Seglitide

sst2 and sst5 agonist CAS# 81377-02-8

Seglitide

Catalog No. BCC7191----Order now to get a substantial discount!

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Chemical structure

Seglitide

3D structure

Chemical Properties of Seglitide

Cas No. 81377-02-8 SDF Download SDF
PubChem ID 3035423 Appearance Powder
Formula C44H56N8O7 M.Wt 808.98
Type of Compound N/A Storage Desiccate at -20°C
Synonyms MK 678
Solubility Soluble to 1 mg/ml in 20% ethanol / water
Sequence AYWKVF

(Modifications: Ala-1 = N-methyl-Ala, Trp-3 = D-Trp, Cyclized)

Chemical Name (2S)-6-amino-2-[[(2R)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-2-(methylideneamino)propanoyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2S)-3-methyl-1-oxo-1-[[(2S)-1-oxo-3-phenylpropan-2-yl]amino]butan-2-yl]hexanamide
SMILES CC(C)C(C(=O)NC(CC1=CC=CC=C1)C=O)NC(=O)C(CCCCN)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(C)N=C
Standard InChIKey AGPBDTZFIQXTPB-LPVZYQQFSA-N
Standard InChI InChI=1S/C44H56N8O7/c1-27(2)39(44(59)48-32(26-53)22-29-12-6-5-7-13-29)52-41(56)36(16-10-11-21-45)49-43(58)38(24-31-25-47-35-15-9-8-14-34(31)35)51-42(57)37(50-40(55)28(3)46-4)23-30-17-19-33(54)20-18-30/h5-9,12-15,17-20,25-28,32,36-39,47,54H,4,10-11,16,21-24,45H2,1-3H3,(H,48,59)(H,49,58)(H,50,55)(H,51,57)(H,52,56)/t28-,32-,36-,37-,38+,39-/m0/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.
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.
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.

Biological Activity of Seglitide

DescriptionPeptide agonist for sst2 and sst5 somatostatin receptors. IC50/Kd values (nM) at cloned human somatostatin receptors are: > 1000 (sst1), 0.2 - 1.5 (sst2), 27 - 36 (sst3), > 127 (sst4), and 0.06 - 23 (sst5).

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References on Seglitide

Antagonist effects of seglitide (MK 678) at somatostatin receptors in guinea-pig isolated right atria.[Pubmed:8104651]

Br J Pharmacol. 1993 Aug;109(4):898-9.

Somatostatin (SS) exerts a negative inotropic effect in isolated atria. Here we report that in guinea-pig isolated right atria, Seglitide, a potent cyclic hexapeptide somatostatin agonist, behaves as a competitive somatostatin receptor antagonist with pA2 values against SS14, SS25 and SS28, of 6.50 +/- 0.40, 6.24 +/- 0.08 and 6.09 +/- 0.06, respectively. Seglitide had little or no effect on the negative inotropic action of carbachol or N6-cyclohexyladenosine. Our findings indicate that the receptor-response coupling characteristics of guinea-pig atria are such that in this preparation Seglitide has low intrinsic activity and behaves specifically as a somatostatin receptor antagonist.

Molecular pharmacology of somatostatin receptors.[Pubmed:7870182]

Naunyn Schmiedebergs Arch Pharmacol. 1994 Nov;350(5):441-53.

The neuropeptide somatostatin (SRIF) is widely expressed in the brain and in the periphery in two main forms, SRIF-14 and SRIF-28. Similarly, the presence of SRIF receptors throughout the whole body has been reported. SRIF produces a variety of effects including modulation of hormone release (e.g. GH, glucagon, insulin), of neurotransmitter release (e.g. acetylcholine, dopamine, 5-HT), and its own release is modulated by many neurotransmitters. SRIF affects cognitive and behavioural processes, the endocrine system, the gastrointestinal tract and the cardiovascular system and also has tumor growth inhibiting effects. Initially, two classes of SRIF receptors have been proposed on the basis of biochemical and functional studies. However, the recent cloning of five putative SRIF receptor subtypes which belong to the G-protein coupled receptor superfamily suggests that SRIF mediates its various effects via a whole family of receptors. Here we review, in this new context, the molecular pharmacology of the SRIF receptor subtypes present in the brain and in the periphery, and address the question of nomenclature of SRIF receptors.

Cloned somatostatin receptors: identification of subtype-selective peptides and demonstration of high affinity binding of linear peptides.[Pubmed:8100350]

Mol Pharmacol. 1993 Jun;43(6):838-44.

The recent molecular cloning of the genes encoding three somatostatin (SRIF) receptor subtypes has allowed for the individual expression of these receptors in mammalian cells and characterization of their respective pharmacological profiles. In the present study, we have investigated the affinities of a battery of SRIF analogues to bind to SRIF receptor subtypes SSTR1 (cloned somatostatin complex), SSTR2, and SSTR3, as well as their abilities to inhibit the release of growth hormone from anterior pituitary cells in vitro. We labeled SSTR1 and SSTR3 receptors expressed in Chinese hamster ovary and COS-1 cells, respectively, with the metabolically stable SRIF analogue 125I-CGP 23996. SSTR2 receptors expressed in Chinese hamster ovary cells were labeled with the SSTR2-specific radioligand 125I-MK-678. Inhibition studies were performed using SRIF analogues of differing structures, including hexapeptide analogues similar to MK-678, octapeptide analogues similar to SMS 201-995, pentapeptide analogues similar to c[Ahep-Phe-D-Trp-Lys-Thr(Bzl)] (SA), and linear SRIF analogues. SSTR1 bound SRIF and SRIF-28 with high affinity and the peptide SA and its structural analogues with low affinity. The hexapeptides did not interact with SSTR1 at concentrations as high as 1 microM, and only a few of the octapeptides or linear peptides bound, with very low affinities. In contrast, 125I-MK-678 binding to SSTR2 was potently inhibited by the hexapeptides, octapeptides, and some of the linear compounds, whereas SA and its analogues did not bind to SSTR2. The potencies of the various SRIF agonists to inhibit growth hormone release in vitro was highly correlated with their potencies to inhibit radioligand binding to SSTR2, but not to SSTR1 or SSTR3. SSTR3 bound analogues of each class but with moderate to low affinities, with the exception of several linear peptides and one of the octapeptides. We report for the first time the binding affinities of linear analogues of SRIF, some of which display subnanomolar affinities and are highly selective for SRIF receptor subtypes. Most importantly, these studies identify several peptide analogues that are highly potent, specific, and selective for individual subtypes of SRIF receptors. Such information, coupled with the knowledge of the distribution of these receptor subtypes in normal and pathological tissues, will be critical for more specific experimental and therapeutic interventions.

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