, rat Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C129H216N42O42 |
| Molecular Weight | 3027.35153999999 |
| Exact Mass | 3025.61 |
| CAS # | 121028-49-7 |
| Related CAS # | Secretin (33-59), rat TFA |
| PubChem CID | 90488725 |
| Appearance | Typically exists as solid at room temperature |
| Density | 1.505 g/cm3 |
| LogP | -14.4 |
| Hydrogen Bond Donor Count | 50 |
| Hydrogen Bond Acceptor Count | 47 |
| Rotatable Bond Count | 107 |
| Heavy Atom Count | 213 |
| Complexity | 6940 |
| Defined Atom Stereocenter Count | 27 |
| SMILES | OCCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC(NCC=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O |
| InChi Key | LKHWQEXKRMDFFJ-NEMWHCQRSA-N |
| InChi Code | InChI=1S/C129H216N42O42/c1-58(2)40-78(119(206)170-99(64(13)14)102(134)189)149-94(181)51-145-105(192)74(29-33-91(131)178)153-113(200)81(43-61(7)8)161-116(203)82(44-62(9)10)159-108(195)72(27-22-38-143-128(137)138)151-110(197)75(30-34-92(132)179)154-114(201)79(41-59(3)4)157-107(194)71(26-21-37-142-127(135)136)150-103(190)65(15)148-121(208)87(53-172)166-118(205)86(49-98(187)188)163-111(198)76(31-35-93(133)180)155-115(202)80(42-60(5)6)158-109(196)73(28-23-39-144-129(139)140)152-122(209)89(55-174)167-117(204)83(45-63(11)12)160-112(199)77(32-36-96(183)184)156-123(210)90(56-175)168-126(213)101(67(17)177)171-120(207)84(46-68-24-19-18-20-25-68)164-125(212)100(66(16)176)169-95(182)52-146-106(193)85(48-97(185)186)162-124(211)88(54-173)165-104(191)70(130)47-69-50-141-57-147-69/h18-20,24-25,50,57-67,70-90,99-101,172-177H,21-23,26-49,51-56,130H2,1-17H3,(H2,131,178)(H2,132,179)(H2,133,180)(H2,134,189)(H,141,147)(H,145,192)(H,146,193)(H,148,208)(H,149,181)(H,150,190)(H,151,197)(H,152,209)(H,153,200)(H,154,201)(H,155,202)(H,156,210)(H,157,194)(H,158,196)(H,159,195)(H,160,199)(H,161,203)(H,162,211)(H,163,198)(H,164,212)(H,165,191)(H,166,205)(H,167,204)(H,168,213)(H,169,182)(H,170,206)(H,171,207)(H,183,184)(H,185,186)(H,187,188)(H4,135,136,142)(H4,137,138,143)(H4,139,140,144)/t65-,66+,67+,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,99-,100-,101-/m0/s1 |
| Chemical Name | (4S)-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[2-[[(2S)-1-[[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S,3R)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Secretin receptor (a G-protein-coupled receptor). Activation stimulates the adenylate cyclase (AC)/protein kinase A (PKA) pathway and increases intracellular Ca²⁺ concentration. Rat and human secretin receptors share 81% identity. Vasoactive intestinal peptide (VIP) binds to secretin receptors with an affinity similar to secretin. [1] |
| ln Vitro |
Rats' release of adrenocorticotropic hormone (ACTH) is inhibited by secretin (33-59), which also specifically blocks the glucocorticoid response to ACTH in zona fasciculata reticularis (ZF/R) cells [1]. In the rat cerebellum, the secretin retrograde messenger facilitates GABA transmission [2]. Secretin (at 10⁻⁷ M) maximally enhanced aldosterone production (2.4-fold increase) by dispersed rat zona glomerulosa (ZG) cells. [1] Secretin did not affect basal corticosterone production by dispersed rat zona fasciculata/reticularis (ZF/R) cells. [1] Secretin inhibited both submaximally (10⁻¹⁰ M ACTH) and maximally (10⁻⁸ M ACTH) stimulated corticosterone secretion from dispersed rat ZF/R cells. [1] Secretin did not stimulate corticosterone secretion in cultured murine adrenal tumor cells. [1] Secretin enhanced catecholamine synthesis in rat PC12 pheochromocytoma cells. [1] |
| ln Vivo |
In rats, a single subcutaneous (SC) bolus of Secretin (30 nmol/kg) moderately attenuated the injection stress-induced rise in plasma ACTH at 60 min, but significantly increased ACTH levels above control at 120 min. [1] Prolonged SC administration of Secretin (10 or 30 nmol/kg/day for 6 days) markedly elevated basal blood ACTH concentration in rats. [1] A single SC bolus of Secretin (30 nmol/kg) increased plasma aldosterone levels at 120 min in rats. [1] Chronic treatment with Secretin (10 or 30 nmol/kg/day for 6 days) stably elevated basal plasma aldosterone in rats. [1] A single SC injection of Secretin (30 nmol/kg) caused a 60% suppression of the stress-induced corticosterone rise at 60 min, followed by a rebound increase above control at 120 min in rats. [1] Chronic Secretin treatment (10 or 30 nmol/kg/day for 6 days) increased basal plasma corticosterone and adrenal gland weight in rats. [1] One study reported no change in rat plasma corticosterone 60 min after an intraperitoneal (IP) bolus of Secretin (dose unspecified). [1] |
| Cell Assay |
Steroidogenic effects were assessed using dispersed adrenocortical cells. Rat adrenal glands were decapsulated to isolate the zona glomerulosa (ZG). The remaining tissue (zona fasciculata/reticularis, ZF/R) was processed separately. Tissues were minced and digested with collagenase to obtain dispersed cells. Cells were incubated in appropriate culture medium. Aldosterone production was measured in ZG cell incubations. Corticosterone production, both basal and in response to ACTH stimulation, was measured in ZF/R cell incubations. Steroid hormone concentrations in the incubation media were quantified by radioimmunoassay. [1] The effect on catecholamine synthesis was studied using the rat PC12 pheochromocytoma cell line. [1] |
| Animal Protocol |
Acute Study: Rats received a single subcutaneous (SC) bolus injection of Secretin at a dose of 30 nmol/kg. Blood samples were collected at 60 and 120 minutes post-injection for the measurement of plasma ACTH, aldosterone, and corticosterone levels. The injection procedure itself served as a mild stressor. [1] Chronic Study: Rats were treated with Secretin via daily subcutaneous (SC) injection for 6 consecutive days at doses of 10 or 30 nmol/kg per day. Following the treatment period, animals were euthanized, and blood was collected to determine basal hormone concentrations. Adrenal glands were excised and weighed. [1] In a separate experiment, Secretin was administered as a single intraperitoneal (IP) bolus injection, and plasma corticosterone was measured 60 minutes later. [1] |
| References |
[1]. Secretin, glucagon, gastric inhibitory polypeptide, parathyroid hormone, and related peptides in the regulation of the hypothalamus- pituitary-adrenal axis. Peptides. 2000 Feb;21(2):309-24. [2]. Secretin as a neuropeptide. Mol Neurobiol. 2002 Aug;26(1):97-107. |
| Additional Infomation |
Secretin is a 27-amino acid peptide belonging to the VIP-secretin-glucagon family. It is expressed in the hypothalamus and pituitary gland. Its receptors are also found in these brain regions, but evidence for their presence in the adrenal gland is indirect, based on functional studies. [1] Secretin regulates the HPA axis through complex mechanisms. It can stimulate ACTH release, likely via hypothalamic receptors activating CRH neurons. It directly stimulates aldosterone secretion from ZG cells but inhibits ACTH-stimulated glucocorticoid production from ZF/R cells. The peptide may also influence adrenal function indirectly by modulating adrenal blood flow or medullary chromaffin cell activity. [1] The physiological secretion of Secretin induced by food intake may be involved in the feeding-associated increase in adrenal steroid secretion. [1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.3303 mL | 1.6516 mL | 3.3032 mL | |
| 5 mM | 0.0661 mL | 0.3303 mL | 0.6606 mL | |
| 10 mM | 0.0330 mL | 0.1652 mL | 0.3303 mL |