Alytesin TFA | CAS#unknown | Frog skin neuropeptide

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

MedKoo CAT#: 465293

CAS#: unknown

Description: Alytesin is a neuropeptide originally isolated from frog (A. obstetricans) skin that has diverse biological activities. It induces hypertension with tachyphylaxis and increases blood glucose levels in dogs. Alytesin reduces gastric acid secretion in rats. It also induces anorexigenic effects in neonatal chicks.

Chemical Structure

Alytesin TFA

CAS# unknown

Instruction

Theoretical Analysis

MedKoo Cat#: 465293
Name: Alytesin TFA
CAS#: unknown
Chemical Formula: C70H107F3N22O19S
Exact Mass: 0.00
Molecular Weight: 1,649.816
Elemental Analysis: C, 50.96; H, 6.54; F, 3.45; N, 18.68; O, 18.43; S, 1.94

Price and Availability

Size	Price	Availability
1mg	USD 220	2 Weeks
5mg	USD 430	2 Weeks
10mg	USD 700	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Alytesin TFA; Alytesin-TFA;

IUPAC/Chemical Name: (S)-N1-((5S,8S,11S,17S,20S,23S)-11-((1H-imidazol-5-yl)methyl)-5-carbamoyl-24-(1H-indol-3-yl)-8-isobutyl-17-isopropyl-20-methyl-7,10,13,16,19,22-hexaoxo-2-thia-6,9,12,15,18,21-hexaazatetracosan-23-yl)-2-((6S,9S,15S)-6-(3-guanidinopropyl)-15-((R)-1-hydroxyethyl)-9-isobutyl-1,4,7,10,13-pentaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14-pentaazahexadecan-16-amido)pentanediamide 2,2,2-trifluoroacetate

InChi Key: UJWINXQOAQAKMA-FNFDJKIRSA-N

InChi Code: InChI=1S/C68H106N22O17S.C2HF3O2/c1-33(2)23-46(86-61(101)43(15-12-21-74-68(71)72)82-52(94)29-76-59(99)44-17-19-51(93)81-44)60(100)77-31-54(96)89-56(37(8)91)67(107)85-45(16-18-50(69)92)62(102)88-48(25-38-27-75-41-14-11-10-13-40(38)41)63(103)80-36(7)58(98)90-55(35(5)6)66(106)78-30-53(95)83-49(26-39-28-73-32-79-39)65(105)87-47(24-34(3)4)64(104)84-42(57(70)97)20-22-108-9;3-2(4,5)1(6)7/h10-11,13-14,27-28,32-37,42-49,55-56,75,91H,12,15-26,29-31H2,1-9H3,(H2,69,92)(H2,70,97)(H,73,79)(H,76,99)(H,77,100)(H,78,106)(H,80,103)(H,81,93)(H,82,94)(H,83,95)(H,84,104)(H,85,107)(H,86,101)(H,87,105)(H,88,102)(H,89,96)(H,90,98)(H4,71,72,74);(H,6,7)/t36-,37+,42-,43-,44-,45-,46-,47-,48-,49-,55-,56-;/m0./s1

SMILES Code: O=C(NCC(N[C@H](C(N[C@H](C(NCC(N[C@H](C(N[C@H](C(N[C@@H](CC1=CNC2=CC=CC=C12)C(N[C@H](C(N[C@H](C(NCC(N[C@@H](CC3=CN=CN3)C(N[C@H](C(N[C@@H](CCSC)C(N)=O)=O)CC(C)C)=O)=O)=O)C(C)C)=O)C)=O)=O)CCC(N)=O)=O)[C@@H](C)O)=O)=O)CC(C)C)=O)CCCNC(N)=N)=O)[C@@H]4CCC(N4)=O.FC(F)(C(O)=O)F

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,649.82 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: König E, Zhou M, Wang L, Chen T, Bininda-Emonds OR, Shaw C. Antimicrobial peptides and alytesin are co-secreted from the venom of the Midwife toad, Alytes maurus (Alytidae, Anura): implications for the evolution of frog skin defensive secretions. Toxicon. 2012 Nov;60(6):967-81. doi: 10.1016/j.toxicon.2012.06.015. Epub 2012 Jul 16. PMID: 22800568.

2: Cline MA, Fouse DN, Prall BC. Central and peripheral alytesin cause short- term anorexigenic effects in neonatal chicks. Neuropeptides. 2008 Jun;42(3):283-91. doi: 10.1016/j.npep.2008.02.004. Epub 2008 Apr 1. PMID: 18384875.

3: Rinnová M, Jezek J, Malon P, Lebl M. Comparative multiple synthesis of fifty linear peptides: evaluation of cotton carrier vs. T bag-benzhydrylamine resin. Pept Res. 1993 Mar-Apr;6(2):88-94. PMID: 8485341.

4: Burgevin MC, Daniel N, Doble A, Blanchard JC. The trophic effect of beta- amyloid 25-35 peptide is not mediated by NK1 or bombesin receptors. Neuroreport. 1992 Dec;3(12):1131-4. doi: 10.1097/00001756-199212000-00025. PMID: 1283535.

5: Vangsted AJ, Schwartz TW. Production of gastrin-releasing peptide-(18-27) and a stable fragment of its precursor in small cell lung carcinoma cells. J Clin Endocrinol Metab. 1990 Jun;70(6):1586-93. doi: 10.1210/jcem-70-6-1586. PMID: 1693372.

6: Kuranova IL, Churkina SI, Liudmirova VL, Filonova EB, Mumulis FK. Bombezin amfibiĭ i ego analog alitezin [Amphibian bombesin and its analog alytesin]. Bioorg Khim. 1989 Jun;15(6):748-62. Russian. PMID: 2783173.

7: Larsen PJ, Saermark T, Mikkelsen JD. An immunohistochemical demonstration of gastrin-releasing peptide (GRP) in the rat substantia nigra. J Chem Neuroanat. 1989 Mar-Apr;2(2):83-93. PMID: 2604912.

8: Roseghini M, Falconieri Erspamer G, Severini C, Simmaco M. Biogenic amines and active peptides in extracts of the skin of thirty-two European amphibian species. Comp Biochem Physiol C Comp Pharmacol Toxicol. 1989;94(2):455-60. doi: 10.1016/0742-8413(89)90097-2. PMID: 2576781.

9: Heikkila R, Trepel JB, Cuttitta F, Neckers LM, Sausville EA. Bombesin-related peptides induce calcium mobilization in a subset of human small cell lung cancer cell lines. J Biol Chem. 1987 Dec 5;262(34):16456-60. PMID: 2824495.

10: Guglietta A, Strunk CL, Irons BJ, Lazarus LH. Central neuromodulation of gastric acid secretion by bombesin-like peptides. Peptides. 1985;6 Suppl 3:75-81. doi: 10.1016/0196-9781(85)90354-7. Erratum in: Peptides 1987 May- Jun;8(3):579. PMID: 3841693.

11: McDonald TJ, Jörnvall H, Ghatei M, Bloom SR, Mutt V. Characterization of an avian gastric (proventricular) peptide having sequence homology with the porcine gastrin-releasing peptide and the amphibian peptides bombesin and alytesin. FEBS Lett. 1980 Dec 15;122(1):45-8. doi: 10.1016/0014-5793(80)80398-x. PMID: 7215543.

12: Rivier JE, Brown MR. Bombesin, bombesin analogues, and related peptides: effects on thermoregulation. Biochemistry. 1978 May 2;17(9):1766-71. doi: 10.1021/bi00602a030. PMID: 656396.

13: Rivier C, Rivier J, Vale W. The effect of bombesin and related peptides on prolactin and growth hormone secretion in the rat. Endocrinology. 1978 Feb;102(2):519-22. doi: 10.1210/endo-102-2-519. PMID: 743973.

14: Broccardo M, Falconieri Erspamer G, Melchiorri P, Negri L, de Castiglione R. Relative potency of bombesin-like peptides. Br J Pharmacol. 1975 Oct;55(2):221-7. doi: 10.1111/j.1476-5381.1975.tb07631.x. PMID: 1201380; PMCID: PMC1666799.

15: Erspamer V, Melchiorri P, Sopranzi N. The action of bombesin on the systemic arterial blood pressure of some experimental animals. Br J Pharmacol. 1972 Jul;45(3):442-50. doi: 10.1111/j.1476-5381.1972.tb08100.x. PMID: 4342029; PMCID: PMC1666167.

16: Erspamer V, Erspamer GF, Inselvini M, Negri L. Occurrence of bombesin and alytesin in extracts of the skin of three European discoglossid frogs and pharmacological actions of bombesin on extravascular smooth muscle. Br J Pharmacol. 1972 Jun;45(2):333-48. doi: 10.1111/j.1476-5381.1972.tb08087.x. PMID: 5048651; PMCID: PMC1666146.

17: Anastasi A, Erspamer V, Bucci M. Isolation and amino acid sequences of alytesin and bombesin, two analogous active tetradecapeptides from the skin of European discoglossid frogs. Arch Biochem Biophys. 1972 Feb;148(2):443-6. doi: 10.1016/0003-9861(72)90162-2. PMID: 4537042.

18: Anastasi A, Erspamer V, Bucci M. Isolation and structure of bombesin and alytesin, 2 analogous active peptides from the skin of the European amphibians Bombina and Alytes. Experientia. 1971 Feb 15;27(2):166-7. doi: 10.1007/BF02145873. PMID: 5544731.

19: Anastasi A. Alytesin and bombesin, two peptide analogs from amphibian skin. Naunyn Schmiedebergs Arch Pharmakol. 1971;269(2):135-9. doi: 10.1007/BF01003031. PMID: 4254272.

20: Erspamer V, Erpamer GF, Inselvini M. Some pharmacological actions of alytesin and bombesin. J Pharm Pharmacol. 1970 Nov;22(11):875-6. doi: 10.1111/j.2042-7158.1970.tb08465.x. PMID: 4395815.

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Alytesin TFA featured