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Dynorphin A(1-13)

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CAT#
10-101-12
Synonyms/Alias
dynorphin (1-13); dinorphinA (1-13); Dynorphin A; DynorphinA; Dynorphin-A; Dynorphin 1-13; Dynorphin1-13; dynorphin(1-13); 1-13-Dynorphin A; LS-63662; LS63662; LS 63662
CAS No.
72957-38-1 (net)
Sequence
H-Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys- Leu-Lys-OH acetate salt
M.W/Mr.
1603.99
Molecular Formula
C75H126N24O15
Source
Synthetic
Long-term Storage Conditions
−20°C
Application
Dynorphin A appears to reduce morphine requirements in postoperative patients.
Description
Dynorphin A(1-13), a version of dynorphin A containing only the first 13 amino acids of the peptide, in the rat spinal cord has additive effects. When dynorphin A1-13 was injected into the intracerebroventriulcar (ICV) region of the brain, it has an antagonist effect on morphine-induced analgesia.
Areas of Interest
Analgesia
  • Background
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  • References

Dynorphin A(1–13), a tridecapeptide of the endogenous opioid peptides, has modest effects in reducing mild opiate withdrawal in humans. Previous studies revealed that dynorphin also potentiates the analgesic effect of morphine in morphine-tolerant rats and mice. The therapeutic potential of dynorphin A(1–13) is limited due to extensive metabolism by human metabolic enzymes resulting in an in vivo half-life of less than one minute. Chemical modifications of dynorphin A(1–13), such as N-methylation of Tyr1 and amidation of the C-terminus have been shown to be effective in protecting against the proteolytic enzymes in human plasma. This article is a general review of the metabolism of dynorphin A(1–13) in human plasma and CSF.

CAS: 80448-90-4
Sequence: H-Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln-OH
M.W: 2147.48
Molecular Formula: C99H155N31O23

Dynorphin A is an endogenous opioid peptide that preferentially activates κ opioid receptors and is antinociceptive at physiological concentrations. Levels of dynorphin A and a major metabolite, dynorphin A (1-13), increase significantly following spinal cord trauma and reportedly contribute to neurodegeneration associated with secondary injury. Interestingly, both κ opioid and N-methyl-D-aspartate (NMDA) receptor antagonists can modulate dynorphin toxicity, suggesting that dynorphin is acting (directly or indirectly) through κ opioid and/or NMDA receptor (NMDAR) types. Despite these findings, few studies have systematically explored dynorphin toxicity at the cellular level in defined populations of neurons co-expressing κ opioid and NMDA receptors.

Hauser, K. F., Foldes, J. K., & Turbek, C. S. (1999). Dynorphin A (1–13) neurotoxicity in vitro: opioid and non-opioid mechanisms in mouse spinal cord neurons. Experimental neurology, 160(2), 361-375.

We describe the opioid properties of a tridecapeptide, the sequence of which corresponds to the NH2-terminal sequence of dynorphin, a novel porcine pituitary endorphin. It contains [Leu]enkephalin. In the guinea pig ileum longitudinal muscle preparation it is about 700 times more potent than [Leu]enkephalin. Its effects in this tissue are blocked completely by naloxone, but the apparent affinity of naloxone is 1/13th that for blockade of [Leu]enkephalin or normorphine. In the mouse vas deferens, this peptide is 3 times more potent than [Leu]enkephalin. Well-washed rat brain membranes degrade the peptide rapidly, suggesting the presence of a membrane-bound degradative enzyme. The peptide displays considerable immunoreactivity in assays with antisera that have been used for the immunohistochemical localization of [Leu]enkephalin. The remarkable enhancement of the potency of [Leu]enkephalin by the COOH-terminal extension -Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-OH suggests new interpretations concerning the structure of opiate receptors and the function of the enkephalin pentapeptides.

Goldstein, A., Tachibana, S., Lowney, L. I., Hunkapiller, M., & Hood, L. (1979). Dynorphin-(1-13), an extraordinarily potent opioid peptide. Proceedings of the National Academy of Sciences, 76(12), 6666-6670.

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