UFP-512

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

MedKoo CAT#: 532869

CAS#: 480446-44-4

Description: UFP-512 is a novel selective delta-opioid (DOP) receptor agonist. UFP-512 is a promising drug prototype for exploring innovative treatments for mood disorders.


Price and Availability

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UFP-512 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 532869
Name: UFP-512
CAS#: 480446-44-4
Chemical Formula: C31H33N5O5
Exact Mass: 555.2482
Molecular Weight: 555.64
Elemental Analysis: C, 67.01; H, 5.99; N, 12.60; O, 14.40


Synonym: UFP-512, UFP 512, UFP512

IUPAC/Chemical Name: (3S)-3-[[(3S)-2-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-3-(1H-benzimidazol-2-yl)propanoic acid

InChi Key: USVQTDLSVBRMCR-YGPDHOBYSA-N

InChi Code: InChI=1S/C31H33N5O5/c1-17-11-21(37)12-18(2)22(17)14-23(32)31(41)36-16-20-8-4-3-7-19(20)13-27(36)30(40)35-26(15-28(38)39)29-33-24-9-5-6-10-25(24)34-29/h3-12,23,26-27,37H,13-16,32H2,1-2H3,(H,33,34)(H,35,40)(H,38,39)/t23-,26-,27-/m0/s1

SMILES Code: O=C(O)C[C@H](NC([C@H]1N(C([C@@H](N)CC2=C(C)C=C(O)C=C2C)=O)CC3=C(C=CC=C3)C1)=O)C4=NC5=CC=CC=C5N4


Technical Data

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).

Harmonized System Code:
293490


References

1: Zhi F, Xue L, Shao N, Deng D, Kang X, Chao D, Xu Y, Wang R, Yang Y, Xia Y. δ-Opioid Receptor Activation and MicroRNA Expression in the Rat Heart Under Prolonged Hypoxia. Cell Physiol Biochem. 2016;39(3):1118-28. doi: 10.1159/000447815. Epub 2016 Aug 29. PubMed PMID: 27576463.

2: Xu Y, Zhi F, Shao N, Wang R, Yang Y, Xia Y. Cytoprotection against Hypoxic and/or MPP⁺ Injury: Effect of δ-Opioid Receptor Activation on Caspase 3. Int J Mol Sci. 2016 Aug 9;17(8). pii: E1179. doi: 10.3390/ijms17081179. PubMed PMID: 27517901; PubMed Central PMCID: PMC5000589.

3: Cao S, Chao D, Zhou H, Balboni G, Xia Y. A novel mechanism for cytoprotection against hypoxic injury: δ-opioid receptor-mediated increase in Nrf2 translocation. Br J Pharmacol. 2015 Apr;172(7):1869-81. doi: 10.1111/bph.13031. Epub 2015 Feb 10. PubMed PMID: 25439010; PubMed Central PMCID: PMC4376463.

4: Liang J, Chao D, Sandhu HK, Yu Y, Zhang L, Balboni G, Kim DH, Xia Y. δ-Opioid receptors up-regulate excitatory amino acid transporters in mouse astrocytes. Br J Pharmacol. 2014 Dec;171(23):5417-30. doi: 10.1111/bph.12857. PubMed PMID: 25052197; PubMed Central PMCID: PMC4294049.

5: Wang Q, Chao D, Chen T, Sandhu H, Xia Y. δ-Opioid receptors and inflammatory cytokines in hypoxia: differential regulation between glial and neuron-like cells. Transl Stroke Res. 2014 Aug;5(4):476-83. doi: 10.1007/s12975-014-0342-1. Epub 2014 May 2. PubMed PMID: 24788819.

6: Chen T, Li J, Chao D, Sandhu HK, Liao X, Zhao J, Wen G, Xia Y. δ-Opioid receptor activation reduces α-synuclein overexpression and oligomer formation induced by MPP(+) and/or hypoxia. Exp Neurol. 2014 May;255:127-36. doi: 10.1016/j.expneurol.2014.02.022. Epub 2014 Mar 5. PubMed PMID: 24613828.

7: Kabli N, Nguyen T, Balboni G, O'Dowd BF, George SR. Antidepressant-like and anxiolytic-like effects following activation of the μ-δ opioid receptor heteromer in the nucleus accumbens. Mol Psychiatry. 2014 Sep;19(9):986-94. doi: 10.1038/mp.2013.115. Epub 2013 Sep 24. PubMed PMID: 24061495.

8: Charfi I, Nagi K, Mnie-Filali O, Thibault D, Balboni G, Schiller PW, Trudeau LE, Pineyro G. Ligand- and cell-dependent determinants of internalization and cAMP modulation by delta opioid receptor (DOR) agonists. Cell Mol Life Sci. 2014 Apr;71(8):1529-46. PubMed PMID: 24022593; PubMed Central PMCID: PMC3952036.

9: Tian X, Hua F, Sandhu HK, Chao D, Balboni G, Salvadori S, He X, Xia Y. Effect of δ-opioid receptor activation on BDNF-TrkB vs. TNF-α in the mouse cortex exposed to prolonged hypoxia. Int J Mol Sci. 2013 Jul 31;14(8):15959-76. doi: 10.3390/ijms140815959. PubMed PMID: 23912236; PubMed Central PMCID: PMC3759895.

10: Yang Y, Zhi F, He X, Moore ML, Kang X, Chao D, Wang R, Kim DH, Xia Y. δ-opioid receptor activation and microRNA expression of the rat cortex in hypoxia. PLoS One. 2012;7(12):e51524. doi: 10.1371/journal.pone.0051524. Epub 2012 Dec 13. PubMed PMID: 23272113; PubMed Central PMCID: PMC3521741.

11: Mabrouk OS, Marti M, Salvadori S, Morari M. The novel delta opioid receptor agonist UFP-512 dually modulates motor activity in hemiparkinsonian rats via control of the nigro-thalamic pathway. Neuroscience. 2009 Dec 1;164(2):360-9. doi: 10.1016/j.neuroscience.2009.08.058. Epub 2009 Sep 1. PubMed PMID: 19729051.

12: Balboni G, Fiorini S, Baldisserotto A, Trapella C, Sasaki Y, Ambo A, Marczak ED, Lazarus LH, Salvadori S. Further studies on lead compounds containing the opioid pharmacophore Dmt-Tic. J Med Chem. 2008 Aug 28;51(16):5109-17. doi: 10.1021/jm800587e. Epub 2008 Aug 5. PubMed PMID: 18680274; PubMed Central PMCID: PMC2812024.

13: Vergura R, Balboni G, Spagnolo B, Gavioli E, Lambert DG, McDonald J, Trapella C, Lazarus LH, Regoli D, Guerrini R, Salvadori S, Caló G. Anxiolytic- and antidepressant-like activities of H-Dmt-Tic-NH-CH(CH2-COOH)-Bid (UFP-512), a novel selective delta opioid receptor agonist. Peptides. 2008 Jan;29(1):93-103. Epub 2007 Oct 23. PubMed PMID: 18069089.

14: Aguila B, Coulbault L, Boulouard M, Léveillé F, Davis A, Tóth G, Borsodi A, Balboni G, Salvadori S, Jauzac P, Allouche S. In vitro and in vivo pharmacological profile of UFP-512, a novel selective delta-opioid receptor agonist; correlations between desensitization and tolerance. Br J Pharmacol. 2007 Dec;152(8):1312-24. Epub 2007 Nov 5. Erratum in: Br J Pharmacol. 2007 Dec;152(8):1325. PubMed PMID: 17982482; PubMed Central PMCID: PMC2189997.