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Merck
CN

C4801

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:
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

Key Documents

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Product Name

Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr[Bzl]), ≥95% (HPLC), powder

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

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 key

YHVHQZYJGWGAKN-ZUWUZHNASA-N

assay

≥95% (HPLC)

form

powder

color

white

solubility

H2O: 1 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Gene Information

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

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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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000331469
0000331469
SLCQ6437
SLCH8129
SLCG1726

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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
J Chuang et al.
Pflugers Archiv : European journal of physiology, 415(5), 606-610 (1990-02-01)
The changes in thermoregulatory effectors produced by an injection of polyriboinosinic acid: polyribocytidylic acid (Poly I:C) or interferon were assessed and compared in control rats, in rats with hypothalamic somatostatin (SS) receptor blockade and in rats with hypothalamic SS depletion.
S Pieretti et al.
Life sciences, 54(15), 1091-1099 (1994-01-01)
The effects were investigated of cysteamine--a well known somatostatin depletor--on the pain induced by chemical stimuli in mice. Cysteamine injected intraperitoneally 4 h before the test at doses of 50 and 100 mg/kg reduced the second phase of the licking
U Smedh et al.
Neuroscience letters, 260(1), 41-44 (1999-02-23)
Corticotropin-releasing factor (CRF) acts centrally to suppress gastric emptying and increase plasma levels of somatostatin in rats. The experiments were conducted to examine whether cyclo(7-aminoheptanoyl-phe-D-TRP-LYS-THR[BZL]), which acts as a somatostatin antagonist in vivo, blocks the effect of CRF on gastric
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