SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 47, Issue 14, 2008, Pages 2595-2599

Improving oral bioavailability of peptides by multiple N-methylation: Somatostatin analogues

(11) Biron, Eric a Chatterjee, Jayanta a Ovadia, Oded b Langenegger, Daniel c Brueggen, Joseph c Hoyer, Daniel c Schmid, Herbert A c Jelinek, Raz d Gilon, Chaim b Hoffman, Amnon b Kessler, Horst a

a TECHNICAL UNIVERSITY OF MUNICH (Germany)

b HEBREW UNIVERSITY OF JERUSALEM (Israel)

c NOVARTIS PHARMA AG (Switzerland)

d BEN GURION UNIVERSITY OF THE NEGEV (Israel)

Author keywords

Bioavailability; Cyclic peptides; N methylation; Peptide drugs; Somatostatin

Indexed keywords

AMINES; CONFORMATIONS;

BIOAVAILABILITY; CYCLIC PEPTIDES; N METHYLATION; PEPTIDE DRUGS; SOMATOSTATIN;

BIOCHEMISTRY;

DRUG DERIVATIVE; SOMATOSTATIN;

ANIMAL; ARTICLE; BIOAVAILABILITY; CELL STRAIN CACO 2; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METHYLATION; ORAL DRUG ADMINISTRATION; RAT;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; HUMANS; METHYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RATS; SOMATOSTATIN;

EID: 41949086504 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200705797 Document Type: Article

Times cited : (308)

References (33)

1
- 0028657017
- J. F. Woodley, Crit. Rev. Ther. Drug Carrier Syst. 1994, 11, 61-95.
- (1994) Crit. Rev. Ther. Drug Carrier Syst , vol.11 , pp. 61-95
- Woodley, J.F.¹

2
- 16244418685
- N. Salamat-Miller, T. P. Johnston, Int. J. Pharm. 2005, 294, 201-216.
- (2005) Int. J. Pharm , vol.294 , pp. 201-216
- Salamat-Miller, N.¹ Johnston, T.P.²

3
- 0037124506
- M. J. Roberts, M. D. Bentley, J. M. Harris, Adv. Drug Delivery Rev. 2002, 54, 459-476.
- (2002) Adv. Drug Delivery Rev , vol.54 , pp. 459-476
- Roberts, M.J.¹ Bentley, M.D.² Harris, J.M.³

4
- 0029743699
- N. Flinn, I. Hussain, A. Shaw, P. Artursson, W. A. Gibbons, I. Toth, Int. J. Pharm. 1996, 138, 167-174.
- (1996) Int. J. Pharm , vol.138 , pp. 167-174
- Flinn, N.¹ Hussain, I.² Shaw, A.³ Artursson, P.⁴ Gibbons, W.A.⁵ Toth, I.⁶

5
- 0010004422
- H. Kessler, Angew. Chem. 1982, 94, 703-703;
- (1982) Angew. Chem , vol.94 , pp. 703-703
- Kessler, H.¹

6
- 0020163940
- Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523.
- (1982) Angew. Chem. Int. Ed. Engl , vol.21 , pp. 512-523

7
- 53549135850
- Eds, M. Goodman, A. Felix, L. Moroder, C. Toniolo, Georg Thieme, Stuttgart
- C. Gilon, M. A. Dechantsreiter, F. Burkhart, A. Friedler, H. Kessler in Houben-Weyl Methods of Organic Chemistry (Eds.: M. Goodman, A. Felix, L. Moroder, C. Toniolo), Georg Thieme, Stuttgart, 2002, pp. 215-291.
- (2002) Houben-Weyl Methods of Organic Chemistry , pp. 215-291
- Gilon, C.¹ Dechantsreiter, M.A.² Burkhart, F.³ Friedler, A.⁴ Kessler, H.⁵

8
- 0025989573
- J. Samanen, F. Ali, T. Romoff, R. Calvo, E. Sorenson, J. Vasko, B. Storer, D. Berry, D. Bennett, M. Strohsacker, D. Powers, J. Stadel, A. Nichols, J. Med. Chem. 1991, 34, 3114-3125.
- (1991) J. Med. Chem , vol.34 , pp. 3114-3125
- Samanen, J.¹ Ali, F.² Romoff, T.³ Calvo, R.⁴ Sorenson, E.⁵ Vasko, J.⁶ Storer, B.⁷ Berry, D.⁸ Bennett, D.⁹ Strohsacker, M.¹⁰ Powers, D.¹¹ Stadel, J.¹² Nichols, A.¹³

9
- 0030936392
- J. Yu, E. R. Butelman, J. H. Woods, B. T. Chait, M. J. Kreek, J. Pharmacol. Exp. Ther. 1997, 280, 1147-1151.
- (1997) J. Pharmacol. Exp. Ther , vol.280 , pp. 1147-1151
- Yu, J.¹ Butelman, E.R.² Woods, J.H.³ Chait, B.T.⁴ Kreek, M.J.⁵

10
- 0030746698
- W. L. Cody, J. X. He, M. D. Reily, S. J. Haleen, D. M. Walker, E. L. Reyner, B. H. Stewart, A. M. Doherty, J. Med. Chem. 1997, 40, 2228-2240.
- (1997) J. Med. Chem , vol.40 , pp. 2228-2240
- Cody, W.L.¹ He, J.X.² Reily, M.D.³ Haleen, S.J.⁴ Walker, D.M.⁵ Reyner, E.L.⁶ Stewart, B.H.⁷ Doherty, A.M.⁸

11
- 33644799946
- E. Biron, J. Chatterjee, H. Kessler, J. Pept. Sci. 2006, 12, 213-219.
- (2006) J. Pept. Sci , vol.12 , pp. 213-219
- Biron, E.¹ Chatterjee, J.² Kessler, H.³

12
- 33845309676
- J. Chatterjee, D. Mierke, H. Kessler, J. Am. Chem. Soc. 2006, 128, 15164-15172.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 15164-15172
- Chatterjee, J.¹ Mierke, D.² Kessler, H.³

13
- 37849035729
- J. Chatterjee, O. Ovadia, G. Zahn, L. Marinelli, A. Hoffman, C. Gilon, H. Kessler, J. Med. Chem. 2007, 50, 5878-5881.
- (2007) J. Med. Chem , vol.50 , pp. 5878-5881
- Chatterjee, J.¹ Ovadia, O.² Zahn, G.³ Marinelli, L.⁴ Hoffman, A.⁵ Gilon, C.⁶ Kessler, H.⁷

14
- 0035289779
- C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 2001, 46, 3-26.
- (2001) Adv. Drug Delivery Rev , vol.46 , pp. 3-26
- Lipinski, C.A.¹ Lombardo, F.² Dominy, B.W.³ Feeney, P.J.⁴

15
- 0019862208
- D. F. Veber, R. M. Freidinger, D. S. Perlow, W. J. Paleveda, F. W. Holly, R. G. Strachan, R. F. Nutt, B. H. Arison, C. Homnick, W. C. Randall, M. S. Glitzer, R. Saperstein, R. Hirschmann, Nature 1981, 292, 55-58
- (1981) Nature , vol.292 , pp. 55-58
- Veber, D.F.¹ Freidinger, R.M.² Perlow, D.S.³ Paleveda, W.J.⁴ Holly, F.W.⁵ Strachan, R.G.⁶ Nutt, R.F.⁷ Arison, B.H.⁸ Homnick, C.⁹ Randall, W.C.¹⁰ Glitzer, M.S.¹¹ Saperstein, R.¹² Hirschmann, R.¹³

16
- 0346328229
- G. Weckbecker, I. Lewis, R. Albert, H. A. Schmid, D. Hoyer, C. Bruns, Nat. Rev. Drug Discovery 2003, 2, 999-1017.
- (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 999-1017
- Weckbecker, G.¹ Lewis, I.² Albert, R.³ Schmid, H.A.⁴ Hoyer, D.⁵ Bruns, C.⁶

17
- 33845560832
- S. F. Brady, S. L. Varga, R. M. Freidinger, D. A. Schwenk, M. Mendlowski, F. W. Holly, D. F. Veber, J. Org. Chem. 1979, 44, 3101-3105.
- (1979) J. Org. Chem , vol.44 , pp. 3101-3105
- Brady, S.F.¹ Varga, S.L.² Freidinger, R.M.³ Schwenk, D.A.⁴ Mendlowski, M.⁵ Holly, F.W.⁶ Veber, D.F.⁷

18
- 0020845060
- H. Kessler, M. Bernd, H. Kogler, J. Zarbock, O. W. Sorensen, G. Bodenhausen, R. R. Ernst, J. Am. Chem. Soc. 1983, 105, 6944-6952.
- (1983) J. Am. Chem. Soc , vol.105 , pp. 6944-6952
- Kessler, H.¹ Bernd, M.² Kogler, H.³ Zarbock, J.⁴ Sorensen, O.W.⁵ Bodenhausen, G.⁶ Ernst, R.R.⁷

19
- 2242467850
- L. A. Carpino, H. Imazumi, A. El-Faham, F. J. Ferrer, C. W. Zhang, Y. S. Lee, B. M. Foxman, P. Henklein, C. Hanay, C. Mugge, H. Wenschuh, K. Klose, M. Beyermann, M. Bienert, Angew. Chem. 2002, 114, 457-461;
- (2002) Angew. Chem , vol.114 , pp. 457-461
- Carpino, L.A.¹ Imazumi, H.² El-Faham, A.³ Ferrer, F.J.⁴ Zhang, C.W.⁵ Lee, Y.S.⁶ Foxman, B.M.⁷ Henklein, P.⁸ Hanay, C.⁹ Mugge, C.¹⁰ Wenschuh, H.¹¹ Klose, K.¹² Beyermann, M.¹³ Bienert, M.¹⁴

20
- 0036462499
- Angew. Chem. Int. Ed. 2002, 41, 441-445.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 441-445

21
- 0036005817
- J. P. Hannon, C. Pertucci, D. Fehlmann, C. Viollet, J. Epelbaum, D. Hoyer, Neuropharmacology 2002, 42, 396-413
- (2002) Neuropharmacology , vol.42 , pp. 396-413
- Hannon, J.P.¹ Pertucci, C.² Fehlmann, D.³ Viollet, C.⁴ Epelbaum, J.⁵ Hoyer, D.⁶

22
- 0024829677
- R. Holmes, R. W. Lobley, Gut 1989, 30, 1667-1678
- (1989) Gut , vol.30 , pp. 1667-1678
- Holmes, R.¹ Lobley, R.W.²

23
- 0033973792
- S. Kolusheva, L. Boyer, R. Jelinek, Nat. Biotechnol. 2000, 18, 225-227.
- (2000) Nat. Biotechnol , vol.18 , pp. 225-227
- Kolusheva, S.¹ Boyer, L.² Jelinek, R.³

24
- 27144548864
- R. Tugyi, G. Mezo, E. Fellinger, D. Andreu, F. Hudecz, J. Pept. Sci. 2005, 11, 642-649.
- (2005) J. Pept. Sci , vol.11 , pp. 642-649
- Tugyi, R.¹ Mezo, G.² Fellinger, E.³ Andreu, D.⁴ Hudecz, F.⁵

25
- 0029742789
- G. Byk, D. Halle, I. Zeltser, G. Bitan, Z. Selinger, C. Gilon, J. Med. Chem. 1996, 39, 3174-3178.
- (1996) J. Med. Chem , vol.39 , pp. 3174-3178
- Byk, G.¹ Halle, D.² Zeltser, I.³ Bitan, G.⁴ Selinger, Z.⁵ Gilon, C.⁶

26
- 0020526697
- J. M. Hows, J. M. Smith, J. Clin. Pathol. 1983, 36, 720-721.
- (1983) J. Clin. Pathol , vol.36 , pp. 720-721
- Hows, J.M.¹ Smith, J.M.²

27
- 0023712859
- L. Sangalli, A. Bortolotti, L. Jiritano, M. Bonati, Drug Metab. Dispos. 1988, 16, 749-753.
- (1988) Drug Metab. Dispos , vol.16 , pp. 749-753
- Sangalli, L.¹ Bortolotti, A.² Jiritano, L.³ Bonati, M.⁴

28
- 33746933183
- K. Zheng, M. Trivedi, T. J. Siahaan, Curr. Pharm. Des. 2006, 12, 2813-2824.
- (2006) Curr. Pharm. Des , vol.12 , pp. 2813-2824
- Zheng, K.¹ Trivedi, M.² Siahaan, T.J.³

29
- 0032075589
- A. Fasano, Mol. Genet. Metab. 1998, 64, 12-18.
- (1998) Mol. Genet. Metab , vol.64 , pp. 12-18
- Fasano, A.¹

30
- 0030853188
- G. T. Knipp, D. G. V. Velde, T. J. Siahaan, R. T. Borchardt, Pharm. Res. 1997, 14, 1332-1340.
- (1997) Pharm. Res , vol.14 , pp. 1332-1340
- Knipp, G.T.¹ Velde, D.G.V.² Siahaan, T.J.³ Borchardt, R.T.⁴

31
- 0032949615
- J. D. Irvine, L. Takahashi, K. Lockhart, J. Cheong, J. W. Tolan, H. E. Selick, J. R. Grove, J. Pharm. Sci. 1999, 88, 28-33.
- (1999) J. Pharm. Sci , vol.88 , pp. 28-33
- Irvine, J.D.¹ Takahashi, L.² Lockhart, K.³ Cheong, J.⁴ Tolan, J.W.⁵ Selick, H.E.⁶ Grove, J.R.⁷

32
- 0031925268
- H. Lennernas, J. Pharm. Sci. 1998, 87, 403-410.
- (1998) J. Pharm. Sci , vol.87 , pp. 403-410
- Lennernas, H.¹

33
- 0027438352
- Y. B. He, Z. W. Huang, K. Raynor, T. Reisine, M. Goodman, J. Am. Chem. Soc. 1993, 115, 8066-8072.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 8066-8072
- He, Y.B.¹ Huang, Z.W.² Raynor, K.³ Reisine, T.⁴ Goodman, M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.