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Galantide

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

Galantide, a neuropeptide, is a reversible and non-specific galanin receptor antagonist. Galantide showed a more than 10-fold higher
affinity to the galanin receptors than did galanin. Galantide was not only the very high-affinity ligand at pancreatic and Rin m 5F cell galanin receptors but it also acted as the first galanin antagonist.

Category

Peptide Inhibitors

Catalog number

BAT-015158

CAS number

138579-66-5

Molecular Formula

C104H151N25O26S

Molecular Weight

2199.53

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-1-[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxybutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-3-hydroxypropanoyl]amino]propanoyl]amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-N-[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]pentanediamide

Synonyms

Galanin (1-13)-Substance P (5-11) amide; H-Gly-Trp-Thr-Leu-Asn-Ser-Ala-Gly-Tyr-Leu-Leu-Gly-Pro-Gln-Gln-Phe-Phe-Gly-Leu-Met-NH2; glycyl-L-tryptophyl-L-threonyl-L-leucyl-L-asparagyl-L-seryl-L-alanyl-glycyl-L-tyrosyl-L-leucyl-L-leucyl-glycyl-L-prolyl-L-glutaminyl-L-glutaminyl-L-phenylalanyl-L-phenylalanyl-glycyl-L-leucyl-L-methioninamide

Appearance

White Powder

Purity

≥95%

Density

1.305±0.06 g/cm3

Boiling Point

2345.4±65.0°C (Predicted)

Sequence

GWTLNSAGYLLGPQQFFGLM-NH2

Storage

Store at -20°C

Solubility

Soluble in DMF, DMSO

InChI

InChI=1S/C104H151N25O26S/c1-54(2)39-70(91(142)113-52-87(139)129-37-20-27-80(129)103(154)120-69(33-35-82(107)134)93(144)119-68(32-34-81(106)133)94(145)124-76(44-61-23-16-13-17-24-61)99(150)123-74(43-60-21-14-12-15-22-60)92(143)112-51-86(138)116-71(40-55(3)4)95(146)118-67(89(109)140)36-38-156-11)121-96(147)72(41-56(5)6)122-98(149)75(45-62-28-30-64(132)31-29-62)117-85(137)50-111-90(141)58(9)114-102(153)79(53-130)127-100(151)78(47-83(108)135)125-97(148)73(42-57(7)8)126-104(155)88(59(10)131)128-101(152)77(115-84(136)48-105)46-63-49-110-66-26-19-18-25-65(63)66/h12-19,21-26,28-31,49,54-59,67-80,88,110,130-132H,20,27,32-48,50-53,105H2,1-11H3,(H2,106,133)(H2,107,134)(H2,108,135)(H2,109,140)(H,111,141)(H,112,143)(H,113,142)(H,114,153)(H,115,136)(H,116,138)(H,117,137)(H,118,146)(H,119,144)(H,120,154)(H,121,147)(H,122,149)(H,123,150)(H,124,145)(H,125,148)(H,126,155)(H,127,151)(H,128,152)/t58-,59+,67-,68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,88-/m0/s1

InChI Key

TZOJVPDIYKRJSM-GKPUQKAJSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(CCSC)C(=O)N)NC(=O)CNC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C3CCCN3C(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)CNC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(C(C)O)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)CN

1.Galanin and galanin-like peptide modulate vasopressin and oxytocin release in vitro: the role of galanin receptors.

Wodowska J;Ciosek J Neuropeptides. 2014 Dec;48(6):387-97. doi: 10.1016/j.npep.2014.10.005. Epub 2014 Nov 10.

Galanin (Gal) and galanin-like peptide (GALP) may be involved in the mechanisms of the hypothalamo-neurohypophysial system. The aim of the present in vitro study was to compare the influence of Gal and GALP on vasopressin (AVP) and oxytocin (OT) release from isolated rat neurohypophysis (NH) or hypothalamo-neurohypophysial explants (Hth-NH). The effect of Gal/GALP on AVP/OT secretion was also studied in the presence of galantide, the non-selective galanin receptors antagonist. Gal at concentrations of 10(-10 )M and 10(-8 )M distinctly inhibited basal and K(+)-stimulated AVP release from the NH and Hth-NH explants, whereas Gal exerted a similar action on OT release only during basal incubation. Gal added to the incubation medium in the presence of galantide did not exert any action on the secretion of either neurohormone from NH and Hth-NH explants. GALP (10(-10 )M and 10(-9 )M) induced intensified basal AVP release from the NH and Hth-NH complex as well as the release of potassium-evoked AVP from the Hth-NH. The same effect of GALP has been observed in the presence of galantide. GALP added to basal incubation medium was the reason for stimulated OT release from the NH as well as from the Hth-NH explants.

2.Stimulation of luteinizing hormone subunit gene expression by pulsatile intracerebroventricular microinjection of galanin in female rats.

Gajewska A;Zwierzchowski L;Kochman K J Neuroendocrinol. 2004 Jun;16(6):558-65.

Although galanin, which exerts its effects both at the hypothalamic and pituitary level, has been implicated as an important neuroendocrine regulator of hypothalamic-pituitary-gonadal axis activity, there is a lack of data concerning its involvement in the regulation of gonadotropin subunit gene expression. To elucidate whether galanin can influence luteinizing hormone (LH) subunit mRNA content, as well as affect gonadotropin-releasing hormone (GnRH) receptor activity, a model based on pulsatile (one pulse per hour over 5 h) galanin (1 nM) microinjections directly into the third cerebral ventricle of ovariectomized (OVX) and/or oestrogen/progesterone-pretreated rats was used. Furthermore, to determine galanin effects on GnRH-induced LH subunit mRNA synthesis, a cocktail of 1 nM GnRH and 1 nM galanin was coadministered in a pulsatile manner to OVX/steroid primed rats. Subsequently, to obtain data concerning the role of galanin receptors in the regulation of pituitary alpha (common to LH, follicle-stimulating hormone, thyroid-stimulating hormone) and LHbeta subunit gene expression, OVX/oestrogen/progesterone rats received microinjections of 1 nM of the receptor antagonist galantide and 1 nM of galanin.

3.Galanin receptors in human hypothalamus: biochemical and structural analysis.

Lorinet AM;Javoy-Agid F;Laburthe M;Amiranoff B Eur J Pharmacol. 1994 Sep 15;269(1):59-64.

Galanin receptors have been characterized in normal human hypothalamus using 125I-galanin binding assays. Competition experiments of porcine 125I-galanin binding to human hypothalamic membranes with native human, porcine and rat galanin (10(-11) M to 10(-8) M) gave comparable results with IC50 close to 0.1 nM. Scatchard analysis indicated one type of high affinity binding sites (Kd = 0.11 nM) with a capacity of 460 fmol/mg protein. Galanin-(1-15) and galanin-(2-29) inhibited tracer binding (IC50 = 1.5 nM), galanin-(3-29) and galanin-(10-29) being inactive. The galanin receptor antagonist, galantide, 10(-14) M to 10(-8) M, also strongly displaced binding of 125I-galanin to the human receptor (IC50 close to 0.15 nM). Guanine nucleotides (from 10(-8) M to 10(-4) M) decreased tracer binding to human membranes by increasing the dissociation of the galanin-receptor complexes. Structural analysis by covalent labelling indicated that the human galanin receptor behaves as a monomeric protein with a molecular mass of 54,000 daltons.