Patent
Methods for collagen imaging
| العنوان: | Methods for collagen imaging |
|---|---|
| Patent Number: | 9,386,938 |
| تاريخ النشر: | July 12, 2016 |
| Appl. No: | 13/229900 |
| Application Filed: | September 12, 2011 |
| مستخلص: | Diagnostic compositions and methods for imaging and/or assessing collagen are described. The diagnostic compositions can include collagen binding peptides. |
| Inventors: | Caravan, Peter D. (Cambridge, MA, US); Kolodziej, Andrew (Winchester, MA, US); Zhang, Zhaoda (Andover, MA, US); Dumas, Stephane (Cambridge, MA, US); Das, Biplab Kumar (Boston, MA, US); Jacques, Vincent (Somerville, MA, US); Looby, Richard (Reading, MA, US); Koerner, Steffi K. (Somerville, MA, US); Sun, Wei-Chuan (Acton, MA, US); Buckler, David R. (Sudbury, MA, US); Abujoub, Aida (Winchester, MA, US); Sato, Aaron K. (Richmond, CA, US) |
| Assignees: | Collagen Medical, LLC (Belmont, MA, US) |
| Claim: | 1. A collagen binding peptide, wherein the collagen binding peptide comprises a cyclic peptide comprising the amino acid sequence: [table included] wherein the peptide has a total length of 16 to 20 amino acids, and wherein one or more of the amino acids in the peptide is derivatized with a non-metallic radionuclide selected from the group consisting of 18 F, 123 I, 125 I, and 131 I. |
| Claim: | 2. A collagen binding peptide, wherein the collagen binding peptide comprises a cyclic peptide comprising the amino acid sequence: [table included] wherein: C* is C or Pen in D or L form; X1=T, A, K, V, I, S, Y, G, R, P, L, 3-NO2 Y, 4-Pal, 4-CO2H-F, 4-tBu-F, F(4-NH2), Y(Bn, 3-Cl), b-h-S, Y(3-I), or Aib, in D or L form; X2=T, A, N, S, Y, R, V, I, K, D, G, b-h-G, Orn, or Dpr, in D or L form; X3=R, A, S, L, Y, D, K, G, P, Aib, Y(3-Cl), I, Cha, Abu, F(4-F), Dopa, Tle, Cit, b-h-D, or K(Boc), in D or L form; X4=F, Bip, F(4-CF3), 4-Pal, 1-Nal, F(4-NO2), Hfe, Bpa, F(4-CN), F(4-NH2), F(3,4-OMe), 2-Nal, Y(3-Cl), Aib, or b-h-E, in D or L form; X5=P, P(3-OH), APro, Pip, N-Me-A, P(3-OH), Y(3-I), b-h-Y, or Aib, in D or L form; X6=H, A, S, K, N, Y, T, D, R, W, P, Aib, or b-h-T, in D or L form; X7=H, A, S, N, D, Y, W, Aib, Dpr, 2-Pal, 1-Nal, thien-W, W(5-OH), or b-h-W, in D or L form; and X8=Y, A, R, T, V, H, D, S, P, 1-Nal, Bip, DOPA, H-Tyr, H-Tyr(Me), F(3-OMe), Y(3-Cl), Y(2,6-Me2), Dip, F(4-NH2), or Aib, in D or L form; and wherein the peptide has a length of 10 to 20 amino acids, and wherein one or more of the amino acids in the peptide is derivatized with a non-metallic radionuclide selected from the group consisting of 18 F, 123 I, 125 I, and 131 I. |
| Claim: | 3. The collagen binding peptide of claim 2 , wherein the cyclic peptide comprises the amino acid sequence: [table included] |
| Claim: | 4. The collagen binding peptide of claim 2 , wherein the cyclic peptide comprises the amino acid sequence: [table included] wherein: X9, X10, and X11 are any amino acid; and wherein the peptide has a length of 13 to 20 amino acids. |
| Claim: | 5. The collagen binding peptide of claim 4 , wherein: X9=L, A, I, K, V, F, N, Y, P, Aib, Hse, Hfe, Bpa, 2-Nal, Y(3-Cl), Dip, or F(4-NH2), in D or L form; X10=Y, A, F, E, Bpa, 2-Nal, Y(3-Cl), Dip, F(4-NH2), or Y(3-I), in D or L form; and X11=G, E, Y, F, V, Bip, F(4-NH2), or Aib, in D or L form. |
| Claim: | 6. The collagen binding peptide of claim 4 , wherein the cyclic peptide comprises the amino acid sequence: [table included] wherein: X11 is any amino acid; X12 is any one or two amino acids; and wherein the peptide has a length of 14 to 20 amino acids. |
| Claim: | 7. The collagen binding peptide of claim 6 , wherein: X11=G, E, Y, F, V, Bip, F(4-NH2), or Aib, in D or L form; and X12=K, KK, Peg K, PEG(1×O), 1,4-AMB, 1,3-AMB, 1,6-Hex, PEG, or GTE, in D or L form. |
| Claim: | 8. The collagen binding peptide of claim 2 , wherein the collagen binding peptide comprises a cyclic peptide comprising the amino acid sequence: [table included] wherein: X13 and X14 are any amino acid; C* is C or Pen, in D or L form; and wherein the peptide has a length of 12 to 20 amino acids. |
| Claim: | 9. The collagen binding peptide of claim 8 , wherein: X13=H, A, S, K, N, D, Y, T, P, or Aib, in D or L form; and X14=W, A, Y, 1-Nal, 2-Nal, thien-W, Tic, or W(5-OH), in D or L form. |
| Claim: | 10. The collagen binding peptide of claim 8 , wherein the collagen binding peptide comprises a cyclic peptide comprising the amino acid sequence: [table included] wherein: X15 and X16 comprise one to three amino acids; and wherein the peptide has a length of 14 to 20 amino acids. |
| Claim: | 11. The collagen binding peptide of claim 10 , wherein: X15=Q, G, A, D, S, P, K, GQ, K(G), K(Y.G), K(V.G), K(F.G), K(H.H), KK(K), Dpr, or Aib, in D or L form; and X16=G, K, PP, GY, GV, GF, GH, GK(G), KK(K), Dpr, EAG, or PPG, in D or L form. |
| Claim: | 12. The collagen binding peptide of claim 11 , wherein: X15=Q, D, or K(G); and X16=G. |
| Claim: | 13. A collagen binding peptide, wherein the collagen binding peptide comprises a cyclic peptide comprising the amino acid sequence: [table included] wherein: X1=any amino acid in L form; X2=W or W*; X3=H, A, K, or S; X4=T, Y, G, K, or Y*; X5=any amino acid in L form; X6=F, Y, Y*; X7=H, A, or Y; X8=Y or Y*; X9=L, V, L*, or Y*; X10=Y, F, or Y*; and X11=G, Y, Bip, or Y*; wherein: W* is 1-Nal, 2-Nal, Bpa, thien-W, W(5-OH), 7-aza-Trp, 1-methyl-Trp, 5-bromo-Tryp, 5-chloro-Tryp, 5-fluor-Trp, 7-methyl-trp, 6-methyl-Trp, 6-flouro-Trp, or 6-hydroxy-trp; Y* is F(4-NH2), F(3,4-OMe2), F(3-OMe), F(4-CF3), F(4-CN), F(4-NO2), F(4-F), F(4-NO2), Hfe, 4-tBu-F, 4-CO2H-F, h-Tyr, h-Tyr(Me), Y(2,6-Me2), Y(3-Cl), Y(3-I), Y(Bn, 3-Cl), 2-substituted L-Tyr, 2,3-substituted-L-Tyr, 2,3,5-substituted-L-tyr, 2,5-substituted-L-Tyr, 2,6-substituted-L-Tyr, 2,3,5,6-substituted-L-Tyr, 3-substituted-L-Tyr, 3,5-substituted-L-Tyr, 2-substituted L-Phe, 2,3-substituted-L-Phe, 2,3,5-substituted-L-Phe, 2,5-substituted-L-Phe, 2,6-substituted-L-Phe, 2,3,5,6-substituted-L-Phe, 3-substituted-L-Phe, 3,5-substituted-L-Phe, L-2-pyridylalanine, L-3-pyridylalanine, or L-4-pyridylalanine; L* is I, V, A, L, G, Tle, L-norvaline, L-norleucine, L-dehydroleucine, L-abu (2-aminobutyric acid), L-tert-leucine, beta-cyclohexyl-L-alanine, L-homoleucine, or L-homo-cyclohexylalanine; C* is C or Pen; P* is P, L-hydroxyproline, piperidine-2-carboxylic acid, or 4-hydroxypiperidine-2-carboxylic acid; and wherein the peptide has a length of 16 to 20 amino acids, and wherein one or more of the amino acids in the peptide is derivatized with a non-metallic radionuclide selected from the group consisting of 18 F, 123 I, 125 I, and 131 I. |
| Claim: | 14. The collagen binding peptide of claim 13 , wherein: X1=Q or K(G); and X5=R, Y, L, D, or K. |
| Claim: | 15. The collagen binding peptide of any one of claims 1 , 2 , and 13 , wherein the non-metallic radionuclide is 18 F. |
| Claim: | 16. The collagen binding peptide of any one of claims 1 , 2 , and 13 , wherein at least one of the one or more derivatized amino acids is a derivatized tyrosine. |
| Claim: | 17. The collagen binding peptide of claim 16 , wherein the derivatized tyrosine is iodinated with 123 I, 125 I, or 131 I. |
| Claim: | 18. The collagen binding peptide of any one of claims 1 , 2 , and 13 , wherein the one or more amino acids are derivatized with a non-metallic radionuclide at the N-terminus, the C-terminus or at an amino acid side chain. |
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| Assistant Examiner: | Hellman, Kristina M |
| Primary Examiner: | Ha, Julie |
| Attorney, Agent or Firm: | Fish & Richardson P.C. |
| رقم الانضمام: | edspgr.09386938 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |