351
Views
16
CrossRef citations to date
0
Altmetric
Review Articles

PRCosomes: pretty reactive complexes formed in liposomes

, , &
Pages 787-796 | Received 25 Feb 2016, Accepted 02 May 2016, Published online: 22 May 2016

References

  • Allen TM , Cullis PR. Liposomal drug delivery systems: from concept to clinical applications. Adv Drug Deliv Rev 2013;65:36–48.
  • Barenholz Y . Doxil® – the first FDA-approved nano-drug: lessons learned. J Control Release 2012;160:117–34.
  • Leonard RC , Williams S , Tulpule A , et al . Improving the therapeutic index of anthracycline chemotherapy: focus on liposomal doxorubicin (Myocet). Breast 2009;18:218–24.
  • Needham D , Anyarambhatla G , Kong G , Dewhirst MW. A new temperature-sensitive liposome for use with mild hyperthermia: characterization and testing in a human tumor xenograft model. Cancer Res 2000;60:1197–201.
  • Mayer LD , Harasym TO , Tardi PG , et al . Ratiometric dosing of anticancer drug combinations: controlling drug ratios after systemic administration regulates therapeutic activity in tumor-bearing mice. Mol Cancer Ther 2006;5:1854–63.
  • Perezsoler R , Priebe W . Anthracycline antibiotics with high liposome entrapment: structural features and biological activity. Cancer Res 1990;50:4260–6.
  • Zhigaltsev IV , Maurer N , Akhong QF , et al . Liposome-encapsulated vincristine, vinblastine and vinorelbine: a comparative study of drug loading and retention. J Control Release 2005;104:103–11.
  • Podhajcer OL , Friedlander M , Graziani Y. Effect of liposome-encapsulated quercetin on DNA-synthesis, lactate production, and cyclic adenosine 3′-5′-monophosphate level in Ehrlich ascites tumor-cells. Cancer Res 1980;40:1344–50.
  • Kapoor B , Singh SK , Gulati M , et al . Application of liposomes in treatment of rheumatoid arthritis: quo vadis. Sci World J 2014;2014:978351.
  • Bally MB , Hope MJ , Vanechteld CJA , Cullis PR. Uptake of safranine and other lipophilic cations into model membrane systems in response to a membrane-potential. Biochim Biophys Acta 1985;812:66–76.
  • Cullis PR , Bally MB , Madden TD , et al . Ph gradients and membrane-transport in liposomal systems. Trends Biotechnol 1991;9:268–72.
  • Redelmeier TE , Mayer LD , Wong KF , et al . Proton flux in large unilamellar vesicles in response to membrane-potentials and Ph gradients. Biophys J 1989;56:385–93.
  • Cheung BCL , Sun THT , Leenhouts JM , Cullis PR. Loading of doxorubicin into liposomes by forming Mn2+–drug complexes. Biochim Biophys Acta 1998;1414:205–16.
  • Hope MJ , Bally MB , Mayer LD , et al . Generation of multilamellar and unilamellar phospholipid-vesicles. Chem Phys Lipids 1986;40:89–107.
  • Hope MJ , Bally MB , Webb G , Cullis PR. Production of large unilamellar vesicles by a rapid extrusion procedure – characterization of size distribution, trapped volume and ability to maintain a membrane-potential. Biochim Biophys Acta 1985;812:55–65.
  • Zhigaltsev IV , Belliveau N , Hafez I , et al . Bottom-up design and synthesis of limit size lipid nanoparticle systems with aqueous and triglyceride cores using millisecond microfluidic mixing. Langmuir 2012;28:3633–40.
  • Madden TD , Harrigan PR , Tai LCL , et al . The accumulation of drugs within large unilamellar vesicles exhibiting a proton gradient: a survey. Chem Phys Lipids 1990;53:37–46.
  • Bally MB , Mayer LD , Loughrey H , et al . Dopamine accumulation in large unilamellar vesicle systems induced by transmembrane ion gradients. Chem Phys Lipids 1988;47:97–107.
  • Tan J , Wang BC , Zhu LC. DNA binding and oxidative DNA damage induced by a quercetin copper(II) complex: potential mechanism of its antitumor properties. J Biol Inorg Chem 2009;14:727–39.
  • Daniel KG , Chen D , Orlu S , et al . Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells. Breast Cancer Res 2005;7:R897–908.
  • Ding WQ , Liu BL , Vaught JL , et al . Anticancer activity of the antibiotic clioquinol. Cancer Res 2005;65:3389–95.
  • San Andres MP , Marina ML , Vera S. Spectrophotometric determination of copper(II), nickel(II) and cobalt(II) as complexes with sodium diethyldithiocarbamate in cationic micellar medium of hexadecyltrimethylammonium salts. Talanta 1994;41:179–85.
  • Skrott Z , Cvek B. Diethyldithiocarbamate complex with copper: the mechanism of action in cancer cells. Mini Rev Med Chem 2012;12:1184–92.
  • Abraham SA , Edwards K , Karlsson G , et al . An evaluation of transmembrane ion gradient-mediated encapsulation of topotecan within liposomes. J Control Release 2004;96:449–61.
  • Fenske DB , Wong KF , Maurer E , et al . Ionophore-mediated uptake of ciprofloxacin and vincristine into large unilamellar vesicles exhibiting transmembrane ion gradients. Biochim Biophys Acta 1998;1414:188–204.
  • Abraham SA , Waterhouse DN , Mayer LD , et al . The liposomal formulation of doxorubicin. Meth Enzymol 2005;391:71–97.
  • Luo X , Li J , Guo L , et al . Preparation of berberine hydrochloride long-circulating liposomes by ionophore A23187-mediated ZnSO4 gradient method. Asian J Pharm Sci 2013;8:261–6.
  • Taggar AS , Alnajim J , Anantha M , et al . Copper-topotecan complexation mediates drug accumulation into liposomes. J Control Release 2006;114:78–88.
  • Ramsay E , Alnajim J , Anantha M , et al . A novel liposomal irinotecan formulation with significant anti-tumour activity: use of the divalent cation ionophore A23187 and copper-containing liposomes to improve drug retention. Eur J Pharm Biopharm 2008;68:607–17.
  • Suwalsky M , Ungerer B , Quevedo L , et al . Cu2+ ions interact with cell membranes. J Inorg Biochem 1998;70:233–8.
  • Monson CF , Cong X , Robison AD , et al . Phosphatidylserine reversibly binds Cu2+ with extremely high affinity. J Am Chem Soc 2012;134:7773–9.
  • Haran G , Cohen R , Bar LK , Barenholz Y. Transmembrane ammonium-sulfate gradients in liposomes produce efficient and stable entrapment of amphipathic weak bases. Biochim Biophys Acta 1993;1151:201–15.
  • Mayer LD , Tai LC , Bally MB , et al . Characterization of liposomal systems containing doxorubicin entrapped in response to pH gradients. Biochim Biophys Acta 1990;1025:143–51.
  • Bouma J , Beijnen JH , Bult A , Underberg WJ. Anthracycline antitumour agents. A review of physicochemical, analytical and stability properties. Pharm Weekbl Sci Ed 1986;8:109–33.
  • Abraham SA , Edwards K , Karlsson G , et al . Formation of transition metal–doxorubicin complexes inside liposomes. Biochim Biophys Acta 2002;1565:41–54.
  • Abraham SA , McKenzie C , Masin D , et al . In vitro and in vivo characterization of doxorubicin and vincristine coencapsulated within liposomes through use of transition metal ion complexation and pH gradient loading. Clin Cancer Res 2004;10:728–38.
  • Li X , Hirsh DJ , Cabral-Lilly D , et al . Doxorubicin physical state in solution and inside liposomes loaded via a pH gradient. Biochim Biophys Acta 1998;1415:23–40.
  • Mayer LD , Janoff AS. Optimizing combination chemotherapy by controlling drug ratios. Mol Interv 2007;7:216–23.
  • Shaikh IM , Tan K-B , Chaudhury A , et al . Liposome co-encapsulation of synergistic combination of irinotecan and doxorubicin for the treatment of intraperitoneally grown ovarian tumor xenograft. J Control Release 2013;172:852–61.
  • Tardi P , Johnstone S , Harasyrn N , et al . In vivo maintenance of synergistic cytarabine:daunorubicin ratios greatly enhances therapeutic efficacy. Leukemia Res 2009;33:129–39.
  • Bayne WF , Mayer LD , Swenson CE. Pharmacokinetics of CPX-351 (cytarabine/daunorubicin HCl) liposome injection in the mouse. J Pharm Sci 2009;98:2540–8.
  • Chiu GNC , Abraham SA , Ickenstein LM , et al . Encapsulation of doxorubicin into thermosensitive liposomes via complexation with the transition metal manganese. J Control Release 2005;104:271–88.
  • Burdett JK , Sevov S. Stability of the oxidation states of copper. J Am Chem Soc 1995;117:12788–92.
  • Santini C , Pellei M , Gandin V , et al . Advances in copper complexes as anticancer agents. Chem Rev 2014;114:815–62.
  • Marzano C , Pellei M , Tisato F , Santini C. Copper complexes as anticancer agents. Anti-Cancer Agents Med Chem 2009;9:185–211.
  • Duncan C , White AR. Copper complexes as therapeutic agents. Metallomics 2012;4:127–38.
  • Iakovidis I , Delimaris I , Piperakis SM. Copper and its complexes in medicine: a biochemical approach. Mol Biol Int 2011;2011:594529.
  • Tardi PG , Gallagher RC , Johnstone S , et al . Coencapsulation of irinotecan and floxuridine into low cholesterol-containing liposomes that coordinate drug release in vivo. Biochim Biophys Acta 2007;1768:678–87.
  • Dicko A , Tardi P , Xie X , Mayer L. Role of copper gluconate/triethanolamine in irinotecan encapsulation inside the liposomes. Int J Pharm 2007;337:219–28.
  • Patankar N , Anantha M , Ramsay E , et al . The role of the transition metal copper and the ionophore A23187 in the development of Irinophore C™. Pharm Res 2011;28:848–57.
  • Patankar NA , Waterhouse D , Strutt D , et al . Topophore C: a liposomal nanoparticle formulation of topotecan for treatment of ovarian cancer. Invest New Drugs 2013;31:46–58.
  • Ramsay EC , Anantha M , Zastre J , et al . Irinophore C: a liposome formulation of irinotecan with substantially improved therapeutic efficacy against a panel of human xenograft tumors. Clin Cancer Res 2008;14:1208–17.
  • Ramsay E , Alnajim J , Anantha M , et al . Transition metal-mediated liposomal encapsulation of irinotecan (CPT-11) stabilizes the drug in the therapeutically active lactone conformation. Pharm Res 2006;23:2799–808.
  • Messerer CL , Ramsay EC , Waterhouse D , et al . Liposomal irinotecan: formulation development and therapeutic assessment in murine xenograft models of colorectal cancer. Clin Cancer Res 2004;10:6638–49.
  • Sriram D , Yogeeswari P , Thirumurugan R , Bal TR. Camptothecin and its analogues: a review on their chemotherapeutic potential. Nat Prod Res 2005;19:393–412.
  • Fassberg J , Stella VJ. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J Pharm Sci 1992;81:676–84.
  • Hsiang YH , Hertzberg R , Hecht S , Liu LF. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem 1985;260:14873–8.
  • Hsiang YH , Liu LF. Identification of mammalian DNA topoisomerase I as an intracellular target of the anticancer drug camptothecin. Cancer Res 1988;48:1722–6.
  • Chou TH , Chen SC , Chu IM. Effect of composition on the stability of liposomal irinotecan prepared by a pH gradient method. J Biosci Bioeng 2003;95:405–8.
  • Wei H , Song J , Li H , et al . Active loading liposomal irinotecan hydrochloride: preparation, in vitro and in vivo evaluation. Asian J Pharm Sci 2013;8:303–11.
  • Liu JJ , Hong RL , Cheng WF , et al . Simple and efficient liposomal encapsulation of topotecan by ammonium sulfate gradient: stability, pharmacokinetic and therapeutic evaluation. Anti-Cancer Drugs 2002;13:709–17.
  • Li C , Cui J , Li Y , et al . Copper ion-mediated liposomal encapsulation of mitoxantrone: the role of anions in drug loading, retention and release. Eur J Pharm Sci 2008;34:333–44.
  • Johansson B. A review of the pharmacokinetics and pharmacodynamics of disulfiram and its metabolites. Acta Psychiatr Scand Suppl 1992;369:15–26.
  • Johansson B , Stankiewicz Z. Bis-(diethyldithiocarbamato) copper complex: a new metabolite of disulfiram? Biochem Pharmacol 1985;34:2989–91.
  • Hothi P , Martins TJ , Chen LP , et al . High-throughput chemical screens identify disulfiram as an inhibitor of human glioblastoma stem cells. Oncotarget 2012;3:1124–36.
  • Pushie MJ , Nienaber KH , Summers KL , et al . The solution structure of the copper clioquinol complex. J Inorg Biochem 2014;133:50–6.
  • Tripathy DR , Roy AS , Dasgupta S. Complex formation of rutin and quercetin with copper alters the mode of inhibition of ribonuclease A. FEBS Lett 2011;585:3270–6.
  • Harris ED. Cellular copper transport and metabolism. Annu Rev Nutr 2000;20:291–310.
  • Denoyer D , Masaldan S , La Fontaine S , Cater MA. Targeting copper in cancer therapy: ‘copper that cancer’. Metallomics 2015;7:1459–76.
  • Matusch A , Depboylu C , Palm C , et al . Cerebral bioimaging of Cu, Fe, Zn, and Mn in the MPTP mouse model of Parkinson’s disease using laser ablation inductively coupled plasma mass spectrometry (LA-ICP-MS). J Am Soc Mass Spectrom 2010;21:161–71.
  • Brewer GJ. The risks of copper toxicity contributing to cognitive decline in the aging population and to Alzheimer’s disease. J Am Coll Nutr 2009;28:238–42.
  • Wang Y , Zeng S , Lin TM , et al . Evaluating the anticancer properties of liposomal copper in a nude xenograft mouse model of human prostate cancer: formulation, in vitro, in vivo, histology and tissue distribution studies. Pharm Res 2014;31:3106–19.
  • Cvek B. Comment on ‘Cytotoxic effect of disulfiram/copper on human glioblastoma cell lines and ALDH-positive cancer-stem-like cells’. Br J Cancer 2013;108:993.
  • Cvek B , Milacic V , Taraba J , Dou QP. Ni(II), Cu(II), and Zn(II) diethyldithiocarbamate complexes show various activities against the proteasome in breast cancer cells. J Med Chem 2008;51:6256–8.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.