Biomaterial Database

Cholecystokinin (pancreozymin). 3. Synthesis and properties of an analogue of the C-terminal heptapeptide with serine sulfate replacing tyrosine sulfate. 1977

M Bodanszky, and S Natarajan, and W Hahne, and J D Gardner

The influence of tyrosine O-sulfate, the 27th residue in the sequence of cholecystokinin (pancreozymin) (CCK-PZ) on calcium outflux in isolated pancreatic cells of guinea pigs, was studied by replacing this residue in the biologically active C-terminal heptapeptide, CCK-PZ-(27--33) (I), with L-serine O-sulfate. The synthetic analogue Ser(SO3H)-Met-Gly-Trp-Met-Asp-Phe-NH2 (IV), produced the half-maximal outflux observed with I, if applied at about 250 times higher concentration. The unsulfated form of IV was about ten times less potent than unsulfated I. Thus, in the effect on the calcium outflux, serince cannot replace tyrosine without a major loss in potency; a sulfate ester group in position 27 is important but in itself not sufficient for full potency. Interestingly, if the terminal amino group of the heptapeptide is left protected by a tert-butyloxycarbonyl group, the potencies of the derivatives of both I and IV were slightly, but significantly, higher than those of the free peptides.

UI	MeSH Term	Description	Entries
D009842	Oligopeptides	Peptides composed of between two and twelve amino acids.	Oligopeptide
D010179	Pancreas	A nodular organ in the ABDOMEN that contains a mixture of ENDOCRINE GLANDS and EXOCRINE GLANDS. The small endocrine portion consists of the ISLETS OF LANGERHANS secreting a number of hormones into the blood stream. The large exocrine portion (EXOCRINE PANCREAS) is a compound acinar gland that secretes several digestive enzymes into the pancreatic ductal system that empties into the DUODENUM.
D002118	Calcium	A basic element found in nearly all tissues. It is a member of the alkaline earth family of metals with the atomic symbol Ca, atomic number 20, and atomic weight 40. Calcium is the most abundant mineral in the body and combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes.	Coagulation Factor IV,Factor IV,Blood Coagulation Factor IV,Calcium-40,Calcium 40,Factor IV, Coagulation
D002132	Calcium Radioisotopes	Unstable isotopes of calcium that decay or disintegrate emitting radiation. Ca atoms with atomic weights 39, 41, 45, 47, 49, and 50 are radioactive calcium isotopes.	Radioisotopes, Calcium
D002766	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.	Pancreozymin,CCK-33,Cholecystokinin 33,Uropancreozymin
D006168	Guinea Pigs	A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research.	Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D012694	Serine	A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.	L-Serine,L Serine
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014443	Tyrosine	A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.	L-Tyrosine,Tyrosine, L-isomer,para-Tyrosine,L Tyrosine,Tyrosine, L isomer,para Tyrosine