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HomeProduct name listSincalide

Sincalide

Synonym(s):CCK-8;Cholecystokinin octapeptide;Pancreozymin C-terminal octapeptide;Sincalide

  • CAS NO.:25126-32-3
  • Empirical Formula: C49H62N10O16S3
  • Molecular Weight: 1143.27
  • MDL number: MFCD00079849
  • EINECS: 246-639-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-14 14:09:35
Sincalide Structural

What is Sincalide?

Originator

Kinevac,Squibb,US,1976

The Uses of Sincalide

Sincalide is used in the biological studies in the preparation of opioid receptors agonistic and CCK receptor antagonistic activity.

The Uses of Sincalide

Choleretic.

Definition

ChEBI: Sincalide is an oligopeptide.

Manufacturing Process

The starting material in the following synthesis is: t-butyloxycarbonyl-Laspartyl- L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-Lphenylalanine amide designated (SM)
.(A) A solution of (SM) (320 mg) in trifluoroacetic acid (7 ml) was kept under nitrogen at room temperature for 15 minutes. Ether (100 ml) was added and the precipitate filtered, washed thoroughly with ether and dried. This material (280 mg) was added to concentrated sulfuric acid (20 ml), cooled at -20°C. The solution was kept in the dry ice-acetone bath at -20°C for 75 minutes. The sulfuric acid solution was poured into ice water (80 ml). The precipitate was centrifuged, resuspended in ice water (30 ml) and 4N sodium hydroxide was added until a clear solution was obtained. After reacidification to pH 4 with dilute sulfuric acid, the precipitate formed was centrifuged, washed twice with ice water and dried. Yield 155 mg. Chromatograph of DEAE Sephadex (with ammonium carbonate buffer) yielded the desired octapeptide sulfate ester: 30 mg.
(B) A solution of (SM) (330 mg) in trifluoroacetic acid (7 ml) was kept under nitrogen at room temperature for 15 minutes. Ether (100 ml) was added and the precipitate was filtered, washed thoroughly with ether and dried. This material (300 mg) was added in portions to concentrated sulfuric acid (18 ml) cooled at -20°C with vigorous stirring. After 15 minutes a solution of potassium bisulfate in concentrated sulfuric acid (408 mg in 3 ml) was added. The reaction mixture was stirred for 75 minutes at -15°C and then stored at - 7°C for 285 minutes. The sulfuric acid solution was poured into cold ether (400 ml); precipitate was filtered, washed with cold ether, and suspended in cold water. Complete solution was then achieved by careful addition of 2N sodium hydroxide. Acidification with N hydrochloric acid led to the precipitation of the desired octapeptide sulfate ester. Yield 200 mg.

brand name

Kinevac (Bracco).

Therapeutic Function

Choleretic

General Description

It was thought originally that cholecystokinin and pancreozyminwere two different hormones. Cholecystokinin wasthought to be responsible for contraction of the gallbladder,whereas pancreozymin was believed to induce secretion ofpancreatic enzymes. It is now clear that both actions arecaused by a single 33-residue polypeptide, referred to ascholecystokinin–pancreozymin (CCK-PZ). CCK-PZ is secretedin the blood in response to the presence of food in theduodenum, especially long-chain fatty acids. The fiveCOOH-terminal amino acid residues are identical with thosein gastrin. The COOH-terminal octapeptide retains full activityof the parent hormone.

Biochem/physiol Actions

Neurotransmitter; predominant form of CCK in CNS and gastrointestinal tract; may play a role in satiety.

storage

Store at -20°C

Properties of Sincalide

Melting point: >193°C (dec.)
alpha  D23 -18.4° (c = 0.7 in 1N NH3)
Density  1.440±0.06 g/cm3(Predicted)
storage temp.  -20°C
solubility  0.05 M ammonium hydroxide: 1 mg/mL, clear, colorless
form  powder
pka -4.17±0.18(Predicted)
color  Off-White
Water Solubility  Soluble in water 1 g/L at 10°C.
Merck  13,8617
BRN  5231801

Safety information for Sincalide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for Sincalide

InChIKey IZTQOLKUZKXIRV-IVVJSLGPSA-N

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