Lantibiotics as probes for phosphatidylethanolamine

Amino Acids

Volumn 41, Issue 5, 2011, Pages 1071-1079

  Zhao, Ming ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

Anticoagulant; Apoptosis; Cinnamycin; Cytokinesis; Duramycin; Imaging probe; Phosphatidylethanolamine

Indexed keywords

COPPER 64; GADOLINIUM; LANCOVUTIDE; LANTHIONINE; LANTHIOPEPTIN; LANTIBIOTIC; MACROGOL; PHOSPHATIDYLETHANOLAMINE; TECHNETIUM 99M;

ANTICOAGULATION; APOPTOSIS; BINDING AFFINITY; CELL LEVEL; CYTOKINESIS; CYTOTOXICITY TEST; DERIVATIZATION; HUMAN; MITOSIS; MOLECULAR PROBE; NECROSIS; NONHUMAN; PHOSPHOLIPID SYNTHESIS; PRIORITY JOURNAL; PROTEIN LIPID INTERACTION; REVIEW; STRUCTURE ANALYSIS; TISSUE LEVEL;

AMINO ACID SEQUENCE; ANIMALS; BACTERIOCINS; HUMANS; MOLECULAR IMAGING; MOLECULAR PROBES; MOLECULAR SEQUENCE DATA; PHOSPHATIDYLETHANOLAMINES;

MAMMALIA;

EID: 84855230886     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-009-0386-9     Document Type: Review

References (61)

1. Aoki Y, Uenaka T, Aoki J, Umeda M, Inoue K (1994) A novel peptide probe for studying the transbilayer movement of phosphatidylethanolamine. J Biochem 116:291-297 (Pubitemid 24265600)
2. Berard M, Chantome R, Marcelli A, Boffa MC (1996) Antiphosphatidylethanolamine antibodies as the only antiphospholipid antibodies. I. Association with thrombosis and vascular cutaneous diseases. J Rheumatol 23:1369-1374 (Pubitemid 26258759)
3. Bevers EM, Comfurius P, Zwaal RF (1996) Regulatory mechanisms in maintenance and modulation of transmembrane lipid asymmetry: pathophysiological implications. Lupus 5:480-487 (Pubitemid 26354072)
4. Bevers EM, Comfurius P, Dekkers DW et al (1999) Lipid translocation across the plasma membrane of mammalian cells. Biochim Biophys Acta 1439:317-330 (Pubitemid 29371798)
5. Bi EF, Lutkenhaus J (1991) FtsZ ring structure associated with division in Escherichia coli. Nature 354:161-164 (Pubitemid 21896803)
6. Blankenberg FG, Katsikis PD, Tait JF, Davis RE, Naumovski L, Ohtsuki K, Kopiwoda S, Abrams MJ, Darkes M, Robbins RC, Maecker HT, Strauss HW (1998) In vivo detection and imaging of phosphatidylserine expression during programmed cell death. Proc Natl Acad Sci USA 95:6349-6354 (Pubitemid 28249015)
7. Bleeker-Rovers CP, Boerman OC, Rennen HJ, Corstens FH, Oyen WJ (2004) Radiolabeled compounds in diagnosis of infectious and inflammatory disease. Curr Pharm Des 10:2935-2950 (Pubitemid 39220313)
8. Brötz H, Josten M, Wiedemann I, Schneider U, Götz F, Bierbaum G, Sahl HG (1998) Role of lipid-bound peptidoglycan precursors in the formation of pores by nisin, epidermin and other lantibiotics. Mol Microbiol 30:317-3127
9. Chandran KB (1993) Flow dynamics in the human aorta. J Biomech Eng 115:611-616 (Pubitemid 24000890)
10. Choung SY, Kobayashi T, Inoue J, Takemoto K, Ishitsuka H, Inoue K (1988) Hemolytic activity of a cyclic peptide Ro09-0198 isolated from Streptoverticillium. Biochim Biophys Acta 940:171-179
11. Devaux PF (1991) Static and dynamic lipid asymmetry in cell membranes. Biochemistry 30:1163-1173
12. Emoto K, Umeda M (2000) An essential role for a membrane lipid in cytokinesis. Regulation of contractile ring disassembly by redistribution of phosphatidylethanolamine. J Cell Biol 149:1215-1224 (Pubitemid 30399675)
13. Emoto K, Kobayashi T, Yamaji A, Aizawa H, Yahara I, Inoue K, Umeda M (1996) Redistribution of phosphatidylethanolamine at the cleavage furrow of dividing cells during cytokinesis. Proc Natl Acad Sci USA 93:12867-12872 (Pubitemid 26382735)
14. Emoto K, Toyama-Sorimachi N, Karasuyama H, Inoue K, Umeda M (1997) Exposure of phosphatidylethanolamine on the surface of apoptotic cells. Exp Cell Res 232:430-434 (Pubitemid 27194059)
15. Emoto K, Inadome H, Kanaho Y, Narumiya S, Umeda M (2005) Local change in phospholipid composition at the cleavage furrow is essential for completion of cytokinesis. J Biol Chem 280:37901-37907 (Pubitemid 41642402)
16. Esmon NL, Smirnov MD, Esmon CT (1997a) Lupus anticoagulants and thrombosis: the role of phospholipids. Haematologica 82:474-477 (Pubitemid 28023292)
17. Esmon NL, Smirnov MD, Esmon CT (1997b) Thrombogenic mechanisms of antiphospholipid antibodies. Thromb Haemost 78:79-82 (Pubitemid 27289220)
18. Esmon NL, Smirnov MD, Safa O, Esmon CT (1999) Lupus anticoagulants, thrombosis and the protein C system. Haematologica 84:446-451 (Pubitemid 29473136)
19. Hachulla E, Harle JR, Sie P, Boffa MC (2007) Antiphosphatidylethanolamine antibodies are associated with an increased odds ratio for thrombosis. A multicenter study with the participation of the European Forum on antiphospholipid antibodies. Thromb Haemost 97:949-954 (Pubitemid 46939208)
20. Hayashi F, Nagashima K, Terui Y, Kawamura Y, Matsumoto K, Itazaki H (1990) The structure of PA48009: the revised structure of duramycin. J Antibiot 43:1421-1430 (Pubitemid 20378500)
21. Hosoda K, Ohya M, Kohno T, Maeda T, Endo S, Wakamatsu K (1996) Structure determination of an immunopotentiator peptide, cinnamycin, complexed with lysophosphatidylethanolamine by 1H-NMR1. J Biochem 119:226-230 (Pubitemid 26063240)
22. Iwamoto K, Kobayashi S, Fukuda R, Umeda M, Kobayashi T, Ohta A (2004) Local exposure of phosphatidylethanolamine on the yeast plasma membrane is implicated in cell polarity. Genes Cells 9:891-903 (Pubitemid 39369022)
23. 99mTc-annexin V imaging for in vivo detection of atherosclerotic lesions in porcine coronary arteries. J Nucl Med 46:1186-1193 (Pubitemid 43741081)
24. Kaletta C, Entian KD, Jung G (1991) Prepeptide sequence of cinnamycin (Ro 09-0198): the first structural gene of a duramycin-type lantibiotic. Eur J Biochem 199:411-415
25. Kato U, Emoto K, Fredriksson C, Nakamura H, Ohta A, Kobayashi T, Murakami-Murofushi K, Kobayashi T, Umeda M (2002) A novel membrane protein, Ros3p, is required for phospholipids translocation across the plasma membrane in Saccharomyces cerevisiae. J Biol Chem 277:37855-37862
26. Kiestelaer BL, Reutelingsperger CPM, Heidendal GAK, Daemen MJAP, Mess WH, Hofstra L (2004) Noninvasive detection of plaque instability with use of radiolabeled annexin A5 in patients with carotid-artery atherosclerosis. N Engl J Med 350:1472-1473 (Pubitemid 38420011)
27. Li Z, Wells CW, Esmon CT, Zhao M (2009) Phosphatidylethanolamine at the endothelial surface of aortic flow dividers. J Thromb Haemost 7:227-229
28. Li Z, Wells CW, North PE, Kumar S, Duris CB, McIntyre JA, Zhao M (2010) Phosphatidylethanolamine at the luminal endothelial surface-implications in hemostasis and thrombotic autoimmunity. Clin Appl Thromb Hem (in press)
29. 99mTc-labeled small peptides as diagnostic radiopharmaceuticals. Chem Rev 99:2235-2268
30. 99mTc-labeled C2A domain of synaptotagmin I in a rat model of ischemia and reperfusion. Nucl Med Biol 34:907-915 (Pubitemid 350061176)
31. Machaidze G, Seelig J (2003) Specific binding of cinnamycin (Ro 09- 0198) to phosphatidylethanolamine. Comparison between micellar and membrane environments. Biochemistry 42:12570-12576 (Pubitemid 37337547)
32. Marconescu A, Thorpe PE (2008) Coincident exposure of phosphatidylethanolamine and anionic phospholipids on the surface of irradiated cells. Biochim Biophys Acta 1778:2217-2224
33. Maulik N, Kagan VE, Tyurin VA, Das DK (1998) Redistribution of phosphatidylethanolamine and phosphatidylserine precedes reperfusion-induced apoptosis. Am J Physiol 274:H242-H248
34. Mileykovskaya E, Sun Q, Margolin W, Dowhan W (1998) Localization and function of early cell division proteins in filamentous Escherichia coli cells lacking phosphatidylethanolamine. J Bacteriol 180:4252-4257 (Pubitemid 28373532)
35. Narula J, Acio ER, Narula N, Samuels LE, Fyfe B, Wood D, Fitzpatrick JM, Raghunath PN, Tomaszewski JE, Kelly C, Steinmetz N, Green A, Tait JF, Leppo J, Blankenberg FG, Jain D, Strauss HW (2001) Annexin-V imaging for noninvasive detection of cardiac allograft rejection. Nat Med 7:1347-1352 (Pubitemid 34007940)
36. Pag U, Sahl HG (2002) Multiple activities in lantibiotics-models for the design of novel antibiotics? Curr Pharm Des 8:815-833 (Pubitemid 34498567)
37. Rouser G, Yamamoto A, Kritchevsky G (1971) Cellular membranes. Structure and regulation of lipid class composition species differences, changes with age, and variations in some pathological states. Arch Intern Med 127:1105-1121
38. Sahl HG, Bierbaum G (1998) Lantibiotics: biosynthesis and biological activities of uniquely modified peptides from gram-positive bacteria. Annu Rev Microbiol 52:41-79 (Pubitemid 28481187)
39. Sahu SK, Gummadi SN, Manoj N, Aradhyam GK (2007) Phospholipid scramblases: an overview. Arch Biochem Biophys 462:103-114 (Pubitemid 46755145)
40. Sanmarco M, Alessi MC, Harle JR, Sapin C, Aillaud MF, Gentile S, Juhan-Vague I, Weiller PJ (2001) Antibodies to phosphatidylethanolamine as the only antiphospholipid antibodies found in patients with unexplained thromboses. Thromb Haemost 85:800-805 (Pubitemid 32421811)
41. Seelig J (2004) Thermodynamics of lipid-peptide interactions. Biochim Biophys Acta 1666:40-50 (Pubitemid 39425197)
42. Smirnov MD, Esmon CT (1994) Phosphatidylethanolamine incorporation into vesicles selectively enhances factor Va inactivation by activated protein C. J Biol Chem 269:816-819 (Pubitemid 24032448)
43. Smirnov MD, Triplett DT, Comp PC, Esmon NL, Esmon CT (1995) On the role of phosphatidylethanolamine in the inhibition of activated protein C activity by antiphospholipid antibodies. J Clin Invest 95:309-316
44. Smirnov MD, Ford DA, Esmon CT, Esmon NL (1999) The effect of membrane composition on the hemostatic balance. Biochemistry 38:3591-3598
45. Song Z, Steller H (1999) Death by design: mechanism and control of apoptosis. Trends Cell Biol 9:M49-M52
46. Sosnovik DE, Schellenberger EA, Nahrendorf M, Novikov MS, Matsui T, Dai G, Reynolds F, Grazette L, Rosenzweig A, Weissleder R, Josephson L (2005) Magnetic resonance imaging of cardiomyocyte apoptosis with a novel magneto-optical nanoparticle. Magn Reson 54:718-724 (Pubitemid 41233769)
47. Spector AA, Yorek MA (1985) Membrane lipid composition and cellular function. J Lipid Res 26:1015-1035 (Pubitemid 16258287)
48. Sugi T, Katsunuma J, Izumi S, McIntyre JA, Makino T (1999) Prevalence and heterogeneity of antiphosphatidylethanolamine antibodies in patients with recurrent early pregnancy losses. Fertil Steril 71:1060-1065 (Pubitemid 29252496)
49. Sugi T, Matsubayashi H, Inomo A, Dan L, Makino T (2004) Antiphosphatidylethanolamine antibodies in recurrent early pregnancy loss and mid-to-late pregnancy loss. J Obstet Gynaecol Res 30:326-332 (Pubitemid 39108450)
50. Thimister PW, Hofstra L, Liem IH, Boersma HH, Kemerink G, Reutelingsperger CP, Heidendal GA (2003) In vivo detection of cell death in the area at risk in acute myocardial infarction. J Nucl Med 44:391-396 (Pubitemid 39586015)
51. Tian Y, Jackson P, Gunter C, Wang J, Rock CO, Jackowski S (2006) Placental thrombosis and spontaneous fetal death in mice deficient in ethanolamine kinase 2. J Biol Chem 281:28438-28449 (Pubitemid 44414557)
52. Umeda M, Emoto K (1999) Membrane phospholipid dynamics during cytokinesis: regulation of actin filament assembly by redistribution of membrane surface phospholipid. Chem Phys Lipids 101:81-91 (Pubitemid 29385553)
53. Vinatier D, Dufour P, Cosson M, Houpeau JL (2001) Antiphospholipid syndrome and recurrent miscarriages. Eur J Obstet Gynecol Reprod Biol 96:37-50 (Pubitemid 32331848)
54. Wakamatsu K, Choung SY, Kobayashi T, Inoue K, Higashijima T, Miyazawa T (1990) Complex formation of peptide antibiotic Ro09-0198 with lysophosphatidylethanolamine: 1H NMR analyses in dimethyl sulfoxide solution. Biochemistry 29:113-118 (Pubitemid 20033712)
55. Widdick DA, Dodd HM, Barraille P, White J, Stein TH, Chater KF, Gasson MJ, Bibb MJ (2003) Cloning and engineering of the cinnamycin biosynthetic gene cluster from Streptomyces cinnamoneus cinnamoneus DSM 40005. Proc Natl Acad Sci USA 100:4316-4321 (Pubitemid 36418200)
56. Williamson P, Schlegel RA (2002) Transbilayer phospholipid movement and the clearance of apoptotic cells. Biochim Biophys 1585:53-63 (Pubitemid 36092068)
57. Wyllie AH (1997) Apoptosis: an overview. Br Med Bull 53:451-465 (Pubitemid 27397303)
58. Zhao M, Beauregard DA, Loizou L, Davletov B, Brindle KM (2001) Non-invasive detection of apoptosis using magnetic resonance imaging and a targeted contrast agent. Nat Med 7:1241-1244 (Pubitemid 33063780)
59. 99mTc-labeled C2A domain of synaptotagmin I as a target-specific molecular probe for noninvasive imaging of acute myocardial infarction. J Nucl Med 47:1367-1374 (Pubitemid 47544893)
60. 99mTc-labeled duramycin as a novel phosphatidylethanolamine-binding molecular probe. J Nucl Med 49:1345-1352
61. Zimmermann N, Freund S, Fredenhagen A, Jung G (1993) Solution structures of the lantibiotics duramycin B and C. Eur J Biochem 216:419-428 (Pubitemid 23276288)