TIPP | CAS#146369-65-5 | delta opioid antagonist

MedKoo Cat#: 597760 | Name: TIPP

Description:

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

TIPP is a delta opioid antagonist.

Chemical Structure

TIPP

CAS#146369-65-5

Theoretical Analysis

MedKoo Cat#: 597760

Name: TIPP

CAS#: 146369-65-5

Chemical Formula: C37H38N4O6

Exact Mass: 634.2791

Molecular Weight: 634.73

Elemental Analysis: C, 70.01; H, 6.03; N, 8.83; O, 15.12

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 #

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Synonym

TIPP; Tyr-Tic-Phe-Phe-OH;

IUPAC/Chemical Name

N-L-tyrosyl-L-phenylalanyl-N-(1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-phenylalanine

InChi Key

BHHDLHZVBBWMKO-NROWOOLRSA-N

InChi Code

InChI=1S/C37H38N4O6/c38-30(19-26-15-17-29(42)18-16-26)34(43)40-32(20-24-9-3-1-4-10-24)36(45)41(33(37(46)47)21-25-11-5-2-6-12-25)35(44)31-22-27-13-7-8-14-28(27)23-39-31/h1-18,30-33,39,42H,19-23,38H2,(H,40,43)(H,46,47)/t30-,31?,32-,33-/m0/s1

SMILES Code

O=C(O)[C@H](CC1=CC=CC=C1)N(C(C2NCC3=C(C=CC=C3)C2)=O)C([C@H](CC4=CC=CC=C4)NC([C@H](CC5=CC=C(O)C=C5)N)=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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 634.73 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.

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: Lian Q, Jiang W, Cheng Y, Cao H, Liu M, Wang J, Li Y, Song X, Wang F. A novel pentapeptide originated from calf thymus named TIPP shows an inhibitory effect on lung allergic inflammation. Int Immunopharmacol. 2015 Feb;24(2):256-266. doi: 10.1016/j.intimp.2014.12.019. Epub 2014 Dec 19. PubMed PMID: 25533504. 2: Lian Q, Cheng Y, Zhong C, Wang F. Inhibition of the IgE-mediated activation of RBL-2H3 cells by TIPP, a novel thymic immunosuppressive pentapeptide. Int J Mol Sci. 2015 Jan 20;16(1):2252-68. doi: 10.3390/ijms16012252. PubMed PMID: 25608657; PubMed Central PMCID: PMC4307361. 3: Koning GG, Adang EM, Stalmeier PF, Keus F, Vriens PW, van Laarhoven CJ. TIPP and Lichtenstein modalities for inguinal hernia repair: a cost minimisation analysis alongside a randomised trial. Eur J Health Econ. 2013 Dec;14(6):1027-34. doi: 10.1007/s10198-012-0453-0. Epub 2012 Dec 28. PubMed PMID: 23271350. 4: Nguyen NP, Mirarab S, Liu B, Pop M, Warnow T. TIPP: taxonomic identification and phylogenetic profiling. Bioinformatics. 2014 Dec 15;30(24):3548-55. doi: 10.1093/bioinformatics/btu721. Epub 2014 Oct 29. PubMed PMID: 25359891; PubMed Central PMCID: PMC4253836. 5: Weltrowska G, Nguyen TM, Chung NN, Wilkes BC, Schiller PW. N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile. Bioorg Med Chem Lett. 2013 Sep 15;23(18):5082-5. doi: 10.1016/j.bmcl.2013.07.036. Epub 2013 Jul 23. PubMed PMID: 23932788; PubMed Central PMCID: PMC3776131. 6: Berezowska I, Lemieux C, Chung NN, Ding J, Schiller PW. Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists. Bioorg Med Chem Lett. 2012 Mar 1;22(5):1899-902. doi: 10.1016/j.bmcl.2012.01.063. Epub 2012 Jan 28. PubMed PMID: 22325949; PubMed Central PMCID: PMC3288262. 7: Pélissier EP, Ngo P, Gayet B. Transinguinal preperitoneal patch (TIPP) under local anesthesia with sedation. Am Surg. 2011 Dec;77(12):1681-4. PubMed PMID: 22273230. 8: Gillion JF. Reply to: invited comment "Chronic pain and quality of life after transinguinal preperitoneal (TIPP) inguinal hernia repair: a few tips on TIPP". D.C. Chen and P. Amid. DOI 10.1007/s10029-013-1138-z. Hernia. 2013 Dec;17(6):697-8. doi: 10.1007/s10029-013-1188-2. Epub 2013 Nov 16. PubMed PMID: 24241328. 9: Martin NA, Terruso MT, Prather PL. Agonist Activity of the delta-antagonists TIPP and TIPP-psi in cellular models expressing endogenous or transfected delta-opioid receptors. J Pharmacol Exp Ther. 2001 Jul;298(1):240-8. PubMed PMID: 11408548. 10: Chen DC, Amid PK. Chronic pain and quality of life after transinguinal preperitoneal (TIPP) inguinal hernia repair: a few tips on TIPP. Hernia. 2013 Dec;17(6):693-5. doi: 10.1007/s10029-013-1138-z. Epub 2013 Jul 23. PubMed PMID: 23877347. 11: Nevin ST, Tóth G, Weltrowska G, Schiller PW, Borsodi A. Synthesis and binding characteristics of tritiated TIPP[psi], a highly specific and stable delta opioid antagonist. Life Sci. 1995;56(10):PL225-30. PubMed PMID: 7885186. 12: Schiller PW, Weltrowska G, Berezowska I, Nguyen TM, Wilkes BC, Lemieux C, Chung NN. The TIPP opioid peptide family: development of delta antagonists, delta agonists, and mixed mu agonist/delta antagonists. Biopolymers. 1999;51(6):411-25. Review. PubMed PMID: 10797230. 13: Fundytus ME, Schiller PW, Shapiro M, Weltrowska G, Coderre TJ. Attenuation of morphine tolerance and dependence with the highly selective delta-opioid receptor antagonist TIPP[psi]. Eur J Pharmacol. 1995 Nov 3;286(1):105-8. PubMed PMID: 8566146. 14: Baumann PS, Crespi S, Marion-Veyron R, Solida A, Thonney J, Favrod J, Bonsack C, Do KQ, Conus P. Treatment and early intervention in psychosis program (TIPP-Lausanne): Implementation of an early intervention programme for psychosis in Switzerland. Early Interv Psychiatry. 2013 Aug;7(3):322-8. doi: 10.1111/eip.12037. Epub 2013 Feb 28. PubMed PMID: 23445318. 15: Koning GG, Koole D, de Jongh MA, de Schipper JP, Verhofstad MH, Oostvogel HJ, Vriens PW. The transinguinal preperitoneal hernia correction vs Lichtenstein's technique; is TIPP top? Hernia. 2011 Feb;15(1):19-22. doi: 10.1007/s10029-010-0744-2. PubMed PMID: 21061139; PubMed Central PMCID: PMC3038218. 16: Gillion JF, Chollet JM. Chronic pain and quality of life (QoL) after transinguinal preperitoneal (TIPP) inguinal hernia repair using a totally extraperitoneal, parietalized, Polysoft ® memory ring patch : a series of 622 hernia repairs in 525 patients. Hernia. 2013 Dec;17(6):683-92. doi: 10.1007/s10029-013-1121-8. Epub 2013 Jun 23. PubMed PMID: 23793928. 17: Nevin ST, Toth G, Nguyen TM, Schiller PW, Borsodi A. Synthesis and binding characteristics of the highly specific, tritiated delta opioid antagonist [3H]TIPP. Life Sci. 1993;53(5):PL57-62. PubMed PMID: 8393120. 18: Schiller PW, Weltrowska G, Nguyen TM, Wilkes BC, Chung NN, Lemieux C. TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity. J Med Chem. 1993 Oct 15;36(21):3182-7. PubMed PMID: 8230106. 19: Martin NA, Ruckle MB, VanHoof SL, Prather PL. Agonist, antagonist, and inverse agonist characteristics of TIPP (H-Tyr-Tic-Phe-Phe-OH), a selective delta-opioid receptor ligand. J Pharmacol Exp Ther. 2002 May;301(2):661-71. PubMed PMID: 11961071. 20: Lee PH, Nguyen TM, Chung NN, Schiller PW, Chang KJ. Tyrosine-iodination converts the delta-opioid peptide antagonist TIPP to an agonist. Eur J Pharmacol. 1995 Jul 4;280(2):211-4. PubMed PMID: 7589188.