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C2175

Sigma-Aldrich

(Tyr[SO3H]27)Cholecystokinin fragment 26-33 Amide

≥97% (HPLC), powder

Synonym(s):
CCK-8, Cholecystokinin octapeptide, Pancreozymin C-terminal octapeptide, Sincalide
Empirical Formula (Hill Notation):
C49H62N10O16S3
CAS Number:
Molecular Weight:
1143.27
Beilstein:
5231801
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥97% (HPLC)

form

powder

UniProt accession no.

storage temp.

−20°C

SMILES string

CSCC[C@H](NC(=O)[C@H](Cc1ccc(OS(O)(=O)=O)cc1)NC(=O)[C@@H](N)CC(O)=O)C(=O)NCC(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)NC(CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](Cc4ccccc4)C(N)=O

InChI

1S/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35?,36-,37-,38-,39-/m0/s1

InChI key

IZTQOLKUZKXIRV-IVVJSLGPSA-N

Gene Information

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Amino Acid Sequence

Asp-Tyr-Met-Gly-Trp-Met-Asp-Phe-NH2

General description

(Tyr[SO3H]27)Cholecystokinin fragment 26-33 amide is a sulfated cholecystokinin(CCK) octapeptide[94] derived from the proCCK.[88] It is present in plasma and endocrine cells.[88]

Application

(Tyr[SO3H]27)Cholecystokinin fragment 26-33 amide has been used to test its effects:
  • to study its effects on β5i/LMP7 immunoproteasome subunit in pancreatitis
[29]
  • on gastric emptying,food intake and c-Fos immunoreactivity in small litter (SL) and normal litter (NL) rats
  • [94]
  • on the intestine and gallbladder motility in fish Ballan Wrasse
  • [03]

    Biochem/physiol Actions

    (Tyr[SO3H]27)Cholecystokinin fragment 26-33 amide activates the cholecystokinin type B receptor and may mediate the blockage of opioid analgesia.[03] It elicits anti-inflammatory effects. It mediates the inhibition on cytokine release, lymphocytes, and macrophages.[88]
    Neurotransmitter; predominant form of CCK in CNS and gastrointestinal tract; may play a role in satiety.

    Other Notes

    C-Terminal octapeptide of cholecystokinin

    Storage Class Code

    13 - Non 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

    Certificate of Analysis

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    Certificate of Origin

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