Positron emission tomography imaging of the stability of Cu-64 labeled dipalmitoyl and distearoyl lipids in liposomes

Journal of Controlled Release

Volumn 151, Issue 1, 2011, Pages 28-34

  Seo, Jai Woong ^a   Qin, Shengping ^a   Mahakian, Lisa M ^a   Watson, Katherine D ^a   Kheirolomoom, Azadeh ^a   Ferrara, Katherine W ^a  

^a University of California   (United States)

Author keywords

Bifunctional chelator; Cu 64; DPPE; DSPE; Half clearance; Lipid desorption; Liposome; Liposome stability; Long circulating liposome; Maleimide lipid; PET; Pharmacokinetics

Indexed keywords

BIFUNCTIONAL; CU-64; DPPE; DSPE; HALF CLEARANCE; LONG-CIRCULATING LIPOSOMES; MALEIMIDES; PET;

BLOOD; CHAIN LENGTH; CHELATION; CHOLESTEROL; DESORPTION; LAKES; LIPOSOMES; LIVER; PHARMACOKINETICS; PHOSPHOLIPIDS; RADIATION; RADIOACTIVITY; STABILITY; TELEMETERING;

POSITRON EMISSION TOMOGRAPHY;

1,2 DIPALMITOYL SN GLYCERO 3 PHOSPHOETHANOLAMINE N [4 (4 MALEIMIDOPHENYL)BUTYRAMIDE]; 1,2 DISTEAROYL SN GLYCERO 3 PHOSPHOETHANOLAMINE N (3 MALEIMIDOPROPYLAMIDE); [6 [6 [3 (2 PYRIDYLDITHIO)PROPIONAMIDO]HEXANAMIDO]BENZYL] 1,4,8,11 TETRAAZACYCLOTETRADECANE 1,4,8,11 TETRAACETIC ACID; CHELATING AGENT; CHOLESTEROL; COPPER 64; DIOLEOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; LIPID; LIPOSOME; MALEIMIDE; THIOL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD; KIDNEY; LIPID METABOLISM; LIVER; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY;

ANIMALS; COPPER RADIOISOTOPES; FEMALE; HALF-LIFE; LIPOSOMES; MALEIMIDES; MICE; PHOSPHATIDYLETHANOLAMINES; POSITRON-EMISSION TOMOGRAPHY;

EID: 79955482984     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2011.01.008     Document Type: Article

References (38)

1. O.P. Medina, Y. Zhu, and K. Kairemo Targeted liposomal drug delivery in cancer Curr. Pharm. Des. 10 2004 2981 2989 (Pubitemid 39214006)
2. V.P. Torchilin Recent advances with liposomes as pharmaceutical carriers Nat. Rev. Drug Discovery 4 2005 145 160 (Pubitemid 40282557)
3. A.S. Abu Lila, T. Ishida, and H. Kiwada Recent advances in tumor vasculature targeting using liposomal drug delivery systems Expert Opin. Drug Deliv. 6 2009 1297 1309
4. A.S. Abu Lila, T. Ishida, and H. Kiwada Targeting anticancer drugs to tumor vasculature using cationic liposomes Pharm. Res. 27 2010 1171 1183
5. K.W. Ferrara, M.A. Borden, and H. Zhang Lipid-shelled vehicles: engineering for ultrasound molecular imaging and drug delivery Acc. Chem. Res. 42 2009 881 892
6. A.L. Klibanov, K. Maruyama, V.P. Torchilin, and L. Huang Amphipathic polyethyleneglycols effectively prolong the circulation time of liposomes FEBS Lett. 268 1990 235 237 (Pubitemid 20233874)
7. V.P. Torchilin, V.G. Omelyanenko, M.I. Papisov, A.A. Bogdanov, V.S. Trubetskoy, J.N. Herron, and C.A. Gentry Poly(ethylene glycol) on the liposome surface - on the mechanism of polymer-coated liposome longevity Biochim. Biophys. Acta 1195 1994 11 20 (Pubitemid 24318086)
8. A. Gabizon, H. Shmeeda, A.T. Horowitz, and S. Zalipsky Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates Adv. Drug Deliv. Rev. 56 2004 1177 1192 (Pubitemid 38496514)
9. W.M. Li, L. Xue, L.D. Mayer, and M.B. Bally Intermembrane transfer of polyethylene glycol-modified phosphatidylethanolamine as a means to reveal surface-associated binding ligands on liposomes Biochim. Biophys. Acta 1513 2001 193 206 (Pubitemid 32706417)
10. N. Dos Santos, C. Allen, A.M. Doppen, M. Anantha, K.A.K. Cox, R.C. Gallagher, G. Karlsson, K. Edwards, G. Kenner, L. Samuels, M.S. Webb, and M.B. Bally Influence of poly(ethylene glycol) grafting density and polymer length on liposomes: relating plasma circulation lifetimes to protein binding Biochim. Biophys. Acta 1768 2007 1367 1377 (Pubitemid 46782695)
11. G.L. Pool, M.E. French, R.A. Edwards, L. Huang, and R.H. Lumb Use of radiolabeled hexadecyl cholesteryl ether as a liposome marker Lipids 17 1982 448 452
12. S.C. Semple, A. Chonn, and P.R. Cullis Interactions of liposomes and lipid-based carrier systems with blood proteins: relation to clearance behaviour in vivo Adv. Drug Deliv. Rev. 32 1998 3 17 (Pubitemid 28277172)
13. A. Gabizon, H. Shmeeda, and Y. Barenholz Pharmacokinetics of pegylated liposomal doxorubicin: review of animal and human studies Clin. Pharmacokinet. 42 2003 419 436 (Pubitemid 36649037)
14. D.J. Hnatowich, B. Friedman, B. Clancy, and M. Novak Labeling of preformed liposomes with Ga-67 and Tc-99m by chelation J. Nucl. Med. 22 1981 810 814 (Pubitemid 11057772)
15. 99mTc to lipid vesicles containing the lipophilic chelate dipalmitoylphosphatidylethanolamine- DTTA Nucl. Med. Biol. 19 1992 831 840
16. 99mTc-labeling of lipid vesicles containing the lipophilic chelator PE-DTTA: effect of tin-to-chelate ratio, chelate content and surface polymer on labeling efficiency and biodistribution behavior Nucl. Med. Biol. 21 1994 89 96 (Pubitemid 24037228)
17. N. Kitamura, N. Shigematsu, T. Nakahara, M. Kanoh, J. Hashimoto, E. Kunieda, and A. Kubo Biodistribution of immunoliposomes labeled with Tc-99m in tumor xenografted mice Ann. Nucl. Med. 23 2009 149 153
18. N. Mirahmadi, M.H. Babaei, A.M. Vali, and S. Dadashzadeh Effect of liposome size on peritoneal retention and organ distribution after intraperitoneal injection in mice Int. J. Pharm. 383 2010 7 13
19. 18F]FDP) Nucl. Med. Biol. 34 2007 165 171 (Pubitemid 46241896)
20. N. Oku, M. Yamashita, Y. Katayama, T. Urakami, K. Hatanaka, K. Shimizu, T. Asai, H. Tsukada, S. Akai, and H. Kanazawa PET imaging of brain cancer with positron emitter-labeled liposomes Int. J. Pharm. 403 2011 170 177
21. H. Zhang, J. Kusunose, A. Kheirolomoom, J.W. Seo, J.Y. Qi, K.D. Watson, H.A. Lindfors, E. Ruoslahti, J.L. Sutcliffe, and K.W. Ferrara Dynamic imaging of arginine-rich heart-targeted vehicles in a mouse model Biomaterials 29 2008 1976 1988
22. M.S. Tartis, D.E. Kruse, H.R. Zheng, H. Zhang, A. Kheirolomoom, J. Marik, and K.W. Ferrara Dynamic microPET imaging of ultrasound contrast agents and lipid delivery J. Control. Release 131 2008 160 166
23. 64Cu for positron emission tomography (PET) imaging Bioconjug. Chem. 19 2008 2577 2584
24. E.E. Paoli, D.E. Kruse, J.W. Seo, H. Zhang, A. Kheirolomoom, K.D. Watson, P. Chiu, H. Stahlberg, and K.W. Ferrara An optical and microPET assessment of thermally-sensitive liposome biodistribution in the Met-1 tumor model: importance of formulation J. Control. Release 143 2010 13 22
25. W.T. Phillips, B.A. Goins, and A. Bao Radioactive liposomes Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 1 2009 69 83
26. 99mTc by the hydrazino nicotinyl derivative J. Nucl. Med. 40 1999 192 197 (Pubitemid 29044191)
27. A. Akinc, A. Zumbuehl, M. Goldberg, E.S. Leshchiner, V. Busini, N. Hossain, S.A. Bacallado, D.N. Nguyen, J. Fuller, R. Alvarez, A. Borodovsky, T. Borland, R. Constien, A. de Fougerolles, J.R. Dorkin, K. Narayanannair Jayaprakash, M. Jayaraman, M. John, V. Koteliansky, M. Manoharan, L. Nechev, J. Qin, T. Racie, D. Raitcheva, K.G. Rajeev, D.W. Sah, J. Soutschek, I. Toudjarska, H.P. Vornlocher, T.S. Zimmermann, R. Langer, and D.G. Anderson A combinatorial library of lipid-like materials for delivery of RNAi therapeutics Nat. Biotechnol. 26 2008 561 569 (Pubitemid 351668042)
28. J.W. Seo, L.M. Mahakian, A. Kheirolomoom, H. Zhang, C.F. Meares, R. Ferdani, C.J. Anderson, and K.W. Ferrara Liposomal Cu-64 labeling method using bifunctional chelators: poly(ethylene glycol) spacer and chelator effects Bioconjug. Chem. 21 2010 1206 1215
29. S.P. Qin, J.W. Seo, H. Zhang, J. Qi, F.R.E. Curry, and K.W. Ferrara An imaging-driven model for liposomal stability and circulation Mol. Pharm. 7 2010 12 21
30. J.R. Silvius, and R. Leventis Spontaneous interbilayer transfer of phospholipids: dependence on acyl chain composition Biochemistry 32 1993 13318 13326 (Pubitemid 24005942)
31. J.R. Silvius, and M.J. Zuckermann Interbilayer transfer of phospholipid-anchored macromolecules via monomer diffusion Biochemistry 32 1993 3153 3161 (Pubitemid 23110161)
32. W.C. Wimley, and T.E. Thompson Transbilayer and interbilayer phospholipid exchange in dimyristoylphosphatidylcholine/dimyristoylphosphatidylethanolamine large unilamellar vesicles Biochemistry 30 1991 1702 1709
33. J.D. Jones, and T.E. Thompson Mechanism of spontaneous, concentration-dependent phospholipid transfer between bilayers Biochemistry 29 1990 1593 1600 (Pubitemid 20063393)
34. A.A. Gabizon Stealth liposomes and tumor targeting: one step further in the quest for the magic bullet Clin. Cancer Res. 7 2001 223 225 (Pubitemid 32183021)
35. D.J. Hnatowich, and P. Schlegel Albumin microspheres labeled with Ga-67 by chelation: concise communication J. Nucl. Med. 22 1981 623 626 (Pubitemid 11067861)
36. 64Cu-TETA-Tyr3-octreotate. A new somatostatin analog with improved target tissue uptake Nucl. Med. Biol. 26 1999 267 273 (Pubitemid 29179869)
37. D.L. Kukis, H. Diril, D.P. Greiner, S.J. DeNardo, G.L. DeNardo, Q.A. Salako, and C.F. Meares A comparative study of copper-67 radiolabeling and kinetic stabilities of antibody-macrocycle chelate conjugates Cancer 73 1994 779 786 (Pubitemid 24046631)
38. H.J. Verkade, J.T. Derksen, A. Gerding, G.L. Scherphof, R.J. Vonk, and F. Kuipers Differential hepatic processing and biliary secretion of head-group and acyl chains of liposomal phosphatidylcholines Biochem. J. 275 Pt 1 1991 139 144