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CRF (human, rat)

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CRF (human, rat) has been found to be an endogenous peptide agonist and could stimulate the release of ACTH from the anterior pituitary.

Category

Peptide Inhibitors

Catalog number

BAT-010010

CAS number

86784-80-7

Molecular Formula

C208H344N60O63S2

Molecular Weight

4758.00

Specification
Reference Reading

IUPAC Name

(4S)-5-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S,3S)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-4-methylsulfanylbutanoyl]amino]propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]amino]-5-oxopentanoic acid

Synonyms

Corticotropin-releasing factor (human); Corticotropin-releasing factor (sheep), 2-L-glutamic acid-22-L-alanine-23-L-arginine-25-L-glutamic acid-38-L-methionine-39-L-glutamic acid-41-L-isoleucinamide-; L-Isoleucinamide, L-seryl-L-α-glutamyl-L-α-glutamyl-L-prolyl-L-prolyl-L-isoleucyl-L-seryl-L-leucyl-L-α-aspartyl-L-leucyl-L-threonyl-L-phenylalanyl-L-histidyl-L-leucyl-L-leucyl-L-arginyl-L-α-glutamyl-L-valyl-L-leucyl-L-α-glutamyl-L-methionyl-L-alanyl-L-arginyl-L-alanyl-L-α-glutamyl-L-glutaminyl-L-leucyl-L-alanyl-L-glutaminyl-L-glutaminyl-L-alanyl-L-histidyl-L-seryl-L-asparaginyl-L-arginyl-L-lysyl-L-leucyl-L-methionyl-L-α-glutamyl-L-isoleucyl-; Corticobiss; Corticorelin; Corticorelin human; Corticotropin-releasing factor (horse); Corticotropin-releasing factor (Mesocricetus auratus); Corticotropin-releasing factor (rat); Human ACTH-releasing factor; Human corticorelin; Human corticotropin-releasing factor; Human corticotropin-releasing hormone; Human corticotropin-releasing hormone-41; Human CRF; Human CRF(1-41); Human/rat CRF; MCI 028; Rat ACTH-releasing hormone; Rat corticotropin-releasing factor; Rat corticotropin-releasing factor-41; Rat CRF; Rat CRF(1-41); Rat CRF-41; Rat hypothalamic CRF; Rat/human corticotropin-releasing factor; Rat/human CRF; rCRF-41; H-Ser-Glu-Glu-Pro-Pro-Ile-Ser-Leu-Asp-Leu-Thr-Phe-His-Leu-Leu-Arg-Glu-Val-Leu-Glu-Met-Ala-Arg-Ala-Glu-Gln-Leu-Ala-Gln-Gln-Ala-His-Ser-Asn-Arg-Lys-Leu-Met-Glu-Ile-Ile-NH2

Related CAS

86297-72-5 (Deleted CAS)

Appearance

White Solid

Purity

≥95% by HPLC

Sequence

SEEPPISLDLTFHLLREVLEMARAEQLAQQAHSNRKLMEII-NH2

Storage

Store at -20°C

InChI

InChI=1S/C208H344N60O63S2/c1-30-106(20)161(165(215)291)263-202(328)163(108(22)32-3)264-184(310)129(58-67-157(285)286)243-182(308)131(70-78-333-29)246-187(313)134(80-99(6)7)250-176(302)118(45-36-37-71-209)237-174(300)120(47-39-73-225-207(218)219)239-194(320)143(89-152(214)276)256-197(323)145(94-270)260-193(319)141(87-115-91-222-96-227-115)248-169(295)112(26)230-172(298)122(51-60-149(211)273)240-177(303)123(52-61-150(212)274)234-168(294)111(25)232-185(311)133(79-98(4)5)249-181(307)124(53-62-151(213)275)241-178(304)125(54-63-153(277)278)235-167(293)110(24)229-171(297)119(46-38-72-224-206(216)217)233-166(292)109(23)231-173(299)130(69-77-332-28)245-179(305)127(56-65-155(281)282)244-188(314)138(84-103(14)15)258-200(326)160(105(18)19)262-183(309)128(57-66-156(283)284)242-175(301)121(48-40-74-226-208(220)221)238-186(312)135(81-100(8)9)251-189(315)136(82-101(10)11)252-192(318)142(88-116-92-223-97-228-116)255-191(317)140(86-114-43-34-33-35-44-114)259-203(329)164(113(27)272)266-196(322)139(85-104(16)17)253-195(321)144(90-159(289)290)257-190(316)137(83-102(12)13)254-198(324)146(95-271)261-201(327)162(107(21)31-2)265-199(325)147-49-41-75-267(147)205(331)148-50-42-76-268(148)204(330)132(59-68-158(287)288)247-180(306)126(55-64-154(279)280)236-170(296)117(210)93-269/h33-35,43-44,91-92,96-113,117-148,160-164,269-272H,30-32,36-42,45-90,93-95,209-210H2,1-29H3,(H2,211,273)(H2,212,274)(H2,213,275)(H2,214,276)(H2,215,291)(H,222,227)(H,223,228)(H,229,297)(H,230,298)(H,231,299)(H,232,311)(H,233,292)(H,234,294)(H,235,293)(H,236,296)(H,237,300)(H,238,312)(H,239,320)(H,240,303)(H,241,304)(H,242,301)(H,243,308)(H,244,314)(H,245,305)(H,246,313)(H,247,306)(H,248,295)(H,249,307)(H,250,302)(H,251,315)(H,252,318)(H,253,321)(H,254,324)(H,255,317)(H,256,323)(H,257,316)(H,258,326)(H,259,329)(H,260,319)(H,261,327)(H,262,309)(H,263,328)(H,264,310)(H,265,325)(H,266,322)(H,277,278)(H,279,280)(H,281,282)(H,283,284)(H,285,286)(H,287,288)(H,289,290)(H4,216,217,224)(H4,218,219,225)(H4,220,221,226)/t106-,107-,108-,109-,110-,111-,112-,113+,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,160-,161-,162-,163-,164-/m0/s1

InChI Key

GBONBLHJMVUBSJ-FAUHKOHMSA-N

Canonical SMILES

CCC(C)C(C(=O)N)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)C(CC1=CNC=N1)NC(=O)C(C)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)O)NC(=O)C(C)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CCSC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC2=CNC=N2)NC(=O)C(CC3=CC=CC=C3)NC(=O)C(C(C)O)NC(=O)C(CC(C)C)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C4CCCN4C(=O)C5CCCN5C(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CO)N

1.Species differences of 11beta-hydroxysteroid dehydrogenase type 2 function in human and rat term placenta determined via LC-MS/MS.

Heussner K1, Ruebner M2, Huebner H2, Rascher W1, Menendez-Castro C1, Hartner A1, Fahlbusch FB3, Rauh M1. Placenta. 2016 Jan;37:79-84. doi: 10.1016/j.placenta.2015.11.009. Epub 2015 Nov 25.

INTRODUCTION: Glucocorticoid-induced fetal programming has been associated with negative metabolic and cardiovascular sequelae in the adult. The placental enzyme 11beta-hydroxysteroid dehydrogenase type 2 (11β-HSD2) shields the fetus from maternal glucocorticoid excess by catalyzing the conversion of these hormones into biologically inactive derivatives. In vivo experiments addressing placental barrier function are mostly conducted in rodents. Therefore we set out to characterize species-specific differences of rat and human placental 11β-HSD2 steroid turnover, introducing Liquid Chromatography Tandem Mass-Spectrometry (LC-MS/MS) as a tool for rat tissue analysis.

2.Increased Hypothalamic Levels of Endozepines, Endogenous Ligands of Benzodiazepine Receptors, in a Rat Model of Sepsis.

Clavier T1, Besnier E, Lefevre-Scelles A, Lanfray D, Masmoudi O, Pelletier G, Castel H, Tonon MC, Compère V. Shock. 2016 Jan 8. [Epub ahead of print]

BACKGROUND: The mechanisms involved in septic anorexia are mainly related to the secretion of inflammatory cytokines. The term endozepines designates a family of neuropeptides, including the octadecaneuropeptide (ODN), originally isolated as endogenous ligands of benzodiazepine receptors. Previous data showed that ODN, produced and released by astrocytes, is a potent anorexigenic peptide. We have studied the effect of sepsis by means of a model of cecal ligation and puncture (CLP) on the hypothalamic expression of endozepines (DBI mRNA and protein levels), as well as on the level of neuropeptides controlling energy homeostasis mRNAs: pro-opiomelanocortin (POMC), neuropeptide Y (NPY) and corticotropin-releasing hormone (CRH). In addition, we have investigated the effects of two inflammatory cytokines, TNF-α and IL-1β, on DBI mRNA levels in cultured rat astrocytes.

3.Traumatic Stress Promotes Hyperalgesia via Corticotropin-Releasing Factor-1 Receptor (CRFR1) Signaling in Central Amygdala.

Itoga CA1, Roltsch Hellard EA1, Whitaker AM1, Lu YL2, Schreiber AL1, Baynes BB1, Baiamonte BA1, Richardson HN3, Gilpin NW1,4. Neuropsychopharmacology. 2016 Mar 25. doi: 10.1038/npp.2016.44. [Epub ahead of print]

Hyperalgesia is an exaggerated response to noxious stimuli produced by peripheral or central plasticity. Stress modifies nociception, and humans with post-traumatic stress disorder (PTSD) exhibit co-morbid chronic pain and amygdala dysregulation. Predator odor stress produces hyperalgesia in rodents. Systemic blockade of corticotropin-releasing factor (CRF) type 1 receptors (CRFR1s) reduces stress-induced thermal hyperalgesia. We hypothesized that CRF-CRFR1 signaling in central amygdala (CeA) mediates stress-induced hyperalgesia in rats with high stress reactivity. Adult male Wistar rats were exposed to predator odor stress in a conditioned place avoidance paradigm and indexed for high (Avoiders) and low (Non-Avoiders) avoidance of predator odor-paired context, or were unstressed Controls. Rats were tested for the latency to withdraw hindpaws from thermal stimuli (Hargreaves test). We used pharmacological, molecular, and immunohistochemical techniques to assess the role of CRF-CRFR1 signaling in CeA in stress-induced hyperalgesia.

4.Effects of acute treadmill running at different intensities on activities of serotonin and corticotropin-releasing factor neurons, and anxiety- and depressive-like behaviors in rats.

Otsuka T1, Nishii A1, Amemiya S1, Kubota N1, Nishijima T1, Kita I2. Behav Brain Res. 2016 Feb 1;298(Pt B):44-51. doi: 10.1016/j.bbr.2015.10.055. Epub 2015 Nov 2.

Accumulating evidence suggests that physical exercise can reduce and prevent the incidence of stress-related psychiatric disorders, including depression and anxiety. Activation of serotonin (5-HT) neurons in the dorsal raphe nucleus (DRN) is implicated in antidepressant/anxiolytic properties. In addition, the incidence and symptoms of these disorders may involve dysregulation of the hypothalamic-pituitary-adrenal axis that is initiated by corticotropin-releasing factor (CRF) neurons in the hypothalamic paraventricular nucleus (PVN). Thus, it is possible that physical exercise produces its antidepressant/anxiolytic effects by affecting these neuronal activities. However, the effects of acute physical exercise at different intensities on these neuronal activation and behavioral changes are still unclear. Here, we examined the activities of 5-HT neurons in the DRN and CRF neurons in the PVN during 30 min of treadmill running at different speeds (high speed, 25 m/min; low speed, 15m/min; control, only sitting on the treadmill) in male Wistar rats, using c-Fos/5-HT or CRF immunohistochemistry.