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Antisauvagine-30

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Antisauvagine-30 is a selective, competitive and potent corticotropin-releasing factor CRF2 receptor antagonist with Kd values of 153.6 and 1.4 nM for binding to rat CRF1 and mouse CRF2β receptors respectively. It prevents stress-enhanced fear conditioning and MEK 1/2-dependent activation of ERK1/2 in mice in vivo. It inhibits sauvagine-stimulated cAMP accumulation in HEK-mCRF2β cells.

Category

Peptide Inhibitors

Catalog number

BAT-015244

CAS number

220673-95-0

Molecular Formula

C161H274N48O46S

Molecular Weight

3650.29

Specification
Reference Reading

IUPAC Name

(2S,3S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]propanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxybutanoyl]amino]-3-methylpentanoic acid

Synonyms

(D-Phe11,His12)-Sauvagine (11-40); H-D-Phe-His-Leu-Leu-Arg-Lys-Met-Ile-Glu-Ile-Glu-Lys-Gln-Glu-Lys-Glu-Lys-Gln-Gln-Ala-Ala-Asn-Asn-Arg-Leu-Leu-Leu-Asp-Thr-Ile-OH; D-phenylalanyl-L-histidyl-L-leucyl-L-leucyl-L-arginyl-L-lysyl-L-methionyl-L-isoleucyl-L-alpha-glutamyl-L-isoleucyl-L-alpha-glutamyl-L-lysyl-L-glutaminyl-L-alpha-glutamyl-L-lysyl-L-alpha-glutamyl-L-lysyl-L-glutaminyl-L-glutaminyl-L-alanyl-L-alanyl-L-asparagyl-L-asparagyl-L-arginyl-L-leucyl-L-leucyl-L-leucyl-L-alpha-aspartyl-L-threonyl-L-isoleucine; 11-D-Phenylalanine-12-L-histidine-11-40-sauvagine (11-40)

Appearance

White Lyophilized Powder

Purity

≥95%

Sequence

FHLLRKMIEIEKQEKEKQQAANNRLLLDTI

Storage

Store at -20°C

Solubility

Soluble in Acetic Acid

InChI

InChI=1S/C161H273N47O47S/c1-21-84(14)126(205-145(240)105(51-58-124(221)222)195-157(252)127(85(15)22-2)206-146(241)106(59-66-256-20)193-137(232)96(42-30-34-63-165)182-138(233)97(43-35-64-177-160(172)173)186-147(242)107(67-79(4)5)199-150(245)110(70-82(10)11)202-152(247)112(73-91-77-176-78-179-91)197-132(227)92(166)72-90-37-25-24-26-38-90)156(251)194-104(50-57-123(219)220)144(239)185-94(40-28-32-61-163)135(230)190-101(47-54-118(169)212)141(236)192-103(49-56-122(217)218)143(238)184-95(41-29-33-62-164)136(231)191-102(48-55-121(215)216)142(237)183-93(39-27-31-60-162)134(229)189-100(46-53-117(168)211)140(235)188-99(45-52-116(167)210)133(228)181-87(17)130(225)180-88(18)131(226)196-113(74-119(170)213)154(249)203-114(75-120(171)214)153(248)187-98(44-36-65-178-161(174)175)139(234)198-108(68-80(6)7)148(243)200-109(69-81(8)9)149(244)201-111(71-83(12)13)151(246)204-115(76-125(223)224)155(250)208-129(89(19)209)158(253)207-128(159(254)255)86(16)23-3/h24-26,37-38,77-89,92-115,126-129,209H,21-23,27-36,39-76,162-166H2,1-20H3,(H2,167,210)(H2,168,211)(H2,169,212)(H2,170,213)(H2,171,214)(H,176,179)(H,180,225)(H,181,228)(H,182,233)(H,183,237)(H,184,238)(H,185,239)(H,186,242)(H,187,248)(H,188,235)(H,189,229)(H,190,230)(H,191,231)(H,192,236)(H,193,232)(H,194,251)(H,195,252)(H,196,226)(H,197,227)(H,198,234)(H,199,245)(H,200,243)(H,201,244)(H,202,247)(H,203,249)(H,204,246)(H,205,240)(H,206,241)(H,207,253)(H,208,250)(H,215,216)(H,217,218)(H,219,220)(H,221,222)(H,223,224)(H,254,255)(H4,172,173,177)(H4,174,175,178)/t84-,85-,86-,87-,88-,89+,92+,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,126-,127-,128-,129-/m0/s1

InChI Key

JDWSXVUWDQFRCE-JBNJRNGTSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)N)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(C(C)O)C(=O)NC(C(C)CC)C(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(C(C)CC)NC(=O)C(CCSC)NC(=O)C(CCCCN)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC1=CNC=N1)NC(=O)C(CC2=CC=CC=C2)N

1.Development of a selective photoactivatable antagonist for corticotropin-releasing factor receptor, type 2 (CRF2).

Bonk I1, Rühmann A. Eur J Biochem. 2002 Nov;269(21):5288-94.

A novel photoactivatable analog of antisauvagine-30 (aSvg-30), a specific antagonist for corticotropin-releasing factor (CRF) receptor, type 2 (CRF2), has been synthesized and characterized. The N-terminal amino-acid d-Phe in aSvg-30 [d-Phe11,His12]Svg(11-40) was replaced by a phenyldiazirine, the 4-(1-azi-2,2,2-trifluoroethyl)benzoyl (ATB) residue. The photoactivatable aSvg-30 analog ATB-[His12]Svg was tested for its ability to displace [125I-Tyr0]oCRF or [125I-Tyr0]Svg from membrane homogenates of human embryonic kidney (HEK) 293 cells stably transfected with cDNA coding for rat CRF receptor, type 1 (rCRF1) or mouse CRF receptor, type 2beta (mCRF2beta). Furthermore, the ability of ATB-[His12]Svg(12-40) to inhibit oCRF- or Svg-stimulated cAMP production of transfected HEK 293 cells expressing either rCRF1 (HEK-rCRF1 cells) or mCRF2beta (HEK-mCRF2beta cells) was determined. Unlike astressin and photo astressin, ATB-[His12]Svg(12-40) showed high selective binding to mCRF2beta (Ki = 3.