Intermedine

Base Information

• Chemical Name: Intermedine
• CAS No.: 581-05-5
• Deprecated CAS: 17107-62-9,4353-59-7
• Molecular Formula: C77H109 N21 O19 S
• Molecular Weight: 1664.91
• UNII: OVF025LA77
• ChEMBL ID: CHEMBL214332
• NCI Thesaurus Code: C174814
• Wikipedia: Alpha-Melanocyte-stimulating_hormone
• Mol file: 581-05-5.mol

Synonyms:(Des-Acetyl)-alpha-MSH;(Desacetyl)alpha-MSH;Acetylated ACTH (1-13)NH2;ACTH (1-13);ACTH (1-13)NH2;ACTH(1-13);Adrenocorticotropin (1-13)NH2;alpha Intermedin;alpha Melanocyte Stimulating Hormone;alpha Melanotropin;alpha MSH;alpha-Melanocyte-Stimulating Hormone;alpha-Melanocyte-Stimulating Hormone, Desacetyl;alpha-Melanotropin;alpha-MSH;alpha-MSH, Desacetyl;DE-alpha-MSH;Des-Acetyl MSH;Desacetyl alpha Melanocyte Stimulating Hormone;Desacetyl alpha MSH;Desacetyl alpha-Melanocyte-Stimulating Hormone;Desacetyl alpha-MSH;Hormone, alpha-Melanocyte-Stimulating;Hormone, Desacetyl alpha-Melanocyte-Stimulating;Intermedin, alpha;MSH, (Desacetyl)alpha-;MSH, alpha;MSH, Des-Acetyl

Chemical Property of Intermedine

Chemical Property:

• Appearance/Colour: WHITE POWDER
• PKA: 4.43±0.10(Predicted)
• PSA: 668.28000
• Density: 1.48g/cm3
• LogP: 2.68340
• Storage Temp.: 2-8°C
• Solubility.: insoluble in EtOH; ≥10.44 mg/mL in H2O with ultrasonic; ≥166.5 mg/mL in DMSO with gentle warming
• Water Solubility.: Soluble in water (~1 mg/ml).
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 23
• Hydrogen Bond Acceptor Count: 23
• Rotatable Bond Count: 51
• Exact Mass: 1663.79293151
• Heavy Atom Count: 118
• Complexity: 3370

Purity/Quality:

98%,99%, ^*data from raw suppliers

Alpha-Melanocyte Stimulating Hormone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(C(=O)N)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)CNC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC4=CC=CC=C4)NC(=O)C(CC5=CNC=N5)NC(=O)C(CCC(=O)O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(CO)NC(=O)C
• Isomeric SMILES: CC(C)[C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CO)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](CO)NC(=O)C
• Biological functions: α-MSH and other MSH peptides are associated with a wide spectrum of biological functions through MC receptors that distribute in many tissues. MC1R is expressed in melanocytes, keratinocytes, macrophages, leukocytes, and adipose tissue; MC3R is expressed in the central nervous system (CNS), kidney, testis, ovary, skeletal muscle, placenta, and mammary gland; MC4R is expressed in the CNS and associated with food intake; and MC5R is expressed in exocrine glands, muscle, and the CNS. The representative physiological functions of MSH peptides mediated by MC receptors are stimulation of melanocytes in the skin to synthesize melanin, including regulation of the eumelaninpheomelanin switch via MC1R; energy homeostasis and natriuresis via MC3R; energy homeostasis and erectile function via MC4R; and synthesis and secretion of exocrine gland products via MC5R.
• Description: A pituitary hormone secreted from the pars intermedia, MSH was one of the first adenohypophysial hormones demonstrated to be present in vertebrates, from jawless fish to mammals, together with adrenocorticotropic hormone (ACTH). The fact that MSH is derived from a precursor protein called proopiomelanocortin (POMC) was demonstrated in 1979, using the pars intermedia from the bovine pituitary.
• Uses: alpha-Melanocyte Stimulating Hormone amide is an endogenous melanocortin receptor agonist (Ki values are 0.12, 31, 660 and 5700 nM for MC1, MC3, MC4 and MC5 receptors respectively). Anti-inflammatory peptide; antagonizes proinflammatory mediators, including TNF-α, IL-6 and NO and induces anti-inflammatory cytokine IL-10. Inhibits food intake and induces penile erections following i.c.v. administration.
• Clinical Use: The measurement of the blood concentration of MSH has not been validated for routine clinical use. MSH analogs have recently been developed for antiobesity medication, treatment of skin diseases, and prevention of actinic keratoses in organ transplant recipients. The potential use of radiolabeled α-MSH peptides in melanoma imaging and the treatment of disseminated disease has also been reported.

Technology Process of Intermedine

There total 3 articles about Intermedine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Glu(OtBu)-OH (71989-18-9) + acetic anhydride (108-24-7) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Fmoc-His(Trt)-OH (109425-51-6) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → α-melanocyte stimulating hormone (581-05-5)

Guidance literature:

Fmoc-Val-OH; With 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime; In N,N-dimethyl-formamide; Sonication;

With piperidine; In N,N-dimethyl-formamide; for 0.0833333h; Sonication;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-Glu(OtBu)-OH; acetic anhydride; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Fmoc-His(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

DOI:10.1021/acs.orglett.9b02283

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Fmoc-Lys-OH (105047-45-8) + Fmoc-His(Trt)-OH (109425-51-6) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → α-melanocyte stimulating hormone (581-05-5)

Guidance literature:

Fmoc-Val-OH; With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.5h;

With piperidine; In N,N-dimethyl-formamide; for 0.333333h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Fmoc-Lys-OH; Fmoc-His(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

DOI:10.1021/acs.jmedchem.7b01295

Reference yield:

→ α-melanocyte stimulating hormone (581-05-5)

Guidance literature:

Aus prot. Base (II);

DOI:10.1111/j.1399-3011.1977.tb01836.x

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH

Fmoc-Pro-OH

N-Fmoc L-Phe

Refernces

• 1、 Zhou, Yang,Mowlazadeh Haghighi, Saghar,Zoi, Ioanna,Sawyer, Jonathon R.,Hruby, Victor J.,Cai, Minying. "Design of MC1R Selective γ-MSH Analogues with Canonical Amino Acids Leads to Potency and Pigmentation". . p. 9320 - 9329. Retrieved 2017/11/30.
• 2、 Smeets,Granger,Van Nispen,Bloemendal,Tesser. "Des-Nalpha-acetyl-alpha-melanotropin: a synthetic substrate for specific N-terminal directed enzymatic acetylation.". . p. 52 - 56. Retrieved 2007/10/05.