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C4801

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

Name: Cyclo(7-aminoheptanoyl-Phe-<SC>D</SC>-Trp-Lys-Thr[Bzl])
Brand: SIGMA

≥95% (HPLC), powder

Synonym(s):

Cyclosomatostatin

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About This Item

Empirical Formula (Hill Notation):

C₄₄H₅₇N₇O₆

CAS Number:

84211-54-1

Molecular Weight:

779.97

NACRES:

NA.32

PubChem Substance ID:

24892727

UNSPSC Code:

12352200

MDL number:

MFCD00076778

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

200

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Quality Level

200

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)

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]), also known as cyclosomatostatin. Inhibition of somatostatin receptors by cyclosomatostatin induces catalepsy in rats.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Evidence that endogenous somatostatin (SRIF) exerts an inhibitory control on the function and growth of rat adrenal zona glomerulosa. The possible involvement of zona medullaris as a source of endogenous SRIF.

P Rebuffat et al.

The Journal of steroid biochemistry and molecular biology, 48(4), 353-360 (1994-03-01)

The effect of SRIF and its antagonist cyclo(7-aminoheptanonyl-Phe-D-Trp-Lys-Thr magnitude of Bzl)(SRIF-A) were studied in sham-operated and bilaterally adrenalectomized rats bearing ACTH- and angiotensin II (ANG-II)-responsive adrenocortical autotransplants. SRIF-A (10(-5) M) completely annulled SRIF (10(-6) M)-induced inhibition of ANG-II (10(-8) M)-evoked

Cholecystokinin type A receptors mediate intestinal fat-induced inhibition of acid secretion through somatostatin-14 in dogs.

L Fung et al.

Endocrinology, 134(6), 2376-2382 (1994-06-01)

This study was designed to examine whether one or both principle molecular forms of somatostatin (SLI), somatostatin-28 (S-28) and somatostatin-14 (S-14), mediate inhibition of stimulated gastric acid by intestinal fat and to determine whether the mode of action includes activation

The putative somatostatin antagonist, cyclo-(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[BZL]), may act as potent antiproliferative agonist.

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

Differential Co-release of Two Neurotransmitters from a Vesicle Fusion Pore in Mammalian Adrenal Chromaffin Cells.

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

Somatostatin antagonist analog increases GH, insulin, and glucagon release in the rat.

J L Fries et al.

Peptides, 3(5), 811-814 (1982-09-01)

We have utilized the relative structural simplicity of several short, cyclic, highly active somatostatin analogs in the search for competitive antagonists of somatostatin. During an attempted synthesis of cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr), catalytic hydrogenation of the protected peptide intermediate unexpectedly gave cyclo [7-aminoheptanoyl-Phe-D-Trp-Lys-Thr(Bzl)]

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Global Trade Item Number

SKU	GTIN
C4801-1MG	04061826152577

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