-
1
-
-
0345678344
-
-
1. The ADAPT approach is an extension of ADEPT (antibody-directed enzyme prodrug therapy) in which non-human enzymes are used instead of catalytic antibodies. However, these enzymes are highly immunogenic in humans. Thus, the focus on human catalytic antibodies. For recent reviews of ADEPT see: Jungheim, L. N.; Sheperd, T. A. Chem. Rev. 1994, 94, 1553 and Adv. Drug Del. Rev. 1996, 22, No.3., K. Bagshawe Ed.
-
(1994)
Chem. Rev.
, vol.94
, pp. 1553
-
-
Jungheim, L.N.1
Sheperd, T.A.2
-
2
-
-
0345678344
-
-
K. Bagshawe Ed.
-
1. The ADAPT approach is an extension of ADEPT (antibody-directed enzyme prodrug therapy) in which non-human enzymes are used instead of catalytic antibodies. However, these enzymes are highly immunogenic in humans. Thus, the focus on human catalytic antibodies. For recent reviews of ADEPT see: Jungheim, L. N.; Sheperd, T. A. Chem. Rev. 1994, 94, 1553 and Adv. Drug Del. Rev. 1996, 22, No.3., K. Bagshawe Ed.
-
(1996)
Adv. Drug Del. Rev.
, vol.22
, Issue.3
-
-
-
3
-
-
0029671436
-
-
2. Wentworth, P.; Datta, A.; Blakey, D.; Partridge, L. J.; Blackburn, G. M. Proc. Natl. Acad. Sci. USA 1996, 93, 799.
-
(1996)
Proc. Natl. Acad. Sci. USA
, vol.93
, pp. 799
-
-
Wentworth, P.1
Datta, A.2
Blakey, D.3
Partridge, L.J.4
Blackburn, G.M.5
-
4
-
-
0010639598
-
-
note
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3. The reaction catalyzed by the antibody must not be catalyzed by human enzymes in order to avoid premature formation of the drug.
-
-
-
-
5
-
-
0025730616
-
-
4. Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659.
-
(1991)
Science
, vol.252
, pp. 659
-
-
Lerner, R.A.1
Benkovic, S.J.2
Schultz, P.G.3
-
6
-
-
0024098393
-
-
5. Lerner, R. A.; Benkovic, S. J. BioEssays 1988, 9, 107. See also: Lerner, R. A., Hosp. Prac. 1993, 53.
-
(1988)
BioEssays
, vol.9
, pp. 107
-
-
Lerner, R.A.1
Benkovic, S.J.2
-
7
-
-
0024098393
-
-
5. Lerner, R. A.; Benkovic, S. J. BioEssays 1988, 9, 107. See also: Lerner, R. A., Hosp. Prac. 1993, 53.
-
(1993)
Hosp. Prac.
, pp. 53
-
-
Lerner, R.A.1
-
8
-
-
0027302510
-
-
6. Miyashita, H.; Karaki, Y.; Kikuchi, M.; Fujii, I. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5337.
-
(1993)
Proc. Natl. Acad. Sci. U.S.A.
, vol.90
, pp. 5337
-
-
Miyashita, H.1
Karaki, Y.2
Kikuchi, M.3
Fujii, I.4
-
9
-
-
0028076759
-
-
7. Campbell, D. A.; Gong, B.; Kochersperger, Yonkovich, S.; Gallop, M. A.; Schultz, P. G. J. Amer. Chem. Soc. 1994, 116, 2165.
-
(1994)
J. Amer. Chem. Soc.
, vol.116
, pp. 2165
-
-
Campbell, D.A.1
Gong, B.2
Kochersperger3
Yonkovich, S.4
Gallop, M.A.5
Schultz, P.G.6
-
10
-
-
0010728254
-
-
note
-
8. Carbamates are stable relatively stable to hydrolysis by most proteases and esterases and have therefore been used extensively as prodrugs and enzyme inhibitors. See references 9 and 1.
-
-
-
-
11
-
-
0027369525
-
-
9. Kato, M.; Agha, B. J.; Abdul-Rakheem, A. K.; Tsuji, K.; Banks, W. R.; Digenis, G. A. J. Enzyme Inhibition 1993, 7, 105.
-
(1993)
J. Enzyme Inhibition
, vol.7
, pp. 105
-
-
Kato, M.1
Agha, B.J.2
Abdul-Rakheem, A.K.3
Tsuji, K.4
Banks, W.R.5
Digenis, G.A.6
-
12
-
-
0030999007
-
-
10. (a) Ma, G. X.; Batey, R. A.; Taylor, S. D.; Hum, G.; Jones, J. B. Syn Commun. 1997, 27, 2445.
-
(1997)
Syn Commun.
, vol.27
, pp. 2445
-
-
Ma, G.X.1
Batey, R.A.2
Taylor, S.D.3
Hum, G.4
Jones, J.B.5
-
13
-
-
0019453510
-
-
(b) The prodrug system described in Scheme 1 is very similar to the self-immolative prodrug linkage developed by Katzenellenbogen and coworkers. See: Carl, P. L.; Chakravarty, P. K.; Katzenellenbogen, J. A. J. Med. Chem. 1981, 24, 479.
-
(1981)
J. Med. Chem.
, vol.24
, pp. 479
-
-
Carl, P.L.1
Chakravarty, P.K.2
Katzenellenbogen, J.A.3
-
14
-
-
0030964433
-
-
11. Wentworth, P.; Datta, A.; Smith, S.; Marshall, A.; Partridge, L. J.; Blackburn, G. M. J. Am. Chem. Soc. 1997, 119, 2315.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 2315
-
-
Wentworth, P.1
Datta, A.2
Smith, S.3
Marshall, A.4
Partridge, L.J.5
Blackburn, G.M.6
-
15
-
-
0028363822
-
-
12. Van Vranken, D. L.; Panomitros, D.; Schultz, P. G. Tetrahedron Lett. 1994, 35, 3873.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 3873
-
-
Van Vranken, D.L.1
Panomitros, D.2
Schultz, P.G.3
-
16
-
-
0025077696
-
-
13. Tawfik, D. S.; Zemel, R. R.; Arad-Yellin, R.; Green, B. S.; Eshhar, Z. Biochemistry 1990, 29, 9916. Liotta, L. J.; Benkovic, P. A.; Miller, G. P. Benkovic, S. J. J. Am. Chem. Soc. 1993, 115, 350.
-
(1990)
Biochemistry
, vol.29
, pp. 9916
-
-
Tawfik, D.S.1
Zemel, R.R.2
Arad-Yellin, R.3
Green, B.S.4
Eshhar, Z.5
-
17
-
-
0001620899
-
-
13. Tawfik, D. S.; Zemel, R. R.; Arad-Yellin, R.; Green, B. S.; Eshhar, Z. Biochemistry 1990, 29, 9916. Liotta, L. J.; Benkovic, P. A.; Miller, G. P. Benkovic, S. J. J. Am. Chem. Soc. 1993, 115, 350.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 350
-
-
Liotta, L.J.1
Benkovic, P.A.2
Miller, G.P.3
Benkovic, S.J.4
-
18
-
-
0003607090
-
-
New York, Wiley Interscience Chp 16
-
14. For an overview of methods for synthesizing this class of compounds see: Kosalopoff, G. M.; Maier, L. "Organic Phosphorus Compounds" New York, Wiley Interscience 1972. Chp 16.
-
(1972)
Organic Phosphorus Compounds
-
-
Kosalopoff, G.M.1
Maier, L.2
-
19
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0010685242
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note
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15. These reagents are prepared using phosphorous oxychloride. By purifying the initial O-phenylphosphoric dichloride or N-phenylphosphoramidic dichloride derivative (rather than reacting the aniline, phenolic and alcohol derivatives consecutively with phosphorus oxychloride) subsequent reactions proceed much cleaner and complex mixtures of products are, to a certain extent, avoided. Alkyldichlorophosphates, such as methyldichlorophosphate, are not commonly used as starting materials due to loss of the alkyl group during the synthesis.
-
-
-
-
20
-
-
0027989427
-
-
16. Martin, S. F.; Josey, J. A.; Wong, Y-L.; Dean, D. W. J. Org. Chem. 1994, 59, 4805.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4805
-
-
Martin, S.F.1
Josey, J.A.2
Wong, Y.-L.3
Dean, D.W.4
-
21
-
-
0028026762
-
-
17. Martin, S. F.; Wong, Y-L.; Wagman, A. S., J. Org. Chem. 1994, 59, 4821.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4821
-
-
Martin, S.F.1
Wong, Y.-L.2
Wagman, A.S.3
-
22
-
-
0025077696
-
-
18. Tawfik, D. S.; Zemel, R. R.; Arad-Yellin, R.; Green, B. S.; Eshar, Z. Biochemistry 1990, 29, 9916.
-
(1990)
Biochemistry
, vol.29
, pp. 9916
-
-
Tawfik, D.S.1
Zemel, R.R.2
Arad-Yellin, R.3
Green, B.S.4
Eshar, Z.5
-
26
-
-
0010642198
-
-
note
-
2 but lower yields were obtained.
-
-
-
-
27
-
-
15144356086
-
-
23. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M-C. Tetrahedron Lett. 1977, 155.
-
(1977)
Tetrahedron Lett.
, pp. 155
-
-
McKenna, C.E.1
Higa, M.T.2
Cheung, N.H.3
McKenna, M.-C.4
-
30
-
-
0010680995
-
-
note
-
26. We had initially avoided this protecting group since we were concerned of the possibility that the nucleophile required for its removal would also cause loss of the benzyl protecting group from the phosphate.
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-
-
-
32
-
-
0024982305
-
-
28. Competition experiments with various activated esters of N-protected amino acids have shown that the Pfp esters are more reactive than the NHS esters for peptide bond formation. See: Hudson, D. Peptide Res. 1990, 3, 51.
-
(1990)
Peptide Res.
, vol.3
, pp. 51
-
-
Hudson, D.1
-
33
-
-
0000768032
-
-
29. Zhang, H. X.; Guibe, F.; Balavione, G. Tetrahedron Lett. 1988, 29, 623.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 623
-
-
Zhang, H.X.1
Guibe, F.2
Balavione, G.3
-
34
-
-
85004826932
-
-
30. DCC is the coupling agent most commonly employed for forming Pfp esters. See: Kisfaludy, L.; Schon, I. Synthesis, 1983, 325.
-
(1983)
Synthesis
, pp. 325
-
-
Kisfaludy, L.1
Schon, I.2
-
35
-
-
0010641041
-
-
note
-
31. Antibody screening and production is being performed by Prof. William Crosby at the Plant Biotechnology Institute, Saskatoon, Canada. For a description of the phage display library see reference 32.
-
-
-
-
36
-
-
0028291823
-
-
32. Griffiths, A. D.; Williams, S. C.; Hartley, O.; Tomlinson, I. M.; Waterhouse, P.; Crosby, W. L.; Konterman, R. E.; Jones, P. T.; Low, N. M.; Allison, T. J.; Prospero, T. D.; Hoogenboom, H. R.; Nissim, A.; Cox, J. P. L.; Harrison, J. L.; Zaccolo, M.; Gherardi, E.; Winter, G. EMBO 1994, 13, 3245.
-
(1994)
EMBO
, vol.13
, pp. 3245
-
-
Griffiths, A.D.1
Williams, S.C.2
Hartley, O.3
Tomlinson, I.M.4
Waterhouse, P.5
Crosby, W.L.6
Konterman, R.E.7
Jones, P.T.8
Low, N.M.9
Allison, T.J.10
Prospero, T.D.11
Hoogenboom, H.R.12
Nissim, A.13
Cox, J.P.L.14
Harrison, J.L.15
Zaccolo, M.16
Gherardi, E.17
Winter, G.18
-
37
-
-
0000371749
-
-
33. Ogilvie, K.; Theriault, N. Y.; Seifert, J-M.; Pon, R. T.; Nemer, M. J. Can. J. Chem. 1980, 58, 2686.
-
(1980)
Can. J. Chem.
, vol.58
, pp. 2686
-
-
Ogilvie, K.1
Theriault, N.Y.2
Seifert, J.-M.3
Pon, R.T.4
Nemer, M.J.5
-
40
-
-
0014878167
-
-
36. Ryan, A. J.; Vermeulen, M. J. N.; Baker, B. R. J. Med. Chem. 1970, 13, 1140.
-
(1970)
J. Med. Chem.
, vol.13
, pp. 1140
-
-
Ryan, A.J.1
Vermeulen, M.J.N.2
Baker, B.R.3
-
41
-
-
0022186670
-
-
37. Smith, P.K.; Krohn, R.I.; Hermanson, G.T.; Mallia, A.K.; Gartner, F.H.; Provenzano, M.D.; Fujimoto, E.K.; Goeke, N.M.; Olson, B.J.; Klenk, D.C. Anal. Biochem. 1985, 150, 76-85.
-
(1985)
Anal. Biochem.
, vol.150
, pp. 76-85
-
-
Smith, P.K.1
Krohn, R.I.2
Hermanson, G.T.3
Mallia, A.K.4
Gartner, F.H.5
Provenzano, M.D.6
Fujimoto, E.K.7
Goeke, N.M.8
Olson, B.J.9
Klenk, D.C.10
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