 1996, 27, S43-S47.
    • (1996) Br. J. Cancer , vol.27
    • Wilson, W.1    Denny, W.2    Pullen, S.3    Thompson, K.4    Li, A.5    Patterson, L.6    Lee, H.7
  • 62
    • 0016770646 scopus 로고
    • Delivery of a quaternary pyridinium salt across the blood-brain barrier by its dihydropyridine derivative
    • Bodor, N.; Sheck, E.; Higuchi, T. Delivery of a quaternary pyridinium salt across the blood-brain barrier by its dihydropyridine derivative. Science 1975, 190, 155-156.
    • (1975) Science , vol.190 , pp. 155-156
    • Bodor, N.1    Sheck, E.2    Higuchi, T.3
  • 63
    • 0019843193 scopus 로고
    • Site-specific, sustained release of drugs to the brain
    • Bodor, N.; Farag, H.; Brewster, M.; Site-specific, sustained release of drugs to the brain. Science 1981, 217, 1370-1372.
    • (1981) Science , vol.217 , pp. 1370-1372
    • Bodor, N.1    Farag, H.2    Brewster, M.3
  • 64
    • 0024827312 scopus 로고
    • Chemical delivery systems for drugs containing an amino group: Synthesis and properties of some pyridine derivatives of desipramine
    • Pop, E.; Wu, M.; Shek, E.; Bodor, N. Chemical delivery systems for drugs containing an amino group: synthesis and properties of some pyridine derivatives of desipramine. Drug. Des. Deliv. 1989, 5, 93-115.
    • (1989) Drug. Des. Deliv , vol.5 , pp. 93-115
    • Pop, E.1    Wu, M.2    Shek, E.3    Bodor, N.4
  • 65
    • 0020571913 scopus 로고
    • Redox delivery system for brain-specific, sustained release of dopamine
    • Bodor, N.; Simpkins J. Redox delivery system for brain-specific, sustained release of dopamine. Science 1983, 221, 65-67.
    • (1983) Science , vol.221 , pp. 65-67
    • Bodor, N.1    Simpkins, J.2
  • 66
    • 0022001038 scopus 로고
    • Direct evidence for brain-specific release of dopamine from a redox delivery system
    • Simpkins, J.; Bodor, N.; Enz A. Direct evidence for brain-specific release of dopamine from a redox delivery system. J. Pharm. Sci. 1985, 10, 1033-1036.
    • (1985) J. Pharm. Sci , vol.10 , pp. 1033-1036
    • Simpkins, J.1    Bodor, N.2    Enz, A.3
  • 67
    • 0028457106 scopus 로고
    • Improved brain delivery of antiviral agents through the use of redox targeting
    • Brewster, M.; Bodor, N. Improved brain delivery of antiviral agents through the use of redox targeting. Adv. Drug Deliv. Rev. 1994, 14, 177-197.
    • (1994) Adv. Drug Deliv. Rev , vol.14 , pp. 177-197
    • Brewster, M.1    Bodor, N.2
  • 68
    • 0029818542 scopus 로고    scopus 로고
    • Redox targeting of LY231617, an antioxidant with potential use in the treatment of brain damage
    • Pop, E.; Sot, F.; Anderson, W.; Panetta, J.; Estes, K.; Bodor, N.; Brewster, M. Redox targeting of LY231617, an antioxidant with potential use in the treatment of brain damage. Int. J. Pharm. 1996, 140, 33-44.
    • (1996) Int. J. Pharm , vol.140 , pp. 33-44
    • Pop, E.1    Sot, F.2    Anderson, W.3    Panetta, J.4    Estes, K.5    Bodor, N.6    Brewster, M.7
  • 69
    • 0033851778 scopus 로고    scopus 로고
    • Targeting drug to the brain by redox chemical delivery systems
    • Prokai, L.; Prokai-Tatri, L.; Bodor, N. Targeting drug to the brain by redox chemical delivery systems. Med. Res. Rev. 2000, 20, 367-416.
    • (2000) Med. Res. Rev , vol.20 , pp. 367-416
    • Prokai, L.1    Prokai-Tatri, L.2    Bodor, N.3
  • 70
    • 0028835703 scopus 로고
    • Drug delivery to the brain. DOPA prodrugs based on a ring-closure reaction to quaternary thiazolium compounds
    • Ishikura, T.; Senou, T.; Ishiara, H.; Kato, T.; Ito, T. Drug delivery to the brain. DOPA prodrugs based on a ring-closure reaction to quaternary thiazolium compounds. Int. J. Pharm. 1995, 116, 51-63.
    • (1995) Int. J. Pharm , vol.116 , pp. 51-63
    • Ishikura, T.1    Senou, T.2    Ishiara, H.3    Kato, T.4    Ito, T.5
  • 71
    • 12244265540 scopus 로고    scopus 로고
    • New carrier for specific delivery of drugs to the brain
    • Sheha, M.; Al-Tayeb, A.; El-Sherief, H.; Farag, H. New carrier for specific delivery of drugs to the brain. Bioorg. Med. Chem. 2003, 11, 1865-1872.
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 1865-1872
    • Sheha, M.1    Al-Tayeb, A.2    El-Sherief, H.3    Farag, H.4
  • 72
    • 0033539039 scopus 로고    scopus 로고
    • Drug delivery systems employing 1,4- or 1,6-elimination: Poly(ethylene glycol) prodrugs of amine-containing compounds
    • Greenwald, R.; Pendri, A.; Conover, C.; Zhao, H.; Choe, Y.; Martinez, A.; Shum, K.; Guan, S. Drug delivery systems employing 1,4- or 1,6-elimination: poly(ethylene glycol) prodrugs of amine-containing compounds. J. Med. Chem. 1999, 42, 3657-3667.
    • (1999) J. Med. Chem , vol.42 , pp. 3657-3667
    • Greenwald, R.1    Pendri, A.2    Conover, C.3    Zhao, H.4    Choe, Y.5    Martinez, A.6    Shum, K.7    Guan, S.8
  • 73
    • 0035816168 scopus 로고    scopus 로고
    • PEG drugs: An overview
    • Greenwald, R. PEG drugs: an overview. J. Control. Release 2001, 74, 159-171.
    • (2001) J. Control. Release , vol.74 , pp. 159-171
    • Greenwald, R.1
  • 74
    • 0034628515 scopus 로고    scopus 로고
    • Drug delivery systems based on trimethyl lock lactonization: Poly(ethylene glycol) prodrugs of amine-containing compounds
    • Greenwald, R.; Choe, Y.; Conover, C.; Shum, K.; Wu, D.; Royzen, M. Drug delivery systems based on trimethyl lock lactonization: poly(ethylene glycol) prodrugs of amine-containing compounds. J. Med. Chem. 2000, 43, 475-487.
    • (2000) J. Med. Chem , vol.43 , pp. 475-487
    • Greenwald, R.1    Choe, Y.2    Conover, C.3    Shum, K.4    Wu, D.5    Royzen, M.6
  • 75
    • 0037659202 scopus 로고    scopus 로고
    • Tripartate poly(ethylene glycol) prodrugs of the open lactone form of camptothecin
    • Greenwald, R.; Zhao, H.; Xia, J. Tripartate poly(ethylene glycol) prodrugs of the open lactone form of camptothecin. Bioorg. Med. Chem. 2003, 11, 2635-2639.
    • (2003) Bioorg. Med. Chem , vol.11 , pp. 2635-2639
    • Greenwald, R.1    Zhao, H.2    Xia, J.3
  • 77
    • 34548026715 scopus 로고    scopus 로고
    • Stella, V.J, Borchardt, R.T, Hageman, M.J, Oliyai, R, Maag, H, Tilley, J.W, Eds, Springer: New York, Chapter 2.3.1, pp
    • .Greenwald, R.B.; Zhao, H. In Prodrugs: Challenges and Rewards Part I; Stella, V.J.; Borchardt, R.T.; Hageman, M.J.; Oliyai, R.; Maag, H.; Tilley, J.W, Eds.; Springer: New York, 2007; Chapter 2.3.1, pp. 283-337.
    • (2007) Prodrugs: Challenges and Rewards Part I , pp. 283-337
    • Greenwald, R.B.1    Zhao, H.2
  • 78
    • 0026734164 scopus 로고
    • Low molecular weight proteins for renal drug targeting. Preparation of Drug-protein conjugates and drug-spacer derivatives and their catabolism in renal cortex homogenates and lysosomal lysates
    • Franssen, E.; Koiter, J.; Kuipers, C.; Bruins, A.; Moolenaar, F.; Zeeuw ,D.; Kruizinga, W.; Kellog, R.; Meijer, D. Low molecular weight proteins for renal drug targeting. Preparation of Drug-protein conjugates and drug-spacer derivatives and their catabolism in renal cortex homogenates and lysosomal lysates. J. Med. Chem. 1992, 35, 1246-1459.
    • (1992) J. Med. Chem , vol.35 , pp. 1246-1459
    • Franssen, E.1    Koiter, J.2    Kuipers, C.3    Bruins, A.4    Moolenaar, F.5    Zeeuw, D.6    Kruizinga, W.7    Kellog, R.8    Meijer, D.9
  • 79
    • 0024461551 scopus 로고
    • Physicochemical Propertiesband Antitumor Activities of Polymeric Prodrugs of Mitomycin C with Different Regeneration Rates
    • Takakura, Y, Matsumoto, S, Hashida, M, Sezaki, H. Physicochemical Propertiesband Antitumor Activities of Polymeric Prodrugs of Mitomycin C with Different Regeneration Rates. J. Control. Release 1989, 10, 97-105.
    • (1989) J. Control. Release , vol.10 , pp. 97-105
    • Takakura, Y.1    Matsumoto, S.2    Hashida, M.3    Sezaki, H.4
  • 80
    • 14144250496 scopus 로고    scopus 로고
    • A new amino-masking group capable of pH-triggered amino-drug release
    • Gilmer, J.F.; Simplício, A.L.; Clancy, J.C. A new amino-masking group capable of pH-triggered amino-drug release. Eur. J. Pharm. Sci. 2005, 24, 315-323.
    • (2005) Eur. J. Pharm. Sci , vol.24 , pp. 315-323
    • Gilmer, J.F.1    Simplício, A.L.2    Clancy, J.C.3
  • 81
    • 34247637637 scopus 로고    scopus 로고
    • β-Aminoketones as prodrugs with pH-controlled activation
    • Gilmer, J.F.; Simplício, A.L.; Clancy, J.C. β-Aminoketones as prodrugs with pH-controlled activation. Int. J. Pharm. 2007, 336, 208-214.
    • (2007) Int. J. Pharm , vol.336 , pp. 208-214
    • Gilmer, J.F.1    Simplício, A.L.2    Clancy, J.C.3
  • 82
    • 0028801105 scopus 로고    scopus 로고
    • Krause, M.; Rouleau, A.; Stark, H.; Luger, P.; Lipp, R.; Garbarg, M.; Schwartz, J-C.; Schunack, W. Synthesis, X-ray christalography and pharmacokinetics of novel azomethine prodrugs of R-α- methylhistamine: highly potent and selective histamine H3-receptor agonists. J. Med. Chem. 1995, 38, 4070-4079.
    • Krause, M.; Rouleau, A.; Stark, H.; Luger, P.; Lipp, R.; Garbarg, M.; Schwartz, J-C.; Schunack, W. Synthesis, X-ray christalography and pharmacokinetics of novel azomethine prodrugs of R-α- methylhistamine: highly potent and selective histamine H3-receptor agonists. J. Med. Chem. 1995, 38, 4070-4079.
  • 83
    • 0034866384 scopus 로고    scopus 로고
    • Azomethine prodrugs of R-α-methylhistamine, a highly potent and selective histamine H3-receptor agonist
    • Krause, M.; Stark, H.; Schunack, W. Azomethine prodrugs of R-α-methylhistamine, a highly potent and selective histamine H3-receptor agonist. Curr. Med. Chem. 2001, 8, 1329-1340
    • (2001) Curr. Med. Chem , vol.8 , pp. 1329-1340
    • Krause, M.1    Stark, H.2    Schunack, W.3
  • 84
    • 0035191953 scopus 로고    scopus 로고
    • Enzyme-catalyzed prodrug approaches for the histamine H3-receptor agonist R-α-methylhistamine
    • Stark, H.; Krause, M.; Rouleau, A.; Garbarg, M.; Schwartz, J-C. Schunack, W. Enzyme-catalyzed prodrug approaches for the histamine H3-receptor agonist R-α-methylhistamine. Bioorg. Med. Chem. 2001, 9, 191-198.
    • (2001) Bioorg. Med. Chem , vol.9 , pp. 191-198
    • Stark, H.1    Krause, M.2    Rouleau, A.3    Garbarg, M.4    Schwartz, J.-C.5    Schunack, W.6
  • 85
    • 0018875952 scopus 로고
    • Prodrugs as drug delivery systems IV: N-mannich bases as potential novel prodrugs for amides, ureides, amines, and other NH-acidic compounds
    • Bundgaard, H.; Johansen, M. Prodrugs as drug delivery systems IV: N-mannich bases as potential novel prodrugs for amides, ureides, amines, and other NH-acidic compounds. J. Pharm. Sci. 1980, 69, 44-46.
    • (1980) J. Pharm. Sci , vol.69 , pp. 44-46
    • Bundgaard, H.1    Johansen, M.2
  • 87
    • 0019122255 scopus 로고
    • Pro-drugs as drug delivery systems. XIII. Kinetics of decomposition of N-Mannich bases of salicylamide and assessment of their suitability as possible pro-drugs for amines
    • Johansen, M.; Bundgaard, H. Pro-drugs as drug delivery systems. XIII. Kinetics of decomposition of N-Mannich bases of salicylamide and assessment of their suitability as possible pro-drugs for amines. Int. J. Pharm. 1980, 7, 119-127.
    • (1980) Int. J. Pharm , vol.7 , pp. 119-127
    • Johansen, M.1    Bundgaard, H.2
  • 88
    • 0022593016 scopus 로고
    • Prodrugs as drug delivery systems. 43. O-acyloxymethyl salicylamide N-Mannich bases as double prodrug forms for amines
    • Bundgaard, H.; Lixbüll, U.; Falch, E. Prodrugs as drug delivery systems. 43. O-acyloxymethyl salicylamide N-Mannich bases as double prodrug forms for amines. Int. J. Pharm. 1986, 29, 19-28.
    • (1986) Int. J. Pharm , vol.29 , pp. 19-28
    • Bundgaard, H.1    Lixbüll, U.2    Falch, E.3
  • 89
    • 0019481186 scopus 로고
    • Hydrolysis of N-Mannich bases and its consequences for the biological testing of such agents
    • Bundgaard, H.; Johansen, M. Hydrolysis of N-Mannich bases and its consequences for the biological testing of such agents. Int. J. Pharm. 1981, 9, 7-16.
    • (1981) Int. J. Pharm , vol.9 , pp. 7-16
    • Bundgaard, H.1    Johansen, M.2
  • 90
    • 41649113642 scopus 로고    scopus 로고
    • Johansen, M.; Bundgaard, H.; Pro-drugs as drug delivery systems. XXIV. N-Mannich bases as bioreversible lipophilic transport forms for ephedrine, phenethylamine and other amines. Arch. Pharm. Chemi. Sci. Ed. 1982, 10, 111-115.
    • Johansen, M.; Bundgaard, H.; Pro-drugs as drug delivery systems. XXIV. N-Mannich bases as bioreversible lipophilic transport forms for ephedrine, phenethylamine and other amines. Arch. Pharm. Chemi. Sci. Ed. 1982, 10, 111-115.
  • 93
    • 38149074045 scopus 로고    scopus 로고
    • Chemotherapeutic bone-targeted bisphosphonate prodrugs with hydrolytic mode of activation
    • Erez, R.; Ebner, S.; Attali, B.; Shabat, D. Chemotherapeutic bone-targeted bisphosphonate prodrugs with hydrolytic mode of activation. Bioorg. Med. Chem. Lett. 2008, 18, 816-820.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 816-820
    • Erez, R.1    Ebner, S.2    Attali, B.3    Shabat, D.4
  • 95
    • 0031920093 scopus 로고    scopus 로고
    • Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent
    • Tougou, K.; Nakamura, A.; Watanabe, S.; Okuyama Y.; Morino, A. Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent, Drug. Metab. Dispos. 1998, 26, 355-359.
    • (1998) Drug. Metab. Dispos , vol.26 , pp. 355-359
    • Tougou, K.1    Nakamura, A.2    Watanabe, S.3    Okuyama, Y.4    Morino, A.5
  • 97
    • 0019868018 scopus 로고
    • Biopharmaceutical study on the oral and rectal administration of enamine prodrugs of amino acid-like β-lactam antibiotics in rabbits
    • Murakami, T.; Tamauchi, H.; Yamazaki, M.; Kubo, K.; Kamada, A.; Yata, K. Biopharmaceutical study on the oral and rectal administration of enamine prodrugs of amino acid-like β-lactam antibiotics in rabbits. Chem. Pharm. Bull. 1981, 29, 1986-1997.
    • (1981) Chem. Pharm. Bull , vol.29 , pp. 1986-1997
    • Murakami, T.1    Tamauchi, H.2    Yamazaki, M.3    Kubo, K.4    Kamada, A.5    Yata, K.6
  • 98
    • 37049132565 scopus 로고
    • A study of the rates of hydrolysis of certain enaminones
    • Dixon, K.; Greenhill, J. A study of the rates of hydrolysis of certain enaminones. J. Chem. Soc. Perkin. Trans. 1I 1974, 2, 164-168.
    • (1974) J. Chem. Soc. Perkin. Trans , vol.1 I , Issue.2 , pp. 164-168
    • Dixon, K.1    Greenhill, J.2
  • 99
    • 0025271073 scopus 로고
    • Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines
    • Naringrekar, V.; Stella, V.J. Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines. J. Pharm. Sci. 1990, 79, 138-146.
    • (1990) J. Pharm. Sci , vol.79 , pp. 138-146
    • Naringrekar, V.1    Stella, V.J.2
  • 100
    • 0022576486 scopus 로고
    • Prodrugs as drug delivery systems. 42. 2-Hydroxymethylbenzamides and 2-acyloxymethylbenzamides as potential prodrug forms for amines
    • Nielsen, N.; Bundgaard, H. Prodrugs as drug delivery systems. 42. 2-Hydroxymethylbenzamides and 2-acyloxymethylbenzamides as potential prodrug forms for amines. Int. J. Pharm. 1986, 29, 9-18.
    • (1986) Int. J. Pharm , vol.29 , pp. 9-18
    • Nielsen, N.1    Bundgaard, H.2
  • 101
    • 0029892257 scopus 로고    scopus 로고
    • Structural Analysis of a facile lactonization system facilitated by a "trimethyl lock
    • Wang B.; Nicolaou, M.; Liu, S.; Borchardt, R.T. Structural Analysis of a facile lactonization system facilitated by a "trimethyl lock". Bioorg. Chem. 1996, 24, 39-49.
    • (1996) Bioorg. Chem , vol.24 , pp. 39-49
    • Wang, B.1    Nicolaou, M.2    Liu, S.3    Borchardt, R.T.4
  • 102
    • 0025907182 scopus 로고
    • Amine prodrugs which utilize hydroxy amide lactonization. II. A potential esterase-sensitive amide prodrug
    • Ameberry, K.; Gerstenberger, A.; Borchardt, R.T. Amine prodrugs which utilize hydroxy amide lactonization. II. A potential esterase-sensitive amide prodrug. Pharm. Res. 1991, 8, 455-461.
    • (1991) Pharm. Res , vol.8 , pp. 455-461
    • Ameberry, K.1    Gerstenberger, A.2    Borchardt, R.T.3
  • 103
    • 0025869654 scopus 로고
    • Amine prodrugs which utilize hydroxy amide lactonization. I. A potential redox-sensitive amide prodrug
    • Amsberry, K.; Borchardt, R.T. Amine prodrugs which utilize hydroxy amide lactonization. I. A potential redox-sensitive amide prodrug. Pharm. Res. 1991, 8, 323-330.
    • (1991) Pharm. Res , vol.8 , pp. 323-330
    • Amsberry, K.1    Borchardt, R.T.2
  • 104
    • 0029989850 scopus 로고    scopus 로고
    • Phosphate prodrugs for amines utilizing a fast intramolecular hydroxy amide lactonization
    • Nicolaou M.; Yuan, C.; Borchardt, R.T. Phosphate prodrugs for amines utilizing a fast intramolecular hydroxy amide lactonization. J. Org. Chem. 1996, 61, 8636-8641.
    • (1996) J. Org. Chem , vol.61 , pp. 8636-8641
    • Nicolaou, M.1    Yuan, C.2    Borchardt, R.T.3
  • 105
    • 0029887595 scopus 로고    scopus 로고
    • Chemical feasibility studies of a potential coumarin-based prodrug system
    • Wang, B.; Zhang, H.; Wang, W. Chemical feasibility studies of a potential coumarin-based prodrug system. Bioorg. Med. Chem. Lett. 1996, 6, 945-950.
    • (1996) Bioorg. Med. Chem. Lett , vol.6 , pp. 945-950
    • Wang, B.1    Zhang, H.2    Wang, W.3
  • 106
    • 0032053499 scopus 로고    scopus 로고
    • Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs for amines
    • Wang, B.; Zhang, H.; Zheng, A.; Wang, W. Coumarin-based prodrugs. Part 3: structural effects on the release kinetics of esterase-sensitive prodrugs for amines. Bioorg. Med. Chem. 1998, 6, 417-426.
    • (1998) Bioorg. Med. Chem , vol.6 , pp. 417-426
    • Wang, B.1    Zhang, H.2    Zheng, A.3    Wang, W.4
  • 107
    • 0033526917 scopus 로고    scopus 로고
    • Substituted coumarins as esterase-sensitive prodrug moieties with improved release rates
    • Liao, Y.; Wang, B.; Substituted coumarins as esterase-sensitive prodrug moieties with improved release rates. Bioorg. Med. Chem. Lett. 1999, 9, 1795-1800.
    • (1999) Bioorg. Med. Chem. Lett , vol.9 , pp. 1795-1800
    • Liao, Y.1    Wang, B.2
  • 108
    • 0033838834 scopus 로고    scopus 로고
    • The effect of phenyl substituents on the release rates of esterase-sensitive coumarin-based prodrugs
    • Liao, Y, Hendrata, S.; Bae, S-Y.; Wang W. The effect of phenyl substituents on the release rates of esterase-sensitive coumarin-based prodrugs. Chem. Pharm. Bul. 2000, 48, 1138-1147.
    • (2000) Chem. Pharm. Bul , vol.48 , pp. 1138-1147
    • Liao, Y.1    Hendrata, S.2    Bae, S.-Y.3    Wang, W.4
  • 109
    • 0034956683 scopus 로고    scopus 로고
    • Coumarin derivatives as protease-sensitive prodrugs
    • Achiles, K. Coumarin derivatives as protease-sensitive prodrugs. Arch. Pharm. 2001, 334, 209-215.
    • (2001) Arch. Pharm , vol.334 , pp. 209-215
    • Achiles, K.1
  • 110
    • 0028011131 scopus 로고
    • Model for delivery of amines through incorporation into a tetrahydro-2H-1,3,5-thiadiazine-2-thione structure
    • El-Shorbagi, A. Model for delivery of amines through incorporation into a tetrahydro-2H-1,3,5-thiadiazine-2-thione structure. Eur. J. Med. Chem. 1994, 29, 11-15.
    • (1994) Eur. J. Med. Chem , vol.29 , pp. 11-15
    • El-Shorbagi, A.1
  • 111
    • 0029998957 scopus 로고    scopus 로고
    • New prodrug approach for amino acids and amino-acid-like drugs
    • Aboul-Fadl, T.; El-Shorbagi, A. New prodrug approach for amino acids and amino-acid-like drugs. Eur. J. Med. Chem. 1996, 31, 165-169.
    • (1996) Eur. J. Med. Chem , vol.31 , pp. 165-169
    • Aboul-Fadl, T.1    El-Shorbagi, A.2
  • 112
    • 0030707821 scopus 로고    scopus 로고
    • New carriers for representative peptides and peptide drugs
    • Aboul-Fadl, T.; El-Shorbagi, A. New carriers for representative peptides and peptide drugs. Arch. Pharm. 1997, 330, 327-332.
    • (1997) Arch. Pharm , vol.330 , pp. 327-332
    • Aboul-Fadl, T.1    El-Shorbagi, A.2
  • 113
    • 0030568115 scopus 로고    scopus 로고
    • Coumarin-based prodrugs. 2. Synthesis and bioreversibility studies of an esterase sensitive cyclic prodrug of Dadle, an opioid peptide
    • Wang, B.; Wang, W.; Zhang, H.; Shan, D.; Smith, T. Coumarin-based prodrugs. 2. Synthesis and bioreversibility studies of an esterase sensitive cyclic prodrug of Dadle, an opioid peptide. Bioorg. Med. Chem. Lett. 1996, 6, 2823-2826.
    • (1996) Bioorg. Med. Chem. Lett , vol.6 , pp. 2823-2826
    • Wang, B.1    Wang, W.2    Zhang, H.3    Shan, D.4    Smith, T.5
  • 114
    • 0030808023 scopus 로고    scopus 로고
    • Prodrug strategies based on intramolecular cyclization reactions
    • Shan, D.; Nicolaou, M.; Borchardt, R.T.; Wang B. Prodrug strategies based on intramolecular cyclization reactions. J. Pharm. Sci. 1997, 86, 765-767.
    • (1997) J. Pharm. Sci , vol.86 , pp. 765-767
    • Shan, D.1    Nicolaou, M.2    Borchardt, R.T.3    Wang, B.4
  • 115
    • 0031041493 scopus 로고    scopus 로고
    • Esterase-sensitive cyclic prodrugs of peptides: Evaluation of a phenylpropionic acid promoiety in a model hexapeptide
    • Pauletti, G.; Gangwar, S.; Wang, B.; Borchardt, R.T. Esterase-sensitive cyclic prodrugs of peptides: evaluation of a phenylpropionic acid promoiety in a model hexapeptide. Pharm. Res. 1997, 14, 11-17.
    • (1997) Pharm. Res , vol.14 , pp. 11-17
    • Pauletti, G.1    Gangwar, S.2    Wang, B.3    Borchardt, R.T.4
  • 116
    • 0030932221 scopus 로고    scopus 로고
    • Synthesis of a novel esterase-sensitive cyclic prodrug system for peptides that utilises a "trimethyl lock"-facilitated lactonization reaction
    • Wang, B.; Gangwar, S.; Pauletti, G.; Siahaan, T.; Borchardt, R.T. Synthesis of a novel esterase-sensitive cyclic prodrug system for peptides that utilises a "trimethyl lock"-facilitated lactonization reaction. J. Org. Chem. 1997, 62, 1363-1367.
    • (1997) J. Org. Chem , vol.62 , pp. 1363-1367
    • Wang, B.1    Gangwar, S.2    Pauletti, G.3    Siahaan, T.4    Borchardt, R.T.5
  • 117
    • 0020080259 scopus 로고
    • Pro-drugs as drug delivery systems XX. Oxazolidines as potential pro-drug types for β-aminoalcohols, aldehydes and ketones
    • Bundgaard, H.; Joahnsen, M. Pro-drugs as drug delivery systems XX. Oxazolidines as potential pro-drug types for β-aminoalcohols, aldehydes and ketones. Int. J. Pharm. 1982, 10, 165-175.
    • (1982) Int. J. Pharm , vol.10 , pp. 165-175
    • Bundgaard, H.1    Joahnsen, M.2
  • 118
    • 0025949443 scopus 로고
    • Prodrugs of peptides 15. 4-imidazolidinone prodrug derivatives of enkephalins to prevent amino-catalyzed peptidase metabolism in plasma and absortive mucosae
    • Rasmussen, G.; Bundgaard, H.; Prodrugs of peptides 15. 4-imidazolidinone prodrug derivatives of enkephalins to prevent amino-catalyzed peptidase metabolism in plasma and absortive mucosae. Int. J. Pharm. 1991, 76, 113-122.
    • (1991) Int. J. Pharm , vol.76 , pp. 113-122
    • Rasmussen, G.1    Bundgaard, H.2
  • 119
    • 0141447807 scopus 로고    scopus 로고
    • Kinetics of degradation of 4-imidazolidinone prodrug types obtained from reacting prilocaine with formaldehyde and acetaldehyde
    • Larsen, S.; Sidenius, M.; Ahkersen, M.; Larsen, C. Kinetics of degradation of 4-imidazolidinone prodrug types obtained from reacting prilocaine with formaldehyde and acetaldehyde. Eur. J. Pharm. Sci. 2003, 20, 233-240.
    • (2003) Eur. J. Pharm. Sci , vol.20 , pp. 233-240
    • Larsen, S.1    Sidenius, M.2    Ahkersen, M.3    Larsen, C.4
  • 120
    • 0033054737 scopus 로고    scopus 로고
    • N-terminal 4-imidazolidinone prodrugs of Leu-enkephalin: Synthesis, chemical and enzymatic stability studies
    • Bak, A.; Fich, M.; Larsen, B.; Frokjaer, S.; Friis, G. N-terminal 4-imidazolidinone prodrugs of Leu-enkephalin: synthesis, chemical and enzymatic stability studies. Eur. J. Pharm. Sci. 1999, 7, 317-323.
    • (1999) Eur. J. Pharm. Sci , vol.7 , pp. 317-323
    • Bak, A.1    Fich, M.2    Larsen, B.3    Frokjaer, S.4    Friis, G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.