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Safety Information

C6352

Sigma-Aldrich

CTAP

≥95%

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About This Item

Empirical Formula (Hill Notation):
C51H69N13O11S2
CAS Number:
103429-32-9
Molecular Weight:
1104.30
MDL number:
MFCD00671434
UNSPSC Code:
12352200
PubChem Substance ID:
329775120
NACRES:
NA.32

Quality Level

200

Assay

≥95%

form

powder

UniProt accession no.

Q62923

storage temp.

−20°C

SMILES string

C[C@@H](O)[C@H](NC(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc4ccc(O)cc4)NC(=O)[C@H](CSSC1(C)C)NC(=O)[C@H](N)Cc5ccccc5)[C@@H](C)O)C(N)=O

InChI

1S/C51H69N13O11S2/c1-26(65)39(42(53)68)62-49(75)41-51(3,4)77-76-25-38(61-43(69)33(52)21-28-11-6-5-7-12-28)47(73)59-36(22-29-16-18-31(67)19-17-29)45(71)60-37(23-30-24-57-34-14-9-8-13-32(30)34)46(72)58-35(15-10-20-56-50(54)55)44(70)63-40(27(2)66)48(74)64-41/h5-9,11-14,16-19,24,26-27,33,35-41,57,65-67H,10,15,20-23,25,52H2,1-4H3,(H2,53,68)(H,58,72)(H,59,73)(H,60,71)(H,61,69)(H,62,75)(H,63,70)(H,64,74)(H4,54,55,56)/t26-,27-,33-,35+,36+,37-,38+,39+,40+,41-/m1/s1

InChI key

OFMQLVRLOGHAJI-FGHAYEPSSA-N

Gene Information

rat ... Pnoc(25516)

Amino Acid Sequence

D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2

Application

CTAP has been used as a μ-opioid receptor (MOR) antagonist:
  • to study the anti-hyperalgesic effect of dipeptidyl peptidase 4 (DPP4) inhibitor isoleucine-proline-isoleucine (IPI) and vildagliptin in carrageenan-induced inflammation
  • to study the role of MOR in glutamate and gamma-aminobutyric acid (GABA) efflux during predator stress in rats
  • to determine the endogenous opioid peptide involved in blocking pain induced by activated gastrin-releasing peptide (Grp+) neurons

Biochem/physiol Actions

CTAP is a peptide antagonist produced from somatostatin analogs.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7841
BCCF0591
BCCC0540
BCBV7821
BCBS0886V

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T J Abbruscato et al.
The Journal of pharmacology and experimental therapeutics, 280(1), 402-409 (1997-01-01)
D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 (CTAP) is a cyclic, penicillamine-containing octapeptide that is structurally similar to somatostatin and displays greater antagonist potency and selectivity for mu-opioid receptors, compared with the classical mu-selective antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2. The aim of this study was to determine whether CTAP
Kevin Caref et al.
eLife, 7 (2018-03-28)
When relatively sated, people (and rodents) are still easily tempted to consume calorie-dense foods, particularly those containing fat and sugar. Consumption of such foods while calorically replete likely contributes to obesity. The nucleus accumbens (NAc) opioid system has long been
Leaky gate model: intensity-dependent coding of pain and itch in the spinal cord
Sun S, et al.
Neuron, 93(4), 840-853 (2017)
Pathology and glia type specific changes of the DPP4 activity in the spinal cord contributes to the development and maintenance of hyperalgesia and shapes opioid signalling in chronic pain states
Kiraly K, et al.
Scientific Reports (2017)
Potency Differences ford-Phe-Cys-Tyr-d-Trp-Arg-Thr-Pen-Thr-NH2as an Antagonist of Peptide and Alkaloid mu-Agonists in an Antinociception Assay
Sterious SN and Walker EA
Journal of Pharmacology and Experimental Therapeutics, 304(1), 301-309 (2003)
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