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Application Area

TIP 39, Tuberoinfundibular Neuropeptide

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

It is a neuropeptide and parathyroid hormone 2 receptor (PTH2R) agonist.

Category

Peptide Inhibitors

Catalog number

BAT-010644

CAS number

277302-47-3

Molecular Formula

C202H325N61O54S

Molecular Weight

4504.17

Specification
Reference Reading

IUPAC Name

(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-carboxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]pyrrolidine-2-carboxylic acid

Synonyms

Ser-Leu-Ala-Leu-Ala-Asp-Asp-Ala-Ala-Phe-Arg-Glu-Arg-Ala-Arg-Leu-Leu-Ala-Ala-Leu-Glu-Arg-Arg-His-Trp-Leu-Asn-Ser-Tyr-Met-His-Lys-Leu-Leu-Val-Leu-Asp-Ala-Pro; TIP 39 (39 mer); L-seryl-L-leucyl-L-alanyl-L-leucyl-L-alanyl-L-alpha-aspartyl-L-alpha-aspartyl-L-alanyl-L-alanyl-L-phenylalanyl-L-arginyl-L-alpha-glutamyl-L-arginyl-L-alanyl-L-arginyl-L-leucyl-L-leucyl-L-alanyl-L-alanyl-L-leucyl-L-alpha-glutamyl-L-arginyl-L-arginyl-L-histidyl-L-tryptophyl-L-leucyl-L-asparagyl-L-seryl-L-tyrosyl-L-methionyl-L-histidyl-L-lysyl-L-leucyl-L-leucyl-L-valyl-L-leucyl-L-alpha-aspartyl-L-alanyl-L-proline

Purity

≥95% by HPLC

Sequence

SLALADDAAFRERARLLAALERRHWLNSYMHKLLVLDAP

Storage

Store in a cool and dry place and at 2-8°C for short term (days to weeks) or store at -20°C for long term (months to years)

Solubility

Soluble in Water

InChI

InChI=1S/C202H325N61O54S/c1-96(2)71-132(243-164(283)111(26)232-177(296)133(72-97(3)4)247-166(285)121(204)92-264)176(295)231-112(27)165(284)246-149(88-157(276)277)192(311)259-147(86-155(272)273)179(298)230-107(22)160(279)227-109(24)163(282)245-141(80-114-43-31-30-32-44-114)186(305)239-127(51-40-67-221-201(212)213)169(288)240-129(58-60-153(268)269)173(292)235-124(48-37-64-218-198(206)207)167(286)228-110(25)161(280)234-125(49-38-65-219-199(208)209)171(290)249-136(75-100(9)10)182(301)250-134(73-98(5)6)178(297)229-106(21)159(278)226-108(23)162(281)244-135(74-99(7)8)181(300)241-130(59-61-154(270)271)174(293)237-126(50-39-66-220-200(210)211)168(287)236-128(52-41-68-222-202(214)215)172(291)255-145(84-118-91-217-95-225-118)190(309)254-143(82-116-89-223-122-46-34-33-45-120(116)122)188(307)251-138(77-102(13)14)184(303)257-146(85-152(205)267)191(310)261-150(93-265)194(313)253-142(81-115-54-56-119(266)57-55-115)187(306)242-131(62-70-318-29)175(294)256-144(83-117-90-216-94-224-117)189(308)238-123(47-35-36-63-203)170(289)248-137(76-101(11)12)183(302)252-140(79-104(17)18)193(312)262-158(105(19)20)195(314)260-139(78-103(15)16)185(304)258-148(87-156(274)275)180(299)233-113(28)196(315)263-69-42-53-151(263)197(316)317/h30-34,43-46,54-57,89-91,94-113,121,123-151,158,223,264-266H,35-42,47-53,58-88,92-93,203-204H2,1-29H3,(H2,205,267)(H,216,224)(H,217,225)(H,226,278)(H,227,279)(H,228,286)(H,229,297)(H,230,298)(H,231,295)(H,232,296)(H,233,299)(H,234,280)(H,235,292)(H,236,287)(H,237,293)(H,238,308)(H,239,305)(H,240,288)(H,241,300)(H,242,306)(H,243,283)(H,244,281)(H,245,282)(H,246,284)(H,247,285)(H,248,289)(H,249,290)(H,250,301)(H,251,307)(H,252,302)(H,253,313)(H,254,309)(H,255,291)(H,256,294)(H,257,303)(H,258,304)(H,259,311)(H,260,314)(H,261,310)(H,262,312)(H,268,269)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,316,317)(H4,206,207,218)(H4,208,209,219)(H4,210,211,220)(H4,212,213,221)(H4,214,215,222)/t106-,107-,108-,109-,110-,111-,112-,113-,121-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,158-/m0/s1

InChI Key

TYWILDUTZVAJDB-IESKOEEDSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC2=CN=CN2)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)NC(CCSC)C(=O)NC(CC6=CN=CN6)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)N7CCCC7C(=O)O)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CO)N

1.Infant positioning in daily life may mediate associations between physiotherapy and child development-video-analysis of an early intervention RCT.

Dirks T1, Hielkema T2, Hamer EG3, Reinders-Messelink HA4, Hadders-Algra M5. Res Dev Disabil. 2016 Jun-Jul;53-54:147-57. doi: 10.1016/j.ridd.2016.02.006. Epub 2016 Feb 23.

BACKGROUND: Paediatric physiotherapy (PPT) in high-risk infants comprises family involvement, but it is unclear whether parents mediate the intervention effect. We demonstrated in a randomized controlled trial in high-risk infants comparing the family centred programme Coping and Caring for infants with special needs (COPCA) and Traditional Infant Physiotherapy (TIP) that process evaluation revealed associations between COPCA-characteristics and outcome.

2.[The PTH/PTHrP receptor: biological implications].

Ureña P1. Nefrologia. 2003;23 Suppl 2:12-7.

Since its discovery in 1923, the parathyroid hormone (PTH), was thought to be the sole hormone capable of stimulating bone resorption, renal tubular calcium reabsorption, calcitriol synthesis, and urinary excretion of phosphate. However, in 1987, the PTHrP (PTH-related peptide), was demonstrated to share most of the biological actions of PTH through the activation of the same receptor. This receptor was cloned in 1992 and named PTH/PTHrP receptor or PTH-R1. Both, PTH and PTHrP bind with great affinity to PTH-R1 and stimulate a signal transduction system involving different G-proteins, phospholipase C, and adenylate cyclase. A third member of the PTH family, the TIP-39 (tuberoinfundibular peptide), binds and activates another PTH receptor (PTH-R2). There is evidence for other PTH receptors, a PTH-R3, probably specific for PTHrP in keratinocytes, kidney, placenta and a PTH-R4 specific for C-terminal PTH fragments. Activating mutations in the PTH-R1 gene cause Jansen type metaphyseal chondrodysplasia, whereas inactivating mutations are responsible for Blomstrand type rare chondrodysplasia and enchondromatosis.

3.Agonist-specific regulation of parathyroid hormone (PTH) receptor type 2 activity: structural and functional analysis of PTH- and tuberoinfundibular peptide (TIP) 39-stimulated desensitization and internalization.

Bisello A1, Manen D, Pierroz DD, Usdin TB, Rizzoli R, Ferrari SL. Mol Endocrinol. 2004 Jun;18(6):1486-98. Epub 2004 Feb 26.

The human PTH receptor type 2 (PTH2R) is activated by PTH and tuberoinfundibular peptide of 39 residues (TIP39), resulting in cAMP and intracellular Ca signaling. We now report that, despite these similarities, PTH and TIP39 elicit distinct responses from PTH2R. First, TIP39 induced beta-arrestin and protein kinase Cbeta mobilization and receptor internalization, whereas PTH did not. However, PTH stimulated trafficking of these molecules for a chimeric PTH2R containing the N terminus and third extracellular loop of PTH receptor type 1 (PTH1R). Second, whereas PTH-stimulated cAMP activity was brief and rapidly resensitized, the response to TIP39 was sustained and partly desensitized for a prolonged period. PTH2R desensitization was mediated by beta-arrestin interaction with the C terminus (amino acids 426-457) of PTH2R, whereas beta-arrestin mobilization had a minor influence on PTH2R internalization in response to TIP39, as shown with C terminus deletion mutants and/or dominant negative forms of beta-arrestin and dynamin.

4.Treatment of patients with cirrhosis and refractory ascites using LeVeen shunt with titanium tip: comparison with therapeutic paracentesis.

Ginès A1, Planas R, Angeli P, Guarner C, Salerno F, Ginès P, Saló J, Rodriguez N, Domènech E, Soriano G, et al. Hepatology. 1995 Jul;22(1):124-31.

It has recently been suggested that insertion of a titanium tip at the venous end of the LeVeen shunt drastically reduces the rate of shunt obstruction. To assess whether the LeVeen shunt with titanium tip improves the results obtained with therapeutic paracentesis, 81 patients with cirrhosis and refractory ascites were randomly assigned to therapy with paracentesis plus intravenous albumin (42 patients) or LeVeen shunt with titanium tip (39 patients). If patients were readmitted for ascites during follow-up, those in the first group were treated with paracentesis, and those in the LeVeen shunt group by the insertion of a new valve or a new shunt if obstruction was demonstrated. During first hospitalization, both treatments were equally effective in removing ascites. Complications were similar in both groups except for a higher rate of severe bacterial infection in the LeVeen shunt group. The mean duration of hospitalization was shorter in the paracentesis group than in the shunt group.