TT2-32 acetate
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MedKoo CAT#: 597971

CAS#: 147159-51-1

Description: TT2-32, also known as TLN-232 and CAP232, is a somatostatin structural derivative with antitumor activity. TT-232 inhibited tyrosine kinase activity of tumor cell lines and this inhibition correlated well with the inhibition of cell proliferation of a large number of cancer cell lines in vitro and reduces the size of different tumors in animal models in vivo. The antitumor efficacy of TT-232 has been found to be associated with the induction of apoptosis in tumor cells, resulting in highly selective elimination of tumor tissue. TT-232 was found to be devoid of GH release inhibitory activity but to possess strong antitumor effects. It binds with a high affinity to SSTR1 and SSTR4. This compound was also found to inhibit inflammation in a number of experimental models.

Chemical Structure

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TT2-32 acetate
CAS# 147159-51-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 597971
Name: TT2-32 acetate
CAS#: 147159-51-1
Chemical Formula: C47H62N10O11S2
Exact Mass: 946.38
Molecular Weight: 1,007.192
Elemental Analysis: C, 56.05; H, 6.20; N, 13.91; O, 17.47; S, 6.37

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
200mg USD 2950 Ready to ship
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Related CAS #: TT2-32 acetate   147159-51-1 (free base)   147159-51-1 (TFA)   d8-TT2-32 acetate    

Synonym: TT2-32; TT2 32; TT232; TT-232; TT 232; CAP 232; CAP-232; CAP232; TLN-232; TLN 232; TLN232;

IUPAC/Chemical Name: (4R,7S,10R,13S,16R)-10-((1H-indol-3-yl)methyl)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)-16-((R)-2-amino-3-phenylpropanamido)-7-(4-aminobutyl)-13-(4-hydroxybenzyl)-6,9,12,15-tetraoxo-1,2-dithia-5,8,11,14-tetraazacycloheptadecane-4-carboxamide acetate

InChi Key: DPXYLBGOBOVJQG-YWCUHKGISA-N

InChi Code: InChI=1S/C45H58N10O9S2.C2H4O2/c1-25(56)38(39(48)58)55-45(64)37-24-66-65-23-36(53-40(59)31(47)19-26-9-3-2-4-10-26)44(63)51-34(20-27-14-16-29(57)17-15-27)42(61)52-35(21-28-22-49-32-12-6-5-11-30(28)32)43(62)50-33(41(60)54-37)13-7-8-18-46;1-2(3)4/h2-6,9-12,14-17,22,25,31,33-38,49,56-57H,7-8,13,18-21,23-24,46-47H2,1H3,(H2,48,58)(H,50,62)(H,51,63)(H,52,61)(H,53,59)(H,54,60)(H,55,64);1H3,(H,3,4)/t25-,31-,33+,34+,35-,36+,37+,38+;/m1./s1

SMILES Code: O=C([C@@H](NC([C@H](CCCCN)NC([C@@H](CC1=CNC2=C1C=CC=C2)NC([C@H](CC3=CC=C(O)C=C3)N4)=O)=O)=O)CSSC[C@H](NC([C@H](N)CC5=CC=CC=C5)=O)C4=O)N[C@@H]([C@H](O)C)C(N)=O.CC(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:

Biological target: TT 232 is a peptide agonist for sst1/sst4 somatostatin receptors.
In vitro activity: The present report describes TT-232-induced signalling events in A431 cells, where a 4-h preincubation with the peptide irreversibly induced a cell death program. Early intracellular signals of TT-232 include a transient two-fold activation of the extracellular signal-regulated kinase (ERK2) and a strong and sustained activation of the stress-activated protein kinases c-Jun NH(2)-terminal kinase (JNK)/SAPK and p38MAPK. Blocking the signalling to ERK or p38MAPK activation had no effect on the TT-232-induced cell killing. At the commitment time for inducing cell death, TT-232 decreased EGFR-tyrosine phosphorylation and prevented epidermial growth factor (EGF)-induced events like cRaf-1 and ERK2 activation. Signalling to ERK activation by FCS, phorbol 12-myristate 13-acetate (PMA) and platelet-derived growth factor (PDGF) was similarly blocked. The data suggest that TT-232 triggers an apoptotic type of cell death, concomitant with a strong activation of JNK and a blockade of cellular ERK2 activation pathways. Reference: Cell Signal. 2001 Oct;13(10):717-25. https://pubmed.ncbi.nlm.nih.gov/11602182/
In vivo activity: The aim of this study was to examine the effects of TT-232, a heptapeptide sst(4)/sst(1) receptor agonist in airway inflammation models in the mouse. Acute pneumonitis was evoked by intranasal lipopolysaccharide 24 h before measurement. Chronic inflammation was induced by ovalbumin inhalation on days 28, 29 and 30 after i.p. sensitization on days 1 and 14. TT-232 induced an about 50% inhibitory action on bronchoconstriction after administration of a single 500 μg/kg i.p. dose. Inhalation of increasing concentrations (5.5–22 mM) of the muscarinic receptor agonist carbachol evoked a concentration-dependent bronchoconstriction shown by the Penh curves. TT-232 (500 μg/kg i.p.) significantly inhibited endotoxin-induced airway hyperreactivity after a single acute administration and after repeated injections. These results suggest that stable, somatostatin sst(4) receptor-selective agonists could be potential candidates for the development of a completely novel group of anti-inflammatory drugs for the treatment of airway inflammation and hyperresponsiveness. Reference: Eur J Pharmacol. 2008 Jan 14;578(2-3):313-22. https://pubmed.ncbi.nlm.nih.gov/17961545/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 0.00

Preparing Stock Solutions

The following data is based on the product molecular weight 1,007.19 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
Formulation protocol: 1.Vántus T, Kéri G, Krivickiene Z, Valius M, Steták A, Keppens S, Csermely P, Bauer PI, Bökönyi G, Declercq W, Vandenabeele P, Merlevede W, Vandenheede JR. The somatostatin analogue TT-232 induces apoptosis in A431 cells: sustained activation of stress-activated kinases and inhibition of signalling to extracellular signal-regulated kinases. Cell Signal. 2001 Oct;13(10):717-25. doi: 10.1016/s0898-6568(01)00194-2. PMID: 11602182. 2.Vántus T, Kéri G, Krivickiene Z, Valius M, Steták A, Keppens S, Csermely P, Bauer PI, Bökönyi G, Declercq W, Vandenabeele P, Merlevede W, Vandenheede JR. The somatostatin analogue TT-232 induces apoptosis in A431 cells: sustained activation of stress-activated kinases and inhibition of signalling to extracellular signal-regulated kinases. Cell Signal. 2001 Oct;13(10):717-25. doi: 10.1016/s0898-6568(01)00194-2. PMID: 11602182.
In vitro protocol: 1.Vántus T, Kéri G, Krivickiene Z, Valius M, Steták A, Keppens S, Csermely P, Bauer PI, Bökönyi G, Declercq W, Vandenabeele P, Merlevede W, Vandenheede JR. The somatostatin analogue TT-232 induces apoptosis in A431 cells: sustained activation of stress-activated kinases and inhibition of signalling to extracellular signal-regulated kinases. Cell Signal. 2001 Oct;13(10):717-25. doi: 10.1016/s0898-6568(01)00194-2. PMID: 11602182.
In vivo protocol: 1.Vántus T, Kéri G, Krivickiene Z, Valius M, Steták A, Keppens S, Csermely P, Bauer PI, Bökönyi G, Declercq W, Vandenabeele P, Merlevede W, Vandenheede JR. The somatostatin analogue TT-232 induces apoptosis in A431 cells: sustained activation of stress-activated kinases and inhibition of signalling to extracellular signal-regulated kinases. Cell Signal. 2001 Oct;13(10):717-25. doi: 10.1016/s0898-6568(01)00194-2. PMID: 11602182.

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1: Varona L, Noguera JL, Casellas J, de Hijas MM, Rosas JP, Ibáñez-Escriche N. A cross-specific multiplicative binomial recursive model for the analysis of perinatal mortality in a diallel cross among three varieties of Iberian pig. Sci Rep. 2020 Dec 3;10(1):21190. doi: 10.1038/s41598-020-78346-7. PMID: 33273670; PMCID: PMC7712833.


2: Sun C, Liu M, Zhang W, Wang S, Qian G, Wang M, Zhang G. Overexpression of enolase 2 is associated with worsened prognosis and increased glycikolysis in papillary renal cell carcinoma. J Cell Physiol. 2021 May;236(5):3821-3831. doi: 10.1002/jcp.30130. Epub 2020 Nov 1. PMID: 33135164.


3: Kuriyama I, Miyazaki A, Tsuda Y, Yoshida H, Mizushina Y. Inhibitory effect of novel somatostatin peptide analogues on human cancer cell growth based on the selective inhibition of DNA polymerase β. Bioorg Med Chem. 2013 Jan 15;21(2):403-11. doi: 10.1016/j.bmc.2012.11.024. Epub 2012 Nov 29. PMID: 23266186.


4: Jung Y, Oh SH, Witek RP, Petersen BE. Somatostatin stimulates the migration of hepatic oval cells in the injured rat liver. Liver Int. 2012 Feb;32(2):312-20. doi: 10.1111/j.1478-3231.2011.02642.x. Epub 2011 Sep 14. PMID: 22098068; PMCID: PMC3253984.


5: Szolcsányi J, Pintér E, Helyes Z, Petho G. Inhibition of the function of TRPV1-expressing nociceptive sensory neurons by somatostatin 4 receptor agonism: mechanism and therapeutical implications. Curr Top Med Chem. 2011;11(17):2253-63. doi: 10.2174/156802611796904852. PMID: 21671870.


6: Kuriyama I, Miyazaki A, Tsuda Y, Yokoi T, Okada Y, Takeuchi T, Sugawara F, Yoshida H, Mizushina Y. Inhibitory effect of somatostatin Peptide analogues on DNA polymerase activity and human cancer cell proliferation. Anticancer Res. 2010 Dec;30(12):4841-9. PMID: 21187461.


7: Tejeda M, Gaal D, Hullán L, Csuka O, Schwab R, Szokoloczi O, Kéri GY. Continuous administration of the somatostatin structural derivative /TT-232/ by subcutaneously implanted osmotic pump improves the efficacy and potency of antitumor therapy in different mouse and human tumor models. Anticancer Res. 2008 Sep-Oct;28(5A):2769-74. PMID: 19035308.


8: Miyazaki A, Tsuda Y, Fukushima S, Yokoi T, Vántus T, Bökönyi G, Szabó E, Horváth A, Kéri G, Okada Y. Synthesis of somatostatin analogues containing C-terminal adamantane and their antiproliferative properties. J Med Chem. 2008 Aug 28;51(16):5121-4. doi: 10.1021/jm701599w. Epub 2008 Aug 5. PMID: 18680358.


9: Tejeda M, Gaál D, Hullán L, Schwab R, Szokoloczi O, Kéri G. Antitumor activity of the somatostatin structural derivative (TT-232), against mouse and human melanoma tumor models. Anticancer Res. 2007 Nov-Dec;27(6B):4015-9. PMID: 18225564.


10: Elekes K, Helyes Z, Kereskai L, Sándor K, Pintér E, Pozsgai G, Tékus V, Bánvölgyi A, Németh J, Szuts T, Kéri G, Szolcsányi J. Inhibitory effects of synthetic somatostatin receptor subtype 4 agonists on acute and chronic airway inflammation and hyperreactivity in the mouse. Eur J Pharmacol. 2008 Jan 14;578(2-3):313-22. doi: 10.1016/j.ejphar.2007.09.033. Epub 2007 Oct 5. PMID: 17961545.


11: Steták A, Veress R, Ovádi J, Csermely P, Kéri G, Ullrich A. Nuclear translocation of the tumor marker pyruvate kinase M2 induces programmed cell death. Cancer Res. 2007 Feb 15;67(4):1602-8. doi: 10.1158/0008-5472.CAN-06-2870. PMID: 17308100.


12: Tejeda M, Gaál D, Hullán L, Hegymegi-Barakonyi B, Kéri G. Evaluation of the antitumor efficacy of the somatostatin structural derivative TT-232 on different tumor models. Anticancer Res. 2006 Sep-Oct;26(5A):3477-83. PMID: 17094470.


13: Tejeda M, Gaál D, Hullán L, Csuka O, Schwab R, Szokoloczi O, Kéri G. A comparison of the tumor growth inhibitory effect of intermittent and continuous administration of the somatostatin structural derivative TT-232 in various human tumor models. Anticancer Res. 2006 Jul-Aug;26(4B):3011-5. PMID: 16886628.


14: Szokolóczi O, Schwab R, Peták I, Orfi L, Pap A, Eberle AN, Szüts T, Kéril G. TT232, a novel signal transduction inhibitory compound in the therapy of cancer and inflammatory diseases. J Recept Signal Transduct Res. 2005;25(4-6):217-35. doi: 10.1080/10799890500464621. PMID: 16393913.


15: Tejeda M, Gaál D, Csuka O, Kéri G. Growth inhibitory effect of the somatostatin structural derivative (TT-232) on leukemia models. Anticancer Res. 2005 Jan-Feb;25(1A):325-30. PMID: 15816555.


16: Szolcsányi J, Bölcskei K, Szabó A, Pintér E, Petho G, Elekes K, Börzsei R, Almási R, Szuts T, Kéri G, Helyes Z. Analgesic effect of TT-232, a heptapeptide somatostatin analogue, in acute pain models of the rat and the mouse and in streptozotocin-induced diabetic mechanical allodynia. Eur J Pharmacol. 2004 Sep 13;498(1-3):103-9. doi: 10.1016/j.ejphar.2004.07.085. PMID: 15363982.


17: Helyes Z, Szabó A, Németh J, Jakab B, Pintér E, Bánvölgyi A, Kereskai L, Kéri G, Szolcsányi J. Antiinflammatory and analgesic effects of somatostatin released from capsaicin-sensitive sensory nerve terminals in a Freund's adjuvant-induced chronic arthritis model in the rat. Arthritis Rheum. 2004 May;50(5):1677-85. doi: 10.1002/art.20184. PMID: 15146439.


18: Simon A, Czajlik A, Perczel A, Kéri G, Nyikos L, Emri Z, Kardos J. Binding crevice for TT-232 in a homology model of type 1 somatostatin receptor. Biochem Biophys Res Commun. 2004 Apr 16;316(4):1059-64. doi: 10.1016/j.bbrc.2004.02.161. PMID: 15044092.


19: Kéri G, Racz G, Magyar K, Orfi L, Horváth A, Schwab R, Hegymegi BB, Szende B. Pro-apoptotic and anti-apoptotic molecules affecting pathways of signal transduction. Ann N Y Acad Sci. 2003 Dec;1010:109-12. doi: 10.1196/annals.1299.018. PMID: 15033704.


20: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jan-Feb;26(1):53-84. PMID: 14988742.