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PMID: 19055415 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S.

Discovery of targeting ligands for breast cancer cells using the one-bead one-compound combinatorial method.

Journal of medicinal chemistry ·Vol. 52 ·No. 1 ·2009-01-08 ·Pages 126-33

Yao N, Xiao W, Wang X, Marik J, Park SH, Takada Y, Lam KS

Abstract

Four "one-bead one-compound" (OBOC) combinatorial libraries were designed, synthesized, and screened against MDA-MB-231 breast cancer cells. A novel cyclic peptide 1 (LXY1) with high binding specificity to alpha3 integrin was identified. Molecular interactions between alpha3 integrin and 1 were characterized by using a series of K562 cells transfected with various mutant alpha3 integrins. Using analytic flow cytometry, the binding affinity (K(d)) of 1 to alpha3 integrin on MDA-MB-231 breast cancer cells was determined to be approximately 0.4 microM. Based on the established structure-activity relationship (SAR) study, two highly focused cyclic peptide libraries were further designed, synthesized, and screened against MDA-MB-231 breast cancer cells under stringent conditions. A novel cyclic peptide 2 (LXY3) with a high binding affinity (IC(50) = 57 nM) was identified. Moreover, the targeting efficiency and specificity of 2 to the breast adenocarcinoma tumors in mouse xenografts were further confirmed by in vivo and ex vivo near-infrared fluorescence optical imaging.

MeSH Terms
Animals Biomimetic Materials/chemical synthesis,chemistry,metabolism Biotinylation Breast Neoplasms/metabolism,pathology Cell Line, Tumor Combinatorial Chemistry Techniques Databases, Protein Drug Design Female Humans Integrin alpha3/metabolism Ligands Magnetic Resonance Spectroscopy Mice Mice, Nude Molecular Structure Peptides/chemical synthesis,chemistry,metabolism Structure-Activity Relationship Substrate Specificity Xenograft Model Antitumor Assays
Chemicals
Integrin alpha3 Ligands Peptides
Authors & Affiliations
7 authors, click to expand affiliations / ORCID
Yao Nianhuan
Department of Internal Medicine, Division of Hematology and Oncology, UC Davis Cancer Center, University of California, Davis, Sacramento, California 95817, USA.
Xiao Wenwu
Wang Xiaobing
Marik Jan
Park See Hyoung
Takada Yoshikazu
Lam Kit S
References (49)
49 references, click to expand
  1. Inhibition of angiogenesis in human glioblastomas by chromosome 10 induction of thrombospondin-1.
    Cancer Res. 1996 Dec 15;56(24):5684-91 PMID: 8971176
  2. Integrins.
    J Clin Invest. 1991 Jan;87(1):1-5 PMID: 1985087
  3. Identification of an alpha(3)beta(1) integrin recognition sequence in thrombospondin-1.
    J Biol Chem. 1999 Aug 20;274(34):24080-6 PMID: 10446179
  4. Automatic Edman microsequencing of peptides containing multiple unnatural amino acids.
    Anal Biochem. 2001 Aug 1;295(1):9-16 PMID: 11476539
  5. A synthetic peptide derived from the carboxy terminus of the laminin A chain represents a binding site for the alpha 3 beta 1 integrin.
    J Cell Biol. 1992 Apr;117(2):449-59 PMID: 1560034
  6. A new type of synthetic peptide library for identifying ligand-binding activity.
    Nature. 1991 Nov 7;354(6348):82-4 PMID: 1944576
  7. In vivo imaging of tumors with protease-activated near-infrared fluorescent probes.
    Nat Biotechnol. 1999 Apr;17(4):375-8 PMID: 10207887
  8. Therapeutic cancer targeting peptides.
    Biopolymers. 2002;66(3):184-99 PMID: 12385037
  9. Rituximab (anti-CD20 monoclonal antibody) for the treatment of patients with relapsing or refractory aggressive lymphoma: a multicenter phase II study.
    Blood. 1998 Sep 15;92(6):1927-32 PMID: 9731049
  10. Organ targeting in vivo using phage display peptide libraries.
    Nature. 1996 Mar 28;380(6572):364-6 PMID: 8598934
  11. Pro-adhesive and chemotactic activities of thrombospondin-1 for breast carcinoma cells are mediated by alpha3beta1 integrin and regulated by insulin-like growth factor-1 and CD98.
    J Biol Chem. 1999 Apr 16;274(16):11408-16 PMID: 10196234
  12. Peptide ligands targeting integrin alpha3beta1 in non-small cell lung cancer.
    Lung Cancer. 2006 Jun;52(3):291-7 PMID: 16635537
  13. Thrombospondin 1 expression in transformed endothelial cells restores a normal phenotype and suppresses their tumorigenesis.
    Proc Natl Acad Sci U S A. 1995 Jul 18;92(15):6788-92 PMID: 7624320
  14. Epiligrin, a new cell adhesion ligand for integrin alpha 3 beta 1 in epithelial basement membranes.
    Cell. 1991 May 17;65(4):599-610 PMID: 2032285
  15. Applications of topologically segregated bilayer beads in 'one-bead one-compound' combinatorial libraries.
    J Pept Res. 2005 Jan;65(1):130-8 PMID: 15686543
  16. Hepatic veno-occlusive disease in two patients with relapsed acute myeloid leukemia treated with anti-CD33 calicheamicin (CMA-676) immunoconjugate.
    Ann Hematol. 2001 Feb;80(2):119-20 PMID: 11261323
  17. A peptide model of basement membrane collagen alpha 1 (IV) 531-543 binds the alpha 3 beta 1 integrin.
    J Biol Chem. 1995 Dec 8;270(49):29047-50 PMID: 7493922
  18. Immunotherapy for non-Hodgkin's lymphoma.
    Oncology (Williston Park). 2001 Feb;15(2):141-7, 151; discussion 152-5 PMID: 11252930
  19. Differential effects of integrin alpha chain mutations on invasin and natural ligand interaction.
    J Biol Chem. 1998 Nov 27;273(48):31837-43 PMID: 9822651
  20. Yttrium-90/indium-111-DOTA-peptide-chimeric L6: pharmacokinetics, dosimetry and initial results in patients with incurable breast cancer.
    Anticancer Res. 1997 May-Jun;17(3B):1735-44 PMID: 9179227
  21. Receptor functions for the integrin VLA-3: fibronectin, collagen, and laminin binding are differentially influenced by Arg-Gly-Asp peptide and by divalent cations.
    J Cell Biol. 1991 Jan;112(1):169-81 PMID: 1986004
  22. The Eugene M. Landis Award Lecture 1996. Delivery of molecular and cellular medicine to solid tumors.
    Microcirculation. 1997 Mar;4(1):1-23 PMID: 9110280
  23. Flow cytometric measurement of kinetic and equilibrium binding parameters of arginine-glycine-aspartic acid ligands in binding to glycoprotein IIb/IIIa on platelets.
    Cytometry. 1997 May 1;28(1):58-65 PMID: 9136756
  24. A novel peptide-based encoding system for "one-bead one-compound" peptidomimetic and small molecule combinatorial libraries.
    J Am Chem Soc. 2002 Jul 3;124(26):7678-80 PMID: 12083920
  25. Engineered antibody fragments and the rise of single domains.
    Nat Biotechnol. 2005 Sep;23(9):1126-36 PMID: 16151406
  26. 124I-labeled engineered anti-CEA minibodies and diabodies allow high-contrast, antigen-specific small-animal PET imaging of xenografts in athymic mice.
    J Nucl Med. 2003 Dec;44(12):1962-9 PMID: 14660722
  27. Nonmyeloablative iodine-131 anti-B1 radioimmunotherapy as outpatient therapy.
    J Nucl Med. 1998 Jul;39(7):1230-6 PMID: 9669400
  28. Radiolabeled estradiol derivatives to predict response to hormonal treatment in breast cancer: a review.
    Eur J Nucl Med. 2000 Sep;27(9):1421-33 PMID: 11007529
  29. Identification of novel targeting peptides for human ovarian cancer cells using "one-bead one-compound" combinatorial libraries.
    Mol Cancer Ther. 2005 May;4(5):806-13 PMID: 15897245
  30. Studies of the HER-2/neu proto-oncogene in human breast and ovarian cancer.
    Science. 1989 May 12;244(4905):707-12 PMID: 2470152
  31. The "One-Bead-One-Compound" Combinatorial Library Method.
    Chem Rev. 1997 Apr 1;97(2):411-448 PMID: 11848877
  32. Radiolabeled-antibody therapy of B-cell lymphoma with autologous bone marrow support.
    N Engl J Med. 1993 Oct 21;329(17):1219-24 PMID: 7692295
  33. Transfection of thrombospondin 1 complementary DNA into a human breast carcinoma cell line reduces primary tumor growth, metastatic potential, and angiogenesis.
    Cancer Res. 1994 Dec 15;54(24):6504-11 PMID: 7527299
  34. Synthesis of hydrophilic and flexible linkers for peptide derivatization in solid phase.
    Bioorg Med Chem Lett. 2004 Jan 5;14(1):161-5 PMID: 14684320
  35. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.
    Int J Pept Protein Res. 1990 Mar;35(3):161-214 PMID: 2191922
  36. Noninvasive imaging of alpha(v)beta3 integrin expression using 18F-labeled RGD-containing glycopeptide and positron emission tomography.
    Cancer Res. 2001 Mar 1;61(5):1781-5 PMID: 11280722
  37. Fluorescence imaging with near-infrared light: new technological advances that enable in vivo molecular imaging.
    Eur Radiol. 2003 Jan;13(1):195-208 PMID: 12541130
  38. Near-infrared optical imaging of epidermal growth factor receptor in breast cancer xenografts.
    Cancer Res. 2003 Nov 15;63(22):7870-5 PMID: 14633715
  39. The role of alpha2 beta1 and alpha3 beta1 integrin receptors in the initial anchoring of MDA-MB-231 human breast cancer cells to cortical bone matrix.
    Biochem Biophys Res Commun. 1998 Sep 29;250(3):735-40 PMID: 9784415
  40. Streptavidin in antibody pretargeting. 4. Site-directed mutation provides evidence that both arginine and lysine residues are involved in kidney localization.
    Bioconjug Chem. 2004 Nov-Dec;15(6):1454-63 PMID: 15546215
  41. Bacteriophage display and discovery of peptide leads for drug development.
    Annu Rev Biophys Biomol Struct. 1997;26:401-24 PMID: 9241425
  42. The PPFLMLLKGSTR motif in globular domain 3 of the human laminin-5 alpha3 chain is crucial for integrin alpha3beta1 binding and cell adhesion.
    Exp Cell Res. 2005 Mar 10;304(1):317-27 PMID: 15707596
  43. Near-infrared optical imaging in glioblastoma xenograft with ligand-targeting alpha 3 integrin.
    Eur J Nucl Med Mol Imaging. 2009 Jan;36(1):94-103 PMID: 18712382
  44. Alpha 3 beta 1 adhesion to laminin-5 and invasin: critical and differential role of integrin residues clustered at the boundary between alpha 3 N-terminal repeats 2 and 3.
    Biochemistry. 1999 Oct 26;38(43):14424-31 PMID: 10572017
  45. Discovery of high-affinity peptide ligands for vancomycin.
    Biopolymers. 2008;90(3):421-32 PMID: 18260149
  46. Charcoal surface-assisted catalysis of intramolecular disulfide bond formation in peptides.
    J Pept Res. 1998 May;51(5):365-9 PMID: 9606016
  47. Real-time vital optical imaging of precancer using anti-epidermal growth factor receptor antibodies conjugated to gold nanoparticles.
    Cancer Res. 2003 May 1;63(9):1999-2004 PMID: 12727808
  48. Control of angiogenesis in fibroblasts by p53 regulation of thrombospondin-1.
    Science. 1994 Sep 9;265(5178):1582-4 PMID: 7521539
  49. Combinatorial chemistry identifies high-affinity peptidomimetics against alpha4beta1 integrin for in vivo tumor imaging.
    Nat Chem Biol. 2006 Jul;2(7):381-9 PMID: 16767086
Article Info
Journal
Journal of medicinal chemistry
Abbr.
J Med Chem
ISSN
1520-4804
Published
2009-01-08
Pages
126-33
Language
English
Region
United States
NLM ID
9716531
PMCID
PMC2836207
Subset
IM
Grants
NCI NIH HHS · R01 CA115483-01 · United States
NCI NIH HHS · U19 CA113298 · United States
NCI NIH HHS · U19CA113298 · United States
NCI NIH HHS · R01CA115483 · United States
NCI NIH HHS · R01 CA115483 · United States
NCI NIH HHS · U19 CA113298-04 · United States
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