The potential of cystine-knot microproteins as novel pharmacophoric scaffolds in oral peptide drug delivery

Journal of Drug Targeting

Volumn 14, Issue 3, 2006, Pages 137-146

  Werle, Martin ^a   Schmitz, Thierry ^b   Huang, Hong Lei ^c   Wentzel, Alexander ^d   Kolmar, Harald ^d,e   Bernkop Schnürch, Andreas ^b  

^a Thiomatrix Forschungs und Beratungs GmbH   (Austria)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c INNSBRUCK MEDICAL UNIVERSITY   (Austria)

^d Selecore GmbH   (Germany)

^e DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Cystine knot; Cystine knot microproteins; Oral peptide delivery; Pharmacophoric scaffolds

Indexed keywords

BACITRACIN; CHYMOTRYPSIN; CYSTINE; ELASTASE; INSULIN; PEPSIN A; PEPTIDE DERIVATIVE; PROTEINASE; TRYPSIN;

ANIMAL TISSUE; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYSTINE KNOT MOTIF; DRUG ADMINISTRATION ROUTE; DRUG DELIVERY SYSTEM; DRUG STABILITY; ENZYME DEGRADATION; ENZYME STABILITY; GASTROINTESTINAL SECRETION; INTESTINE MUCOSA; ISOELECTRIC POINT; MEMBRANE BINDING; MEMBRANE PERMEABILITY; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN STABILITY; RAT;

ADMINISTRATION, ORAL; AMINO ACID SEQUENCE; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTINE; ISOELECTRIC POINT; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEINS; RATS;

EID: 33745098362     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.1080/10611860600648254     Document Type: Article

References (27)

1. Athaudaa, SB and Takahashia, K. (2002) Cleavage specificities of aspartic proteinases toward oxidized insulin B chain at different pH values Protein Pept Lett, 9(4), pp. 289-294.
2. Bernkop-Schnürch, A. (1998) The use of inhibitory agents to overcome the enzymatic barrier to perorally administered therapeutic peptides and proteins J Control Release, 52(1-2), pp. 1-16.
3. Bernkop-Schnürch, A and Fragner, R. (1996) Investigations into the diffusion behaviour of polypeptides in native intestinal mucus with regard to their peroral administration Pharm Sci, 2(1), pp. 361-363.
4. Bernkop-Schnürch, A and Apprich, I. (1997) Synthesis and evaluation of a modified mucoadhesive polymer protecting from a-chymotrypsinic degradation Int J Pharm, 146(2), pp. 247-254.
5. Bernkop-Schnürch, A and Bratengeyer, I and Valenta, C. (1997) Development and in vitro evaluation of a drug delivery system protecting from trypsinic degradation Int J Pharm, 157(1), pp. 17-25.
6. Bernkop-Schnürch, A and Clausen, AE and Hnatyszyn, M. (2001) Thiolated polymers: Synthesis and in vitro evaluation of polymer-cysteamine conjugates Int J Pharm, 226(1-2), pp. 185-194.
7. Bernkop-Schnürch, A and Kast, CE and Guggi, D. (2003) Permeation enhancing polymers in oral delivery of hydrophilic macromolecules: Thiomer/GSH systems J Control Release, 93(2), pp. 95-103.
8. Bernkop-Schnürch, A and Guggi, D and Y. (2004) Thiolated chitosans: Development and in vitro evaluation of a mucoadhesive, permeation enhancing oral drug delivery system J Control Release, 94(1), pp. 177-186.
9. Bernkop-Schnürch, A and Pinter, Y and Guggi, D and Kahlbacher, H and Schöffmann, G and Schuh, M and Schmerold, I and Del Curto, MD and D'Antonio, M and Huck, C. (2005) The use of Thiolated polymers as carrier matrix in oral peptide delivery-proof of concept J Control Release, 106(1-2), pp. 26-33.
10. Chiche, L and Heitz, A and Gelly, JC and Gracy, J and Chau, PT and Ha, PT and Hernandez, JF and Le-Nguyen, D. (2004) Squash inhibitors: From structural motifs to macrocyclic knottins Curr Protein Pept Sci, 5(5), pp. 341-349.
11. Clausen, AE and Bernkop-Schnürch, A. (2000) In vitro evaluation of the permeation-enhancing effect of thiolated polycarbophil J Pharm Sci, 89(10), pp. 1253-1261.
12. Clausen, AE and Bernkop-Schnürch, A. (2001) Thiolated carboxymethylcellulose: In vitro evaluation of its permeation enhancing effect on peptide drugs Eur J Pharm Biopharm, 51(1), pp. 25-32.
13. Colgrave, ML and Craik, DJ. (2004) Thermal, chemical, and enzymatic stability of the cyclotide kalata B1: The importance of the cyclic cystine knot Biochemistry, 43(20), pp. 5965-5975.
14. Craik, DJ and Daly, NL and Waine, C. (2001) The cystine knot motif in toxins and implications for drug design Toxicon, 39(1), pp. 43-60.
15. Doggrell, SA. (2004) Intrathecal ziconotide for refractory pain Expert Opin Investig Drugs, 13(7), pp. 875-877.
16. Guggi, D and Krauland, AH and Bernkop-Schnürch, A. (2003) Systemic peptide delivery via the stomach: In vivo evaluation of an oral dosage form for salmon calcitonin J Control Release, 92(1-2), pp. 125-135.
17. Guo, J and Ping, Q and Jiang, G and Dong, J and Qi, S and Feng, L and Li, Z and Li, C. (2004) Transport of leuprolide across rat intestine, rabbit intestine and Caco-2 cell monolayer Int J Pharm, 278(2), pp. 415-422.
18. Hentz, NG and Richardson, JM and Sportsman, JR and Daijo, J and Sittampalam, GS. (1997) Synthesis and characterization of insulin-fluorescein derivatives for bioanalytical applications Anal Chem, 69(24), pp. 4994-5000.
19. Jackson, PJ and McNulty, JC and Yang, YK and Thompson, DA and Chai, B and Gantz, I and Barsh, GS and Millhauser, GL. (2002) Design, pharmacology, and NMR structure of a minimized cystine knot with agouti-related protein activity Biochemistry, 41(24), pp. 7565-7572.
20. Krauland, AH and Guggi, D and Bernkop-Schnürch, A. (2004) Oral insulin delivery: The potential of thiolated chitosan-insulin tablets on non-diabetic rats J Control Release, 95(3), pp. 547-555.
21. Nourse, A and Trabi, M and Daly, NL and Craik, DJ. (2003) A comparison of the self-association behavior of the plant cyclotides kalata B1 and kalata B2 via analytical ultracentrifugation J Biol Chem, 279(1), pp. 562-570.
22. Pantzar, N and Lundin, S and Wester, L and Westrom, BR. (1994) Bidirectional small-intestinal permeability in the rat to some common marker molecules in vitro Scand J Gastroenterol, 29(8), pp. 703-709.
23. Roumi, M and Kwong, E and Deghenghi, R and Locatelli, V and Marleau, S and Du, SP and Beliveau, R and Ong, H. (2001) Permeability of the peptidic GH secretagogues hexarelin and EP 51389, across rat jejunum Peptides, 22(7), pp. 1129-1138.
24. Sinko, PJ and Lee, Y-H and Makhey, V and Leesman, GD and Sutyak, JP and Yu, H and Perry, B and Smith, CL and Hu, P and Wagner, EJ and Falzone, LM and McWhorter, LT and Gilligan, JP and Stern, W. (1999) Biopharmaceutical approaches for developing and assessing oral peptide delivery strategies and systems: In vitro permeability and in vivo oral absorption of salmon calcitonin (sCT) Pharm Res, 16(4), pp. 527-533.
25. Swarbrick, J and Boylan, JC. (2002) Encyclopedia of pharmaceutical Technology 2nd ed. New York: Marcel Dekker Inc.
26. Woodley, JF. (1994) Enzymatic Barriers for GI Peptide and Protein Delivery Crit Rev Ther Drug Carrier Syst, 11(2-3), pp. 61-95.
27. Yamamoto, A. (2001) Improvement of transmucosal absorption of biologically active peptide drugs Yakugaku Zasshi, 121(12), pp. 929-948.