Mesotocin
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Mesotocin

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Mesotocin, an oxytocin analogue, is produced in birds, reptiles and amphibians, as well as in most marsupials.

Category
Others
Catalog number
BAT-014441
CAS number
362-39-0
Molecular Formula
C43H66N12O12S2
Molecular Weight
1007.19
Mesotocin
IUPAC Name
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-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
L-cysteinyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-isoleucyl-glycinamide (1->6)-disulfide; (Ile8)-Oxytocin; H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Ile-Gly-NH2 (Disulfide bridge: Cys1-Cys6); 8-Ile-oxytocin; Oxytocin, 8-L-isoleucine-; 1-{[(4R,7S,10S,13S,16S,19R)-19-Amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-2-butanyl]-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-isoleucylglycinamide
Appearance
White Powder
Purity
≥95%
Density
1.3±0.1 g/cm3
Boiling Point
1533.3±65.0°C at 760 mmHg
Sequence
CYIQNCPIG-NH2 (Disulfide bridge: Cys1-Cys6)
Storage
Store at -20°C
InChI
InChI=1S/C43H66N12O12S2/c1-5-21(3)34(41(65)48-18-33(47)59)54-40(64)30-8-7-15-55(30)43(67)29-20-69-68-19-25(44)36(60)50-27(16-23-9-11-24(56)12-10-23)39(63)53-35(22(4)6-2)42(66)49-26(13-14-31(45)57)37(61)51-28(17-32(46)58)38(62)52-29/h9-12,21-22,25-30,34-35,56H,5-8,13-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,65)(H,49,66)(H,50,60)(H,51,61)(H,52,62)(H,53,63)(H,54,64)/t21-,22-,25-,26-,27-,28-,29-,30-,34-,35-/m0/s1
InChI Key
SILDPWPVKZETMP-AMUMSSSMSA-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)CCC(=O)N
1. Measurement of urinary mesotocin in large-billed crows by enzyme-linked immunosorbent assay
Akiko Seguchi, Kazutaka Mogi, Ei-Ichi Izawa J Vet Med Sci. 2022 Apr 13;84(4):520-524. doi: 10.1292/jvms.21-0635. Epub 2022 Feb 14.
Mesotocin (MT) is an avian homologue of oxytocin (OT). Behavioral pharmacological studies in birds have suggested the involvement of MT in socially affiliative behavior. However, investigations of peripheral MT levels associated with social behavior are lacking because non-invasive methods to measure surrogate plasma MT have yet to be established. This study aimed to measure urinary MT in crows using a commercially available OT enzyme-linked immunosorbent assay kit. Urine samples were collected after intravenous injection of MT and centrifuged to separate urine and fecal components. We found that urinary MT was significantly elevated 15-30 min after MT injection. These results validate our method for the use of urine samples for the measurement of peripheral MT levels in crows.
2. Measuring salivary mesotocin in birds - Seasonal differences in ravens' peripheral mesotocin levels
Martina Stocker, Jonathan Prosl, Lisa-Claire Vanhooland, Lisa Horn, Thomas Bugnyar, Virginie Canoine, Jorg J M Massen Horm Behav. 2021 Aug;134:105015. doi: 10.1016/j.yhbeh.2021.105015. Epub 2021 Jun 15.
Oxytocin is involved in a broad array of social behaviours. While saliva has been used regularly to investigate the role of oxytocin in social behaviour of mammal species, so far, to our knowledge, no-one has tried to measure its homolog, mesotocin, in birds' saliva. Therefore, in this study we measured salivary mesotocin in common ravens (Corvus corax), and subsequently explored its link to three aspects of raven sociality. We trained ravens (n = 13) to voluntarily provide saliva samples and analysed salivary mesotocin with a commercial oxytocin enzyme-immunoassay kit, also suitable for mesotocin. After testing parallelism and recovery, we investigated the effect of bonding status, sex and season on mesotocin levels. We found that mesotocin was significantly more likely to be detected in samples taken during the breeding season (spring) than during the mating season (winter). In those samples in which mesotocin was detected, concentrations were also significantly higher during the breeding than during the mating season. In contrast, bonding status and sex were not found to relate to mesotocin detectability and concentrations. The seasonal differences in mesotocin correspond to behavioral patterns known to be associated with mesotocin/oxytocin, with ravens showing much more aggression during the mating season while being more tolerant of conspecifics in the breeding season. We show for the first time that saliva samples can be useful for the non-invasive determination of hormone levels in birds. However, the rate of successfully analysed samples was very low, and collection and analysis methods will benefit from further improvements.
3. Mesotocin influences pinyon jay prosociality
J F Duque, W Leichner, H Ahmann, J R Stevens Biol Lett. 2018 Apr;14(4):20180105. doi: 10.1098/rsbl.2018.0105.
Many species exhibit prosocial behaviour, in which one individual's actions benefit another individual, often without an immediate benefit to itself. The neuropeptide oxytocin is an important hormonal mechanism influencing prosociality in mammals, but it is unclear whether the avian homologue mesotocin plays a similar functional role in birds. Here, we experimentally tested prosociality in pinyon jays (Gymnorhinus cyanocephalus), a highly social corvid species that spontaneously shares food with others. First, we measured prosocial preferences in a prosocial choice task with two different pay-off distributions: Prosocial trials delivered food to both the subject and either an empty cage or a partner bird, whereas Altruism trials delivered food only to an empty cage or a partner bird (none to subject). In a second experiment, we examined whether administering mesotocin influenced prosocial preferences. Compared to choices in a control condition, we show that subjects voluntarily delivered food rewards to partners, but only when also receiving food for themselves (Prosocial trials), and administration of high levels of mesotocin increased these behaviours. Thus, in birds, mesotocin seems to play a similar functional role in facilitating prosocial behaviours as oxytocin does in mammals, suggesting an evolutionarily conserved hormonal mechanism for prosociality.
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