Method for delivery of molecules to intracellular targets

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S013800, C514S014800, C514S015800, C514S016700, C514S017400, C530S324000, C530S325000, C530S326000, C530S327000, C530S328000, C530S329000, C530S332000, C530S345000

Reexamination Certificate

active

06914048

ABSTRACT:
Disclosed are β-peptides and β-peptide conjugates that are capable of diffusing or otherwise being transported across the cell membranes of living cells. The β-peptides contain at least six β-amino acid residues, at leastsix of which are preferably β3-homoarginine residues. It has been found that when pharmacologically-active agents are conjugated to these types of β-peptides, the resulting conjugates (also disclosed herein) are also capable of diffusing or otherwise being transported across the cell membranes of living cells, including mammalian cells.

REFERENCES:
patent: 2002/0132766 (2002-09-01), DeGrado et al.
Barron, A. E.; Zuckerman, R. N., Bioinspired polymeric materials: in-between porteins and plastics,Curr. Opin. Chem. Biol. 1999, 3, 681-87.
DeGrado, W.F.; Schneider, J. P.; Hamuro, Y., The twists and turns of β-peptides,J. Pept. Res. 1999, 54, 206-17.
Derossi, D.; Joliot, A.H.; Chassaing, G.; Prochiantz, A., Trojan peptides; the penetratin system for intracellular delivery,J. Biol. Chem. 1994, 269, 10444-47.
Derossi, D.; Calvet, S.; Trembleau, A.; Brunissen, A.; Chassaing, G.; Prochiantz, A., Cell Internalization of the Third Helix of the Antennapedia Homeodomain Is Receptor-independent,J. Biol. Chem. 1996, 271, 18188-93.
Fawell, S.; Seery, J.; Kaikh, Y.; Moore, C.; Chen, L. L.; Pepinsky, B.; Barsoum, J., Tat-mediated delivery of heterologous proteins into cells,Proc. Natl. Acad. Sci. USA1994, 91, 664-68.
Frankel, A. D.; Pabo, C. O., Cellular Uptake of the Tat Protein from Human Immunodeficiency Virus,CEll1988, 22, 1189-93.
Futaki, S.; Suzuki, T.; Ohashi, W.; Yagami, T.; Tanaka, S.; Ueda, K.; Sugiura, Y., Arginine-rich Peptides,J. Biol. Chem.2001, 276, 5836-40.
Gademann, K.; Hintermann, T.; Schreiber, J. V., β-Piptides: Twisting and Turning,Curr. Med. Chem. 1999, 6, 905-25.
Gellman, S. H., Foldamers: A Maniffesto,Acc. Chem. Res. 1998, 31, 173-80.
Green, M.; Loewenstein, P. M., Autonomous Functional Domains of Chemically Synthesized Human Immunodeficiency Virus TatTrans-Actovator Protein,Cell1988, 55, 1179-88.
Guichard, G.; Abele, S.; Seebach, D., Preparatio ofN-Fmoc-Protected β2- and β3- Amino Acids and Their Use as Building Blocks for the Solid-Phase Synthesis of β-Peptides,Helv. Chim. Acta1998, 81, 187-98.
Hamuro, Y.; Schneider, J. P.; DeGrado, W. F., De Novo Design of Antibacterial β- Peptides,J. Am. Chem. Soc. 1999, 121, 12200-01.
Hawiger, J. , Noninvasive intracellular delivery of functional pepides and proteins,Curr. Opin. Chem. Biol. 1999, 3, 89-94.
Kirshenbaum, K.; Zuckermann, R. N.; Dill, K. A., Designing polymers that mimic biomolecules,Curr. Opin. Struct. Biol. 1999, 9, 530-535.
Lindgren, M.; Hallbrink, M.; Prochiantz, A.; Langel, Ü., Cell-penetrating peptides,Trends Pharmacol. Sci. 2000, 21, 99-103.
Mitchell, D. J.; Kim, D. T.; Steinman, L.; Fathman, C. G.; Rothbard, J. B., Polyarginine enters cells more efficiently than other polcationic homopolymers,J. Pept. Res. 2000, 56, 318-25.
Pooga, M.; Soomets, U.; Hällbrink, M.; Valkna, A.; Saar, K.; Rezaei, K.; Kahl, U.; Hao, J.-X.; Xu, X.-J.; Wiesenfeld-Hallin, Z.; Hökfelt, T.; Bartfai, T.; Langel, Ü., Cell penetrating PNA constructs regulate galanin receptor levels and modify pain transmission in vivo,Nat. Biotechnol. 1998, 16, 857-61.
Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H., Non-haemolytic β-amino-acid oligomers,Nature2000, 404, 565.
Prochiantz, A., Messenger proteins: homeoproteins, TAT and others,Curr. Opin. Cell Biol. 2000, 12, 400-06.
Rothbard, J. B.; Garlington, S.; Lin, Q.; Kirschberg, T.; Kreider, E.; McGrane, P. L.; Wender, P. A.; Khavari, P. A., Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation,Nat. Medicine2000, 6, 1253-57.
Rouselle, C.; Clair, P.; Lefauconnier, J.-M.; Kaczorek, M.; Scherrmann, J.-M.; Temsamani, J., New Advances in the Transport of Doxorubicin through the Blood-Brain Barrier by a Peptide Vector-Mediated Strategy,Mol. Pharmacol. 2000, 57, 679-686.
Rueping, M.; Mahajan, Y.; Sauer, M; and Seebach, D.,Cellular Uptake Studies with β-Peptides,ChemBioChem2002, No. 02-03, 257-259.
Schwarze, S. R.; Ho, A.; Vocero-Akbani, A.; Dowdy, S. F., In Vivo Protein Transduction: Delivery of a Biologically Active Protein into the Mouse,Science1999, 285, 1569-72.
Schwarze, S. R.,; Hruska, K. A.; Dowdy, S. F., Protein transduction: unrestricted delivery into all cells!,Trends Cell Biol. 2000, 10, 290-95.
Schwarze, S.R. and Dowdy, S.F., In vivo protein transduction: intracellular delivery of biologically active proteins, compounds and DNA,TiPS, 2000, 21, 45-48.
Seebach, D.; Matthews, J. L., β-Peptides: a surprise at every turn,J. Chem. Soc., Chem. Commun. 1997, 2015-22.
Seebach, D.; Abele, S.; Schreiber, J. V.; Martinoni, B.; Nussbaum, A. K.; Schild, H.; Schulz, H.; Hennecke, H.; Woessner, R; Bitsch, F., Biological and Pharmacokinetic Studies with β-Peptides,Chimia1998, 52, 734-39.
Stigers, K. D.; Soth, M.J.; Nowick, J. S., Designed molecules that fold to mimic protein secondary structures,Curr. Opin. Chem. Biol. 1999, 3, 714-23.
Tamilarasu, N.; Huq, I.; Rana, T. M., High Affinity and Specific Binding of HIV-1 TAR RNA by a Tat-Derived Oligourea,J. Am. Chem. Soc. 1999, 121, 1597-98.
Umezawa, N.; Gelman, M.A.; Haigis, M.C.; Rainer, R.T.; and Gellman, S.H.,, Translocation of a β-Peptide Across Cell Membranes,J. Am. Chem.Soc. 2002, vol. 24, No. 3, 368-369.
Vivés, E.; Brodin, P.; Lebleu, B., A Truncated HIV-1 Tat Protein Basic Domain Rapidly Translocates through the Plasma Membrane and Accumulates in the Cell Nucleus,J. Biol. Chem. 1997, 272, 16010-17.
Vivés, E.; Granier, C.; Prevot, P.; Lebleu, B., Structure-activity relationship study of the plasma membrane translocating potential of a short peptide from HIV-1 Tat protein,Lett. Pept. Sci. 1997, 4, 429-436.
Wang, X.; Huq, I.; Rana, T. M., HIV-1 TAR RNA Recognition by Unnatural Biopolymer,J. Am. Chem. Soc. 1997, 119, 6444-45.
Wender, P.A.; Mitchell, D. J.; Pattabiraman, K.; Pelkey, E. T.; Steinman, L.; Rothbard, J. B., the design , synthesis, and evaluation of molecules that enable or enhance cellular uptake: Peptoid molecular transporters,Proc. Natl. Acad. Sci. USA2000, 97, 13003-08.
Werder, M.; Hausre, H.; Abele, S.; Seebach, D., β-Peptides as Inhibitors of Small-Intestinal Cholesterol and Fat Absorption,Helv. Chim. Acta1999, 82, 1774-83.
Zhang, L.; Torgerson, T. R.; Liu, X.-Y.; Timmons, S.; Colosia, A. D.; Hawiger, J.; Tam, J. P., Preparation of functionality active cell-permeable peptide by sinlge-step ligation of two peptides modules,Proc. Natl. Acad. Sci. USA1998, 95, 9184-89.
Bastiaans, Harold M., A facile conversion of arginine into β-homoarginine dipeptides,Tetrahedron Letters, 1994, vol. 35, No. 41, pp. 7659-7660.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Method for delivery of molecules to intracellular targets does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for delivery of molecules to intracellular targets, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for delivery of molecules to intracellular targets will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3412027

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.