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Isotocin

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Isotocin is a peptide hormone particularly used in the research of psychiatric afflictions, drug addiction and post-traumatic stress disorder.

Category
Peptide Inhibitors
Catalog number
BAT-015176
CAS number
550-21-0
Molecular Formula
C41H63N11O12S2
Molecular Weight
966.14
Isotocin
IUPAC Name
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-10-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S,3S)-1-[(2-amino-2-oxoethyl)amino]-3-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
Synonyms
(Ser4,Ile8)-Oxytocin; H-Cys-Tyr-Ile-Ser-Asn-Cys-Pro-Ile-Gly-NH2 (Disulfide bridge: Cys1-Cys6); L-cysteinyl-L-tyrosyl-L-isoleucyl-L-seryl-L-asparagyl-L-cysteinyl-L-prolyl-L-isoleucyl-glycinamide (1->6)-disulfide; [4-Serine,8-Isoleucine]Oxytocin; 4-L-serine-8-L-isoleucineoxytocin; (2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxo-ethyl)-10-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-sec-butyl-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(1S,2S)-1-[(2-amino-2-oxo-ethyl)carbamoyl]-2-methyl-butyl]pyrrolidine-2-carboxamide
Appearance
White Powder
Purity
≥95%
Density
1.277±0.06 g/cm3 (Predicted)
Boiling Point
1483.4±65.0°C (Predicted)
Sequence
CYISNCPIG-NH2 (Disulfide bridge: Cys1-Cys6)
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C41H63N11O12S2/c1-5-20(3)32(39(62)45-16-31(44)56)51-38(61)29-8-7-13-52(29)41(64)28-19-66-65-18-24(42)34(57)46-25(14-22-9-11-23(54)12-10-22)36(59)50-33(21(4)6-2)40(63)48-27(17-53)37(60)47-26(15-30(43)55)35(58)49-28/h9-12,20-21,24-29,32-33,53-54H,5-8,13-19,42H2,1-4H3,(H2,43,55)(H2,44,56)(H,45,62)(H,46,57)(H,47,60)(H,48,63)(H,49,58)(H,50,59)(H,51,61)/t20-,21-,24-,25-,26-,27-,28-,29-,32-,33-/m0/s1
InChI Key
XMINXPSYULINQV-XPLLYYSMSA-N
Canonical SMILES
CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(C(C)CC)C(=O)NCC(=O)N)CC(=O)N)CO
1. Isotocin neuronal phenotypes differ among social systems in cichlid fishes
Peter L Hurd, Douglas R Wylie, Sigal Balshine, Constance M O'Connor, Jason Cameron, Jennifer K Hellmann, Erin Nesjan, Isaac Y Ligocki, Ian M Hamilton, Susan E Marsh-Rollo, Adam R Reddon R Soc Open Sci . 2017 May 17;4(5):170350. doi: 10.1098/rsos.170350.
Social living has evolved numerous times across a diverse array of animal taxa. An open question is how the transition to a social lifestyle has shaped, and been shaped by, the underlying neurohormonal machinery of social behaviour. The nonapeptide neurohormones, implicated in the regulation of social behaviours, are prime candidates for the neuroendocrine substrates of social evolution. Here, we examined the brains of eight cichlid fish species with divergent social systems, comparing the number and size of preoptic neurons that express the nonapeptides isotocin and vasotocin. While controlling for the influence of phylogeny and body size, we found that the highly social cooperatively breeding species (n= 4) had fewer parvocellular isotocin neurons than the less social independently breeding species (n= 4), suggesting that the evolutionary transition to group living and cooperative breeding was associated with a reduction in the number of these neurons. In a complementary analysis, we found that the size and number of isotocin neurons significantly differentiated the cooperatively breeding from the independently breeding species. Our results suggest that isotocin is related to sociality in cichlids and may provide a mechanistic substrate for the evolution of sociality.
2. Immunohistochemical description of isotocin neurons and the anatomo-functional comparative analysis between isotocin and vasotocin systems in the weakly electric fish, Gymnotus omaroum
Rossana Perrone, Ana Silva, Paula Pouso Gen Comp Endocrinol . 2021 Nov 1;313:113886. doi: 10.1016/j.ygcen.2021.113886.
The vasopressin-vasotocin (AVP-AVT) and oxytocin-mesotocin-isotocin (OT-MT-IT) families of nonapeptides are of great importance in shaping context-dependent modulations of a conserved and yet highly plastic network of brain areas involved in social behavior: the social behavior network. The nonapeptide systems of teleost fish are highly conserved and share a common general organization. In this study, we first describe the presence of IT cells and projections in the brain of an electric fish, Gymnotus omarorum. Second, we confirm that IT neuron types and distribution in the preoptic area (POA) follow the same general pattern previously described in other teleost species. Third, we show that although IT and AVT neurons occur intermingled within the POA of G. omarorum and can be classified into the same subgroups, they present subtle but remarkable differences in size, number, and location. Finally, we show that unlike AVT, IT has no effect on basal electric signaling, reinforcing the specificity in the actions that each one of these nonapeptides has on social behavior and communication.
3. Isotocin increases female avoidance of males in a coercive mating system: Assessing the social salience hypothesis of oxytocin in a fish species
Molly E Cummings, Dustin Fry, Mary E Ramsey Horm Behav . 2019 Jun;112:1-9. doi: 10.1016/j.yhbeh.2019.03.001.
The nonapeptide oxytocin (and its fish homolog isotocin (IT)) is an evolutionarily-conserved hormone associated with social behaviors across most vertebrate taxa. Oxytocin has traditionally been regarded as a prosocial hormone, but studies on social cognition in mammalian models suggest it may play a more nuanced role in modulating social discrimination based on social salience and stimulus valence. Here we test IT and its role in regulating female social decision-making and anxiety behaviors in a live-bearing fish with a male coercive mating system. Gambusia affinis males engage in a forced mating strategy, with frequent harassment and attempted copulatory thrusts directed towards unwilling females. Exogenous IT produced anxiolytic responses in female G. affinis that altered exploration (time in center of tank) but not time in dark vs. light regions of the tank. Exogenous IT also produced context-specific changes in social tendency: IT-treated G. affinis females spent less time associating with males while association time with conspecific females was not altered. Further, while overall activity levels were not changed by IT treatment, the amount of social behaviors IT-treated females directed towards males, but not females, was reduced. Our results support the social salience hypothesis of oxytocin action in a teleost and suggest that oxytocin's critical input into social cognitive processing is conserved across vertebrate taxa.
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