Enhanced antiproliferative activity of the new anticancer candidate LPSF/AC04 in cyclodextrin inclusion complexes encapsulated into liposomes

AAPS PharmSciTech

Volumn 13, Issue 4, 2012, Pages 1355-1366

  Mendonça, Elisângela A M ^a,b   Lira, Mariane C B ^b,c   Rabello, Marcelo M ^b   Cavalcanti, Isabella M F ^b   Galdino, Suely L ^b   Pitta, Ivan R ^b   Do Carmo A Lima, Maria ^b   Pitta, Maira G R ^b   Hernandes, Marcelo Z ^b   Santos Magalhães, Nereide S ^c  

^a STATE UNIVERSITY OF PARAÍBA   (Brazil)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^c Centro Acadêmico de Vitoria CAV   (Brazil)

Author keywords

acridine; cyclodextrins; cytotoxicity; liposomes; modeling

Indexed keywords

(5Z) [5 ACRIDIN 9 YLMETHYLENE 3 (4 METHYL BENZYL)THIAZOLIDINE 2,4 DIONE]; ANTINEOPLASTIC AGENT; CYCLODEXTRIN; LIPOSOME; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CYTOTOXICITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG FORMULATION; DRUG PENETRATION; HUMAN; HUMAN CELL; IN VIVO STUDY; INFRARED SPECTROMETRY; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAMAN SPECTROMETRY; SCANNING ELECTRON MICROSCOPY; THERMOGRAVIMETRY;

ABSORPTION; ACRIDINES; ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG STABILITY; EXCIPIENTS; GAMMA-CYCLODEXTRINS; HUMANS; LIPOSOMES; SOLUBILITY; THIAZOLIDINEDIONES; WATER;

EID: 84871647217     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-012-9853-9     Document Type: Article

References (35)

1. Denny WA. Acridine derivatives as chemotherapeutic agents. Curr Med Chem. 2002;9:1655-65.
2. Goodell JR, Ougolkov AV, Hiasa H, Kaur H, Remmel R, Billadeu DD, et al. Acridine-based agents with topoisomerase II activity inhibit pancreatic cancer cell proliferation and induce apoptosis. J Med Chem. 2008;51:179-82.
3. Vispe S, Vandenberghe I, Robin M, Annereau JP, Créancier L, Pique V, et al. Novel tetra-acridine derivatives as dual inhibitors of topoisomerase II and the human proteasome. Biochem Pharmacol. 2007;73:1863-72.
4. Loise AC, Issel BF. Amsacrine (AMSA) - a clinical review. J Clin Oncol. 1985;3:562-92.
5. Chilin A, Marzaro G, Marzano C, Via LD, Ferlin MG, Pastorin G, et al. Synthesis and antitumor activity of novel amsacrine analogs: the critical role of the acridine moiety in determining their biological activity. Bioorg Med Chem. 2009;17:523-9.
6. Mourão RH, Silva TG, Soares AL, Vieira ES, Santos JN, Lima MCA, et al. Synthesis and biological activity of novel acridinylidene and benzylidene thiazolidinediones. Eur J Med Chem. 2005;40:1129-33.
7. Pitta IR, Galdino SL, Lima MCA. Acridine derivatives with antitumoral activity. Patent number WO/2007/109871. PCT/BR2007/000074. 2007.04.10. Federal University of Pernambuco, Recife, Brazil.
8. Pigatto MC, Lima MCA, Galdino SL, Pitta IR, Vessecchi R, Assis MD, et al. Metabolism evaluation of the anticancer candidate AC04 by biomimetic oxidative model and rat liver microsomes. Eur J Med Chem. 2011;46:4245-51.
9. Loftsson T, Hreinsdóttir D, Másson M. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm. 2005;302:18-28.
10. Loftsson T, Duchêne D. Cyclodextrins and their pharmaceutical applications. Int J Pharm. 2007;329:1-11.
11. Schuette JM, Dou TN, de la Peña AM, Greene KL, Williamson CK, Warner IM. Characterization of the β-cyclodextrin/acridine complex. J Phys Chem. 1991;95:4897-902.
12. Correia I, Bezzenine N, Ronzani N, Platzer N, Beloeil J-C, Doan B-T. Study of inclusion complexes of acridine with β-and (2,6-di-o-methyl)- β-cyclodextrin by use of solubility diagrams and NMR spectroscopy. J Phys Org Chem. 2002;15:647-59.
13. Mishur RJ, Griffin ME, Battle CH, Shan B, Jayawickramrajah J. Molecular recognition and enhancement of aqueous solubility and bioactivity of CD437 by β-cyclodextrin. Bioorg Med Chem Lett. 2011;21:857-60.
14. Al Omari AA, Al Omari MM, Badwan AA, Al-Sou'od KA. Effect of cyclodextrins on the solubility and stability of candesartan cilexetil in solution and solid state. J Pharm Biomed Anal. 2011;54:503-9.
15. Torchilin VP. Multifunctional nanocarriers. Adv Drug Deliv Rev. 2006;58:1532-55.
16. McCormack B, Gregoriadis G. Drugs-in-cyclodextrins-in-liposomes: an approach to controlling the fate of water insoluble drugs in vivo. Int J Pharm. 1998;162:59-69.
17. Loukas YL, Vraka V, Gregoriadis G. Drugs, in cyclodextrins, in liposomes: a novel approach to the chemical stability of drugs sensitive to hydrolysis. Int J Pharm. 1998;162:137-42.
18. Maestrelli F, Gonzalez-Rodriguez ML, Rabasco AM, Mura P. New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anesthetics. Int J Pharm. 2010;395:222-31.
19. Lira MCB, Ferraz MS, da Silva DGVC, Cortes ME, Teixeira KI, Caetano NP, et al. Inclusion complex of usnic acid with β-cyclodextrin: characterization and nanoencapsulation into liposomes. J Incl Phenom Macrocycl Chem. 2009;64:215-24.
20. Cavalcanti IMF, Mendonça EAM, Lira MCB, Honrato SB, Amorim C, Amorim RVS, et al. The encapsulation of β-lapachone in 2-hydroxypropyl- β-cyclodextrin inclusion complex into liposomes: a physicochemical evaluation and molecular modeling approach. Eur J Pharm Sci. 2011;44:332-40.
21. Higuchi T, Connors KA. Phase-solubility techniques. Adv Anal Chem. 1965;4:117-212.
22. Mura P, Bettinetti G, Melani F, Manderioli A. Interaction between naproxen and chemically modified β-cyclodextrins in the liquid and solid state. Eur J Pharm Sci. 1995;3:347-55.
23. Aicart E, Junqueira E. Complex formation between purine derivatives and cyclodextrins: a fluorescence spectroscopy study. J Incl Phenom Macrocycl Chem. 2003;47:161-5.
24. Illapakurthy AC, Sabnis YA, Avery BA, Avery MA, Wyandt CM. Interaction of artemisinin and its related compounds with hydroxypropyl-β-cyclodextrin in solution state: experimental and molecular-modeling studies. J Pharm Sci. 2003;92:649-55.
25. Araújo MVG, Vieira EKB, Lázaro GS, Conegero LS, Almeida LE, Barreto LS, et al. Sulfadiazine/hydroxypropyl-β-cyclodextrin host-guest system: characterization, phase-solubility and molecular modeling. Bioorg Med Chem. 2008;16:5788-94.
26. Hao SY, Molnar LF, Jung Y, Kussmann J, Ochsenfeld C, Brown ST, et al. Advances in methods and algorithms in a modern quantum chemistry program package. Phys Chem Chem Phys. 2006;8:3172-91.
27. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application of proliferation and cytotoxicity assay. J Immunol Methods. 1983;65:55-63.
28. Pralhad T, Rajendrakumar K. Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J Pharm Biomed Anal. 2004;34:333-9.
29. Ribeiro A, Figueiras A, Santos D, Veiga F. Preparation and solid-state characterization of inclusion complex formed between miconazole and methyl-β-cyclodextrin. AAPS PharmSciTech. 2008;9:1102-9.
30. Aigner Z, Berkesi O, Farkas G, Szabo-Revesz P. DSC, X-ray and FTIR studies of a gemfibrozil/dimethyl-β-cyclodextrin inclusion complex produced by co-grinding. J Pharm Biomed Anal. 2012;57:62-7.
31. Sardo M, Amado AM, Ribeiro-Claro PJA. Inclusion compounds of phenol derivatives with cyclodextrins: a combined spectroscopic and thermal analysis. J Raman Spectrosc. 2009;40:1624-33.
32. Loftsson T, Masson M, Brewster ME. Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci. 2004;93:1091-9.
33. Upadhyay AK, Singh S, Chhipa RR, Vijayakumar MV, Ajay AK, Bhat MK. Methyl-β-cyclodextrin enhances the susceptibility of human breast cancer cells to carboplatin and 5-fluorouracil: involvement of Akt, NF-κB and Bcl-2. Toxicol Appl Pharmacol. 2006;2:177-85.
34. Pourgholami MH, Wangoo KT, Morris DL. Albendazole-cyclodextrin complex: enhanced cytotoxicity in ovarian cancer cells. Anticancer Res. 2008;28:2775-80.
35. Dhule SS, Penfornis P, Frazier T, Walker R, Feldman J, Tan G, et al. Curcumin-loaded γ-cyclodextrin liposomal nanoparticles as delivery vehicles for osteosarcoma. Nanomedicine. 2012;8:440-51. doi: 10.1016/j.nano2011.07.011.