Stable and sensitive probes for lysosomes: Cell-penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

Cytometry Part A

Volumn 79 A, Issue 2, 2011, Pages 126-136

  Mueller, Anja ^a   Lalor, Ruth ^a   Cardaba, Clara Moyano ^a   Matthews, Susan E ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Calixarene; Cell penetration; Immunofluorescence; Lysosome

Indexed keywords

BAFILOMYCIN A1; BREFELDIN A; CALIX(4)ARENE; CALIXARENE; CLATHRIN; FLUORESCENT DYE; MACROLIDE; MONENSIN; PHENOL DERIVATIVE; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATE SYNTHASE; SODIUM AZIDE;

ANIMAL; ARTICLE; CAVEOLA; CHO CELL; CRICETULUS; DRUG ANTAGONISM; DRUG EFFECT; ENDOSOME; GOLGI COMPLEX; HAMSTER; HELA CELL; HUMAN; LYSOSOME; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL CULTURE;

ANIMALS; BIOLOGICAL TRANSPORT; BREFELDIN A; CALIXARENES; CAVEOLAE; CHO CELLS; CLATHRIN; CRICETINAE; CRICETULUS; ENDOSOMES; FLUORESCENT DYES; GOLGI APPARATUS; HELA CELLS; HUMANS; LYSOSOMES; MACROLIDES; MONENSIN; PHENOLS; SODIUM AZIDE; TUMOR CELLS, CULTURED; VACUOLAR PROTON-TRANSLOCATING ATPASES;

EID: 79251480735     PISSN: 15524922     EISSN: 15524930     Source Type: Journal    
DOI: 10.1002/cyto.a.21002     Document Type: Article

References (39)

1. Böhmer V. Calixarenes, macrocycles with (almost) unlimited possibilities. Angew Chem Int Ed Engl 1995; 34: 713.
2. Quinlan E, Matthews SE, Gunnlaugsson T. Anion sensing using colorimetric amidourea based receptors incorporated into a 1, 3-disubstituted calix[4]arene. Tetrahedron Lett 2006; 47: 9333-9338.
3. Quinlan E, Matthews SE, Gunnlaugsson T. Colorimetric recognition of anions using preorganized tetra-amidourea derived calix[4]arene sensors. J Org Chem 2007; 72: 7497-7503.
4. Matthews SE, Schmitt P, Felix V, Drew MGB, Beer PD. Calix[4]tubes: A new class of potassium-selective ionophore. J Am Chem Soc 2002; 124: 1341-1353.
5. 2+. J Org Chem 2008; 73: 8212-8218.
6. Cecioni S, Lalor R, Blanchard B, Praly JP, Imberty A, Matthews SE, Vidal S. Achieving high affinity towards a bacterial lectin through multivalent topological isomers of calix[4]arene glycoconjugates. Chemistry 2009; 15: 13232-13240.
7. Cornforth JW, Hart PD, Nicholls GA, Rees RJ, Stock JA. Antituberculous effects of certain surface-active polyoxyethylene ethers. Br J Pharmacol Chemother 1955; 10: 73-88.
8. Loiseau FA, Hill AM, Hii KK. Preparation of macrocyclon analogues: Calix[8]arenes with extended polyethylene glycol chains. Tetrahedron 2007; 63: 9947-9959.
9. Geraci C, Consoli GML, Galante E, Bousquet E, Pappalardo M, Spadaro A. Calix[4]arene decorated with four Tn antigen glycomimetic units and P~3CS immunoadjuvant: Synthesis, characterization, and anticancer immunological evaluation. Bioconjug Chem 2008; 19: 751-758.
10. Sun J, Blaskovich MA, Jain RK, Delarue F, Paris D, Brem S, Wotoczek-Obadia M, Lin Q, Coppola D, Choi K. Blocking angiogenesis and tumorigenesis with GFA-116, a synthetic molecule that inhibits binding of vascular endothelial growth factor to its receptor. Cancer Res 2004; 64: 3586-3592.
11. Bagnacani V, Sansone F, Donofrio G, Baldini L, Casnati A, Ungaro R. Macrocyclic nonviral vectors: High cell transfection efficiency and low toxicity in a lower rim guanidinium calix[4]arene. Org Lett 2008; 10: 3953-3956.
12. Horiuchi S, Aoyama Y. Systematic lactose-functionalization of amphiphilic octaamine macrocycle as a gene carrier. Optimization of the charge, size, toxicity, and receptor factors for hepatocyte targeting. J Control Release 2006; 116: 107-114.
13. Sansone F, Dudic M, Donofrio G, Rivetti C, Baldini L, Casnati A, Cellai S, Ungaro R. DNA condensation and cell transfection properties of guanidinium calixarenes: Dependence on macrocycle lipophilicity, size, and conformation. J Am Chem Soc 2006; 128: 14528-14536.
14. Lalor R, DiGesso J, Mueller A, Matthews S. Efficient gene transfection with functionalised multicalixarenes. Chem Commun 2007: 4907-4909.
15. 3+ complex endowed with high stability, relaxivity, and binding affinity to serum albumin. Angew Chem Int Ed Engl 2001; 40: 4737-4739.
16. Bryant LH, Yordanov AT, Linnoila JJ, Brechbiel MW, Frank JA. First noncovalently bound calix[4]arene-Gd̂ÎÎI-albumin complex. Angew Chem Int Ed Engl 2000; 39: 1641-1643.
17. Shahgaldian P, Coleman AW. Miscibility studies on amphiphilic calix[4]arene-natural phospholipid mixed films. Langmuir 2003; 19: 5261-5265.
18. 3+ chelators. Bioconjug Chem 1999; 10: 613-623.
19. Paclet MH, Rousseau Cc, Yannick C, Morel Fo, Coleman AW. An absence of non-specific immune response towards para-sulphonato-calix[n]arenes. J Incl Phenom Macrocycl Chem 2006; 55: 353-357.
20. Lalor R, Baillie-Johnson H, Redshaw C, Matthews SE, Mueller A. Cellular uptake of a fluorescent calix[4]arene derivative. J Am Chem Soc 2008; 130: 2892-2893.
21. Holman DH, Turner LS, El-Zawahry A, Elojeimy S, Liu X, Bielawski J, Szulc ZM, Norris K, Zeidan YH, Hannun YA, Bielawska A, Norris JS. Lysosomotropic acid ceramidase inhibitor induces apoptosis in prostate cancer cells. Cancer Chemother Pharmacol 2008; 61: 231-242.
22. Pourahmad J, O'Brien PJ, Chan K, Shakouri A. Tetramethylphenylenediamine-induced hepatocyte cytotoxicity caused by lysosomal labilisation and redox cycling with oxygen activation. Chem Biol Interact 2008; 172: 39-47.
23. Mueller A. Strange PG CCL3, acting via the chemokine receptor CCR5, leads to independent activation of Janus kinase 2 (JAK2) and Gi proteins. FEBS Lett 2004; 570: 126-132.
24. Mueller A, Kelly E, Strange PG. Pathways for internalization and recycling of the chemokine receptor CCR5. Blood 2002; 99: 785-791.
25. Soulet D, Gagnon B, Rivest S, Audette M, Poulin R. A fluorescent probe of polyamine transport accumulates into intracellular acidic vesicles via a two-step mechanism. J Biol Chem 2004; 279: 49355-49366.
26. Richard JP, Melikov K, Vives E, Ramos C, Verbeure B, Gait MJ, Chernomordik LV, Lebleu B. Cell-penetrating peptides. A reevaluation of the mechansim of cellular uptake. J Biol Chem 2003; 278: 585-590.
27. Cardaba CM, Kerr JS, Mueller A. CCR5 internalisation and signalling have different dependence on membrane lipid raft integrity. Cell Signal 2008; 20: 1687-1694.
28. Soulet D, Gagnon B, Rivest S, Audette M, Poulin R. A fluorescent probe of polyamine transport accumulates into intracellular acidic vesicles via a two-step mechanism. J Biol Chem 2004; 279: 49355-49366.
29. Forgac M. Vacuolar ATPases: Rotary proton pumps in physiology and pathophysiology. Nat Rev Mol Cell Biol 2007; 8: 917-929.
30. Aridor M, Hannan LA. Traffic jams II: An update of diseases of intracellular transport. Traffic 2002; 3: 781-790.
31. Marshansky V, Futai M. The V-type H+-ATPase in vesicular trafficking: Targeting, regulation and function. Curr Opin Cell Biol 2008; 20: 415-426.
32. Raghunand N, Mahoney B, van Sluis R, Baggett B, Gillies RJ. Acute metabolic alkalosis enhances response of C3H mouse mammary tumors to the weak base mitoxantrone. Neoplasia 2001; 3: 227-235.
33. Morita T, Nagaki T, Fukuda I, Okumura K. Clastogenicity of low pH to various cultured mammalian cells. Mutat Res 1992; 268: 297-305.
34. Martinez-Zaguilan R, Seftor EA, Seftor RE, Chu YW, Gillies RJ, Hendrix MJ. Acidic pH enhances the invasive behavior of human melanoma cells. Clin Exp Metastasis 1996; 14: 176-186.
35. De Milito A, Fais S. Tumor acidity, chemoresistance and proton pump inhibitors. Future Oncol 2005; 1: 779-786.
36. +)-ATPases-Nature's most versatile proton pumps. Nat Rev Mol Cell Biol 2002; 3: 94-103.
37. +-ATPase in cancer biology. Cell Biochem Biophys 2004; 40: 185-206.
38. Ivanov A, Beers SA, Walshe CA, Honeychurch J, Alduaij W, Cox KL, Potter KN, Murray S, Chan CH, Klymenko T, Erenpreisa J, Glennie MJ, Illidge TM, Cragg MS. Monoclonal antibodies directed to CD20 and HLA-DR can elicit homotypic adhesion followed by lysosome-mediated cell death in human lymphoma and leukemia cells. J Clin Invest 2009; 119: 2143-2159.
39. de Duve C, de Barsy T, Poole B, Trouet A, Tulkens P, Van Hoof F. Commentary. Lysosomotropic agents. Biochem Pharmacol 1974; 23: 2495-2531.