Improvement of tetracaine antinociceptive effect by inclusion in cyclodextrins

Journal of Drug Targeting

Volumn 20, Issue 1, 2012, Pages 85-96

  Franco De Lima, Roberta Aline ^a   De Jesus, Marcelo Bispo ^a   Saia Cereda, Cntia Maria ^a   Tofoli, Giovana Radomille ^a,b   Cabeça, Luis Fernando ^c   Mazzaro, Irineu ^d   Fraceto, Leonardo Fernandes ^e   De Paula, Eneida ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSIDADE SÃO FRANCISCO   (Brazil)

^c EMBRAPA CERRADOS   (Brazil)

^d FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^e Julio de Mesquisa Filho State University   (Brazil)

Author keywords

Cyclodextrin; Cytotoxicity; in vivo; Inclusion complex; Tetracaine

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; BETA CYCLODEXTRIN; TETRACAINE;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DELIVERY SYSTEM; DRUG STRUCTURE; FIBROBLAST; FLUORESCENCE; INFRAORBITAL NERVE; LIGHT ABSORPTION; MALE; NOCICEPTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; NUCLEAR OVERHAUSER EFFECT; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RAT; STOICHIOMETRY; TIME TO MAXIMUM PLASMA CONCENTRATION; X RAY DIFFRACTION;

ANALGESICS; ANIMALS; CHEMISTRY, PHARMACEUTICAL; CYCLODEXTRINS; MALE; MICE; NIH 3T3 CELLS; PAIN MEASUREMENT; RATS; RATS, WISTAR; TETRACAINE; X-RAY DIFFRACTION;

EID: 83155183254     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.3109/1061186X.2011.622400     Document Type: Article

References (50)

1. Arantes LM, Scarelli C, Marsaioli AJ, de Paula E, Fernandes SA. (2009). Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied 1H-NMR approaches. Magn Reson Chem 47, 757-763.
2. Banerjee R, Chakraborty H, Sarkar M. (2004). Host-guest complexation of oxicam NSAIDs with beta-cyclodextrin. Biopolymers, 75, 355-365. (Pubitemid 39452438)
3. Biczok L, Jicsinszky L, Linschitz H. (1994). Solvent-Dependent Radiationless Transitions in Fluorenone - a Probe for Hydrogen- Bonding Interactions in the Cyclodextrin Cavity. J Inclusion Phenom Macrocyclic Chem 18, 237-245.
4. Bragagni M, Maestrelli F, Mennini N, Ghelardini C, Mura P. (2010). Liposomal formulations of prilocaine: effect of complexation with hydroxypropyl-β-cyclodextrin on drug anesthetic efficacy. J Liposome Res, 20, 315-322.
5. Cabeca LF, Fernandes SA, de Paula E, Marsaioli AJ. (2008). Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR. Magn Reson Chem, 46, 832-837.
6. Cereda CM, Brunetto GB, de Araújo DR, de Paula E. (2006). Liposomal formulations of prilocaine, lidocaine and mepivacaine prolong analgesic duration. Can J Anaesth, 53, 1092-1097. (Pubitemid 44756155)
7. Cereda CM, de Araujo DR, Brunetto GB, De Paula E. (2004). Liposomal prilocaine: preparation, characterization, and in vivo evaluation. J Pharm Pharm Sci, 7, 235-240. (Pubitemid 41528897)
8. Chalam KV, Murthy RK, Agarwal S, Gupta SK, Grover S. (2009). Comparative efficacy of topical tetraVisc versus lidocaine gel in cataract surgery. BMC Ophthalmol, 9, 7.
9. De Araujo DR, Tsuneda SS, Cereda CM, Del G F Carvalho F, Preté PS, Fernandes SA, Yokaichiya F, Franco MK, Mazzaro I, Fraceto LF, de F A Braga A, de Paula E. (2008). Development and pharmacological evaluation of ropivacaine-2-hydroxypropyl-beta-cyclodextrin inclusion complex. Eur J Pharm Sci, 33, 60-71. (Pubitemid 350235192)
10. De Paula E, Cereda CM, Tofoli GR, Franz-Montan M, Fraceto LF, de Araújo DR. (2010). Drug delivery systems for local anesthetics. Recent Pat Drug Deliv Formul, 4, 23-34.
11. De Paula E, de Araújo DR, Fraceto, LF. (2010b). Nuclear Magnetic Resonance Spectroscopy tools for the physicochemical characterization of cyclodextrins inclusion complexes. Cyclodextrins: Chemistry and Physics J. Hu, Research Signpost/Transworld Research Network: 1-21.
12. Deyhimi F, Ebrahimi A. et al. (2004). Determination of activity coefficients, osmotic coefficients, and excess Gibbs free energies of HCl in N,N-dimethylformamide-water mixed solvent systems by potentiometric measurements. J Chem Eng Data 49, 1185-1188.
13. Dollo G, Le Corre P. et al. (1996). Inclusion complexation of amidetyped local anaesthetics with [beta]-cyclodextrin and its derivatives. I. Physicochemical characterization. Int J Pharm 131, 219-228.
14. Dollo G, Le Corre P, Chevanne F, Le Verge R. (2004). Bupivacaine containing dry emulsion can prolong epidural anesthetic effects in rabbits. Eur J Pharm Sci, 22, 63-70. (Pubitemid 38543014)
15. Dollo G, Thompson DO, Le Corre P, Chevanne F, Le Verge R. (1998). Inclusion complexation of amide-typed local anesthetics with [beta]-cyclodextrin and its derivatives. III. Biopharmaceutics of bupivacaine-SBE7-[beta]CD complex following percutaneous sciatic nerve administration in rabbits. Int J Pharm 164, 11-19. (Pubitemid 28160093)
16. Duchêne D. (2011). Cyclodextrins And Their Inclusion Complexes. Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicine: Current and Future Industrial Applications. E. Bilensoy, Wiley.
17. Fernandes SA, Cabe?a LF, Marsaioli, AJ, de Paula E. (2007). Investigation of tetracaine complexation with beta-cyclodextrins and β-sulphonic acid calyx[6]arenes by nOe and PGSE NMR. J Incl Phen Macrocycl Chem 57, 395-401.
18. Fink BR, Aasheim G, Kish SJ, Croley TS. (1975). Neurokinetics of lidocaine in the infraorbital nerve of the rat in vivo: Relation to sensory block. Anesthesiology, 42, 731-736.
19. Fotakis G, Timbrell JA. (2006). In vitro cytotoxicity assays: comparison of LDH, neutral red, MTT and protein assay in hepatoma cell lines following exposure to cadmium chloride. Toxicol Lett, 160, 171-177. (Pubitemid 41578961)
20. Fraceto LF, Goncalves MM. et al. (2007). Characterization of the inclusion complex ropivacaine: beta-cyclodextrin. Quim Nova 30, 1203-1207.
21. Frömming KH, Szejtli J. (1994). Cyclodextrins in pharmacy. Dordrecht, Kluwer academic Publishers.
22. Gantenbein M, Abat C, Attolini L, Pisano P, Emperaire N, Bruguerolle B. (1997). Ketamine effects on bupivacaine local anaesthetic activity and pharmacokinetics of bupivacaine in mice. Life Sci, 61, 2027-2033. (Pubitemid 27461512)
23. Giordano F, Novak C, Moyano JR. (2001). Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim Acta 380, 123-151. (Pubitemid 33100003)
24. Gou M, Wu L, Yin Q, Guo Q, Guo G, Liu J, Zhao X, Wei Y, Qian Z. (2009). Transdermal anaesthesia with lidocaine nano-formulation pretreated with low-frequency ultrasound in rats model. J Nanosci Nanotechnol, 9, 6360-6365.
25. Gould S, Scott RC. (2005). 2-Hydroxypropyl-beta-cyclodextrin (HP-beta-CD): a toxicology review. Food Chem Toxicol, 43, 1451-1459.
26. Grant GJ, Barenholz Y, Bolotin EM, Bansinath M, Turndorf H, Piskoun B, Davidson EM. (2004). A novel liposomal bupivacaine formulation to produce ultralong-acting analgesia. Anesthesiology, 101, 133-137. (Pubitemid 38833273)
27. Hassan HG, Renck H, Lindberg B, Akerman B, Hellquist R. (1985). Effects of adjuvants to local anaesthetics on their duration. I. Studies of dextrans of widely varying molecular weight and adrenaline in rat infraorbital nerve block. Acta Anaesthesiol Scand, 29, 375-379. (Pubitemid 15088664)
28. Hassan HG, Renck H, Lindberg B, Lindquist B, Akerman B. (1985). Effects of adjuvants to local anaesthetics on their duration. II. Studies of some substituted dextrans and other macromolecules in rat infraorbital nerve block. Acta Anaesthesiol Scand, 29, 380-383. (Pubitemid 15079163)
29. Iglesias E. (2008). Investigation of physico-chemical behaviour of local anaesthetics in aqueous SDS solutions. New J Chem 32, 517-524. (Pubitemid 351342283)
30. Iglesias-Garcia I, Brandaris I, Iglesias E. (2010). Fluorescence study of tetracaine-cyclodextrin inclusion complexes. Supramol Chem, 22, 228-236.
31. Jug M, Maestrelli F, Bragagni M, Mura P. (2010). Preparation and solidstate characterization of bupivacaine hydrochloride cyclodextrin complexes aimed for buccal delivery. J Pharm Biomed Anal, 52, 9-18.
32. Lee WY, Park CJ, Shin TJ, Yum KW, Yoon TG, Seo KS, Kim HJ. (2009). Only tetracaine and not other local anaesthetics induce apoptosis in rat cortical astrocytes. Br J Anaesth, 103, 719-725.
33. Li S, Purdy WC. (1992). Cyclodextrins and their applications in analytical chemistry. Chem Rev 92, 1457-1470.
34. Loftsson T, Masson M. (2001). Cyclodextrins in topical drug formulations: theory and practice. Int J Pharm, 225, 15-30. (Pubitemid 32728196)
35. Malheiros SV, Pinto LM, Gottardo L, Yokaichiya DK, Fraceto LF, Meirelles NC, de Paula E. (2004). A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partitioning at pH 7.4. Biophys Chem, 110, 213-221. (Pubitemid 38844675)
36. Matsui Y, Tokunaga S. (1996). Internal Reference Compounds Available for the Determination of Binding Constants for Cyclodextrin Complexes by 1H NMR Spectrometry. Bull Chem Soc Jpn 69, 2477-2480. (Pubitemid 126476784)
37. Moraes CM, Abrami P, de Paula E, Braga AFA, Fraceto, LF. (2007). Study of the interaction between S(-) bupivacaine and 2-hydroxypropylbeta- cyclodextrin. Int J Pharm 331, 99-106. (Pubitemid 46195167)
38. Mosmann T. (1983). Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods, 65, 55-63. (Pubitemid 14203433)
39. OBrien L, Taddio A, Lyszkiewicz DA, Koren G. (2005). A critical review of the topical local anesthetic amethocaine (Ametop) for pediatric pain. Paediatr Drugs, 7, 41-54. (Pubitemid 40444228)
40. Oikarinen VJ, Ylipaavalniemi P, Evers H. (1975). Pain and temperature sensations related to local analgesia. Int J Oral Surg, 4, 151-156.
41. Pinto LM, Fraceto LF, Santana MH, Pertinhez TA, Junior SO, de Paula E. (2005). Physico-chemical characterization of benzocaine-betacyclodextrin inclusion complexes. J Pharm Biomed Anal, 39, 956-963. (Pubitemid 41441724)
42. Ready LB, Fink BR. (1980). Experimental evaluation of local anaesthetic solutions using rat infraorbital nerve block. Can Anaesth Soc J, 27, 58-61. (Pubitemid 10141766)
43. Sadlej-Sosnowska N. (1997). Fluorometric determination of association constants of three estrogens with cyclodextrins. J Fluoresc 7, 195-200. (Pubitemid 127722569)
44. Schmidt AC, Schwarz I. (2006). Solid-state characterization of nonstoichiometric hydrates of ester-type local anaesthetics. Part XI. Crystal polymorphism of local anaesthetic drugs. Int J Pharm, 320, 4-13. (Pubitemid 44128705)
45. Schneider HJ, Hacket F, Rüdiger V, Ikeda H. (1998). NMR Studies of Cyclodextrins and Cyclodextrin Complexes. Chem Rev, 98, 1755-1786.
46. States DJ, Haberkorn RA, Ruben DJ. (1982). A Two-Dimensional Nuclear Overhauser Experiment with Pure Absorption Phase in 4 Quadrants. J Magn Reson 48, 286-292.
47. Werdehausen R, Fazeli S, Braun S, Hermanns H, Essmann F, Hollmann MW, Bauer I, Stevens MF. (2009). Apoptosis induction by different local anaesthetics in a neuroblastoma cell line. Br J Anaesth, 103, 711-718.
48. Wyman IW, Macartney DH. (2010). Host-guest complexations of local anaesthetics by cucurbit[7]uril in aqueous solution. Org Biomol Chem, 8, 247-252.
49. Yanagidate F, Strichartz GR. (2007). Local anesthetics. Handb Exp Pharmacol 177, 95-127.
50. Yang C, Liu L. Mu T-W, Guo Q-X. (2000). The Performance of the Benesi-Hildebrand Method in Measuring the Binding Constants of the Cyclodextrin Complexation. Anal Sci 16, 537-539.