CH 275Potent and selective sst1 receptor agonist CAS# 174688-78-9 |
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| Cas No. | 174688-78-9 | SDF | Download SDF |
| PubChem ID | 90488765 | Appearance | Powder |
| Formula | C74H96N14O15S2 | M.Wt | 1485.8 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 0.30 mg/ml in water | ||
| Sequence | CKFFWXTFTSC (Modifications: Cyclic Cys1-Cys11, X=4-[[(1-methylethyl)amino]met | ||
| Chemical Name | (4R,7R,10R,13S,16R,19R,22S,25S,28S,31R,34R)-34-amino-31-(4-aminobutyl)-13,25,28-tribenzyl-10,16-bis[(1R)-1-hydroxyethyl]-7-(hydroxymethyl)-22-(1H-indol-3-ylmethyl)-9,12,15,18,21,24,27,30,33-nonaoxo-19-[[4-[(propan-2-ylamino)methyl]phenyl]methyl]-1,2-dithia-5,8,11,14,17,20,23,26,29,32-decazacyclopentatriacontane-4-carboxylic acid | ||
| SMILES | CC(C)NCC1=CC=C(C=C1)CC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CNC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC3=CNC4=CC=CC=C43)CC5=CC=CC=C5)CC6=CC=CC=C6)CCCCN)N)C(=O)O)CO)C(C)O)CC7=CC=CC=C7)C(C)O | ||
| Standard InChIKey | LFOPEPKKBBIGHF-RXUBGYFDSA-N | ||
| Standard InChI | InChI=1S/C74H98N14O14S2/c1-43(2)77-37-50-29-27-49(28-30-50)35-59-70(97)88-64(45(4)91)73(100)86-60(34-48-22-12-7-13-23-48)71(98)87-63(44(3)90)72(99)80-52(40-89)39-79-62(74(101)102)42-104-103-41-54(76)65(92)81-56(26-16-17-31-75)66(93)82-57(32-46-18-8-5-9-19-46)67(94)83-58(33-47-20-10-6-11-21-47)68(95)85-61(69(96)84-59)36-51-38-78-55-25-15-14-24-53(51)55/h5-15,18-25,27-30,38,43-45,52,54,56-64,77-79,89-91H,16-17,26,31-37,39-42,75-76H2,1-4H3,(H,80,99)(H,81,92)(H,82,93)(H,83,94)(H,84,96)(H,85,95)(H,86,100)(H,87,98)(H,88,97)(H,101,102)/t44-,45-,52-,54+,56-,57+,58+,59-,60+,61+,62+,63-,64-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent somatostatin receptor 1 (sst1) agonist; displays selectivity for sst1 (IC50 values are 30.9 nM, 345 nM, > 1 μM, > 10 μM and > 10μM for human sst1, sst3, sst4, sst2 and sst5 respectively). Attenuates somatostatin release in the rat nucleus accumbens. |
CH 275 Dilution Calculator
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A comparative analysis of human and mouse islet G-protein coupled receptor expression.[Pubmed:28422162]
Sci Rep. 2017 Apr 19;7:46600.
G-protein coupled receptors (GPCRs) are essential for islet function, but most studies use rodent islets due to limited human islet availability. We have systematically compared the GPCR mRNA expression in human and mouse islets to determine to what extent mouse islets can be used as surrogates for human islets to study islet GPCR function, and we have identified species-specific expression of several GPCRs. The A3 receptor (ADORA3) was expressed only in mouse islets and the A3 agonist MRS 5698 inhibited glucose-induced insulin secretion from mouse islets, with no effect on human islets. Similarly, mRNAs encoding the galanin receptors GAL1 (GALR1), GAL2 (GALR2) and GAL3 GALR3) were abundantly expressed in mouse islets but present only at low levels in human islets, so that it reads (GALR3) and galanin inhibited insulin secretion only from mouse islets. Conversely, the sst1 receptor (SSTR1) was abundant only in human islets and its selective activation by CH 275 inhibited insulin secretion from human islets, with no effect on mouse islets. Our comprehensive human and mouse islet GPCR atlas has demonstrated that species differences do exist in islet GPCR expression and function, which are likely to impact on the translatability of mouse studies to the human context.
The somatostatin receptor (sst1) modulates the release of somatostatin in the nucleus accumbens of the rat.[Pubmed:15380378]
Neuropharmacology. 2004 Sep;47(4):612-8.
The aim of the present study was to examine the function of the somatostatin receptor (sst(1)) in the nucleus accumbens (NAc) of the basal ganglia. Radioligand binding studies were performed in rats to assess the presence of the receptor, while in vivo microdialysis studies were performed to examine its role in somatostatin release. CH-275, which is selective for sst(1), MK-678, selective for sst(2) and L-803,087, selective for sst(4) receptors displaced [(125)I]-Tyr(11)-somatostatin specific binding in a concentration-dependent manner with IC(50) values of 75, 0.21 and 11 nM, respectively. Infusion of CH-275 (10(-5), 10(-6) or 10(-7) M) in the NAc of freely moving rats resulted in a decrease in somatostatin levels only at the concentration of 10(-5) M. This effect was reversed by 10(-5) M of the selective sst(1) antagonist SRA-880. The sst(1) agonist L-797,591 (10(-5) M) mimicked the effect of CH-275, while MK-678 and L-803,087 at the same concentration were unable to influence somatostatin levels. These results provide functional evidence to demonstrate that the sst(1) receptor modulates somatostatin release in the basal ganglia.
Potent somatostatin undecapeptide agonists selective for somatostatin receptor 1 (sst1).[Pubmed:11405660]
J Med Chem. 2001 Jun 21;44(13):2238-46.
A family of analogues of des-AA(1,2,5)-[DTrp(8)/D2Nal(8)]-SRIF that contain a 4-(N-isopropyl)-aminomethylphenylalanine (IAmp) at position 9 was identified that has high affinity and selectivity for human somatostatin receptor subtype 1 (sst1). The binding affinities of des-AA(1,2,5)-[DTrp(8),IAmp(9)]-SRIF (c[H-Cys-Lys-Phe-Phe-DTrp-IAmp-Thr-Phe-Thr-Ser-Cys-OH], CH-275) (7), des-AA(1,5)-[Tyr(2),DTrp(8),IAmp(9)]-SRIF (CH-288) (16), des-AA(1,2,5)-[Tyr(7),DTrp(8),IAmp(9)]-SRIF (23), and des-AA(1,2,5)-[DTrp(8),IAmp(9),Tyr(11)]-SRIF (25) are about (1)/(7), (1)/(4), (1)/(125), and (1)/(4) that of SRIF-28 (1) to sst1, respectively, about (1)/(65), (1)/(130), <(1)/(1000), and <(1)/(150) that of 1 to sst3, respectively, and about or less than (1)/(1000) that of 1 to the other three human SRIF receptor subtypes. A substitution of DTrp(8) by D2Nal(8) in 7 to yield des-AA(1,2,5)-[D2Nal(8),IAmp(9)]-SRIF (13) and in 16 to yield des-AA(1,5)-[Tyr(2),D2Nal(8),IAmp(9)]-SRIF (17) was intended to increase chemical stability, selectivity, and affinity and resulted in two analogues that were less potent or equipotent with similar selectivity, respectively. Carbamoylation of the N-terminus as in des-AA(1,2,5)-[DTrp(8),IAmp(9),Tyr(11)]-Cbm-SRIF (27) increased affinity slightly as well as improved selectivity. Monoiodination of 25 to yield 26 and of 27 to yield 28 resulted in an additional 4-fold increase in affinity at sst1. Desamination of the N-terminus of 17 to yield 18, on the other hand, resulted in significant loss of affinity. Attempts at reducing the size of the ring with maintenance of selectivity failed in that des-AA(1,4,5,13)-[Tyr(2),DTrp(8),IAmp(9)]-SRIF (33) and des-AA(1,4,5,6,12,13)-[Tyr(2),DTrp(8),IAmp(9)]-SRIF (34) progressively lost affinity for all receptors. Both des-AA(1,2,5)-[DTrp(8),IAmp(9),Tyr(11)]-Cbm-SRIF (27) and des-AA(1,2,5)-[DCys(3),DTrp(8),IAmp(9),Tyr(11)]-Cbm-SRIF (29) show agonistic activity in a cAMP assay; therefore, the structural basis for the agonist property of this family of analogues is not contingent upon the chirality of the Cys residue at position 3 as shown to be the case in 18-membered ring SRIF octapeptides. None of the high affinity structures described here showed receptor antagonism. We have prepared the radiolabeled des-AA(1,2,5)-[DTrp(8),IAmp(9),(125)ITyr(11)]-SRIF ((125)I-25) and des-AA(1,2,5)-[DTrp(8),IAmp(9), (125)ITyr(11)]-Cbm-SRIF ((125)I-27), used them as in vitro tracers, and found them to be superior to des-AA(1,5)-[(125)ITyr(2),DTrp(8),IAmp(9)]-SRIF ((125)I-16) for the detection of sst1 tumors in receptor autoradiography studies.
Structural basis for the binding specificity of a SSTR1-selective analog of somatostatin.[Pubmed:10329447]
Biochem Biophys Res Commun. 1999 May 19;258(3):689-94.
The availability of subtype-specific agonists and antagonists for somatostatin (SS) receptors (SSTRs) will be important for elucidation of the function of each receptor isoform in vivo. A SS analog, des-AA1,2,5-[D-Trp8, IAmp9]SS (CH275), has been shown previously to bind preferentially to SSTR1. In this report, we identify structural determinants in the ligand and receptor responsible for the selective binding of CH275 to SSTR1 by modifying both the ligand and the receptor. We propose that IAmp9 in CH275, like Lys9 in SS, interacts with Asp137 in the middle of the third transmembrane domain of SSTR1 to form an ion pair, while other residues unique to SSTR1 conbribute to binding selectivity of CH275 for SSTR1. Replacement of Asp137 with Asn resulted in loss of binding of radiolabeled SS and decreased potencies of both SS and CH275 to induce a change in the extracellular acidification rate measured by microphysiometry. The structural determinants for specific binding to SSTR1 were mapped in chimeric SSTR1/SSTR2 receptors. One chimera, 2beta, with the N-terminus to second transmembrane domain (TM2) from SSTR2 and the remainder of the receptor from SSTR1, had low affinity for CH275. Furthermore, when a single residue, Leu107, in TM2 of SSTR1 was replaced with Phe, the corresponding residue in SSTR2, a 20-fold decrease in affinity for CH275 with no significant change in affinity for SS was observed. A reciprocal change from Phe to Leu in the chimeric receptor 2beta resulted in a 10-fold increase in affinity for CH275. Thus, Leu107 is an important determinant for CH275 binding to SSTR1. To identify the moiety in CH275 which could interact with Leu107, a new analog des-AA1,2,5-[D-Trp8, Amp9]SS was prepared. This analog bound to both SSTR1 and SSTR2 with similar affinities; thus, subtype selectivity was lost. Collectively, these data support a binding model for CH275 in which the positively charged IAmp interacts with the negatively charged Asp137 in TM3 of SSTR1 and the isopropyl group of IAmp forms a hydrophobic interaction with Leu107 in TM2.
