Conjugation of thymopentin (TP5) with lipoamino acid residues increases the hydrolytic stability and preserves the biological activity

Pharmazie

Volumn 62, Issue 9, 2007, Pages 663-667

  Pignatello, Rosario ^a   Pecora, T M G ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOTETRADECANOIC ACID; AMINO ACID; DENDRIMER; DIMER; LIPOAMINO ACID; LIPOSOME; PENTAPEPTIDE; THYMOPENTIN; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; BIOLOGICAL ACTIVITY; CELL MEMBRANE; DRUG CONJUGATION; DRUG STABILITY; DRUG STRUCTURE; FETAL CALF SERUM; HUMAN; HUMAN CELL; HYDROLYSIS; INCUBATION TIME; LIPOPHILICITY; LYMPHOBLASTOID CELL LINE; MEMBRANE MODEL; MEMBRANE PERMEABILITY;

EID: 34848901053     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: 10.1691/ph.2007.9.7002     Document Type: Article

References (36)

1. Aiuti F, Businco L, Fiorilli M, Galli E, Quinti I, Le Moli S, Seminara R, Goldstein G (1983) Therapy with thymopoietin pentapeptide (TP5) in 26 patients with primary immunodeficiences. Birth Defects Orig Artic Ser 19: 267-272.
2. Baker B, Viamontes G, Audhya T, Goldstein G (1988) Selected human T cell lines respond to thymopoietin with intracellular cyclic GMP elevations. Immunopharmacology 16: 115-122.
3. Bodey B, Bodey B Jr, Siegel SE, Kaiser HE (2000) Review of thymic hormones in cancer diagnosis and treatment. Int J Immunopharmacol 22: 261-273.
4. Castelli F, Raudino A, Fresta M (2005) A mechanistic study of the permeation kinetics through biomembrane models: Gemcitabine-phospholipid bilayer interaction. J Colloid Interface Sci 285: 110-117.
5. Conant MA, Calabrese LH, Thompson SE, Poiesz BJ, Rasheed S, Hirsch RL, Meyerson LA, Kremer AB, Wang CC, Goldstein G (1992) Mainteinance of CD4+ cells by thymopentin in asymptomatic HIV-infected subjects: results of a double-blind, placebo-controlled study. AIDS 6: 1335-1339.
6. De Graw JL, Almquist RG, Hiebert CK, Judd AK, Dousman L, Smith RL, Wand WR, Uchida I (1997) Stabilized analogs of thymopentin. 2. 1,2-and 3,4-ketomethylene pseudopeptides. J Med Chem 40: 2398-2406.
7. Denes L, Szende B, Hajos G, Szporny L, Lapis K (1987) Therapeutic possibilities of thymopoietin fragments (TP3 and TP4) based on experimental animal models. Drugs Exptl Clin Res 13: 279-287.
8. Fan YZ, Chang H, Yu Y, Liu J, Zhao L, Yang DJ, Wang R (2006) Thymopentin (TP5), an immunomodulatory peptide, suppresses proliferation and induces differentiation in HL-60 cells. Biochim Biophys Acta 1763: 1059-1066.
9. Gibbons WA, Hughes RA, Charalambous M, Christodoulou M, Szeto A, Aulabaugh AE, Mascagni P, Toth I (1990) Synthesis, resolution and structural elucidation of lipidic amino acids and their homo- and hetero-oligomers. Liebigs Ann Chem 1990: 1175-1183.
10. Goldstein G, Audhya TK (1985) Thymopoietin to thymopentin: experimental studies. Surv Immunol Res 4 (suppl. 1): 1-10.
11. Goldstein G, Scheid MP, Boyse EA, Schlesinger DH, Van Wauwe J (1979) A synthetic pentapeptide with biological activity characteristic of the thymic hormone thymopoietin. Science 204: 1309-1310.
12. Gonser S, Weber E, Folkers G (1999) Peptides and polypeptides as modulators of the immune response: thymopentin - an example with unknown mode of action. Pharm Acta Helv 73: 265-273.
13. Heavner GA, Kroon DJ, Audhya T, Goldstein G (1986) Biologically active analogs of thymopentin with enhanced enzymatic stability. Peptides 7: 1015-1019.
14. Heizmann J, Langguth P, Biber A, Oschmann R, Merkle HP, Wolffram S (1996) Enzymatic cleavage of thymopoietin oligopeptides by pancreatic and intestinal brush-border enzymes. Peptides 17: 1083-1089.
15. Hussain R, Toth I, Gibbons WA (1991a) Lipidic peptides VII. Synthesis and structure elucidation of γ-amino-butyric acid conjugates with lipidic acids, lipidic amino acids and lipidic peptides. Liebigs Ann Chem 1991: 963-966.
16. Hussain R, Toth I, Bowery NG, Gibbons WA (1991b) Brain uptake of lipidic γ-amino-butyric acid conjugates. J Pharm Pharmacol 43: 129P.
17. Kellam B, Drouillat B, Dekany G, Starr MS, Toth I (1998) Synthesis and in vitro evaluation of lipoamino acid and carbohydrate-modified enkephalins as potential antinociceptive agents. Int J Pharm 161: 55-64.
18. Lee ML, Stavchansky S (1998) Isothermal and nonisothermal decomposition of thymopentin and its analogs in aqueous solution. Pharm Res 15: 1702-1707.
19. Panico AM, Pignatello R, Mazzone S, Puglisi G, Mazzone G, Campo ME, Stivala F, Bernardini A (1991) Liposomal thymostimulin formulations: in vitro activity on human erythroleukemic cells. J Chemotherapy 3 (Suppl. 3): 308-310.
20. Panico AM, Pignatello R, Puglisi G, Mazzone G, Petrone G (1992) Use of liposomes as carriers for immunomodulatory polypeptides: Studies on thymostimulin encapsulation and retention. Int J Pharm 80: 93-100.
21. Panico AM, Pignatello R, Mazzone S, Cardile V, Bindoni M, Cordopatri F, Villari A, Micali N, Mazzone G (1993) Lipid vesicles loaded with thymopentin: characterization and in vitro activity on tumoral cells. Int J Pharm 98: 19-28.
22. Pignatello R, Toth I, Puglisi G (2001) Structural effects of lipophilic methotrexate conjugates on model phospholipid biomembranes. Thermochimica Acta 380: 255-264.
23. Pignatello R, Guccione S, Castelli F, Sarpietro MG, Giurato L, Lombardo M, Puglisi G, Toth I (2006a) Enhancement of drug affinity for cell membranes by conjugation with lipoamino acids. II. Experimental and computational evidence using biomembrane models. Int J Pharm 310: 53-63.
24. Pignatello R, Intravaia VD, Puglisi G (2006b) A calorimetric evaluation of the interaction of amphiphilic prodrugs of idebenone with a biomembrane model. J Colloid Interface Sci 299: 626-635.
25. Pignatello R, Noce C, Campisi A, Acquaviva R, Bucolo C, Puglisi G, Toth I (2007) Evaluation of cell tolerability of a series of lipoamino acids using biological membranes and a biomembrane model. Curr Drug Del 4: 109-121.
26. Puglisi G, Fresta M, Pignatello R (1998) Synthesis of methotrexate α,γ-bis(amides) and correlation of thermotropic and DPPC biomembrane interaction parameters with their anticancer activity. Drug Dev Res 44: 62-69.
27. Rogalski C, Dummer R, Burg G (1999) Immunomodulators in the treatment of cutaneous lymphoma. J Eur Acad Dermatol Venereol 113: 83-90.
28. Saija A, Tomaino A, Trombetta D, Pellegrino ML, Tita B, Caruso S, Castelli F (2002) Interaction of melatonin with model membranes and possible implications in its photoprotective activity. Eur J Pharm Biopharm 53: 209-215.
29. Schlesinger DH, Goldstein G (1975) The amino acid sequence of thymopoietin II. Cells 5: 361-365.
30. Singh VK, Biswas S, Mathur KB, Haq W, Garg SK, Agarwal SS (1998) Thymopentin and splenopentin as immunomodulators. Current status. Immunol Res 17: 345-368.
31. Toth I (1994) A novel chemical approach to drug delivery: lipidic amino acid conjugates. J Drug Targeting 2: 217-239.
32. Toth I, Flinn N, Hillery AM, Gibbons WA, Artursson P (1994) Lipidic conjugates of luteinizing hormone releasing hormone (LHRH) and thyrotropin releasing hormone (TRH) that release and protect the native hormones in homogenates of human intestinal epithelial (Caco-2) cells. Int J Pharm 105: 241-246.
33. Toth I, Christodoulou M, Bankowsky K, Flinn N, Gibbons WA, Godeau G, Moczar E, Hornebeck W (1995) Design of potent lipidic-peptide inhibitors of human neutrophil elastase. In vitro and in vivo studies. Int J Pharm 125: 117-122.
34. Toth I, Malkinson JP, Flinn NS, Drouillat B, Horváth A, Érchegyi J, Idei M, Venetianer A, Artursson P, Lazorova L, Szende B, Kéri G (1999) Novel lipoamino acid- and liposaccharide-based system for peptide delivery: application for oral administration of tumor-selective somatostatin analogues. J Med Chem 42: 4010-4013.
35. Wong A, Toth I (2001) Lipid, sugar and liposaccharide based delivery systems. Curr Med Chem 8: 1123-1136.
36. Zheng A-P, Wang J-C, Lu W-L, Zhang X, Zhang H, Wang X-Q, Zhang Q (2006) Thymopentin-loaded pH-sensitive chitosan nanoparticles for oral administration: preparation, characterization, and pharmacodynamics. J Nanosci Nanotechnol 6: 2936-2944.