Dérivés d'acides aminés

µ-Conotoxin GIIIA from the Conus geographus L. venom blocks with very high selectivity the muscle subtype of sodium channels.

Antiinflammatory peptide with high homology to somatostatin.

Cell-penetrating peptide, a dimer of the protein transduction domain (47-58) of HIV-tat protein.

Active molecules as peptides can be readily conjugated to this cell-permeable peptide by the mercapto moiety.

The amyloidogenic peptide hormone amylin 1-37 (or Islet Amyloid Polypeptide, IAPP), KCNTATCATQRLANFLVHSSNNFGAILSSTNVGSNTY amide, has been isolated from the amyloid-rich pancreases of diabetic patients. hIAPP forms fibrillar peptide deposits in the pancreatic islets of Langerhans, which may be related to death of the insulin-producing islet β-cells in type 2 diabetes mellitus.

<p>Bachem ID: 4012616.</p>

This product is used for the attachment of the FLAG-tag by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), the prototypical reaction of click chemistry, as described for example by Wang and coworkers. In addition, Azido-PEG3-FLAG contains a PEG-linker. The resulting FLAG-tagged molecules can be detected or purified immunologically, using dye labeled, enzyme coupled or, for purification, immobilized anti-FLAG antibodies.

<p>Bachem ID: 4012222.</p>

The orphan G protein-coupled receptor APJ has been shown to be a coreceptor for human and simian immunodeficiency virus (HIV and SIV) strains. As long as apelin is an endogenous ligand for the APJ receptor, inhibitory effects of apelin peptides on HIV infection have been examined and it has been found that the apelin peptides inhibit the entry of some HIV-1 and HIV-2 strains into NP-2/CD4 cells expressing APJ. For apelin-36 the strongest inhibitory efficiency has been reported.

Potent and long-acting CRF antagonist.

<p>Bachem ID: 4034491.</p>

<p>Bachem ID: 4095874.</p>

<p>Bachem ID: 4030533.</p>

Orexin A (OXA, hypocretin-1) is a hypothalamic neuropeptide regulating the feeding behavior. Central administration of orexin A to rats stimulated food consumption in a dose-dependent manner. The effect persisted at 4 h after injection, as orexin A seems to be resistant to peptidases. Orexin A specifically binds a G protein-coupled receptor, OX₁R (IC₅₀ = 20 nM to displace 50 % of radiolabeled orexin A bound to this receptor). Orexin A produced in the amygdala induces wakefulness and plays a role in the induction of human emotions. Narcolepsy has been associated with orexin deficiency. The peptide also corresponds to bovine, canine, ovine, and porcine orexin A.

Peptide YY (3-36) and peptide YY are both synthesized by the gastrointestinal tract and released into the circulation after a meal. Peptide YY (3-36) is a Y₂ receptor subtype agonist, whereas peptide YY is non-selective for Y₁ and Y₂ receptor subtypes. It has been suggested that Y₁ and Y₂ receptor subtype binding affinities depend on their secondary and tertiary solution state structures.

<p>Bachem ID: 4034865.</p>

<p>Bachem ID: 4029353.</p>

Glucagon sulfoxide shows the same maximal glucose mobilizing activity in rat hepatocytes as native glucagon, but it is less potent, suggesting a crucial role of methionine in the binding of glucagon to its hepatic receptor.

Exendin (9-39) is a potent glucagon-like peptide 1 (GLP-1) receptor antagonist. It has also been described as an antagonist of the putative exendin receptor. Exendin (9-39) blocks the stimulatory action of GLP-1 (7- 36) amide and of exendin-4 on cAMP production in pancreatic acini. Moreover, exendin (9-39) was shown to be safely used to abolish the incretin effect of GLP-1 without interfering with the control of insulin secretion by circulating nutrients.

Potential impurity of exenatide.

GLP-2 administration to mice or rats promotes stimulation of crypt cell proliferation and inhibition of enterocyte apoptosis resulting in hyperplasia of the small bowel villous epithelium. It also exerts trophic effects in animal models of both small and large bowel injury such as experimental small bowel resection or chemically induced colitis. In addition to stimulation of epithelial proliferation, GLP-2 also acutely regulates gastric emptying and exerts rapid metabolic effects promoting stimulation of intestinal hexose transport. The actions of GLP-2 are transduced via the GLP-2 receptor, a member of the glucagon-secretin G protein-coupled receptor superfamily.

α-Conotoxin MI has been isolated from the venom of the sea snail Conus imperialis. The conotoxin is a ligand for nicotinic acetylcholine receptors. It is highly active against the neuromuscular receptor in frogs but not in mice.

Iberiotoxin (IbTx), from the venom of the scorpion Buthus tamulus, shows 68% sequence homology with charybdotoxin, another scorpion-derived peptidyl toxin. Although these two toxins both inhibit the high conductance Ca²⁺ activated K⁺ channel, they appear to bind at different sites on the channel and modulate channel activity by different mechanisms. Thus, iberiotoxin can be used to selectively study the function of the high conductance Ca²⁺ activated K⁺ channel.

<p>Bachem ID: 4034554.</p>

KALA amphipathic peptide, a low-molecular weight cationic amphipathic peptide was able to bind to DNA, to destabilize membranes and to mediate transfection of plasmid DNA in various cell lines. Thus, KALA provides a starting point for a family of peptides that incorporate other functions to improve DNA delivery systems.

GLP-1 (7-36) amide is secreted from the lower small intestine and shows a strong insulinotropic effect. GLP-1 (7-36) amide is considered as the most important incretin hormone. Its action is mediated by receptors expressed by the endocrine pancreatic B-cells. Considerable interest has focused on the development of this peptide as a therapeutic strategy for non-insulin-dependent (type 2 ) diabetes mellitus and associated neuropathy.

GRF is the hypothalamic peptide hormone that specifically stimulates synthesis and release of the growth hormone by somatotropic cells of the anterior pituitary gland.

<p>Bachem ID: 4011654.</p>

Potential degradation product of exenatide resulting from aspartimide formation and cleavage.

Rat amylin (rIAPP) lacks the fibril-forming capacity of human amylin (hIAPP). As a consequence, toxic effects have been reported for the human but not for the rat peptide amide.

As antagonist of CCK, PP inhibits pancreatic sedretion. PP also acts on the gastrointestinal motility, food intake, and metabolism.

A synthetic chromogenic substrate for the determination of serinic and thiol proteases, e.g. urokinase, trypsin, cathepsin B, cathepsin L, and papain.

The cyclic MSH analog HS024 showed about 20-fold selectivity and very high affinity (Ki = 0.29 nM) for the melanocortin-4 (MC4) receptor and also increased the food intake, indicating that blockade of the MC4 receptor is a highly effective way to increase feeding.

Competitive inhibitor of alanine racemase, Ki 0.005 mM.

<p>Bachem ID: 4031196.</p>

This GIP fragment has potent insulinotropic activity in the isolated, perfused rat pancreas but greatly reduced somatostatinotropic activity in the isolated perfused rat stomach. The site responsible for insulinotropic activity apparently lies between residues 19 and 30 of GIP.

GRF antagonist.

<p>Bachem ID: 4037181.</p>

<p>Bachem ID: 4030885.</p>

Bombesin-like peptide from porcine spinal cord; exhibits a potent stimulant effect on smooth muscle of rat uterus. Neuromedin C microinjected into the amygdala inhibited feeding in rats.

Fmoc-D-AzF can be incorporated in peptides as precursor of p-aminophenylalanine. Levinson et al. reduced the azido group on-resin with a large excess of tributylphosphine in DMF.

Substrate for FK-506 binding proteins (FKBPs, also called macrophilins) and cyclophilins, which belong to the group of peptidyl prolyl cis-trans isomerases (PPIases). Suc-AFPF-pNA has been used for an uncoupled protease-free assay of PPIase activity.

<p>Bachem ID: 4002971.</p>

Ac-RGK(Ac)-AMC, fluorogenic substrate for assaying histone deacetylase (HDAC) activity in a two-step enzymatic reaction. The assay consists of the initial lysine deacetylation by HDAC followed by the release of the fluorescent group by trypsin.

<p>Bachem ID: 4027358.</p>

Special fluorogenic substrate for aminopeptidase M (microsomal alanyl aminopeptidase, membrane aminopeptidase, APN). Furthermore, the major aminopeptidase from human skeletal muscle showed highest activity with this substrate.

Z-GGL-AMC, a fluorogenic substrate for the chymotrypsin-like activity of the 20S proteasome. Sensitive fluorogenic substrate for subtilisins BPN’ and Carlsberg. Also cleaved by ClpP protease from M. tuberculosis.

In search of competitive α-MSH antagonists, the hexapeptide GHRP-6 has been recognized as a selective inhibitor of α-MSH activity in the frog skin bioassay. It is identical in sequence with a growth hormone-releasing peptide analog, (His¹,Lys⁶)-GHRP, which selectively releases GH in vitro and in a wide variety of species in vivo. GHRP-6 also acts as a functional antagonist of somatostatin in the somatotrope cells.

Suc-LLVY-pNA, chromogenic substrate analog to the proteasome substrate Suc-LLVY-AMC.

A substrate for flavivirus proteases such as West Nile virus protease, yellow fever virus NS3 protease, and dengue virus NS2B-NS3 protease.Boc-GRR-AMC is cleaved by type II Metacaspases Atmc4 and Atmc9 of Arabidopsis thaliana. Stock solutions of Boc-GRR-AMC are best prepared in DMSO.

Desamidation of neuropeptide Y suppresses almost all of NPY effects.

DL-APNE (or NAPNE), a chromogenic substrate for chymotrypsin and microbial serine proteases, e.g. subtilisin. It is also hydrolyzed by cathepsin G. NAPNE was used by Yakoby and Raskin to determine the inhibitory activity of trypsin and chymotrypsin.

<p>Bachem ID: 4096166.</p>

Impurity of tetracosactide, which is a synthetic peptide analog of the human adrenocorticotropic hormone that stimulates the production of cortisol.

Chemotactic peptide antagonist.

(Trp⁶³,Trp⁶⁴)-C3a (63-77), synthetic superagonist analog of complement 3a, exhibited the greatest biological potency of all peptides tested. The peptide was 12-15 times more active than natural C3a. Such an optimal potency was obtained by introducing a bulky hydrophobic group such as Trp-Trp which binds more strongly to the hydrophobic site on the receptor than does the corresponding site on the natural ligand.

Chromogenic substrate for dipeptidyl aminopeptidase II (DPPII), also cleaved by a dipeptidyl peptidase V (DPP V) from Aspergillus fumigatus.

Substrate for urokinase.

Ac-WEHD-CHO, a very potent reversible inhibitor of caspase-1 (ICE). It bears the optimal tetrapeptide recognition motif for this enzyme. With a Ki of 56 pM it belongs to the most potent reversible, peptide-based inhibitors described for any protease. For caspase-8 a Ki of 21.1 nM has been reported.

This enzyme substrate was used to test the concept of substrate-assisted catalysis with an engineered bacterial serine endopeptidase, subtilisin. Suc-FAAF-pNA has been employed for assaying subtilisins from psychrophilic bacteria and myroilysin, a metalloproteinase from the deep sea bacterium Myroides profundi.

ACTH (1–14) is a fragment of the ACTH hormone, which stimulates the adrenal cortex and the secretion of glucocorticoids such as cortisol. ACTH (1–14) is an agonist of the melanocortin-1 and 3 receptor (K1 = 0.836 ± 0.33 and 48,3 ± 9,0 nmol/L respectively).

Competitive inhibitor of acyl peptide hydrolase.

Short-term administration of deslorelin stimulates the formation of LH and FSH, which induce an increase in the production of testosterone and estradiol. Prolonged administration of the GnRH agonist causes a sustained down-regulation of circulating LH and FSH levels and hence suppression of steroidogenesis.

Substrate for leucine aminopeptidase.

N-terminal sequence of dynorphin A and the neoendorphins.

Nafarelin is a synthetic decapeptide agonist of the luteinizing hormone-releasing hormone (LHRH) which is approximately 200 times more potent than the natural peptide. Like LHRH nafarelin stimulates the release of the gonadotrophins luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the anterior pituitary which in turn results in an initial increase of testosterone and estradiol synthesis. Continuous administration of LHRH or one of its analogs causes a sustained down-regulation of circulating LH and FSH levels leading to a suppression of testicular and ovarian steroidogenesis. Currently, nafarelin is indicated for the treatment of endometriosis and for the use in reproductive medicine. CAS Number (nafarelin acetate): 86220-42-0.

Z-VEID-AFC, fluorogenic substrate for caspase-6 (Mch2).

Suc-AAPL-pNA, a sensitive substrate for human and especially porcine pancreatic elastases. Substrate for leucine endopeptidase from the psychrotropic bacillus B. cereus.

A ghrelin receptor antagonist. Asakawa et al. found that peripherally administered (D-Lys³)-GHRP-6 (HwkWfK-amide) decreased food intake in lean mice, in mice with diet induced obesity, and in ob/ob obese mice, and that repeated administration of this GHS-R antagonist decreased body weight gain and improved glycaemic control in ob/ob obese mice.

RR-AMC, fluorogenic substrate for dipeptidyl peptidase III (DPP III).

AAF-AMC, fluorogenic substrate for tripeptidyl peptidases I and II and for tripeptide aminopeptidase EC 3.4.11.4.

Suc-AAVA-pNA has been used for assaying hamster chymase 2.

Substrate for aminopeptidase M and leucine aminopeptidase.

Human ghrelin (GHR), the endogenous ligand of the growth hormone secretagogue receptor (GHS-R), potently stimulates GH release. The Ser³ octanoyl ester turned out to be essential for generating this activity. Ghrelin plays an important role in the short-time regulation of appetite and in the long-time regulation of energy balance and glucose homeostasis. A number of studies showed that ghrelin is also involved in the regulation of gastrointestinal, cardiovascular, and immune functions as well as in bone metabolism.

In contrast to the octanoylated peptide, the non-acylated ghrelin does not activate growth hormone secretagogue receptor-expressing cells. The peptide decreases food intake and gastroduodenal motility in conscious rats, probably by crossing the blood-brain barrier and activating the brain receptor directly.

Fluorogenic substrate for farnesyl diphosphate farnesyltransferase (FTase). The pentapeptide is based on the C-terminal region of H-Ras with a dansyl group attached to the N-terminus. Due to farnesylation of the cysteine thiol group the dansyl group is placed from a polar to a non-polar molecular environment which is accompanied by an enhancement of fluorescence and a shift to a lower wavelength emission maximum of the dansyl group. Complete conversion of the product results in a decrease of the emission maximum wavelength from 565 nm to 515 nm together with a 13-fold enhancement in fluorescence intensity at 505 nm. Dansyl-GCVLS can be used for continuously monitoring FTase activity in the presence of farnesyl diphosphate (FPP) at 505 nm using an excitation wavelength of 340 nm (kcat = 0.5 s⁻¹; Km = 1.4 µM). It represents a useful tool for screening potential FTase inhibitors. The substrate is highly specific to FTase and is not recognized by geranylgeranyl transferse type I (GGTase I). Concentrations of stock solutions of Dns-GCVLS can be calculated from the extinction coefficient of the dansyl moiety (ε₃₄₀ = 4250 M⁻¹cm⁻¹ in 20 mM Tris-HCl, pH 7.5, 10 mM EDTA).

CTAP, an analog of CTOP, is a selective µ-opioid receptor antagonist.

<p>Bachem ID: 4002476.</p>

Bz-VGR-AMC has been employed as substrate for the tricorn core protease from Thermoplasma acidophilum. Bz-VGR-AMC is used for measuring the trypsin-like activity of the 20S proteasome, in combination with e.g. Suc-LLVY-AMC (for assaying its chymotrypsin-like activity) and Z-LLE-AMC (for determining its PGPH activity).

Ac-DEVD-CMK irreversibly inhibits caspase-3. It is also active towards caspases-6, -7, -8, and -10.

A specific substrate for dipeptidyl aminopeptidase IV (DPP IV). Gly-Pro-MNA is very suitable for histochemical purposes.

Leu-OMe (LME) causes lysosomal disruption and death of human monocytes (M phi). In addition, LME removed natural killer cell (NK) activity from human peripheral mononuclear cells (PBM). During incubation of human lymphocytes with Leu-OMe, the dipeptide Leu-Leu-OMe which is responsible for the NK-toxicity, is formed.

Substrate for aminopeptidase B (arginine aminopeptidase) and cathepsin H.

<p>Bachem ID: 4096177.</p>

CCK-8 exhibits various gastrointestinal effects as contraction of the gallbladder and stimulation of pancreatic secretion and gastrointestinal transit. In rats, CCK-8 facilitated the uptake of leptin from peripheral circulation to cerebrospinal fluid and its access to the hypothalamus.

Rat pTH (1-34) suppressed appositional bone formation by cultured rat cranial osteoblasts.

<p>Bachem ID: 4012160.</p>

A good substrate for carboxypeptidase Y. Educt for the synthesis of fluorinated α-keto carboxylic inhibitors of chymotrypsin published by Parisi and Abeles.

<p>Bachem ID: 4030687.</p>

A good substrate for carboxypeptidase Y, the Streptomyces griseus carboxypeptidase, and the membrane-associated carboxypeptidase ysc-lambda.

Substrate for chymotrypsin and carboxypeptidase Y.

The prolyl oligopeptidase (POP) substrate Z-AP-pNA was used in combination with Z-GP-pNA and Z-AA-pNA for characterizing the prolyl oligopeptide of of the hyperthermophile Pyrococcus furiosus.

<p>Bachem ID: 4003545.</p>

Chimeric rabies virus glycoprotein fragment peptide (RVG-9R peptide) was able to bind and transduce siRNA to neuronal cells in vitro, resulting in efficient gene silencing. Repeated administration of RVG-9R-bound siRNA did not induce inflammatory cytokines nor anti-peptide antibodies.

Suc-AAPR-pNA, a substrate for wild-type and K188D/D189K trypsins (Km = 32.8 mM respectively 50.8 mM).

<p>Bachem ID: 4104812.</p>

PEG acrylate-based hydrogels have been modified with the RGD peptide YRGDS to improve their biocompatibility. YRGDS can be radioiodinated.

Apelin-17 is an endogenous ligand of the human orphan G protein-coupled receptor APJ, reported to act as a coreceptor of CD4 for human and simian immunodeficiency viruses. Apelin-17 and apelin-13 represent the predominant molecular forms of apelin present in the whole brain, hypothalamus, and plasma. Like apelin-13, apelin-17 exhibited a high activity on extracellular acidification rate and strongly inhibited forskolin-stimulated cAMP production in CHO cells expressing the human or the rat apelin receptor. The peptide might play a crucial role in the maintenance of body fluid homeostasis by counteracting AVP (arginine vasopressin) actions through inhibition of AVP neuron activity and AVP release.

This peptide is the pp60 c-src carboxy-terminal phosphoregulatory peptide phosphorylated at Tyr⁵²⁷. The peptide fragment is involved in the regulation of kinase activity by binding intramolecularly or intermolecularly to the SH2 domain of the pp60 c-src protein.

FAM-HIV-1 Tat 47-57 was used as a fluorescent probe for studying the interaction between the p53 tetramerization domain and HIV-1 Tat protein.

Muramyl dipeptide (MDP) inhibits HIV replication in CD4⁺ H9 lymphocytes..

Caloxin 2A1 is a selective extracellular inhibitor of the plasma membrane Ca²⁺-pump.

AFP-pNA, substrate for prolyl tripeptidyl aminopeptidases from the periodontal pathogens Porphyromonas gingivalis and Prevotella nigrescens.