Dafphedyn

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MedKoo CAT#: 581224

CAS#: 111846-43-6

Description: Dafphedyn, [D-Ala2, (F5) Phe4]-dynorphin 1-13-NH2 (DAFPHEDYN) is a potent analog of dynorphin 1-13. Intracerebroventricular administration of the dynorphin analog, [D-Ala2,(F5)Phe4]-dynorphin 1-13-NH2 (DAFPHEDYN) in rats produced diuresis and profound analgesia. Both effects were antagonized by central administration of naltrexone or naloxone. Intravenous administration of 10, 25, and 50 mg/kg of DAFPHEDYN failed to induce diuresis. The increased potency of DAFPHEDYN was apparent from the failure of an equal dose of the parent compound (dynorphin 1-13) to produce diuresis and the failure of [D-Ala2]-dynorphin 1-13-NH2 to produce analgesia. Radioligand binding studies indicated the DAFPHEDYN retains the same degree of kappa selectivity as the parent compound (dynorphin 1-13) though a drop in affinity occurred. DAFPHEDYN may be of significant interest because it retains the essential pharmacology of the parent compound and exhibits marked in vivo potency.


Chemical Structure

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Dafphedyn
CAS# 111846-43-6

Theoretical Analysis

MedKoo Cat#: 581224
Name: Dafphedyn
CAS#: 111846-43-6
Chemical Formula: C76H124F5N25O14
Exact Mass: 1705.968
Molecular Weight: 1706.98
Elemental Analysis: C, 53.48; H, 7.32; F, 5.56; N, 20.51; O, 13.12

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
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Synonym: Dafphedyn; Dynorphin amide (1-13), ala(2)-(F(5)-phe)(4)-; Dynorphin amide (1-13), alanyl(2)-(5-fluorophenylalanine)(4)-;

IUPAC/Chemical Name: (S)-N-((S)-6-amino-1-(((S)-1-(((S)-1,6-diamino-1-oxohexan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxohexan-2-yl)-1-(((S)-2-(2-((R)-2-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)propanamido)acetamido)-3-(perfluorophenyl)propanoyl)-L-leucyl-L-arginyl-L-arginyl-L-isoleucyl-L-arginyl)pyrrolidine-2-carboxamide

InChi Key: GONRGWUCZCUEAR-NGBXKCEBSA-N

InChi Code: InChI=1S/C76H124F5N25O14/c1-8-40(6)61(72(119)102-50(21-15-31-94-76(90)91)73(120)106-32-16-22-54(106)71(118)101-47(18-10-12-28-83)66(113)103-51(33-38(2)3)68(115)98-46(62(85)109)17-9-11-27-82)105-67(114)49(20-14-30-93-75(88)89)99-65(112)48(19-13-29-92-74(86)87)100-69(116)52(34-39(4)5)104-70(117)53(36-44-56(77)58(79)60(81)59(80)57(44)78)97-55(108)37-95-63(110)41(7)96-64(111)45(84)35-42-23-25-43(107)26-24-42/h23-26,38-41,45-54,61,107H,8-22,27-37,82-84H2,1-7H3,(H2,85,109)(H,95,110)(H,96,111)(H,97,108)(H,98,115)(H,99,112)(H,100,116)(H,101,118)(H,102,119)(H,103,113)(H,104,117)(H,105,114)(H4,86,87,92)(H4,88,89,93)(H4,90,91,94)/t40-,41+,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,61-/m0/s1

SMILES Code: c1(c(c(c(c(c1F)F)F)F)F)C[C@@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N1CCC[C@H]1C(N[C@@H](CCCCN)C(N[C@@H](CC(C)C)C(=O)N[C@H](C(N)=O)CCCCN)=O)=O)=O)=O)[C@H](CC)C)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CC(C)C)=O)NC(CNC([C@H](NC([C@H](Cc1ccc(cc1)O)N)=O)C)=O)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 1706.98 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

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1: Walker JM, Coy DH, Young EA, Baldrighi G, Siegel SF, Bowen WD, Akil H. [D-Ala2, (F5) Phe4]-dynorphin 1-13-NH2 (DAFPHEDYN): a potent analog of dynorphin 1-13. Peptides. 1987 Sep-Oct;8(5):811-7. PubMed PMID: 2893357.

2: Gosnell BA, Majchrzak MJ, Krahn DD. Effects of preferential delta and kappa opioid receptor agonists on the intake of hypotonic saline. Physiol Behav. 1990 Mar;47(3):601-3. PubMed PMID: 1972796.

3: Kostrzewa RM, Brus R, Coy DH, Criswell H, Coogan PS, Kastin AJ. D-Ala2,F5Phe4-dynorphin amide, an opiate with analgesic and toxic properties. Pol J Pharmacol Pharm. 1992 Mar-Apr;44(2):109-20. PubMed PMID: 1357636.

4: Solin AV, Lyashev AY, Lyashev YD. Effects of Opioid Peptides on Changes in Lipid Metabolism in Rats Subjected to Swimming Stress. Bull Exp Biol Med. 2017 Jan;162(3):313-315. doi: 10.1007/s10517-017-3603-7. Epub 2017 Jan 14. PubMed PMID: 28091903.