67
Views
9
CrossRef citations to date
0
Altmetric
Review

Twenty years of non-peptide CCK1 receptor antagonists: all that glitters is not gold

&
Pages 1193-1213 | Published online: 31 Aug 2006

Bibliography

  • WILLIAMS JA: Cholecystokinin: a hormone and neurotransmitter. Biomed. Res. (1982) 3:107-115.
  • DOUGLAS BR, JANSEN JB, DE JONG AJ et al.: Effect of various triglycerides on plasma cholecystokinin levels in rats. J. Nutr. (1990) 120:686-690.
  • LEWIS LD, WILLIAMS JA: Regulation of cholecystokinin secretion by food, hormones, and neural pathways in the rat. Am. J. Physiol. (1990) 258:G512-G518.
  • SCHWARTZ GJ, MORAN TH, WHITE WO et al.: Relationships between gastric motility and gastric vagal afferent responses to CCK and GRP in rats differ. Am. J. Physiol. (1997) 272:R1726-R1733.
  • GRIDER JR: Role of cholecystokinin in the regulation of gastrointestinal motility. J. Nutr. (1994) 124:1334S-1339S.
  • WANK SA: G-protein-coupled receptors in gastrointestinal physiology I. CCK receptors: An exemplary family. Am. J. Physiol. (1998) 274:G607-G613.
  • DEGEN L, MATZINGER D, DREWE J et al.: The effect of cholecystokinin in controlling appetite and food intake in humans. Peptides (2001) 22:1265-1269.
  • WIESENFELD-HALLIN Z, XU XJ: The role of cholecystokinin in nociception, neuropathic pain and opiate tolerance. Regul. Pept. (1996) 65:23-28.
  • SZELENYI Z: Cholecystokinin and thermoregulation: a mini review. Peptides (2001) 22:1245-1250.
  • GRIEBEL G: Is there a future for neuropeptide receptor ligands in the treatment of anxiety disorders? Pharmacol. Ther. (1999) 82:1-61.
  • REHFELD JF: Cholecystokinin and panic disorder: three unsettled questions. Regul. Pept. (2000) 93:79-83.
  • VILLANUEVA ML, COLLINS SM, JENSEN RT et al.: Structural requirements for action of cholecystokinin on enzyme secretion from pancreatic acini. Am. J. Physiol. (1982) 242:G416-G422.
  • DESCHENES RJ, LORENZ LJ, HAUN RS et al.: Cloning and sequence analysis of a cDNA encoding rat pre-procholecystokinin. Proc. Natl. Acad. Sci. USA (1984) 81:726-730
  • INNIS RB, SNYDER SH: Distinct cholecystokinin receptors in brain and pancreas. Proc. Natl. Acad. Sci. USA (1980) 77:6917-6912.
  • NOBLE F, WANK SA, CRAWLEY JN et al.: International Union of Pharmacology. XXI. Structure, distribution, and functions of cholecystokinin receptors. Pharmacol. Rev. (1999) 51:745-781.
  • PISEGNA JR, DEWEERTH A, HUPPI K et al.: Molecular cloning, functional expression, and chromosomal localization of the human cholecystokinin type A receptor. Ann. N. Y. Acad. Sci. (1994) 713:338-342.
  • LEE YM, BEINBORN M, McBRIDE EW et al.: The human brain cholecystokinin-B/gastrin receptor. Cloning and characterization. J. Biol. Chem. (1993) 268:8164-8169.
  • DUNLOP J: CCK receptor antagonists. Gen. Pharmac. (1998) 31:519-524.
  • DE TULLIO P, DELARGE J, PIROTTE B: Recent advances in the chemistry of cholecystokinin receptor ligands (agonists and antagonists). Curr. Med. Chem. (1999) 6:433-455.
  • HERRANZ R: Cholecystokinin antagonists: pharmacological and therapeutic potential. Med. Res. Rev. (2003) 23:559-605.
  • HILL DR, CAMPBELL NJ, SHAW TM et al.: Autoradiographic localisation and biochemical characterisation of peripheral type CCK receptors in rat CNS using highly selective non-peptide CCK antagonists. J. Neurosci. (1987) 7:2967-2976.
  • WOODRUFF GN, HILL DR, BODEN P et al.: Functional role of brain CCK receptors. Neuropeptides (1991) 19(Suppl.):45-56.
  • WANK SA: Cholecystokinin receptors. Am. J. Physiol. (1995) 269:G628-G646.
  • FELICIANO LF, MAZZINI BK, CACHEIRO RG et al.: Stimulation of either cholecystokinin receptor subtype reduces while antagonists potentiate or sensitize a morphine-induced excitatory response. Peptides (2001) 22:1299-1304.
  • CRAWLEY JN: Cholecystokinin–dopamine interactions. Trends Pharmacol. Sci. (1991) 12:232-236.
  • WANK SA, HARKINS R, JENSEN RT et al.: Purification, molecular cloning, and functional expression of the cholecystokinin receptor from rat pancreas. Proc. Natl. Acad. Sci. USA (1992) 89:3125-3129.
  • DE WEERTH A, PISEGNA JR, HUPPI K et al.: Molecular cloning, functional expression and chromosomal localization of the human cholecystokinin type A receptor. Biochem. Biophys. Res. Commun. (1993) 194:811-818.
  • DUNLOP J, ZHANG Y, EVANS N: Full and partial agonist activity of C-terminal cholecystokinin peptides at the cloned human CCKA receptor expressed in Chinese hamster ovary cells. Peptides (1997) 18:865-868.
  • YULE DI, TSENG MJ, WILLIAMS JA et al.: A cloned CCKA receptor transduces multiple signals in response to full and partial agonists. Am. J. Physiol. (1993) 265:G999-G1004.
  • YOSHIDA H, TSUNODA Y, OWYANG C: Cholecystokinin peptides stimulate pancreatic secretion by multiple signal transduction pathways. Am. J. Physiol. (1997) 273:G735-G747.
  • MARINO CR, LEACH SD, SCHAEFER JF et al.: Characterization of cAMP-dependent protein kinase activation by CCK in rat pancreas. FEBS Lett. (1993) 316:48-52.
  • DUFRESNE M, SEVA C, FOURMY D: Cholecystokinin and gastrin receptors. Physiol. Rev. (2006) 86:805-847.
  • FREIDINGER RM: Cholecystokinin and gastrin antagonists. Med. Res. Rev. (1989) 9:271-290.
  • NADZAN AM, KERWIN JF: Cholecystokinin agonists and antagonists. Ann. Rep. Med. Chem. (1991) 26:191-201.
  • D’AMATO M, ROVATI LC: Cholecystokinin-A receptor antagonists: Therapies for gastrointestinal disorders. Exp. Opin. Invest. Drugs (1997) 6:819-836.
  • DE TULLIO P, DELARGE J, PIROTTE B: Therapeutic and chemical developments of cholecystokinin receptor ligands. Exp. Opin. Invest. Drugs (2000) 9:129-146.
  • KENNEDY K, GIGOUX V, ESCRIEUT C et al.: Identification of two amino acids of the human cholecystokinin-A receptor that interact with the N-terminal moiety of cholecystokinin. J. Biol. Chem. (1997) 272:2920-2926.
  • PELLEGRINI M, MIERKE DF: Molecular complex of cholecystokinin-8 and N terminus of the cholecystokinin A receptor by NMR spectroscopy. Biochemistry (1999) 38:14775-14783.
  • CHANG RS, LOTTI VJ, MONAGHAN RL et al.: A potent nonpeptide cholecystokinin antagonist selective for peripheral tissues isolated from Aspergillus alliaceus. Science (1985) 230:177-179.
  • EVANS BE, RITTLE KE, BOCK MG et al.: Design of nonpeptidal ligands for peptide receptor: cholecystokinin antagonists. J. Med. Chem. (1987) 30:1229-1239.
  • EVANS BE, RITTLE KE, BOCK MG et al.: Methods for drug discovery: development of potent, selective orally effective cholecystokinin antagonists. J. Med. Chem. (1988) 31:2235-2246.
  • WOLTMAN TA, HULCE M, REIDELBERGER RD: Relative blood–brain barrier permeabilties of the cholecystokinin receptor antagonists devazepide and A-65186 in rats. J. Pharm. Pharmacol. (1999) 51:917-920.
  • SATOH Y, MATSUO T, SOGABE H et al.: Studies on a novel, potent and orally effective cholecystokinin A antagonist, FK-480. Synthesis and structure–activity relationships of FK-480 and related compounds. Chem. Pharm. Bull. (Tokyo) (1994) 42:2071-2083.
  • EVANS BE, RITTLE KE, CHANG RSL et al.: Multipurpose receptor ligands: β-carboline cholecystokinin antagonists. Bioorg. Med. Chem. Lett. (1993) 3:867-870
  • FLYNN DL, VILLAMIL CI, BECKER DP et al.: 1,3,4-trisubstituted pyrrolidinones as scaffolds for construction of peptidomimetic cholecystokinin antagonists. Bioorg. Med. Chem. Lett. (1992) 2:1251-1256.
  • HOWBERT JJ, LOBB KL, BRITTON TC et al.: Diphenylpyrazolidinone and benzodiazepine cholecystokinin antagonists: a case of convergent evolution in medicinal chemistry. Bioorg. Med. Chem. Lett. (1993) 5:875-880.
  • MCCLURE K, HACK M, HUANG L et al.: Pyrazole CCK1 receptor antagonists. Part 1: solution-phase library synthesis and determination of Free–Wilson additivity. Bioorg. Med. Chem. Lett. (2006) 16:72-76.
  • SEHON C, McCLURE K, HACK M et al.: Pyrazole CCK1 receptor antagonists. Part 2: SAR studies by solid-phase library synthesis and determination of Free–Wilson additivity. Bioorg. Med. Chem. Lett. (2006) 16:77-80.
  • GULLY D, FREHEL D, MARCY C et al.: Peripheral biological activity of SR 27897: a new potent non-peptide antagonist of CCKA receptors. Eur. J. Pharmacol. (1993) 232:13-19.
  • TANIGUCHI H, YAZAKI N, YOMOTA E et al.: Pharmacological profile of T-0632, a novel potent and selective CCKA receptor antagonist, in vivo. Eur. J. Pharmacol. (1996) 312:227-233.
  • VARNAVAS A, LASSIANI L, VALENTA V et al.: Anthranilic acid derivatives: a new class of non-peptide CCK1 receptor antagonists. Bioorg. Med. Chem. (2003) 11:741-751.
  • VARNAVAS A, LASSIANI L, VALENTA V et al.: Antranilic acid based CCK1 antagonists: the 2-indole moiety may represent a “needle” according to the recent homonymous concept. Eur. J. Med. Chem. (2004) 39:85-97.
  • VARNAVAS A, LASSIANI L, VALENTA V et al.: N-terminal anthranoyl-phenylalanine derivatives as CCK1 receptor antagonists: the final approach. Med. Chem. (2005) 1:501-517
  • DE LUCA S, SAVIANO M, LASSIANI L et al.: Anthranilic acid based CCK1 receptor antagonists and CCK8 have a common step in their “receptor desmodynamic processes”. J. Med. Chem. (2006) 49:2456-2462.
  • ROVATI AL, CASULA PL, DA RE G: Pharmacological and experimental toxicology of a new nonanticholinergic product with antisecretory and gastroprotective activity (CR 242, xylamide-Milid). Minerva Med. (1967) 58:3656-3670.
  • HAHNE WF, JENSEN RT, LEMP GF et al.: Proglumide and benzotript: members of a different class of cholecystokinin receptor antagonists. Proc. Natl. Acad. Sci. USA (1981) 78:6304-6308.
  • MATON PN, SUTLIFF VE, JENSEN RT et al.: Carbobenzoxy amino acids: structural requirements for cholecystokinin receptor antagonist activity. Am. J. Physiol. (1985) 248:G479-G484.
  • MAKOVEC F, CHISTE R, BANI M et al.: New glutamic and aspartic derivatives with potent CCK-antagonistic activity. Eur. J. Med. Chem. (1986) 21:9-20.
  • MAKOVEC F, BANI M, CEREDA R et al.: Pharmacological properties of lorglumide as a member of a new class of cholecystokinin antagonists. Arzneimittel-Forsch. (1987) 37:1265-1268.
  • SETNIKAR I, BANI M, CEREDA R et al.: Anticholecystokinin activities of loxiglumide. Arzneimittel-Forsch. (1987) 37:1168-1171.
  • SETNIKAR I, CHISTE R, MAKOVEC F et al.: Pharmacokinetics of loxiglumide after single intravenous or oral doses in man. Arzneimittel-Forsch. (1988) 38:716-720.
  • PERSIANI S, D’AMATO M, MAKOVEC F et al.: Pharmacokinetics of dexloxiglumide after administration of single and repeat oral escalating doses in healthy young males. Int. J. Clin. Pharmacol. Ther. (2002) 40:198-206.
  • KERWIN JF, NADZAN AM, KOPECKA H et al.: Hybrid cholecistokinin (CCK) antagonists: new implications in the design and modification of CCK antagonists. J. Med. Chem. (1989) 32:739-742.
  • FREIDINGER RM, WHITTER WL, GOULD NP et al.: Novel glutamic acid derived cholecystokinin receptor ligands. J. Med. Chem. (1990) 33:591-595.
  • YAMAZI Y, AKAHANE M, KOBAYASHI M et al.: Pharmacological profile of KSG-504, a new cholecystokinin-A-receptor antagonist. Jpn. J. Pharmacol. (1993) 63:219-225.
  • HULL RA, SHANKLEY NP, HARPER EA et al.: 2-Naphthalenesulphonyl-L- aspartyl-(2-phenyl)amide (2-NAP) a selective cholecystokinin CCKA-receptor antagonist. Br. J. Pharmacol. (1993) 108:734-740.
  • AKIYAMA T, TACHIBANA I, HIROHATA Y et al.: Pharmacological profile of TP-680, a new cholecystokinin A receptor antagonist. Br. J. Pharmacol. (1996) 117:1558-1564.
  • TACHIBANA I, KANAGAWA K, YAMAMOTO Y et al.: Pharmacological profile of a new serine derivative cholecystokinin receptor antagonist TP-680 on pancreatic, biliary and gastric function. J. Pharmacol. Exp. Ther. (1996) 279:1404-1412.
  • HORWELL DC, BEEBY A, CLARK CR et al.: Synthesis and binding affinities of analogues of cholecystokinin-(30-33) as probes for CNS cholecystokinin receptors. J. Med. Chem. (1987) 30:729-732.
  • HORWELL DC, BIRCHMORE B, BODEN PR et al.: α-Methyl tryptophanylphenylalanines and their arylethylamine ‘‘dipeptoid’’ analogues of the tetrapeptide cholecystokinin (30-33). Eur. J. Med. Chem. (1990) 25:53-60.
  • HORWELL DC, HUGHES J, HUNTER JC et al.: Rationally designed ‘‘dipeptoid’’ analogues of CCK. α-Methyltryptophan derivatives as highly selective and orally active gastrin and CCKB antagonists with potent anxiolytic properties. J. Med. Chem. (1991) 34:404-414.
  • BODEN PR, HIGGINBOTTOM M, HILL DR et al.: Cholecystokinin dipeptoid antagonists: design, synthesis, and anxiolytic profile of some novel CCKA and CCKB selective and ‘‘mixed’’ CCKA/CCKB antagonists. J. Med. Chem. (1993) 36:552-565.
  • MARTÍN-MARTÍNEZ M, DE LA FIGUERA N, LATORRE M et al.: β-Turned dipeptoids as potent and selective CCK1 receptor antagonists. J. Med. Chem. (2000) 43:3770-3777.
  • MARTÍN-MARTÍNEZ M, DE LA FIGUERA N, LATORRE M et al.: Conformationally constrained CCK4 analogues incorporating IBTM and BTD β-turn mimetics. J. Med. Chem. (2005) 48:7667-7674.
  • GONZÁLEZ-MUÑIZ R, DOMÍNGUEZ MJ, MARTÍN-MARTÍNEZ M et al.: CCK4 restricted analogues containing a 3-oxoindolizidine skeleton. Bioorg. Med. Chem. Lett. (1996) 6:967-972.
  • MARTÍN-MARTÍNEZ M, BARTOLOMÉ-NEBREDA JM, GÓMEZ-MONTERREY I et al.: Synthesis and stereochemical structure–activity relationships of 1,3-dioxoperhydropyrido[1,2-c]-pyrimidine derivatives: potent and selective cholecystokinin-A receptor antagonists. J. Med. Chem. (1997) 40:3402-3407.
  • BALLAZ S, BARBER A, FORTUÑO A et al.: Pharmacological evaluation of IQM-95,333, a highly selective CCKA receptor antagonist with anxiolytic-like activity in animal models. Br. J. Pharmacol. (1997) 121:759-767.
  • BARTOLOMÉ-NEBREDA JM, GÓMEZ-MONTERREY I, GARCÍA-LÓPEZ MT et al.: 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-based potent and selective CCK1 receptor antagonists: structural modifications at the tryptophan domain. J. Med. Chem. (1999) 42:4659-4668.
  • BARTOLOMÉ-NEBREDA JM, PATIÑO-MOLINA R, MARTÍN-MARTÍNEZ M et al.: 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-based potent and selective CCK1 receptor antagonists: structure–activity relationship studies on the substituent at N2-position. J. Med. Chem. (2001) 44:2219-2228.
  • BARTOLOMÉ-NEBREDA JM, GARCÍA-LÓPEZ MT, GONZÁLEZ-MUÑIZ R et al.: 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-based potent and selective CCK1 receptor antagonists: structure–activity relationship studies on the central 1,3-dioxoperhydropyrido- [1,2-c]pyrimidine scaffold. J. Med. Chem. (2001) 44:4196-4206.
  • MARTÍN-MARTÍNEZ M, MARTY A, JOURDAN M et al.: Combination of molecular modeling, site-directed mutagenesis, and SAR studies to delineate the binding site of pyridopyrimidine antagonists on the human CCK1 receptor. J. Med. Chem. (2005) 48:4842-4850.
  • KONTUREK JW, KONTUREK SJ, AKUREK AR et al.: CCK receptor antagonism by loxiglumide and gallbladder contractions response to cholecystokinin, sham feeding and ordinary feeding in man. Gut (1989) 30:1136-1142.
  • MASELLI MA, PIEPOLI AL, PEZZOLLA F et al.: Effect of three nonpeptide cholecystokinin antagonists on human isolated gallbladder. Dig. Dis. Sci. (2001) 46:2773-2778.
  • XU QW, LE MANTLE M, PAULETZKI JG et al.: Sustained gallbladder stasis promotes cholesterol gallstone formation in the ground squirrel. Hepatology (1997) 26:831-836.
  • SATO N, MIYASAKA K, SUZUKI S et al.: Lack of cholecystokinin-A receptor enhanced gallstone formation: a study in CCKA receptor gene knockout mice. Dig. Dis. Sci. (2003) 48:1944-1947.
  • KERSTENS PJ, LAMERS CB, JANSEN JB et al.: Physiological plasma concentrations of cholecystokinin stimulate pancreatic enzyme secretion and gallbladder contraction in man. Life Sci. (1985) 36:565-569.
  • WILLIAMS JA.: Intracellular signaling mechanisms activated by cholecystokinin-regulating synthesis and secretion of digestive enzymes in pancreatic acinar cells. Annu. Rev. Physiol. (2001) 63:77-97.
  • OWYANG C, LOGSDON CD: New insights into neurohormonal regulation of pancreatic secretion. Gastroenterology (2004) 127:957-969.
  • REHFELD JF: Cholecystokinin. Best Practice & Research Clin. Endocrinol. & Metabolism (2004) 18:569-586.
  • D’AMATO M, MAKOVEC F, ROVATI LC: Potential clinical applications of CCKA receptor antagonists in gastroenterology. DN&P (1994) 7:87-95.
  • HOLLOWAY RH, PENAGINI R, IRELAND AC: Criteria for objective definition of transient lower esophageal sphincter relaxation. Am. J. Physiol. (1995) 268:G128-G138.
  • WYMAN JB, DENT J, HEDDLE R et al.: Control of belching by the lower oesophageal sphincter. Gut (1990) 31:639-646.
  • MITTAL RK, HOLLOWAY RH, PENAGINI R et al.: Transient lower esophageal sphincter relaxation. Gastroenterology (1995) 109:601-61010.
  • BOECKXSTAENS GE, HIRSCH DP, FAKHRY N et al.: Involvement of cholecystokinin A receptors in transient lower esophageal sphincter relaxations triggered by gastric distension. Am. J. Gastroenterol. (1998) 93:182-1828.
  • PARKMAN HP, HASLER WL, FISHER RS: American gastroenterological association technical review on the diagnosis and treatment of gastroparesis. Gastroenterology (2004) 127:1592-1622.
  • TALLEY NJ, VAKIL NB, MOAYYEDI P: American gastroenterological association technical review on the evaluation of dyspepsia. Gastroenterology (2005) 129:1756-1780.
  • STACHER G, LENGLINGER J, BERGMANN H et al.: Gastric emptying: a contributory factor in gastro-oesophageal reflux activity? Gut (2000) 47:661-666.
  • CHOWDHURY RS, FORSMARK CE, DAVIS RH et al.: Prevalence of gastroparesis in patients with small duct chronic pancreatitis. Pancreas (2003) 26:235-238.
  • SARNELLI G, CAENEPEEL P, GEYPENS B et al.: Symptoms associated with impaired gastric emptying of solids and liquids in functional dyspepsia. Am. J. Gastroenterol. (2003) 98:783-788.
  • LEMANN M, DEDERDING JP, FLOURIE B et al.: Abnormal perception of visceral pain in response to gastric distension in chronic idiopathic dyspepsia. Dig. Dis. Sci. (1991) 36:1249-1254.
  • HOLTMANN G: IBS: a syndrome or many diseases? Best Pract. Res. Cl. Ga. (2004) 18:91-97.
  • GILKIN RJ Jr: The spectrum of irritable bowel syndrome: a clinical review. Clin. Ther. (2005) 27:1696-1709.
  • WOODS SC: Signals that influence food intake and body weight. Physiol. Behav. (2005) 86:709-716.
  • STRADER AD, WOODS SC: Gastrointestinal hormones and food intake. Gastroenterology (2005) 128:175-191.
  • BEGLINGER C, DEGEN L, MATZINGER D et al.: Loxiglumide, a CCKA receptor antagonist, stimulates calorie intake and hunger feelings in humans. Am. J. Physiol. (2001) 280:R1149-R1154.
  • KATSCHINSKI M: Drug evaluations: loxiglumide. rotta research. IDrugs (2002) 5:469-474.
  • VARGA G: Dexloxiglumide (Rotta Research Lab). Curr. Opin. Investig. Drugs (2002) 3:621-626.
  • LEE YS, AGNES RS, BADGHISI H et al.: Design and synthesis of novel hydrazide-linked bifunctional peptides as δμ opioid receptor agonists and CCK-1/CCK-2 receptor antagonists. J. Med. Chem. (2006) 49:1773-1780.
  • AGNES RS, LEE YS, DAVIS P et al.: Structure–activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors. J. Med. Chem. (2006) 49:2868-2875.

Patents

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.