Compounds > cholecystokinin (27-33), tert-butyloxycarbonyl-nle(28,31)-
Page last updated: 2024-12-10

cholecystokinin (27-33), tert-butyloxycarbonyl-nle(28,31)-

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Description

cholecystokinin (27-33), tert-butyloxycarbonyl-Nle(28,31)-: cholecystokinin agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3086453
CHEMBL ID384035
MeSH IDM0137671

Synonyms (17)

Synonym
cholecystokinin (27-33), tert-butyloxycarbonyl-nle(28,31)-
CHEMBL384035 ,
(s)-3-{(s)-2-[(s)-2-(2-{(s)-2-[(s)-2-tert-butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1h-indol-3-yl)-propionylamino]-hexanoylamino}-n-((s)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid
3-{2-[2-(2-{2-[2-tert-butoxycarbonylamino-3-(4-sulfooxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1h-indol-3-yl)-propionylamino]-hexanoylamino}-n-(1-carbamoyl-2-phenyl-ethyl)-succinamic acid
bdbm50016425
3-{2-[2-(2-{2-[2-(tert-butoxycarbonyl-methyl-amino)-3-(4-sulfonyl-oxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1h-indol-3-yl)-propionylamino]-hexanoylamino}-n-(1-carbamoyl-2-phenyl-ethyl)-succinamic acid
boc-tyr(so3h)-nle-gly-trp-nle-asp-phe-nh2
l-phenylalaninamide, n-((1,1-dimethylethoxy)carbonyl)-o-sulfo-l-tyrosyl-l-norleucylglycyl-l-tryptophyl-l-norleucyl-l-alpha-aspartyl-
cholecystokinin (27-33), tert-butyloxycarbonylnorleucyl(28,31)-
98640-66-5
tert-butyloxycarbonyl-28,31-nle-cholecystokinin (27-33)
boc-tyr(so3h)nle-gly-trp-nle-asp-phenh2
boc-28,31-nle-cck-7
t-boc(nle(28,31))-cck (27-33)
tert-butoxycarbonyltyrosyl(sulfo)-norleucyl-glycyl-tryptophyl-norleucyl-aspartyl-phenylalaninamide
DTXSID90243747
PD184215

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"Lys-Trp-Nle-Asp-Phe-NH2) was ineffective to modify the self-stimulation behaviour when administered alone while a 150 pmol BC-197 dosage was able to antagonize the decreasing effect of 150 pmol CCK-8 on ICSS."( Similar potencies of CCK-8 and its analogue BOC(Nle28;Nle31)CCK27-33 on the self-stimulation behaviour both are antagonized by a newly synthesized cyclic CCK analogue.
De Witte, P; Heidbreder, C; Roques, BP, )		0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cholecystokinin receptor type ARattus norvegicus (Norway rat)IC50 (µMol)0.00150.00000.43624.3000AID52409
Gastrin/cholecystokinin type B receptorRattus norvegicus (Norway rat)IC50 (µMol)0.00190.00010.24801.4000AID51450; AID52409
Gastrin/cholecystokinin type B receptorHomo sapiens (human)IC50 (µMol)0.00020.00010.36154.0000AID50822; AID50971
Cholecystokinin receptor type ACavia porcellus (domestic guinea pig)IC50 (µMol)0.00090.00041.13803.5000AID52566
Cholecystokinin receptor type ACavia porcellus (domestic guinea pig)Ki0.00090.00030.13770.6310AID52252
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Pancreatic alpha-amylaseHomo sapiens (human)EC50 (µMol)0.00000.00000.00000.0000AID38533
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
carbohydrate catabolic processPancreatic alpha-amylaseHomo sapiens (human)
polysaccharide digestionPancreatic alpha-amylaseHomo sapiens (human)
carbohydrate metabolic processPancreatic alpha-amylaseHomo sapiens (human)
gastric acid secretionGastrin/cholecystokinin type B receptorHomo sapiens (human)
cell surface receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationGastrin/cholecystokinin type B receptorHomo sapiens (human)
positive regulation of cell population proliferationGastrin/cholecystokinin type B receptorHomo sapiens (human)
cholecystokinin signaling pathwayGastrin/cholecystokinin type B receptorHomo sapiens (human)
pH reductionGastrin/cholecystokinin type B receptorHomo sapiens (human)
digestive tract developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
gland developmentGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
alpha-amylase activityPancreatic alpha-amylaseHomo sapiens (human)
calcium ion bindingPancreatic alpha-amylaseHomo sapiens (human)
chloride ion bindingPancreatic alpha-amylaseHomo sapiens (human)
cholecystokinin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
protein bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
gastrin receptor activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
peptide hormone bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
type B gastrin/cholecystokinin receptor bindingGastrin/cholecystokinin type B receptorHomo sapiens (human)
1-phosphatidylinositol-3-kinase regulator activityGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
extracellular regionPancreatic alpha-amylaseHomo sapiens (human)
extracellular spacePancreatic alpha-amylaseHomo sapiens (human)
extracellular exosomePancreatic alpha-amylaseHomo sapiens (human)
extracellular spacePancreatic alpha-amylaseHomo sapiens (human)
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
intracellular membrane-bounded organelleGastrin/cholecystokinin type B receptorHomo sapiens (human)
plasma membraneGastrin/cholecystokinin type B receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID175694Evaluated for agonist activity measured as amylase secretion by rat pancreas1987Journal of medicinal chemistry, Jun, Volume: 30, Issue:6
Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogues of CCK26-33: synthesis and biological properties.
AID175324Ability of compound to stimulate in vitro amylase release from rat pancreatic acini1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and biological activity of some partially modified retro-inverso analogues of cholecystokinin.
AID75932Agonist activity by measuring the effect on amylase secretion from guinea pig acini.1988Journal of medicinal chemistry, May, Volume: 31, Issue:5
Synthesis and biological activity of CCK26-33-related analogues modified in position 31.
AID52409Ability of compound to Inhibit the binding of [125I]BH-CCK-8 to Cholecystokinin receptor in isolated rat pancreatic acini1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and biological activity of some partially modified retro-inverso analogues of cholecystokinin.
AID52411Evaluated for binding affinity measured by inhibiting [3H]Boc[Nle28,31]CCK27-33 specific binding to Cholecystokinin receptor in rat pancreas membranes at a KD concentration of 4.4 nM1987Journal of medicinal chemistry, Jun, Volume: 30, Issue:6
Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogues of CCK26-33: synthesis and biological properties.
AID52274Ability of compound to Inhibit the binding of [125I]BH-CCK-8 to Cholecystokinin receptor in isolated guinea pig brain membranes1989Journal of medicinal chemistry, Oct, Volume: 32, Issue:10
Synthesis and biological activity of some partially modified retro-inverso analogues of cholecystokinin.
AID77909Potency in displacing [3H]Boc(Nle28,Nle31)-CCk27-33 from guinea pig pancreatic acini.1988Journal of medicinal chemistry, May, Volume: 31, Issue:5
Synthesis and biological activity of CCK26-33-related analogues modified in position 31.
AID50946Displacement of 0.2 nM [3H]pCCK-8 from guinea pig brain membranes1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Synthesis and binding affinities of cyclic and related linear analogues of CCK8 selective for central receptors.
AID52406Binding affinity measured by inhibiting [3H]Boc[Nle28,31]CCK27-33 specific binding to Cholecystokinin receptor in mouse brain membranes at a KD concentration of 0.19 nM1987Journal of medicinal chemistry, Jun, Volume: 30, Issue:6
Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogues of CCK26-33: synthesis and biological properties.
AID50971Inhibition of [125I]BH-CCK- binding to cholecystokinin type B receptor from jurkat Tcells1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Synthesis and biological evaluation of cholecystokinin analogs in which the Asp-Phe-NH2 moiety has been replaced by a 3-amino-7-phenylheptanoic acid or a 3-amino-6-(phenyloxy)hexanoic acid.
AID134214Potency in displacing [3H]propionyl-CCK-8 from mouse brain membranes.1988Journal of medicinal chemistry, May, Volume: 31, Issue:5
Synthesis and biological activity of CCK26-33-related analogues modified in position 31.
AID75931Agonist activity by measuring the ability to stimulate the contraction of the isolated guinea pig ileum.1988Journal of medicinal chemistry, May, Volume: 31, Issue:5
Synthesis and biological activity of CCK26-33-related analogues modified in position 31.
AID52252Displacement of 0.1 nM [3H]pCCK-8 from guinea pig pancreatic membranes1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Synthesis and binding affinities of cyclic and related linear analogues of CCK8 selective for central receptors.
AID38533Tested in vitro for amylase release from rat pancreatic acini1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Synthesis and biological evaluation of cholecystokinin analogs in which the Asp-Phe-NH2 moiety has been replaced by a 3-amino-7-phenylheptanoic acid or a 3-amino-6-(phenyloxy)hexanoic acid.
AID51450Inhibition of [125I]BH-CCK- binding to peripheral cholecystokinin type B receptor from rat pancreatic acini1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Synthesis and biological evaluation of cholecystokinin analogs in which the Asp-Phe-NH2 moiety has been replaced by a 3-amino-7-phenylheptanoic acid or a 3-amino-6-(phenyloxy)hexanoic acid.
AID223181Evaluated for contractile activities of guinea pig ileum for agonistic activity1987Journal of medicinal chemistry, Jun, Volume: 30, Issue:6
Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogues of CCK26-33: synthesis and biological properties.
AID50822Inhibition of [125I]BH-CCK- binding to cholecystokinin type B receptor from guinea pig brain membranes1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Synthesis and biological evaluation of cholecystokinin analogs in which the Asp-Phe-NH2 moiety has been replaced by a 3-amino-7-phenylheptanoic acid or a 3-amino-6-(phenyloxy)hexanoic acid.
AID52566In vitro ability to inhibit [3H]propionyl-CCK-8 binding to Cholecystokinin type A receptor in guinea pig pancreas1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Tetrapeptide CCK-A agonists: effect of backbone N-methylations on in vitro and in vivo CCK activity.
AID52255Relative affinity for guinea pig membranes of pancreas and brain1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Synthesis and binding affinities of cyclic and related linear analogues of CCK8 selective for central receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (46.15)18.7374
1990's7 (53.85)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.77

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.77 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.3920amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
rb 101
RB 101: structure given in first source; inhibits enkephalinase and aminopeptidases; biologically cleaved at disulfide to produce inhibitors of both aminopeptidase N and neutral endopeptidase		2.3920
tyrosyl-seryl(o-t-butyl)-glycyl-phenylalanyl-leucyl-threonine(o-t-butyl)
tyrosyl-seryl(O-t-butyl)-glycyl-phenylalanyl-leucyl-threonine(O-t-butyl): RN given refers to L-Thr-L-Tyr-D-Ser-Gly-L-Phe-L-Leu cpd; RN for cpd without isomeric designation not available 3/90		2.3920
cholecystokinin 9
cholecystokinin 9: nonapeptide		1.9710
devazepide
Devazepide: A derivative of benzodiazepine that acts on the cholecystokinin A (CCKA) receptor to antagonize CCK-8's (SINCALIDE) physiological and behavioral effects, such as pancreatic stimulation and inhibition of feeding.. devazepide : An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders.		2.67301,4-benzodiazepinone;
indolecarboxamide		antineoplastic agent;
apoptosis inducer;
cholecystokinin antagonist;
gastrointestinal drug
tetragastrin
Tetragastrin: L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamide. The C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin.. tetragastrin : A tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence.		1.9810peptidyl amide;
tetrapeptide		anxiogenic;
human metabolite
enkephalin, leucine
Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.		2.3920pentapeptide;
peptide zwitterion		analgesic;
delta-opioid receptor agonist;
human metabolite;
mu-opioid receptor agonist;
neurotransmitter;
rat metabolite
naloxone
Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.		2.3920morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist
bc 264
BC 264: a selective CCK-B agonist; do not confuse with pBC 264 (propionyl-BC 264)		2.6730
l 365260
L 365260: a CCK-B antagonist; structure given in first source; potent & selective CCK-B & gastrin receptor ligand; L 365260 and L 365346 are (R)- and (S)-stereoisomers, respectively		2.3820benzodiazepine
naltrexone
Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.		1.9810cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic
enkephalin, ala(2)-mephe(4)-gly(5)-
Enkephalin, Ala(2)-MePhe(4)-Gly(5)-: An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.		2.3920
naltrindole
naltrindole: delta opioid receptor antagonist		1.9810isoquinolines
sincalide
Sincalide: An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.		3.68100oligopeptide
cholecystokinin
Cholecystokinin: A peptide, of about 33 amino acids, secreted by the upper INTESTINAL MUCOSA and also found in the central nervous system. It causes gallbladder contraction, release of pancreatic exocrine (or digestive) enzymes, and affects other gastrointestinal functions. Cholecystokinin may be the mediator of satiety.		3.2360
ConditionIndicatedRelationship StrengthStudiesTrials
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.3720
Ache
[description not available]		02.3820
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		02.3820
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9910