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MedKoo Cat#: 597027 | Name: Pressinoic acid

Description:

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

Pressinoic acid is a potent corticotrophin-releasing peptide. Arginine-vasopressin metabolite. Inhibits oxytocin and the blood-brain barrier permeability of vasopressin in vivo.

Chemical Structure

Pressinoic acid
CAS#35748-51-7

Theoretical Analysis

MedKoo Cat#: 597027

Name: Pressinoic acid

CAS#: 35748-51-7

Chemical Formula: C33H42N8O10S2

Exact Mass: 774.2465

Molecular Weight: 774.86

Elemental Analysis: C, 51.15; H, 5.46; N, 14.46; O, 20.65; S, 8.27

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
Pressinoic acid; L-Cysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-cysteine-cyclic (1-6)-disulfid;
IUPAC/Chemical Name
(4R,7S,10S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carboxylic acid
InChi Key
ICSANXSPLDFBSA-ZUYRUSJRSA-N
InChi Code
InChI=1S/C33H42N8O10S2/c34-20-15-52-53-16-25(33(50)51)41-32(49)24(14-27(36)44)40-29(46)21(10-11-26(35)43)37-30(47)23(12-17-4-2-1-3-5-17)39-31(48)22(38-28(20)45)13-18-6-8-19(42)9-7-18/h1-9,20-25,42H,10-16,34H2,(H2,35,43)(H2,36,44)(H,37,47)(H,38,45)(H,39,48)(H,40,46)(H,41,49)(H,50,51)/t20-,21-,22-,23?,24-,25-/m0/s1
SMILES Code
O=C(N[C@@H](CCC(N)=O)C(N[C@@H](CC(N)=O)C(N[C@H](C(O)=O)CSSC[C@H](N)C(N[C@@H](Cc1ccc(O)cc1)C(N2)=O)=O)=O)=O)C2Cc3ccccc3
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 774.86 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: Slusarz R, Kaźmierkiewicz R, Lammek B. Theoretical conformational analysis of six arginine vasopressin analogs with the L-naphthylalanine in position 3. J Pept Res. 2000 Dec;56(6):352-9. PubMed PMID: 11152294. 2: Walse B, Kihlberg J, Drakenberg T. Conformation of desmopressin, an analogue of the peptide hormone vasopressin, in aqueous solution as determined by NMR spectroscopy. Eur J Biochem. 1998 Mar 15;252(3):428-40. PubMed PMID: 9546658. 3: Liwo A, Tempczyk A, Ołdziej S, Shenderovich MD, Hruby VJ, Talluri S, Ciarkowski J, Kasprzykowski F, Lankiewicz L, Grzonka Z. Exploration of the conformational space of oxytocin and arginine-vasopressin using the electrostatically driven Monte Carlo and molecular dynamics methods. Biopolymers. 1996 Feb;38(2):157-75. PubMed PMID: 8589250. 4: Bharadwaj M, Bizzozero OA. Myelin P0 glycoprotein and a synthetic peptide containing the palmitoylation site are both autoacylated. J Neurochem. 1995 Oct;65(4):1805-15. PubMed PMID: 7561879. 5: Kaźmierkiewicz R, Liwo A, Lammek B. Theoretical conformational analysis of three vasopressin antagonists with a modified cyclohexyl ring in the first thioacid residue. Int J Pept Protein Res. 1995 May;45(5):451-8. PubMed PMID: 7591484. 6: Liu JW, Ben-Jonathan N. Prolactin-releasing activity of neurohypophysial hormones: structure-function relationship. Endocrinology. 1994 Jan;134(1):114-8. PubMed PMID: 8275925. 7: Yeo PL, Rabenstein DL. Characterization of the thiol/disulfide chemistry of neurohypophyseal peptide hormones by high-performance liquid chromatography. Anal Chem. 1993 Nov 1;65(21):3061-6. PubMed PMID: 8256869. 8: Boyd SK. Effect of vasotocin on locomotor activity in bullfrogs varies with developmental stage and sex. Horm Behav. 1991 Mar;25(1):57-69. PubMed PMID: 2045091. 9: Zlokovic BV, Segal MB, McComb JG, Hyman S, Weiss MH, Davson H. Kinetics of circulating vasopressin uptake by choroid plexus. Am J Physiol. 1991 Feb;260(2 Pt 2):F216-24. PubMed PMID: 1899978. 10: Zlokovic BV, Hyman S, McComb JG, Lipovac MN, Tang G, Davson H. Kinetics of arginine-vasopressin uptake at the blood-brain barrier. Biochim Biophys Acta. 1990 Jun 27;1025(2):191-8. PubMed PMID: 2364078. 11: Crankshaw D. [Arg8]vasopressin-induced contractions of rabbit urinary bladder smooth muscle. Eur J Pharmacol. 1989 Dec 7;173(2-3):183-8. PubMed PMID: 2625135. 12: Johnson HM, Torres BA. A novel arginine vasopressin-binding peptide that blocks arginine vasopressin modulation of immune function. J Immunol. 1988 Oct 1;141(7):2420-3. PubMed PMID: 3139759. 13: Tripp SK, Moore FL. Autoradiographic characterization of binding sites labelled with vasopressin in the brain of a urodele amphibian. Neuroendocrinology. 1988 Jul;48(1):87-92. PubMed PMID: 3173642. 14: Koike TI, Shimada K, Cornett LE. Plasma levels of immunoreactive mesotocin and vasotocin during oviposition in chickens: relationship to oxytocic action of the peptides in vitro and peptide interaction with myometrial membrane binding sites. Gen Comp Endocrinol. 1988 Apr;70(1):119-26. PubMed PMID: 3371647. 15: Torres BA, Johnson HM. Arginine vasopressin (AVP) replacement of helper cell requirement in IFN-gamma production. Evidence for a novel AVP receptor on mouse lymphocytes. J Immunol. 1988 Apr 1;140(7):2179-83. PubMed PMID: 2965181. 16: Banks WA, Kastin AJ, Horvath A, Michals EA. Carrier-mediated transport of vasopressin across the blood-brain barrier of the mouse. J Neurosci Res. 1987;18(2):326-32. PubMed PMID: 3694715. 17: Lang MA, Handler JS, Gainer H. Neurohypophysial peptide potencies in cultured anuran epithelia (A6). Am J Physiol. 1986 Jul;251(1 Pt 2):R77-81. PubMed PMID: 3014910. 18: Langs DA, Smith GD, Stezowski JJ, Hughes RE. Structure of pressinoic acid: the cyclic moiety of vasopressin. Science. 1986 Jun 6;232(4755):1240-2. PubMed PMID: 3704648. 19: Le-Nguyen D, Rivier J. Use of carboethoxysulfenyl chloride for disulfide bond formation. Int J Pept Protein Res. 1986 Mar;27(3):285-92. PubMed PMID: 2872176. 20: Johnson HM, Torres BA. Regulation of lymphokine production by arginine vasopressin and oxytocin: modulation of lymphocyte function by neurohypophyseal hormones. J Immunol. 1985 Aug;135(2 Suppl):773s-775s. PubMed PMID: 3925016.

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