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L9761

Sigma-Aldrich

[D-Trp6]-LH-RH

≥97% (HPLC), powder

Synonym(s):

[D-Trp6]-Luteinizing hormone releasing hormone

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About This Item

Empirical Formula (Hill Notation):
C64H82N18O13
CAS Number:
57773-63-4
Molecular Weight:
1311.45
MDL number:
MFCD00167541
UNSPSC Code:
12352209
PubChem Substance ID:
329817674
NACRES:
NA.32

assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01148
P30968

storage temp.

−20°C

SMILES string

CC(C)C[C@H](NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CO)NC(=O)[C@H](Cc4c[nH]c5ccccc45)NC(=O)[C@H](Cc6c[nH]cn6)NC(=O)[C@@H]7CCC(=O)N7)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N8CCC[C@H]8C(=O)NCC(N)=O

InChI

1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1

InChI key

VXKHXGOKWPXYNA-PGBVPBMZSA-N

Gene Information

human ... GNRH1(2796) , GNRHR(2798)

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Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-Trp-Leu-Arg-Pro-Gly-NH2

Application

[D-Trp6]-LH-RH (luteinizing hormone releasing hormone) has been used to study whether the (M. – X) region in electron capture dissociation provides information on amino acid composition of polypeptides. It is also used to study the effect of LH-RH on the production of progesterone (P), estradiol (E2) or human chorionic gonadotropin (hCG) by JEG-3 choriocarcinoma cells.

Biochem/physiol Actions

Potent LH-RH agonist with enhanced biological activity due to its slower rate of degradation. Like [D-Lys6]-LH-RH, the D-Trp6 analog has been shown to be effective against cancers expressing the LH-RH receptor. However, unlike the D-Lys6 analog, it is generally used in the unconjugated form.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J M Arencibia et al.
International journal of oncology, 16(5), 1009-1013 (2000-04-14)
Agonistic and antagonistic analogs of luteinizing hormone-releasing hormone (LHRH) inhibit the growth of various cancers in vivo. This effect is mainly exerted through the suppression of the pituitary-gonadal axis and the creation of a state of sex steroid deprivation. In
J F Nagao et al.
Animal reproduction science, 136(1-2), 69-73 (2012-11-28)
This study aimed to determine whether deslorelin acetate could induce double ovulation in mares. In Experiment 1, eight mares were treated with prostaglandin on Day 8 (D8) after ovulation, then treated with saline or with 100 μg of a controlled-release
Barbara Wolters et al.
Hormone research in paediatrics, 78(5-6), 304-311 (2012-12-22)
We studied the effect of gonadotropin-releasing hormone analogues (GnRHa) on weight gain as a possible side effect. We analyzed longitudinally changes in BMI-SDS in 92 children [median age 8.0 years (IQR 7.1-8.9), 88% females, mean BMI-SDS 0.69 ± 1.30] with
C Asa et al.
Reproduction in domestic animals = Zuchthygiene, 47 Suppl 6, 377-380 (2013-01-04)
North American zoos began using melengestrol acetate (MGA) implants to control reproduction in wild felids in the mid-1970s. Research linking MGA and other progestin-based contraceptives to uterine and mammary pathology in canids as well as felids resulted in a shift
Sandra Goericke-Pesch et al.
Theriogenology, 79(4), 640-646 (2012-12-26)
Although slow release GnRH-agonist implants have been shown to effectively suppress the estrous cycle in queens, there are still several remaining questions about their use: if the probability and frequency of estrus induction because of initial stimulation is dependent on
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