Small molecule complementarity as a source of novel pharmaceutical agents and combination therapies

Current Pharmaceutical Design

Volumn 14, Issue 1, 2008, Pages 55-62

  Root Bernstein, Robert S ^a   Dillon, Patrick F ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Antisense peptides; Binding; Catecholamines; Charge transfer complex; Complexation; Drug interactions; Indoleamines; Pi pi bonding; Vitamins

Indexed keywords

ADRENERGIC RECEPTOR STIMULATING AGENT; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ASCORBIC ACID; ATYPICAL ANTIPSYCHOTIC AGENT; CHLORPROMAZINE; CLOZAPINE; ELLAGIC ACID; FENFLURAMINE; FLUOROURACIL; GENTAMICIN; HALOPERIDOL; IMIPRAMINE; ISOPRENALINE; METHOTREXATE; MORPHINE; NARCOTIC ANALGESIC AGENT; PENICILLIN DERIVATIVE; PHENOTHIAZINE DERIVATIVE; PHENYLEPHRINE; PROMAZINE; PROMETHAZINE; PROPIOMAZINE; QUERCETIN; RIBOFLAVIN; TETRACYCLINE; TRICYCLIC ANTIDEPRESSANT AGENT; TRIFLUPROMAZINE; TRIPTAN DERIVATIVE; UNINDEXED DRUG;

ALZHEIMER DISEASE; ANTINEOPLASTIC ACTIVITY; BINDING KINETICS; COMPLEX FORMATION; DRUG ANTAGONISM; DRUG COMPETITION; DRUG DESIGN; DRUG EFFICACY; DRUG POTENTIATION; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG SCREENING; DRUG TARGETING; HORMONE BINDING; HUMAN; MIGRAINE; NEOPLASM; NONHUMAN; PRIORITY JOURNAL; REVIEW;

DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG INTERACTIONS; HUMANS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN BINDING;

EID: 39449091701     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161208783330727     Document Type: Review

References (136)

1. Root-Bernstein RS, Dillon PF. Molecular complementarity I. The complementarity theory of life and its origins. J Theor Biol 1997; 188: 447-79.
2. Orts RJ, Burot BC, Sartin JL. Inhibitory properties of a bovine pineal tripeptide, threonylsery Ilysine, on serum follicle-stimulating hormone. Neuroendocrinology 1980; 31: 92-5.
3. Orts RJ, Liao T-H, Sartin JL, Bruot BC. Isolation, purification and amino acid sequence of a tripeptide from bovine pineal tissue displaying antigonadotropic properties. Biochim Biophys Acta 1980; 628: 201-8.
4. Vaughn MK, Johnson LY, Blask DE, Brainard GC, Dinh DT, Petterborg LJ, et al. Effect of synthetic threonylseryllysine (TSL), a proposed pineal peptide, on reproductive organ weights and plasma and pituitary levels of LH, FSH, and prolactin in intact and castrated immature and adult male rodents. Neuroendocr Lett 1980; 2: 235-40.
5. Benson B. Bovine pineal tripeptide threonylseryllysine retards puberty in female rats. J Pineal Res 1989; 6: 351-7.
6. Chan WY, Ng TB. Actions of selected proteins, peptides and amino acid derivatives on mouse embryonic development in vitro. Gen Pharmacol 1994; 25: 1611-6.
7. Root-Bernstein RS, Westall FC. Bovine pineal antireproductive tripeptide binds to luteinizing hormone-releasing hormone: A model for peptide modulation by sequence specific peptide interactions? Brain Res Bull 1986; 17: 519-28.
8. Root-Bernstein RS, Dobbelstein C. Insulin binds to glucagon forming a complex that is hyper-antigenic and inducing complementary antibodies having an idiotype-antiidiotype relationship. Autoimmunity 2001; 33: 153-69.
9. Dillon PF, Root-Bernstein, RS, Lieder CM. Molecular shielding of electric field complex dissociation. Biophys J 2006; 90: 1432-8.
10. Root-Bernstein RS. Molecular complementarity III. Peptide complementarity as a basis for peptide receptor evolution: A bioinformatic case study of insulin, glucagon and gastrin. J Theor Biol 2002; 218: 71-84.
11. Jones DS. Polypeptides. Part XIII. Peptides related to the C-terminal tetrapeptide sequence of gastrins by complementary reading of the genetic message. J Chem Soc Perkin 1972; 1: 1407-15.
12. Mekler LB. On the specific selective interaction between amino acid residues of polypeptide chains. Biofizika 1969; 14: 581-4.
13. Ildis RG. The principle of cross-stereocomplementarity and the symmetry of the genetic code. Mendeloev Chemistry, J 1980; 25: 126-31.
14. Biro J. Comparative analyses of specificity in protein-protein interactions. Part II. The complementarity coding of some proteins as a possible source of specificity.in protein-protein interactions. Med Hypoth 1983; 7: 981-93.
15. Root-Beinstein RS. Amino acid pairing. J Theor Biol 1982; 94: 885-94
16. Root-Bernstein RS. On the origin of the genetic code. J Theor Biol 1982; 94: 895-904.
17. Blalock JE. Complementarity of peptides specified by sense and antisense strands of DNA. Trends Biotechnol 1990; 8: 140-4.
18. Blalock JE, Bost KL. Ligand receptor characteristics of peptides encoded by complementary nucleic acids: Implications for a molecular recognition code. Recent Prog Horm Res 1988; 44: 199-222.
19. Chaiken I. Interactions and uses of antisense peptides in affinity technology. J Chormotogr 1992; 597: 29-36.
20. Root-Bernstein RS, Holsworth DD. Antisense peptides: A critical mini-review. J Theor Biol 1998; 190: 107-19.
21. Blalock JE, Smith EM. Hydropathic anti-complementarity of amino acids based on the genetic code. Biochem Biophys Res Commun 1984; 121: 203-7.
22. Holsworth DD, Kiely JS, Root-Bernstein RS, Overhiser, RW. Antisense-designed peptides: A comparative study focusing on possible complements to angiotensin II. Pept Res 1994; 7: 185-93.
23. Loo JA, Holsworth DD, Root-Bernstein RS. Use of electrospray ionization mass spectrometry to probe antisense peptide interactions. Biol Mass Spect 1994; 23: 6-12.
24. Heal JR, Roberts GW, Christie G, Miller AD. Inhibition of beta-amyloid aggregation and neurotoxicity by complementary (antisense) peptides. Chembiochem 2002; 3: 86-92.
25. Sautebin L, rombola L, Di Rosa M, Caliendo G, Perissuitti E, Grieco P, et al. Synthesis and structure-activity of antisense peptides corresponding to the region for CaM-binding domain of the inducible nitric oxide synthase. Eur J Med Chem 2000; 35: 727-32.
26. Davids JW, El Bakri A, Heal J, Christie G, Roberts GW, Raynes JG, et al. Design of antisense (complementary) peptides as selective inhibitors of cytokine interleukin-1. Angew Chem 1997; 3: 962-7.
27. Dillon PF, Root-Bernstein RS, Holsworth, DD. Augmentation of aortic ring contractions by antiotensin II antisense peptide. Hypertension 1998; 31: 854-60.
28. Misra PK, Hq W, Katti SB, Mathur KB, Raghubir R, Patnaik GK, et al. Enkephalin-antisense peptides: Design, synthesis, and biological activity. Pharm Res 1993; 10: 660-1.
29. Chaiken IM, Abercrombie DM, Kanmera T, Sequeira RP. Neuronal peptide-protein complexes: Neurophysins and associated neuropeptide hormones. Pept Protein Rev 1983; 1: 139-209.
30. Root-Bernstein RS "Molecular sandwiches" as a basis for the structural and functional similarities of interferons, MSH, ACTH, LHRH, myelin basic protein and albumins. FEBS Lett 1984; 168: 208-12.
31. Adachi DK, Kalivas PW, Schenk JO. Neurotensin binding to dopamine. J Neurochem 1990; 54: 1321-8.
32. Schenk JO, Morocco MT, Ziemba VA. Interactions between the argininyl moieties of neurtensin and the catechol protons of dopamine. J Neurochem 1991; 57: 1787-95.
33. Field EJ, Caspary EA, Carnegie PR. Lymphocyte sensitization to basic protein of brain in malignant neoplasia: Experiments with serotonin and related compounds. Nature 1971; 233: 284-6.
34. Caspary EA, Field EJ. Specific lymphocyte sensitization in cancer: Is there a common antigen in human malignant neoplasia? Br Med J 1971; 2: 613-7.
35. Root-Bernstein RS. Structure of a serotonin and LSD binding site on myelin basic protein. J Theor Biol 1983; 100: 373-8.
36. Root-Bernstein RS, Westall FC. Serotonin binding sites I. Structures of sites on myelin basic protein, LHRH, MSH, ACTH, interferon, serum albumin, ovalbumin and re pigment concentrating hormone. Brain Res Bull 1984; 12: 425-36.
37. Takeuchi Y, Root-Bernstein RS, Shih JC. Peptide displacement of [3H]5-hydroxytryptamine binding to bovine cortical membranes. Brain Res Bull 1990; 25: 817-20.
38. Krieger DT. Serotonin regulation of ACTH secretion. Ann NY Acad Sci 1977; 297: 527-35.
39. Kordon C, Hery M, Szafarczyk A, Ixart G, Assenmacher I. Serotonin and the regulation of pituitary hormone secretion and of neuroendocrine rhythms. J Physiol (Paris) 1981; 77: 489-96.
40. Marko M, Fluckiger E. Role of serotonin in the regulation of ovulation Neuroendocrinology 1980; 30: 228-31.
41. Lederer E. Synthetic muramyl peptides. Science 1982; 218: 330.
42. Kotani S. Tsujimoto M, Koga T, Nagao S, Tanaka A, Kawata S. Chemical structure and biological activity relationship of bacterial cell walls and-muramyl peptides. Fed Proc 1986; 45: 2534-40.
43. Kreuger JM, Pappenheimer JR, Kamovsky ML. Sleep promoting effects of muramyl peptides Proc Natl Acad Sci USA 1982; 79: 6102-6.
44. Kreuger JM, Pappenheimer JR, Karnovsky ML. The composition of sleep-promoting factor isolated from human drine. J Biol Chem 1982; 257: 1664-9.
45. Krueger JM, Kamovsky ML, Martin SA, Pappenheimer JR, Walter J, Biemann K. Peptidoglycans as promoters of slow-wave sleep. J Biol Chem 1984; 259: 12659-62.
46. Root-Bernstein RS, Westall FC. Serotonin binding sites II. Muramyl dipeptide binds to serotonin binding sites on myelin basic protein, LHRH, and MSH-ACTH 4-10, Brain Res Bull 1990; 25: 827-41.
47. Root-Bernstein RS, Westall FC. Sleep factors: Do muramyl peptides activate serotonin binding site? Lancet 1983; i(8325): 653.
48. Silverman DH, Wu H, Karnovsky ML. Muramyl peptides and serotonin interct at specific brinding sites on macrophages and enhance superoxide release. Biochem Biophys Res Commun 1985; 131: 1160-7.
49. Silverman DH, Imam K, Karnovsky ML. Muramyl peptide/serotonin receptors in brain-derived preparations. Pept Res 1989; 2: 338-44.
50. Sevcik J, Masek K. The interaction of immunomodulatory muramyl dipeptide with peripheral 5-HT receptors: Overview of the current state. Int J Immunopharmacol 1999; 21: 227-32.
51. Kadlec O, Masek K, Gulda O, Ruzicka V, Parant M, Chedid L. Smooth muscle stimulation by an immunomodulatory compound muramyl dipeptide: Does it involve the serotoninergic system? Pharmacology 1984; 29:31-9.
52. Masek K, Petrovicky P. Morphological and pharmacological evidence for the existence of brain regulatory circuits in the immune response. Int J Immunopharmacol 1997; 19: 507-10.
53. Polanki M, Vermeulen MW, Wu J. Karhovsky ML. Muramyl dipeptide mimicry in the regulation of murine macrophage activation by serotonin. Int J Immunopharmacol 1995; 17: 225-32.
54. Andren J, Andrews K, Brown L, Chidgey J, Geary N, King MG, et al. Muramyl peptides and the functions of sleep. Behav Brain Res. 1995; 69: 85-90.
55. Polanski M, Karnovsky ML. Serotonergic aspects of the response of human platelets to immune-adjuvant muramyl dipeptide. J Neuroimmunol 1992; 37: 149-60.
56. Horak P, Masek K. Analgesic activity of two synthetic immunomodulators, muramyl dipeptide and adamantylamide dipeptide in mice and rats. Methods Find Exp Clin Pharmacol 1998; 10: 569-74.
57. Root-Bernstein RS. Catecholamines bind to enkephalins, morphiceptin and morphine. Brain Res Bull 1987; 18: 509-32.
58. Rotsztejn WH, Drouva SV, Patton E, Kordon C. Met-enkaphalin inhibits in vitro dopamine-induced LHRH release from mediobasal hypothalamus of male rats. Nature 1978; 274: 281-2.
59. Saland LC, Mennin SP, Selinfreund R, Rasmussen P. Interaction of beta-endorphin, naloxone and dopamine: Effects on melanocyte-stimulating hormone secretion of amphibian pituitaries in vitro. Regul Pept 1982; 3: 371-81.
60. Gedulsky GA, Porter JC. Morphine and opiate peptide-induced inhibition of the release of dopamine from tuberoinfundibular neurons. Life Sci 1979; 25: 1697-702.
61. Caffrey JL, Hodges DH. Catecholamine mediated inhibition of enkephalin metabolism. Endocrinology 1982; 110: 291-3.
62. Suh JJ, Rhee HM. Effect of norepinephrine on the binding of [3H]methiorine-enkephalinamide in brain tissue Ann N.Y Acad Sci 1986 463: 356-8.
63. Kindman LA, Kates RE, Ginsburg R. Opioids potentiate-contractile response of rabbit myocardium to the beta-adrenergic agonist isoproterenol. J Cardiovasc Pharmacol 1991; 17: 61-7.
64. Lechner RB. Naloxone potentiates the inotropic effects of isoproterenol in vitro by a nonopiate receptor mechanism. Circ Shock 1992; 38: 157-64.
65. Pende A, Ioverno A, Musso NR, Vergassola C, Lotti G. Effects of opioid substances on cAMP response to the beta-adrenergic agonist isoproterenol in human mononuclear leukocytes. Biomed Pharmacother 1995; 49: 33-7.
66. Guo Xh, Fairbandks CA, Stone LS, Loh HH. DPDPE-UK14,304 synergy is retained in mu opioid receptor knockout mice. Pain 2003; 104: 209-17.
67. Takada K, Clark DJ, Davies MF, Tonner PH, Krause TK, Bertaccini E, et al. Meperidine exerts agonist activity at the alpha(2B)- adrenoceptor subtype. Anesthesiology 2002; 96: 1420-6.
68. Tejwani GA, Rattan AK. Antagonism of antinociception produced by intrathecal clonidine by ketorolac in the rat: The role of the opioid system. Anesth Anal 2000; 90: 1152-6.
69. Paul D, Tran JG. Differential cross-tolerance between analgesia produced by alpha-2-adrenoceptor agonists and receptor subtype selective opiod treatments. Eur J Pharmacol 1995; 272: 1111-4.
70. Pende A, Ioverno A, Musso NR, Vergassola C, Lotti G. Effects of opioid subtances on cAMP response to the beta-adrenergic agonist isoproterenol inhuman mononuclear leukocytes. Biomed Pharmacol 1995; 49: 33-7.
71. Reggiani A, Carenzi A, Della-Bella D. Influence of opioids on beta-receptors down-regulation: Studies in cultured C6 glioma cells. Brain Res 1987; 423: 254-60.
72. Goodman AG, Rall TW, Nies AS, Taylor P. Goodman and Gilmans The Pharmacological Basis of Therapeutics. Eighth Edition, New York: Pergamon Press 1990; pp, 498-9.
73. Root-Bernstein RS, Dillon PF. Fostering venture research: A case study of the discovery that ascorbate enhances adrenergic drug activity. Drug Devel Res 2002; 57: 58-74.
74. Clineschmidt BV, Zacchei AG, Todaro JA, Pfleuger AB, McGuffin JC, Wishousky TI. Fenfluarmine and brain serotonin. Ann NY Acad Sci 1978; 305: 222-41.
75. Geller E, Ritvo ER, Freeman BJ, Yuwiler A. Preliminary observations on the effect of fenfluramine on blood serotonin and symptoms in three autistic boys. N Engl J Med 1982; 307: 165-9.
76. Root-Bernstein RS, Westall FC. Fenfluramine binds 5-hydroxytryptophan. Brain Res Bull 1983; 12: 17-22.
77. Patterson TA, Schenk JO. Effects of acute and chronic systemic administration of some typical antipsychotic drugs on turnover of dopamine and potassium ion-induced release of dopamine in the striatum of the rat in vivo. Neuropharmacology 1991; 30: 943-52.
78. McElvain JS, Schenk JO. Blockade of dopamine autoreceptors by haloperidol and the apparent dynamics of potassium-stimulated endogenous release of dopamine from and reuptake into striatal suspensions in the rat. Neuropharmacology 1992; 13: 649-59.
79. Schenk JO, Patterson T. Dopamine (DA) complexes with typical antipsychotic drugs, (AD) and weakly, or not at all, with the atypical antipychotic drugs: Abstr Soc Neurosci 1987; 13: 481.
80. Patterson T, Schenk JO. Haloperidol forms molecular complexes with dopamine in vivo. Abstr Soc Neurosci 1988; 14(2): 1214.
81. Wilson JE. Studies on the electronic nature of flavin-indole and flavin-purine complexes. Biochemistry 1966; 5: 1351-9.
82. Pereira JF, Tollin G. Molecular complexes of flavins: A comparison of flavin-indole and flavin-phenol interactions. Biochim Biophys Acta 1967; 143: 79-87.
83. Budinia R, Marinangeli A. Interactions between some psychodrugs and flavins. Z Naturforsch B 1970; 25: 505-9.
84. Inoue M, Okuda Y, Ishida T, Nakagaki M. On the interaction between flavin-adenine rings and between flavin-indole rings by X-ray structural studies. Arch Biochem Biophys 1983; 227: 52-70.
85. Karen A, Ikeda N, Mataga N, Tanaka F. Picosecond laser photolysis studies of fluorescence quencing mechanisms of flavin: A direct observation of indole-flavin single charge transfer state formation in solutions and flavoenzymes. Photochem Photobiol 1983; 37: 455-502
86. Munoz MA, Carmona C, Hidalgo J, Guardado P, Balon M. Molecular associations of flavins with betacarbolines and related indoles: Bioorg Med Chem 1995; 3: 41-7.
87. Martin CB, Tsao ML, Hadad CM, Platz MS. The reaction of triplet flavin with indole. A study of the cascade of reactive intermediates using density functional theory and time resolved infrared spectroscopy. J Am Chem Soc 2002; 124: 7226-34.
88. Khanna P, Schuman-Joms M. Characterization of the FAD-containing N-methyltryptophan oxididase from Escherichia coli. Biochemistry 2001; 40: 1441-50.
89. Hubbard PA, Shen AL, Paschke R, Kasper CB, Kim JJ. NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer. J Biol Chem 2001; 276: 29163-70.
90. Cashman JR, Xiong Y, Lin J, Verhagen H, van Poppel G, van Bladeren PJ, et al. In vitro and in vivo inhibiation of human falvin-containing monooxygenase from 3 (FMO3) in the presence of dietary indoles. Biochem Pharmcol 1999; 58: 1047-55.
91. Katchamart S., Stresser DM, Dehal SS, Kupfer D, Williams DE. Concurrent falvin-containing monooxygenase down-regulation and cytochrome P-450 induction by dietary indoles in rat: Implications for drug-drug interaction. Drug Metab Dispos 2000; 28: 930-6.
92. Chelala CA, Margolin P. Bactericidal photoproducts in medium containing riboflavin plus aromatic compounds and MnC12. Can J Microbiol 1983; 29: 670-5.
93. Edwards AM, Barredo F, Silva E, De Ioannes AE, Becker MI. Apoptosis induction in nonirradiated human HL-60 and murine NSO/2 tumor cells by photoproducts of indole-3-acetic acid and riboflavin. Photochem Photobiol 1999; 70: 645-9.
94. Krymchantowski AV, Bigal ME, Moreira PF. New and emerging prophylactic agents for migraine. CNS Drugs 2002; 46: 611-34.
95. Sandor PS, Afra J, Ambrosini A, Schoenen J. Prophylactic treatment of migraine with beta-blockers and riboflavin: Differential effects on the intensity dependence of auditory evoked cortical potentials. Headache 2000; 40: 30-5.
96. Tepper SJ, Rapoport A, Shefteil F. The pathophysiology of migraine. Neurology 2001; 7: 279-86.
97. Dobson CF, Tohyama Y, Diksic M, Hamel E. Effects of acute or chronic administration of anti-migraine drugs sumatriptan and zolmitriptan on serotonin synthesis in the rat brain. Cephalalgia 2004; 24: 2-11.
98. Dahlof C. Clinical applications of new therapeutic deliveries, in migraine. Neurology 2003; 61(8 Suppl 4): S31-4.
99. Root-Bernstein RS. Discovering. Cambridge MA, Harvard University Press, 1987; 263.
100. Dillon PF, Root-Bernstein RS, Sears PR, Olson LK. Natural electrophoresis of norepinephrine and ascorbic acid. Biophys J 2000; 79: 370-6.
101. Root-Bernstein RS, Dillon PF. Fostering venture research: A case study of the discovery that ascorbate enhances adrenergic drug activity. Drug Devel Res 2002; 57: 58-74.
102. Dillon PF, Root-Bernstein RS, Lieder CM. Anti-oxidant independent ascorbate enhancement of catecholamine-induced contractions of vascular smooth muscle. Am J Physiol, Heart Circ Physiol 2004; 286: H2353-60.
103. Grossmann M, Dobrev D, Himmel HM, Ravens U, Kirch W Ascorbic acid-induced modulation of venous tone in humans. Hypertension 2001; 37: 949-54.
104. Piccirillo G, Nocca M, Moise A, Lionetti M, Naso C, di Carlo S, et al. Influence of vitamin C on baroreflex sensitivity in chronic heart failure. Hypertension 2003; 41: 1240-5.
105. Monahan KD, Eskurza I, Seals DR. Ascorbic acid increases cardiovagal baroreflex sensitivity in healthy older men. Am J Physiol Heart Circ Physiol 2004; 556: 315-24.
106. Mak S, Newton GE. Vitamin C augments theinotropic response to doputamine in humans with normal left ventricular function. Circulation 2001; 103: 826-31.
107. Houston JB, Wilkens HJ, Levy G. Potentiation of isoproterenol effect by ascorbic acid. Res Commun Chem Pathol Pharmacol 1976; 14: 643-50.
108. Dillon PF, Root-Bernstein RS, Lieder CM. Ascorbate enhancement of H1 histamine receptor coincides with ascorbate oxidation inhibition by histamine receptors. Am J Physiol Cell Physiol 2006; 291: C977-84.
109. Dillon PF, Root-Bernstein RS, Robinson NE, Abraham WM, Lieder CM, Berney C. Ascorbate binding to the adrenergic receptor enhances in vivo and in vitro beta-adrenergic sensitivity. Am J Physiol; (in press).
110. Huang J, Agus DB, Winfree CJ, Kiss S, Mack WJ, McTaggart RA, et al. Dehydroascorbic acid, a blood-brain barrier transportable form of vitamin C, mediates potent cerebroprotection in experimental stroke. Proc Natl Acad Sci USA 2001; 98: 11720-4.
111. Root-Bernstein RS, Dillon PF. Catecholamine pharmaceutical compositions and methods. International Patent Application, World Intellectual Property Organization Number WO 02/26223 A2 (4 April 2002).
112. Johnston PA, Chahl LA. Chronic treatment with ascorbic acid inhibits the morphine withdrawal response in guinea pigs. Neurosci Lett 1992; 135: 23-7.
113. Evangelou A, Kalfakakou V, Georgakas P, Koutras V, Vezyraki P, Iliopoulou L, et al. Ascorbic acid (vitamin C) effects on withdrawal syndrome of heroin abusers. In Vivo 2000; 14: 363-6.
114. Desole MS, Esposito G, Fresu L, Migheli, R, Enrico P, Mura Ma, et al. Effects of morphine treatment and withdrawal on striatal and limbic monoaminergic activity and ascorbic acid oxidation in the rat. Brain Res 1996; 723: 154-61.
115. Kleber HD, Riordan CE. The treatment of narcotic withdrawal: A historical review. J Clin Psychiatry 1982; 43: 30-4.
116. Colter AK, Wang SS, Megerle GH, Ossip PS. J Am Chem Soc 1964; 86: 3106-13.
117. Colter AK, Hui SH. Chemical behavior of charge transfer complexes. J Org Chem 1968; 33: 1935-40.
118. Wood AW, Sayler JM, Newmark HL, Yagi H, Michaud DP, Jerina DM, et al. Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7,8- diol 9,10-epoxide by riboflavin 5′-phosphate. Proc Natl Acad Sci USA 1982; 79: 5122-6.
119. Sayer JM, Yagi H, Wood AW, Conney AH, Jerina DM. Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene, (+)-7,8-diol 9, 10-epoxide and ellagic acid. J Am Chem Soc 1982; 104: 5564-6.
120. Kahnduja KL, Gandi RK, Pathania V, Syal N. Prevention of N-nitrosodiethylamine-induced lung tumorigenesis by ellagic acid and quercetin in mice. Food Chem Toxicol 1999; 37: 313-8.
121. Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW. p53/p21(WAF1/ C1P1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells. Cancer Lett 1999; 136: 215-21.
122. Smith WA, Freeman JW, Gupta RC. Effect of chemopreventive agents on DNA adduction induced by the potent mammary carcinogen dibeno[a,1]pyreine in the human breast cells MCF-7. Mutat Res 2001; 480-481: 97-108.
123. Lin SS, Hung CF, Tyan YS, Yang CC, Hsia TC, Yang MD, et al. Ellagic acid inhibits arylamine N-acetyltransferase activity and DNA adduct formation in human bladder tumor cell lines (T24 and TSGH 8301). Urol Res 2001; 29: 371-6.
124. Ho CC, Tsai HY, Lai YS, Chung JG, Ellagic acid inhibited 2-aminofluorene and p-aminobenzoic acid acetylation by mononu-clear leucocytes from Sprague-Dawley rats. Cytobios 2001; 104: 107-17.
125. Mishra KP, Nosaka Y, Akasaka K, Nagata C, Hatano H. Solubilization of 6-oxybenzo[a]pyrene radical by caffeine and DNA as studied by magnetic resonance. Observation of intermolecular charge transfer. Biochim Biophys Acta 1978; 520: 679-87.
126. D'Amato RJ, Lipman ZP, Snyder SH. Selectivity of the Parkinsonian neurotoxin MPTP: Toxic metabolite MPP+ binds to neuromelanin. Science 1986; 231: 987-9.
127. Molnar J, Foldeak S, Nakamura MJ, Gaizer F, Gutmann F. The influence of charge transfer complex formation on the antibacterial activity of some tricyclic drugs. Xenobiotica 1991; 21: 309-16.
128. Molnar J, Batho N, Csik V, Chevalier J, Cremieux A. Interaction between tricyclic psychopharmacons and some antibiotics. Acta Microbiol Immumol Hung 1995; 42: 277-85.
129. Flores VC, Keyzer H, Kim HK, Molnar J. Interaction of protonated anticancer thiazines with water-insoluble phospholipids and anti-neoplastic agents. Anticancer Res 202; 22: 959-67.
130. Abdel-Gawad FM. Spectrophotometric determination of some pharmaceutical piperazine derivatives through charge-transfer and ion-pair complexation reactions. J Pharm Biomed Anal 1997; 15: 1679-85.
131. Adikwu MU, Ofokans KC. Spectrophotometric determination of moclobemide by charge-transfer complexation. J Pharm Biomed Anal 1997; 16: 529-32.
132. El-Zeany BA, Moustafa AA, Farid NF. Determination of imipramine in presence of imodibenzyl and in pharmaceutical dosage form. J Pharm Biomed Anal 2003; 33: 775-82.
133. Amin AS, Ragab GH Saleh H. Colorimetric determination of beta-blockers in pharmaceutical formulations. J Pharm Biomed Anal 202; 30: 1347-53.
134. Gresh N. Development, validation, and applications of anisotropic polarizable molecular mechanics to study ligand and drug-receptor interactions. Curr Pharm Des 2006; 12(17): 2121-58.
135. Leonetti C, Zupi G. Targeting different signaling pathways with antisense oligonucleotides combination for cancer therapy. Curr Pharm Des 2007; 13(5): 463-70.
136. Uccello-Barretta G, Balzano F, Salvadori P. Enantiodiscrimination by NMR spectroscopy. Curr Pharm Des 2006; 12(31): 4023-45.