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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

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

Certificates of Analysis (COA)

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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
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)
E J Bilsky et al.
The Journal of pharmacology and experimental therapeutics, 277(1), 484-490 (1996-04-01)
Previous studies measuring opioid inhibition of cyclic adenosine monophosphate in SH-SY5Y cells supported the hypothesis that continuous agonist stimulation causes a gradual conversion of the mu opioid receptor to a sensitized or constitutively active state termed mu*. Conversion to mu*
Christine E Engeland et al.
Virology, 460-461, 194-206 (2014-07-11)
Human immunodeficiency virus Gag drives assembly of virions in infected cells and interacts with host factors which facilitate or restrict viral replication. Although several Gag-binding proteins have been characterized, understanding of virus-host interactions remains incomplete. In a series of six
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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