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MedKoo Cat#: 526870 | Name: CJ-15208

Description:

WARNING: This product is for research use only, not for human or veterinary use.

CJ-15208 is a potent and selective κ-opioid receptor antagonist from a fungus, Ctenomyces serratus ATCC15502. CJ-15208 was a selective binding inhibitor for the kappa opioid receptor: 47 nM (IC50) for kappa, 260 nM for mu, and 2,600 nM for delta. In the electrically-stimulated twitch response assay of rabbit vas deferens I recovered the suppression by a kappa agonist asimadoline with an ED50 of 1.3 microM, indicating that it is a kappa antagonist.

Chemical Structure

CJ-15208
CJ-15208
CAS#210236-47-8

Theoretical Analysis

MedKoo Cat#: 526870

Name: CJ-15208

CAS#: 210236-47-8

Chemical Formula: C34H35N5O4

Exact Mass: 577.2689

Molecular Weight: 577.69

Elemental Analysis: C, 70.69; H, 6.11; N, 12.12; O, 11.08

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
CJ-15208; CJ15208; CJ 15208; CJ-15,208; CJ15,208; CJ 15,208.c[Phe-D-Pro-Phe-Trp].
IUPAC/Chemical Name
(3S,6S,9S,14aR)-6-((1H-indol-3-yl)methyl)-3,9-dibenzyldecahydropyrrolo[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10-tetraone
InChi Key
GIZJWWQFOGQPRY-GCXHJFECSA-N
InChi Code
InChI=1S/C34H35N5O4/c40-31-27(18-22-10-3-1-4-11-22)37-33(42)30-16-9-17-39(30)34(43)29(19-23-12-5-2-6-13-23)38-32(41)28(36-31)20-24-21-35-26-15-8-7-14-25(24)26/h1-8,10-15,21,27-30,35H,9,16-20H2,(H,36,40)(H,37,42)(H,38,41)/t27-,28-,29-,30+/m0/s1
SMILES Code
O=C(N1[C@H](CCC1)C(N[C@@H](CC2=CC=CC=C2)C(N[C@H]3CC4=CNC5=CC=CC=C54)=O)=O)[C@@H](NC3=O)CC6=CC=CC=C6
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 577.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: De Marco R, Bedini A, Spampinato S, Cavina L, Pirazzoli E, Gentilucci L. Versatile Picklocks To Access All Opioid Receptors: Tuning the Selectivity and Functional Profile of the Cyclotetrapeptide c[Phe-d-Pro-Phe-Trp] (CJ-15,208). J Med Chem. 2016 Sep 22. [Epub ahead of print] PubMed PMID: 27607020. 2: Khaliq T, Williams TD, Senadheera SN, Aldrich JV. Development of a robust, sensitive and selective liquid chromatography-tandem mass spectrometry assay for the quantification of the novel macrocyclic peptide kappa opioid receptor antagonist [D-Trp]CJ-15,208 in plasma and application to an initial pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Aug 15;1028:11-5. doi: 10.1016/j.jchromb.2016.05.043. Epub 2016 Jun 2. PubMed PMID: 27318293; PubMed Central PMCID: PMC4956519. 3: Aldrich JV, Senadheera SN, Ross NC, Reilley KA, Ganno ML, Eans SE, Murray TF, McLaughlin JP. Alanine analogues of [D-Trp]CJ-15,208: novel opioid activity profiles and prevention of drug- and stress-induced reinstatement of cocaine-seeking behaviour. Br J Pharmacol. 2014 Jul;171(13):3212-22. doi: 10.1111/bph.12664. PubMed PMID: 24588614; PubMed Central PMCID: PMC4080975. 4: Bidlack JM. Mixed κ/μ partial opioid agonists as potential treatments for cocaine dependence. Adv Pharmacol. 2014;69:387-418. doi: 10.1016/B978-0-12-420118-7.00010-X. Review. PubMed PMID: 24484983. 5: Eans SO, Ganno ML, Reilley KJ, Patkar KA, Senadheera SN, Aldrich JV, McLaughlin JP. The macrocyclic tetrapeptide [D-Trp]CJ-15,208 produces short-acting κ opioid receptor antagonism in the CNS after oral administration. Br J Pharmacol. 2013 May;169(2):426-36. doi: 10.1111/bph.12132. PubMed PMID: 23425081; PubMed Central PMCID: PMC3651667. 6: Aldrich JV, Senadheera SN, Ross NC, Ganno ML, Eans SO, McLaughlin JP. The macrocyclic peptide natural product CJ-15,208 is orally active and prevents reinstatement of extinguished cocaine-seeking behavior. J Nat Prod. 2013 Mar 22;76(3):433-8. doi: 10.1021/np300697k. Epub 2013 Jan 17. PubMed PMID: 23327691; PubMed Central PMCID: PMC3879116. 7: Aldrich JV, Kulkarni SS, Senadheera SN, Ross NC, Reilley KJ, Eans SO, Ganno ML, Murray TF, McLaughlin JP. Unexpected opioid activity profiles of analogues of the novel peptide kappa opioid receptor ligand CJ-15,208. ChemMedChem. 2011 Sep 5;6(9):1739-45. doi: 10.1002/cmdc.201100113. Epub 2011 Jul 14. PubMed PMID: 21761566; PubMed Central PMCID: PMC3667675. 8: Ross NC, Reilley KJ, Murray TF, Aldrich JV, McLaughlin JP. Novel opioid cyclic tetrapeptides: Trp isomers of CJ-15,208 exhibit distinct opioid receptor agonism and short-acting κ opioid receptor antagonism. Br J Pharmacol. 2012 Feb;165(4b):1097-108. doi: 10.1111/j.1476-5381.2011.01544.x. PubMed PMID: 21671905; PubMed Central PMCID: PMC3346240. 9: Ross NC, Kulkarni SS, McLaughlin JP, Aldrich JV. Synthesis of CJ-15,208, a novel κ-opioid receptor antagonist. Tetrahedron Lett. 2010 Sep 20;51(38):5020-5023. PubMed PMID: 22865937; PubMed Central PMCID: PMC3411353. 10: Dolle RE, Michaut M, Martinez-Teipel B, Seida PR, Ajello CW, Muller AL, DeHaven RN, Carroll PJ. Nascent structure-activity relationship study of a diastereomeric series of kappa opioid receptor antagonists derived from CJ-15,208. Bioorg Med Chem Lett. 2009 Jul 1;19(13):3647-50. doi: 10.1016/j.bmcl.2009.04.105. Epub 2009 May 3. PubMed PMID: 19464172. 11: Kulkarni SS, Ross NC, McLaughlin JP, Aldrich JV. Synthesis of cyclic tetrapeptide CJ 15,208: a novel kappa opioid receptor antagonist. Adv Exp Med Biol. 2009;611:269-70. PubMed PMID: 19400188. 12: Saito T, Hirai H, Kim YJ, Kojima Y, Matsunaga Y, Nishida H, Sakakibara T, Suga O, Sujaku T, Kojima N. CJ-15,208, a novel kappa opioid receptor antagonist from a fungus, Ctenomyces serratus ATCC15502. J Antibiot (Tokyo). 2002 Oct;55(10):847-54. PubMed PMID: 12523817.