TT2-32 acetate

Catalog Number
ACMA00027302
Category
Others
Molecular Weight
1007.19
Molecular Formula
C47H62N10O11S2

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Specification

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.
Synonyms
TT2-32; TT2 32; TT232; TT-232; TT 232; CAP 232; CAP-232; CAP232; TLN-232; TLN 232; TLN232
IUPAC 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
Canonical SMILES
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
InChI
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
InChI Key
DPXYLBGOBOVJQG-YWCUHKGISA-N
Solubility
Soluble in DMSO
Appearance
Solid powder
Shelf Life
>3 years if stored properly
Storage
Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
Alternative CAS
147159-51-1 (free base)
Biological Target
TT 232 is a peptide agonist for sst1/sst4 somatostatin receptors.
Drug Formulation
This drug may be formulated in DMSO
Elemental Analysis
C, 56.05; H, 6.20; N, 13.91; O, 17.47; S, 6.37
Exact Mass
946.383
HS Tariff Code
2934.99.03.00
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/
Shipping
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.
Stock Solution Storage
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
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