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Key Documents

C4801

Sigma-Aldrich

Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl])

≥95% (HPLC), powder

Synonym(s):

Cyclosomatostatin

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About This Item

Empirical Formula (Hill Notation):
C44H57N7O6
CAS Number:
Molecular Weight:
779.97
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

Quality Level

Assay

≥95% (HPLC)

form

powder

color

white

solubility

H2O: 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

O=C(N[C@H](C(N[C@@]1([H])[C@@H](C)OCC2=CC=CC=C2)=O)CCCCN)[C@H](NC([C@@H](NC(CCCCCCNC1=O)=O)CC3=CC=CC=C3)=O)CC4=CNC5=C4C=CC=C5

InChI

1S/C44H57N7O6/c1-30(57-29-32-18-8-5-9-19-32)40-44(56)46-25-15-3-2-10-23-39(52)48-37(26-31-16-6-4-7-17-31)42(54)50-38(27-33-28-47-35-21-12-11-20-34(33)35)43(55)49-36(41(53)51-40)22-13-14-24-45/h4-9,11-12,16-21,28,30,36-38,40,47H,2-3,10,13-15,22-27,29,45H2,1H3,(H,46,56)(H,48,52)(H,49,55)(H,50,54)(H,51,53)/t30-,36+,37+,38-,40+/m1/s1

InChI key

YHVHQZYJGWGAKN-ZUWUZHNASA-N

Gene Information

human ... SST(6750)
mouse ... SST(20604)
rat ... SST(24797)

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Amino Acid Sequence

cyclo-Phe-Trp-Lys-Thr-Bzl

Application

Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]) has been used as a somatostatin antagonist to study its effects on sleep in rats to infer the role of endogenous somatostatin in the physiologic modulation of REM sleep (REMS) , as an somatostatin (SST) antagonist to study its effects on elemental-induced intestinal atrophy in rats , as an SST receptor antagonist to eliminate the effect of somatostatin on catecholamine .

Biochem/physiol Actions

Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]) (cSSTA) is a cyclic somatostatin (SST) analog and is a somatostatin receptor antagonist. It is involved in blocking the effect of somatostatin, such as airway β-adrenergic function and regulation of acetylcholine release. cSSTA is also involved in blocking the effect of somatostatin of hormone release and corticotropin-releasing factor-induced suppression of gastric emptying.
Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]), also known as cyclosomatostatin. Inhibition of somatostatin receptors by cyclosomatostatin induces catalepsy in rats.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Quanfeng Zhang et al.
Neuron, 102(1), 173-183 (2019-02-19)
Co-release of multiple neurotransmitters from secretory vesicles is common in neurons and neuroendocrine cells. However, whether and how the transmitters co-released from a single vesicle are differentially regulated remains unknown. In matrix-containing dense-core vesicles (DCVs) in chromaffin cells, there are
Jörg Stirnweis et al.
Peptides, 23(8), 1503-1506 (2002-08-17)
The cyclic somatostatin (SST) analogue, cyclo-(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[BZL]) (cSSTA), has been widely used as somatostatin antagonist. In the human neuroblastoma cell line SH-SY5Y the cyclopeptide acts as a somatostatin receptor agonist. Similar to SST, cSSTA inhibits cell proliferation, activates the protein tyrosine
Somatostatin antagonism prevents elemental diet-induced intestinal atrophy in the rat
De Segura IA G, et al.
Digestive Diseases and Sciences, 46(9) (2001)
Z Monnier et al.
Experientia, 51(8), 824-830 (1995-08-16)
Isolated snail gonadal cells were cultured in the presence of synthetic neuropeptides in order to determine the subsequent effect of these substances on gonadal synthetic activities. Gonadal cells were incubated for 24 h in concentrations of methionine-enkephalin, somatostatin and insulin
Kevin Vivot et al.
Molecular metabolism, 5(10), 988-996 (2016-10-01)
G protein-coupled receptor (GPCR) signaling regulates insulin secretion and pancreatic β cell-proliferation. While much knowledge has been gained regarding how GPCRs are activated in β cells, less is known about the mechanisms controlling their deactivation. In many cell types, termination

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