15-28-Somatostatin-28 Property

Melting point:

>211°C (dec.)

Boiling point:

1970.9±65.0 °C(Predicted)

Density 

1.43±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

H₂O: 1 mg/mL

form 

powder

pka

2.94±0.70(Predicted)

color 

White to Off-White

Water Solubility 

Soluble in water(25,00°C 1,00 g/L), Methanol.

Merck 

13,8788

BRN 

6436064

Sequence

Ala-Gly-c[Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys]-OH,(Disulfide bridge: Cys-Cys)

InChI

InChI=1/C76H104N18O19S2/c1-41(79)64(100)82-37-61(99)83-58-39-114-115-40-59(76(112)113)92-72(108)57(38-95)91-75(111)63(43(3)97)94-71(107)54(33-46-23-11-6-12-24-46)90-74(110)62(42(2)96)93-66(102)51(28-16-18-30-78)84-69(105)55(34-47-36-81-49-26-14-13-25-48(47)49)88-68(104)53(32-45-21-9-5-10-22-45)86-67(103)52(31-44-19-7-4-8-20-44)87-70(106)56(35-60(80)98)89-65(101)50(85-73(58)109)27-15-17-29-77/h4-14,19-26,36,41-43,50-59,62-63,81,95-97H,15-18,27-35,37-40,77-79H2,1-3H3,(H2,80,98)(H,82,100)(H,83,99)(H,84,105)(H,85,109)(H,86,103)(H,87,106)(H,88,104)(H,89,101)(H,90,110)(H,91,111)(H,92,108)(H,93,102)(H,94,107)(H,112,113)/t41-,42+,43+,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,62-,63-/s3

InChIKey

NHXLMOGPVYXJNR-ATOGVRKGSA-N

SMILES

C12C=CC=CC=1NC=C2C[C@H]1C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@H](C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](N)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC2C=CC=CC=2)C(=O)N[C@@H](CC2C=CC=CC=2)C(=O)N1)C(=O)O)CC1C=CC=CC=1 |&1:10,14,23,24,30,34,35,41,47,52,60,66,75,83,94,r|

Safety

WGK Germany 

3

RTECS 

WF8751700

F 

3-10-21

Hazard and Precautionary Statements (GHS)

15-28-Somatostatin-28 Chemical Properties,Usage,Production

Chemical Properties

White Powder

Uses

Growth hormone-release inhibiting factor; treatment of severe, acute hemorrhage of gastroduodenal ulcers; experimental antidiabetic.

Definition

ChEBI: A fourteen-membered heterodetic cyclic peptide comprising the sequence Ala-Gly-Cys-Lys-Asn-Phe-Phe-Trp-Lys-Thr-Phe-Thr-Ser-Cys cyclised by a disulfide bridge between the two Cys residues at positions 3 and 14.

Biological Functions

Somatostatin is a cyclic 14-peptide that was first isolated by Guillemin in 1973 and is probably the most thoroughly investigated and most important of the inhibitory factors produced by the hypothalamus. The principal activity of somatostatin, which is of hypothalamic origin, is inhibition of the release of growth hormone (GH) from the anterior pituitary. Too much GH, as in pituitary tumors, causes acromegaly, a form of giantism. On the other hand, too little GH leads to dwarfism. Somatostatin also has been found in the pancreas and the GI tract, where it inhibits the secretion of both insulin and glucagon from the pancreas as well as the secretion of a variety of intestinal peptides (e.g., gastrin, secretin, pepsin, and renin). The short half-life of somatostatin, which is less than 3 minutes, has precluded its use as a therapeutic agent. Many derivatives of somatostatin have been prepared to increase its duration of action and/or to enhance its selectivity of action. The culmination of these structure–activity studies was the development of octreotide acetate.

General Description

Somatostatin (SST) is a peptide.

Biochem/physiol Actions

Somatostatin regulates the secretion of hormones and bioactive peptides. It acts as an inhibitor in the digestive tract by inhibiting gastrin release. In the pancreatic islets, it inhibits glucagon and insulin release. Somatostatin and its synthetic analogs have been used in the treatment of neuroendocrine tumors.

Purification Methods

Somatostatin is a tetradecapeptide which is purified by gel filtration on Sephadex G-25, eluting with 2N AcOH, and then by liquid partition chromatography on Sephadex G-25 using n-BuOH/AcOH/H2O (4:1:5) and has RF = 0.4. It is a brain growth hormone releasing-inhibiting factor which has also been synthesised. [Burgus et al. Proc Natl Acad Sci USA 70 684 1973, Sorantakis & McKinley Biochem Biophys Res Commun 54 234 1973, Hartridt et al. Pharmazie 37 403 1982.]