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(Des-Gly10,D-Ala6,Pro-NHEt9)-LHRH (salmon)

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

Category

Others

Catalog number

BAT-015805

CAS number

88848-87-7

Molecular Formula

C61H76N14O12

Molecular Weight

1197.34

(Des-Gly10,D-Ala6,Pro-NHEt9)-LHRH (salmon)

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide

Synonyms

PYR-HIS-TRP-SER-TYR-D-ALA-TRP-LEU-PRO-NHET; L-Prolinamide, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-alanyl-L-tryptophyl-L-leucyl-N-ethyl-

Density

1.359±0.06 g/cm3

Boiling Point

1714.8±65.0 °C at 760 mmHg

Sequence

XHWSYAWLP

Storage

Store at -20°C

InChI

InChI=1S/C61H76N14O12/c1-5-63-60(86)51-15-10-22-75(51)61(87)49(23-33(2)3)73-56(82)46(25-36-28-64-42-13-8-6-11-40(36)42)69-53(79)34(4)67-55(81)45(24-35-16-18-39(77)19-17-35)70-59(85)50(31-76)74-57(83)47(26-37-29-65-43-14-9-7-12-41(37)43)71-58(84)48(27-38-30-62-32-66-38)72-54(80)44-20-21-52(78)68-44/h6-9,11-14,16-19,28-30,32-34,44-51,64-65,76-77H,5,10,15,20-27,31H2,1-4H3,(H,62,66)(H,63,86)(H,67,81)(H,68,78)(H,69,79)(H,70,85)(H,71,84)(H,72,80)(H,73,82)(H,74,83)/t34-,44+,45+,46+,47+,48+,49+,50+,51+/m1/s1

InChI Key

DTPOGFHWOZMRIR-BXSMXDOGSA-N

Canonical SMILES

CCNC(=O)C1CCCN1C(=O)C(CC(C)C)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(C)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8

1. Effects of LH-RH and Des-Gly10[D-Ala6]LH-RH-ethylamide on plasma sex steroid profiles in adult female coho salmon (Oncorhynchus kisutch)

G Van der Kraak, H M Dye, E M Donaldson Gen Comp Endocrinol. 1984 Jul;55(1):36-45. doi: 10.1016/0016-6480(84)90126-6.

17 beta-Estradiol, testosterone, and 17 alpha, 20 beta dihydroxy-4-pregnen-3-one (17 alpha 20 beta P) levels were measured in plasma samples obtained from coho salmon (Oncorhynchus kisutch) during the preovulatory period and following the injection of mammalian gonadotropin releasing hormones. Spontaneous reproductive activity was characterized by a rapid decline in plasma 17 beta-estradiol 10 days prior to ovulation and a large increase in plasma 17 alpha 20 beta P 6 days before ovulation. Testosterone levels remained high (greater than 125 ng/ml) throughout the preovulatory period, with a small peak evident 6 days prior to ovulation. Oocyte development was not accelerated in fish injected with mammalian LH-RH, whereas des-Gly10[D-Ala6]LH-RH-ethylamide (LH-RHA DAla6) promoted germinal vesicle breakdown (GVBD) in 10 out of 14 fish within 96 hr. Only LH-RHA DAla6-injected fish which completed GVBD displayed the characteristic steroid changes observed during spontaneous reproductive activity. In LH-RH-injected fish, there was a transient increase in plasma 17 alpha 20 beta P levels which persisted for less than 24 hr. LH-RHA DAla6-injected fish which failed to complete GVBD maintained high 17 alpha 20 beta P levels, but the peak concentrations were lower than those in fish which completed GVBD. These fish also maintained high plasma 17 beta-estradiol levels when compared to fish which completed GVBD. The appearance of high plasma 17 alpha 20 beta P levels during spontaneous and LH-RHA DAla6-induced reproductive activity was coincident with the time of GVBD. This finding was consistent with the view that 17 alpha 20 beta P functions as the maturation-inducing steroid in salmonids. The induction of GVBD using gonadotropin-releasing hormones was related to the elevation of plasma gonadotropin levels for greater than 24 hr [G. Van Der Kraak, H. R. Lin, E. M. Donaldson, H. M. Dye, and G. A. Hunter (1983) Gen. Comp. Endocrinol. 49, 470-476] and a decrease in 17 beta-estradiol production.

2. Effects of LH-RH and des-Gly10[D-Ala6]LH-RH-ethylamide on plasma gonadotropin levels and oocyte maturation in adult female coho salmon (Oncorhynchus kisutch)

G Van der Kraak, H R Lin, E M Donaldson, H M Dye, G A Hunter Gen Comp Endocrinol. 1983 Mar;49(3):470-6. doi: 10.1016/0016-6480(83)90210-1.

Plasma gonadotropin (GtH) levels and state of oocyte development were determined in adult female coho salmon following single intraperitoneal injections of LH-RH or its superactive analog des-Gly10[D-Ala6]LH-RH-ethylamide (LH-RHA DAla6). The peptides injected at dosages of 1.0 or 0.2 mg LH-RH and 0.2 or 0.02 mg LH-RHA DAla6/kg bw elevated plasma GtH by 1.5 hr postinjection. The response to the analog was of longer duration. Plasma GtH levels returned to basal levels 24 hr following LH-RH injection while elevated plasma GtH levels were maintained for at least 96 hr in response to the analog. Only those fish injected with LH-RHA DAla6 showed an accelerated rate of germinal vesicle breakdown (GVBD). Based on their relative effects on GVBD, LH-RHA DAla6 has at least 50 times the biological potency of LH-RH in adult female coho salmon.