Illuminating the lipidome to advance biomedical research: Peptide-based probes of membrane lipids

Future Medicinal Chemistry

Volumn 5, Issue 8, 2013, Pages 947-959

  Gao, Jianmin ^a   Zheng, Hong ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTADHERIN; LANTHIOPEPTIN; LIPID BINDING PROTEIN; LIPIDOME; LIPOCORTIN 5; NISIN; SCAFFOLD PROTEIN;

BIOMIMETICS; CELL CULTURE; DIAGNOSTIC IMAGING; DRUG POTENCY; HUMAN; LIPID MEMBRANE; MEDICAL RESEARCH; MEMBRANE BINDING; PRIORITY JOURNAL; PROTEIN TARGETING; REVIEW;

BACTERIOCINS; BIOMIMETIC MATERIALS; GRAM-POSITIVE BACTERIA; MEMBRANE LIPIDS; PEPTIDES; PHOSPHATIDYLSERINES; PROTEIN BINDING;

EID: 84878343219     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.13.66     Document Type: Review

References (61)

1. van Meer G, Voelker DR, Feigenson GW. Membrane lipids: where they are and how they behave. Nat. Rev. Mol. Cell Biol. 9(2), 112-124 (2008).
2. Shevchenko A, Simons K. Lipidomics: coming to grips with lipid diversity. Nat. Rev. Mol. Cell Biol. 11(8), 593-598 (2010).
3. Wenk MR. Lipidomics: new tools and applications. Cell 143(6), 888-895 (2010).
4. Lingwood D, Simons K. Lipid rafts as a membrane-organizing principle. Science 327(5961), 46-50 (2010).
5. Balasubramanian K, Schroit AJ. Aminophospholipid asymmetry: a matter of life and death. Annu. Rev. Physiol. 65, 701-734 (2003).
6. Schutters K, Reutelingsperger C. Phosphatidylserine targeting for diagnosis and treatment of human diseases. Apoptosis 15(9), 1072-1082 (2010).
7. Lemmon MA. Membrane recognition by phospholipid-binding domains. Nat. Rev. Mol. Cell Biol. 9(2), 99-111 (2008).
8. Niu G, Chen X. Apoptosis imaging: beyond annexin V. J. Nucl. Med. 51(11), 1659-1662 (2010).
9. Lambert TN, Smith BD. Synthetic receptors for phospholipid headgroups. Coordination Chem. Rev. 240(1-2), 129-141 (2003).
10. Tseng CY, Ashrafuzzaman M, Mane JY, Kapty J, Mercer JR, Tuszynski JA. Entropic fragment-based approach to aptamer design. Chem. Biol. Drug Design 78(1), 1-13 (2011).
11. Willey JM, Van Der Donk WA. Lantibiotics: peptides of diverse structure and function. Annu. Rev. Microbiol. 61, 477-501 (2007).
12. Cotter PD, Hill C, Ross RP. Bacteriocins: developing innate immunity for food. Nat. Rev. 3(10), 777-788 (2005).
13. Breukink E, Wiedemann I, Van Kraaij C, Kuipers OP, Sahl H, De Kruijff B. Use of the cell wall precursor lipid II by a pore-forming peptide antibiotic. Science 286(5448), 2361-2364 (1999).
14. Hsu ST, Breukink E, Tischenko E et al. The nisin-lipid II complex reveals a pyrophosphate cage that provides a blueprint for novel antibiotics. Nat. Struct. Mol. Biol. 11(10), 963-967 (2004).
15. Kessler H, Steuernagel S, Will M et al. The structure of the polycyclic nonadecapeptide Ro-09-0198. Helv. Chim. Acta 71(8), 1924-1929 (1988).
16. Navarro J, Chabot J, Sherrill K, Aneja R, Zahler SA, Racker E. Interaction of duramycin with artificial and natural membranes. Biochemistry 24(17), 4645-4650 (1985).
17. Zhao M. Lantibiotics as probes for phosphatidylethanolamine. Amino Acids 41(5), 1071-1079 (2011).
18. Emoto K, Kobayashi T, Yamaji A et al. Redistribution of phosphatidylethanolamine at the cleavage furrow of dividing cells during cytokinesis. Proc. Natl. Acad. Sci. USA 93(23), 12867-12872 (1996).
19. Emoto K, Umeda M. An essential role for a membrane lipid in cytokinesis. Regulation of contractile ring disassembly by redistribution of phosphatidylethanolamine. J. Cell. Biol. 149(6), 1215-1224 (2000).
20. Maulik N, Kagan VE, Tyurin VA, Das DK. Redistribution of phosphatidylethanolamine and phosphatidylserine precedes reperfusioninduced apoptosis. Am. J. Physiol. 274(1 Pt 2), H242-H248 (1998).
21. Machaidze G, Ziegler A, Seelig J. Specific binding of Ro 09-0198 (cinnamycin) to phosphatidylethanolamine: a thermodynamic analysis. Biochemistry 41(6), 1965-1971 (2002).
22. Machaidze G, Seelig J. Specific binding of cinnamycin (Ro 09-0198) to phosphatidylethanolamine. Comparison between micellar and membrane environments. Biochemistry 42(43), 12570-12576 (2003).
23. Choung SY, Kobayashi T, Takemoto K, Ishitsuka H, Inoue K. Interaction of a cyclic peptide, Ro09-0198, with phosphatidylethanolamine in liposomal membranes. Biochim. Biophys. Acta 940(2), 180-187 (1988).
24. Zhao M, Li Z, Bugenhagen S. 99mTc-labeled duramycin as a novel phosphatidylethanolamine-binding molecular probe. J. Nucl. Med. 49(8), 1345-1352 (2008).
25. Wakamatsu K, Choung SY, Kobayashi T, Inoue K, Higashijima T, Miyazawa T. Complex formation of peptide antibiotic Ro09-0198 with lysophosphatidylethanolamine: 1H NMR analyses in dimethyl sulfoxide solution. Biochemistry 29(1), 113-118 (1990).
26. Hosoda K, Ohya M, Kohno T, Maeda T, Endo S, Wakamatsu K. Structure determination of an immunopotentiator peptide, cinnamycin, complexed with lysophosphatidylethanolamine by 1H-NMR1. J. Biochem. 119(2), 226-230 (1996).
27. Yeung T, Gilbert GE, Shi J, Silvius J, Kapus A, Grinstein S. Membrane phosphatidylserine regulates surface charge and protein localization. Science 319(5860), 210-213 (2008).
28. Shi J, Pipe SW, Rasmussen JT, Heegaard CW, Gilbert GE. Lactadherin blocks thrombosis and hemostasis in vivo: correlation with platelet phosphatidylserine exposure. J. Thromb. Haemost. 6(7), 1167-1174 (2008).
29. Meers P, Mealy T. Calcium-dependent annexin V binding to phospholipids: stoichiometry, specificity, and the role of negative charge. Biochemistry 32(43), 11711-11721 (1993).
30. Meers P, Mealy T. Relationship between annexin V tryptophan exposure, calcium, and phospholipid binding. Biochemistry 32(20), 5411-5418 (1993).
31. Swairjo MA, Concha NO, Kaetzel MA, Dedman JR, Seaton BA. Ca(2+)-bridging mechanism and phospholipid head group recognition in the membrane-binding protein annexin V. Nat. Struct. Biol. 2(11), 968-974 (1995).
32. Kamp D, Sieberg T, Haest CW. Inhibition and stimulation of phospholipid scrambling activity. Consequences for lipid asymmetry, echinocytosis, and microvesiculation of erythrocytes. Biochemistry 40(31), 9438-9446 (2001).
33. Blankenberg FG, Katsikis PD, Tait JF et al. In vivo detection and imaging of phosphatidylserine expression during programmed cell death. Proc. Natl. Acad. Sci. USA 95(11), 6349-6354 (1998).
34. Ntziachristos V, Schellenberger EA, Ripoll J et al. Visualization of antitumor treatment by means of fluorescence molecular tomography with an annexin V-Cy5.5 conjugate. Proc. Natl. Acad. Sci. USA 101(33), 12294-12299 (2004).
35. Hanshaw RG, Smith BD. New reagents for phosphatidylserine recognition and detection of apoptosis. Bioorg. Med. Chem. 13(17), 5035-5042 (2005).
36. Ojida A, Mito-Oka Y, Inoue MA, Hamachi I. First artificial receptors and chemosensors toward phosphorylated peptide in aqueous solution. J. Am. Chem. Soc. 124(22), 6256-6258 (2002).
37. Koulov AV, Stucker KA, Lakshmi C, Robinson JP, Smith BD Detection of apoptotic cells using a synthetic fluorescent sensor for membrane surfaces that contain phosphatidylserine. Cell. Death Differ. 10(12), 1357-1359 (2003).
38. Lakshmi C, Hanshaw RG, Smith BD. Fluorophore-linked zinc(II) dipicolylamine coordination complexes as sensors for phosphatidylserine- containing membranes. Tetrahedron 60(49), 11307-11315 (2004).
39. Hanshaw RG, Lakshmi C, Lambert TN, Johnson JR, Smith BD. Fluorescent detection of apoptotic cells by using zinc coordination complexes with a selective affinity for membrane surfaces enriched with phosphatidylserine. ChemBioChem 6(12), 2214-2220 (2005).
40. Smith BA, Akers WJ, Leevy WM et al. Optical imaging of mammary and prostate tumors in living animals using a synthetic near infrared zinc(II)-dipicolylamine probe for anionic cell surfaces. J. Am. Chem. Soc. 132(1), 67-69 (2010).
41. Smith BA, Xiao S, Wolter W, Wheeler J, Suckow MA, Smith BD. In vivo targeting of cell death using a synthetic fluorescent molecular probe. Apoptosis 16(7), 722-731 (2011).
42. Smith BA, Gammon ST, Xiao S et al. In vivo optical imaging of acute cell death using a near-infrared fluorescent zinc-dipicolylamine probe. Mol. Pharm. 8(2), 583-590 (2011).
43. Divittorio KM, Johnson JR, Johansson E, Reynolds AJ, Jolliffe KA, Smith BD. Synthetic peptides with selective affinity for apoptotic cells. Org. Biomol. Chem. 4(10), 1966-1976 (2006).
44. Shi J, Heegaard CW, Rasmussen JT, Gilbert GE. Lactadherin binds selectively to membranes containing phosphatidyl-l-serine and increased curvature. Biochim. Biophys. Acta 1667(1), 82-90 (2004).
45. Hanayama R, Tanaka M, Miwa K, Shinohara A, Iwamatsu A, Nagata S. Identification of a factor that links apoptotic cells to phagocytes. Nature 417(6885), 182-187 (2002).
46. Lin L, Huai Q, Huang M, Furie B, Furie BC. Crystal structure of the bovine lactadherin C2 domain, a membrane binding motif, shows similarity to the C2 domains of factor V and factor VIII. J. Mol. Biol. 371(3), 717-724 (2007).
47. Shao C, Novakovic VA, Head JF, Seaton BA, Gilbert GE. Crystal structure of lactadherin C2 domain at 1.7A resolution with mutational and computational analyses of its membrane-binding motif. J. Biol. Chem. 283(11), 7230-7241 (2008).
48. Zheng H, Wang F, Wang Q, Gao J. Cofactorfree detection of phosphatidylserine with cyclic peptides mimicking lactadherin. J. Am. Chem. Soc. 133(39), 15280-15283 (2011).
49. Killian JA, von Heijne G. How proteins adapt to a membrane-water interface. Trends Biochem. Sci. 25(9), 429-434 (2000).
50. Igarashi K, Kaneda M, Yamaji A et al. A novel phosphatidylserine-binding peptide motif defined by an anti-idiotypic monoclonal antibody. Localization of phosphatidylserinespecific binding sites on protein kinase C and phosphatidylserine decarboxylase. J. Biol. Chem. 270(49), 29075-29078 (1995).
51. Xiong C, Brewer K, Song S et al. Peptidebased imaging agents targeting phosphatidylserine for the detection of apoptosis. J. Med. Chem. 54(6), 1825-1835 (2011).
52. Shao R, Xiong C, Wen X, Gelovani JG, Li C. Targeting phosphatidylserine on apoptotic cells with phages and peptides selected from a bacteriophage display library. Mol. Imaging 6(6), 417-426 (2007).
53. Burtea C, Laurent S, Lancelot E et al. Peptidic targeting of phosphatidylserine for the MRI detection of apoptosis in atherosclerotic plaques. Mol. Pharm. 6(6), 1903-1919 (2009).
54. Thapa N, Kim S, So IS et al. Discovery of a phosphatidylserine- recognizing peptide and its utility in molecular imaging of tumour apoptosis. J. Cell. Mol. Med. 12(5A), 1649-1660 (2008).
55. Mcmahon HT, Gallop JL. Membrane curvature and mechanisms of dynamic cell membrane remodelling. Nature 438(7068), 590-596 (2005).
56. Drin G, Casella JF, Gautier R, Boehmer T, Schwartz TU, Antonny B A general amphipathic alpha-helical motif for sensing membrane curvature. Nature Struct. Mol. Biol. 14(2), 138-146 (2007).
57. Yang L, Gordon VD, Trinkle DR et al. Mechanism of a prototypical synthetic membrane-active antimicrobial: efficient hole-punching via interaction with negative intrinsic curvature lipids. Proc. Natl Acad. Sci. USA 105(52), 20595-20600 (2008).
58. Balaj L, Lessard R, Dai L et al. Tumour microvesicles contain retrotransposon elements and amplified oncogene sequences. Nat. Commun. 2, 180 (2011).
59. Saludes JP, Morton LA, Ghosh N et al. Detection of highly curved membrane surfaces using a cyclic peptide derived from synaptotagmin-I. ACS Chem. Biol. 7(10), 1629-1635 (2012).
60. Hui E, Johnson CP, Yao J, Dunning FM, Chapman ER. Synaptotagmin-mediated bending of the target membrane is a critical step in Ca(2+)-regulated fusion. Cell 138(4), 709-721 (2009).
61. Morton LA, Yang H, Saludes JP et al. MARCKS-ED peptide as a curvature and lipid sensor. ACS Chem. Biol. 8(1), 218-225 (2013).