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CART (55-102) (rat)

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Cocaine- and amphetamine-regulated transcript (CART) is a neuropeptide protein with potent appetite-suppressing activity. It inhibits normal and starvation-induced feeding and blocks the neuropeptide Y-induced feeding response.

Category

Peptide Inhibitors

Catalog number

BAT-015138

CAS number

209615-79-2

Molecular Formula

C226H367N65O65S7

Molecular Weight

5259.21

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(1R,1aS,4aS,6R,9S,10aS,12S,13aS,15S,18S,21S,24S,27R,32R,35S,38R,41S,44S,50S,53S,56S,62S,65S,68S,71S,76S,79S,85S,88S,91R)-91-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-2-[[2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-carboxybutanoyl]amino]hexanoyl]amino]hexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]-5-oxopentanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-4-methylsulfanylbutanoyl]amino]-24,44,62-tris(4-aminobutyl)-9-(2-amino-2-oxoethyl)-76-(3-amino-3-oxopropyl)-15-benzyl-50-[(2S)-butan-2-yl]-4a,53,65-tris(3-carbamimidamidopropyl)-79-(2-carboxyethyl)-35,88-bis(carboxymethyl)-10a-[(1R)-1-hydroxyethyl]-12,13a-bis(hydroxymethyl)-56,71,85-trimethyl-18,21,41-tris(2-methylpropyl)-2a,5a,7,8a,10,11a,13,14a,16,19,22,25,34,37,40,43,46,49,52,55,58,61,64,67,70,73,75,78,81,84,87,90,96-tritriacontaoxo-68-propan-2-yl-3,4,29,30,93,94-hexathia-3a,6a,8,9a,11,12a,14,15a,17,20,23,26,33,36,39,42,45,48,51,54,57,60,63,66,69,72,74,77,80,83,86,89,97-tritriacontazatetracyclo[36.35.22.206,32.097,101]pentadecahectane-27-carbonyl]amino]-4-methylpentanoic acid

Synonyms

H-Ile-Pro-Ile-Tyr-Glu-Lys-Lys-Tyr-Gly-Gln-Val-Pro-Met-Cys-Asp-Ala-Gly-Glu-Gln-Cys-Ala-Val-Arg-Lys-Gly-Ala-Arg-Ile-Gly-Lys-Leu-Cys-Asp-Cys-Pro-Arg-Gly-Thr-Ser-Cys-Asn-Ser-Phe-Leu-Leu-Lys-Cys-Leu-OH (Disulfide bridge: Cys14-Cys32, Cys20-Cys40, Cys34-Cys37); L-isoleucyl-L-prolyl-L-isoleucyl-L-tyrosyl-L-alpha-glutamyl-L-lysyl-L-lysyl-L-tyrosyl-glycyl-L-glutaminyl-L-valyl-L-prolyl-L-methionyl-L-cysteinyl-L-alpha-aspartyl-L-alanyl-glycyl-L-alpha-glutamyl-L-glutaminyl-L-cysteinyl-L-alanyl-L-valyl-L-arginyl-L-lysyl-glycyl-L-alanyl-L-arginyl-L-isoleucyl-glycyl-L-lysyl-L-leucyl-L-cysteinyl-L-alpha-aspartyl-L-cysteinyl-L-prolyl-L-arginyl-glycyl-L-threonyl-L-seryl-L-cysteinyl-L-asparagyl-L-seryl-L-phenylalanyl-L-leucyl-L-leucyl-L-lysyl-L-cysteinyl-L-leucine (14->32),(20->40),(34->47)-tris(disulfide)

Appearance

White Lyophilized Solid

Purity

≥95%

Sequence

IPIYEKKYGQVPMCDAGEQCAVRKGARIGKLCDCPRGTSCNSFLLKCL (Disulfide bridge: Cys14-Cys32, Cys20-Cys40, Cys34-Cys47)

Storage

Store at -20°C

Solubility

Soluble in Water

Application

appetite suppressant

InChI

InChI=1S/C226H367N65O65S7/c1-24-117(16)175(235)221(353)290-85-44-58-162(290)215(347)288-179(119(18)26-3)218(350)274-147(94-126-61-65-128(296)66-62-126)202(334)262-140(70-74-172(307)308)193(325)259-132(50-32-37-78-229)188(320)258-133(51-33-38-79-230)190(322)269-145(93-125-59-63-127(295)64-60-125)186(318)248-100-168(302)254-137(67-71-163(232)297)197(329)286-177(116(14)15)222(354)291-86-45-57-161(291)214(346)264-141(75-87-357-23)195(327)280-155-106-359-360-107-156-211(343)273-150(97-174(311)312)205(337)283-159-110-363-362-109-158(212(344)275-151(223(355)356)91-114(10)11)279-191(323)134(52-34-39-80-231)260-199(331)142(88-111(4)5)267-200(332)143(89-112(6)7)268-203(335)146(92-124-46-28-27-29-47-124)270-206(338)152(103-292)276-204(336)148(95-165(234)299)271-209(341)157(282-207(339)153(104-293)277-219(351)180(123(22)294)284-170(304)102-247-185(317)130(53-40-81-242-224(236)237)263-213(345)160-56-43-84-289(160)220(159)352)108-361-358-105-154(278-194(326)139(68-72-164(233)298)261-192(324)138(69-73-171(305)306)255-167(301)99-245-181(313)120(19)251-198(330)149(96-173(309)310)272-210(155)342)208(340)252-122(21)183(315)285-176(115(12)13)217(349)265-135(54-41-82-243-225(238)239)189(321)257-129(48-30-35-76-227)184(316)246-98-166(300)250-121(20)182(314)256-136(55-42-83-244-226(240)241)196(328)287-178(118(17)25-2)216(348)249-101-169(303)253-131(49-31-36-77-228)187(319)266-144(90-113(8)9)201(333)281-156/h27-29,46-47,59-66,111-123,129-162,175-180,292-296H,24-26,30-45,48-58,67-110,227-231,235H2,1-23H3,(H2,232,297)(H2,233,298)(H2,234,299)(H,245,313)(H,246,316)(H,247,317)(H,248,318)(H,249,348)(H,250,300)(H,251,330)(H,252,340)(H,253,303)(H,254,302)(H,255,301)(H,256,314)(H,257,321)(H,258,320)(H,259,325)(H,260,331)(H,261,324)(H,262,334)(H,263,345)(H,264,346)(H,265,349)(H,266,319)(H,267,332)(H,268,335)(H,269,322)(H,270,338)(H,271,341)(H,272,342)(H,273,343)(H,274,350)(H,275,344)(H,276,336)(H,277,351)(H,278,326)(H,279,323)(H,280,327)(H,281,333)(H,282,339)(H,283,337)(H,284,304)(H,285,315)(H,286,329)(H,287,328)(H,288,347)(H,305,306)(H,307,308)(H,309,310)(H,311,312)(H,355,356)(H4,236,237,242)(H4,238,239,243)(H4,240,241,244)/t117-,118-,119-,120-,121-,122-,123+,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,175-,176-,177-,178-,179-,180-/m0/s1

InChI Key

XXBSYMBQWAWYIX-ZCQIAPNTSA-N

Canonical SMILES

CCC(C)C1C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC2CSSCC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(CSSCC3C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)N4CCCC4C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N3)CO)C(C)O)CCCNC(=N)N)NC(=O)C(NC2=O)CC(=O)O)C(=O)NC(CC(C)C)C(=O)O)CCCCN)CC(C)C)CC(C)C)CC5=CC=CC=C5)CO)CC(=O)N)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1)CCCNC(=N)N)C)CCCCN)CCCNC(=N)N)C(C)C)C)CCC(=O)N)CCC(=O)O)C)CC(=O)O)NC(=O)C(CCSC)NC(=O)C6CCCN6C(=O)C(C(C)C)NC(=O)C(CCC(=O)N)NC(=O)CNC(=O)C(CC7=CC=C(C=C7)O)NC(=O)C(CCCCN)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CC8=CC=C(C=C8)O)NC(=O)C(C(C)CC)NC(=O)C9CCCN9C(=O)C(C(C)CC)N)CC(C)C)CCCCN

1.Microinjection of CART (cocaine- and amphetamine-regulated transcript) peptide into the nucleus accumbens inhibits the cocaine-induced upregulation of dopamine receptors and locomotor sensitization.

Peng Q1, Sun X2, Liu Z3, Yang J2, Oh KW4, Hu Z5. Neurochem Int. 2014 Sep;75:105-11. doi: 10.1016/j.neuint.2014.06.005. Epub 2014 Jun 19.

Repeated exposure to addictive drugs enhances dopamine receptor (DR) signaling and the ultimate phosphorylation of the cyclic adenosine 5'-monophosphate (cAMP)-response element-binding protein (CREB)-regulated cocaine- and amphetamine-regulated transcript (CART) expression in the nucleus accumbens (NAcc). These effects are known to contribute to the expression of behavioral sensitization. CART peptides are neuropeptides that modulate drug reward and reinforcement. The present experiments investigated the effects of CART 55-102 microinjection into the NAcc on (1) the phosphorylation of CREB, (2) cAMP/protein kinase A (PKA) signaling and (3) extracellular signal-regulated kinase (ERK) phosphorylated kinase signaling. Here, we show that repeated microinjections into the NAcc of CART 55-102 peptides (1.0 or 2.5μg, 0.5μl/side) attenuates cocaine-induced enhancements of D1R, D2R and D3R phosphorylation in this sites. Furthermore, the microinjection of CART 55-102 followed by repeated injections of cocaine (15mg/kg) dose-dependently blocked the enhancement of cAMP levels, PKA activity and pERK and pCREB levels on the fifth day of cocaine administration.

2.Efferent projections of neuropeptide Y-expressing neurons of the dorsomedial hypothalamus in chronic hyperphagic models.

Lee SJ1, Kirigiti M, Lindsley SR, Loche A, Madden CJ, Morrison SF, Smith MS, Grove KL. J Comp Neurol. 2013 Jun 1;521(8):1891-914. doi: 10.1002/cne.23265.

The dorsomedial hypothalamus (DMH) has long been implicated in feeding behavior and thermogenesis. The DMH contains orexigenic neuropeptide Y (NPY) neurons, but the role of these neurons in the control of energy homeostasis is not well understood. NPY expression in the DMH is low under normal conditions in adult rodents but is significantly increased during chronic hyperphagic conditions such as lactation and diet-induced obesity (DIO). To understand better the role of DMH-NPY neurons, we characterized the efferent projections of DMH-NPY neurons using the anterograde tracer biotinylated dextran amine (BDA) in lactating rats and DIO mice. In both models, BDA- and NPY-colabeled fibers were limited mainly to the hypothalamus, including the paraventricular nucleus of the hypothalamus (PVH), lateral hypothalamus/perifornical area (LH/PFA), and anteroventral periventricular nucleus (AVPV). Specifically in lactating rats, BDA-and NPY-colabeled axonal swellings were in close apposition to cocaine- and amphetamine-regulated transcript (CART)-expressing neurons in the PVH and AVPV.

3.Cocaine-and-Amphetamine Regulated Transcript (CART) peptide attenuates dopamine- and cocaine-mediated locomotor activity in both male and female rats: lack of sex differences.

Job MO1, Perry J2, Shen LL2, Kuhar MJ2. Neuropeptides. 2014 Apr;48(2):75-81. doi: 10.1016/j.npep.2014.01.002. Epub 2014 Jan 10.

Cocaine-and-Amphetamine Regulated Transcript peptide (CART peptide) is known for having an inhibitory effect on dopamine (DA)- and cocaine-mediated actions and is postulated to be a homeostatic, regulatory factor in the nucleus accumbens (NAc). Some sex differences in cocaine-mediated locomotor activity (LMA) and in the expression and function of CART peptide have been reported. However, it is not known if the inhibitory effect of CART peptide on cocaine-mediated LMA is sexually dimorphic. In this study, the effects of CART 55-102 on LMA due to intra-NAc DA and i.p. cocaine were determined in male and female Sprague-Dawley rats. The results show that CART 55-102 blunted or reduced both the DA- and cocaine-induced LMA in both males and females. In conclusion, CART peptide is effective in blunting DA- and cocaine-mediated LMA in both males and females.

4.Nucleus accumbens cocaine-amphetamine regulated transcript mediates food intake during novelty conflict.

Burghardt PR1, Krolewski DM2, Dykhuis KE2, Ching J2, Pinawin AM2, Britton SL3, Koch LG4, Watson SJ5, Akil H5. Physiol Behav. 2016 May 1;158:76-84. doi: 10.1016/j.physbeh.2016.02.035. Epub 2016 Feb 27.

Obesity is a persistent and pervasive problem, particularly in industrialized nations. It has come to be appreciated that the metabolic health of an individual can influence brain function and subsequent behavioral patterns. To examine the relationship between metabolic phenotype and central systems that regulate behavior, we tested rats with divergent metabolic phenotypes (Low Capacity Runner: LCR vs. High Capacity Runner: HCR) for behavioral responses to the conflict between hunger and environmental novelty using the novelty suppressed feeding (NSF) paradigm. Additionally, we measured expression of mRNA, for peptides involved in energy management, in response to fasting. Following a 24-h fast, LCR rats showed lower latencies to begin eating in a novel environment compared to HCR rats. A 48-h fast equilibrated the latency to begin eating in the novel environment. A 24-h fast differentially affected expression of cocaine-amphetamine regulated transcript (CART) mRNA in the nucleus accumbens (NAc), where 24-h of fasting reduced CART mRNA in LCR rats.