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Purity: ≥98%
α-MSH (α-Melanocyte-Stimulating Hormone; CZEN-002) is a novel and peptide-based NF-κB activation inhibitor with the potential to be used for the treatment of vulvovaginal candidiasis. As an endogenous neuropeptide, it is a melanocortin receptor 4 (MC4R) agonist with anti-inflammatory and antipyretic activities. α-MSH is a post-translational derivative of pro-opiomelanocortin (POMC).
| Targets |
MC4R (melanocortin receptor 4)
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|---|---|
| ln Vitro |
α-MSH directly affects neuroastrocyte melanoma receptors to regulate CNS factors. NFκB activation is controlled by α-MSH. The transport of factor κB to the nucleus is regulated by α-MSH [3].
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| ln Vivo |
α-MSH (50 μg/0.2 ml saline; ip) is an effective way to modify the regulatory response when given systemically [3].
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| Cell Assay |
Alpha-melanocyte-stimulating hormone (α-MSH) is an endogenous neuropeptide that is known for its anti-inflammatory and antipyretic activities. We recently demonstrated that α-MSH possesses staphylocidal activity and causes bacterial membrane damage. To understand the role of its amino acid sequences in the staphylocidal mechanism, in the present study we investigated the antimicrobial activities of different fragments of α-MSH, i.e., α-MSH(6-13), α-MSH(11-13), and α-MSH(1-5), and compared them with that of the entire peptide. Our results showed that peptides containing the C-terminal region of α-MSH, namely, α-MSH(6-13) and α-MSH(11-13), efficiently killed >90% of both methicillin-sensitive and -resistant Staphylococcus aureus cells in the micromolar range and ∼50% of these cells in the nanomolar range; their efficiency was comparable to that of the entire α-MSH, whereas the peptide containing the N-terminal region, α-MSH(1-5), was found to be ineffective against S. aureus. The antimicrobial activity of α-MSH and its C-terminal fragments was not affected by the presence of NaCl or even divalent cations such as Ca2+ and Mg2+. Similar to the case for the parent peptide, α-MSH(6-13) and α-MSH(11-13) also depolarized and permeabilized Staphylococcus cells (∼70 to 80% of the cells were depolarized and lysed after 2 h of peptide exposure at micromolar concentrations). Furthermore, scanning and transmission electron microscopy showed remarkable morphological and ultrastructural changes on S. aureus cell surface due to exposure to α-MSH-based peptides. Thus, our observations indicate that C-terminal fragments of α-MSH retain the antimicrobial activity of entire peptide and that their mechanism of action is similar to that of full-length peptide. These observations are important and are critical in the rational design of α-MSH-based therapeutics with optimal efficacy[1].
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| Animal Protocol |
Animal/Disease Models: IL-10–deficient mice [3]
Doses: 50 μg/0.2 ml Saline Route of Administration: Ip Experimental Results: Systemic administration effectively regulates inflammatory responses. The melanocortin-4 receptor (MC4R) in the hypothalamus is thought to be important in physiological regulation of food intake. We investigated which hypothalamic areas known to express MC4R are involved in the regulation of feeding by using alpha-melanocyte-stimulating hormone (alpha-MSH), an endogenous MC4R agonist, and agouti-related peptide (Agrp), an endogenous MC4R antagonist. Cannulae were inserted into the rat hypothalamic paraventricular (PVN), arcuate (Arc), dorsomedial (DMN), and ventromedial (VMN) nuclei; the medial preoptic (MPO), anterior hypothalamic (AHA), and lateral hypothalamic (LHA) areas; and the extrahypothalamic central nucleus of the amygdala (CeA). Agrp (83-132) (0.1 nmol) and [Nle4, D-Phe7]alpha(-MSH (NDP-MSH) (0.1 nmol), a stable alpha-MSH analog, were administered to fed and fasted rats, respectively. The PVN, DMN, and MPO were the areas with the greatest response to Agrp and NDP-MSH. At 8 h postinjection, Agrp increased feeding in the PVN by 218 +/- 23% (P < 0.005), in the DMN by 268 +/- 42% (P < 0.005), and in the MPO by 236 +/- 31% (P < 0.01) compared with a saline control group for each nucleus. NDP-MSH decreased food intake in the PVN by 52 +/- 6% (P < 0.005), in the DMN by 44 +/- 6% (P < 0.0001), and in the MPO by 55 +/- 6% (P < 0.0001) at 1 h postinjection. Injection into the AHA and CeA resulted in smaller alterations in food intake. No changes in feeding were seen after the administration of Agrp into the Arc, LHA, or VMN, but NDP-MSH suppressed food intake in the Arc and LHA. This study indicates that the hypothalamic nuclei expressing MC4R vary in their sensitivity to Agrp and alpha-MSH with regard to their effect on feeding[2]. |
| References |
[1]. Madhuri Singh, et al. C-terminal amino acids of alpha-melanocyte-stimulating hormone are requisite for its antibacterial activity against Staphylococcus aureus. Antimicrob Agents Chemother. 2011 May;55(5):1920-9.
[2]. M S Kim, et al. Hypothalamic localization of the feeding effect of agouti-related peptide and alpha-melanocyte-stimulating hormone. Diabetes. 2000 Feb;49(2):177-82. [3]. Lipton JM, et al. Mechanisms of antiinflammatory action of alpha-MSH peptides. In vivo and in vitro evidence. Ann N Y Acad Sci. 1999;885:173-182. |
| Molecular Formula |
C77H109N21O19S
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|---|---|
| Molecular Weight |
1664.9
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| Exact Mass |
1663.7929
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| Elemental Analysis |
C, 55.55; H, 6.60; N, 17.67; O, 18.26; S, 1.93
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| CAS # |
581-05-5
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| Related CAS # |
171869-93-5 (TFA salt)
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| Sequence |
Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2
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| SequenceShortening |
Ac-SYSMEHFRWGKPV-NH2
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| Appearance |
Typically exists as solids (or liquids in special cases) at room temperature
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| LogP |
-1.77
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| tPSA |
668.28
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| SMILES |
CC(C)[C@@H](C(N)=O)NC([C@H]1N(C([C@H](CCCCN)NC(CNC([C@H](CC2=CNC3=C2C=CC=C3)NC([C@H](CCCNC(N)=N)NC([C@H](CC4=CC=CC=C4)NC([C@H](CC5=CNC=N5)NC([C@H](CCC(O)=O)NC([C@H](CCSC)NC([C@H](CO)NC([C@H](CC6=CC=C(O)C=C6)NC([C@H](CO)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC1)=O
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| InChi Key |
WHNFPRLDDSXQCL-UAZQEYIDSA-N
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| InChi Code |
InChI=1S/C77H109N21O19S/c1-42(2)64(65(79)106)97-75(116)61-20-13-30-98(61)76(117)54(18-10-11-28-78)88-62(103)38-85-66(107)57(34-46-36-84-50-17-9-8-16-49(46)50)94-67(108)51(19-12-29-83-77(80)81)89-70(111)55(32-44-14-6-5-7-15-44)92-72(113)58(35-47-37-82-41-86-47)95-68(109)52(25-26-63(104)105)90-69(110)53(27-31-118-4)91-74(115)60(40-100)96-71(112)56(33-45-21-23-48(102)24-22-45)93-73(114)59(39-99)87-43(3)101/h5-9,14-17,21-24,36-37,41-42,51-61,64,84,99-100,102H,10-13,18-20,25-35,38-40,78H2,1-4H3,(H2,79,106)(H,82,86)(H,85,107)(H,87,101)(H,88,103)(H,89,111)(H,90,110)(H,91,115)(H,92,113)(H,93,114)(H,94,108)(H,95,109)(H,96,112)(H,97,116)(H,104,105)(H4,80,81,83)/t51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,64-/m0/s1
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| Chemical Name |
(4S,7S,10S,13S,16S,22S)-7-((1H-imidazol-4-yl)methyl)-16-((1H-indol-3-yl)methyl)-26-amino-22-((S)-2-(((S)-1-amino-3-methyl-1-oxobutan-2-yl)carbamoyl)pyrrolidine-1-carbonyl)-10-benzyl-13-(3-guanidinopropyl)-4-((2S,5S,8S,11S)-8-(4-hydroxybenzyl)-5,11-bis(hydroxymethyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazatetradecanamido)-5,8,11,14,17,20-hexaoxo-6,9,12,15,18,21-hexaazahexacosanoic acid
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| Synonyms |
CZEN 002 ALPHA-MSH a-MSHCZEN002 CZEN-002Melanotropin a-Melanotropin a-Melanocyte Stimulating Hormone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~25 mg/mL (~15.02 mM)
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.6006 mL | 3.0032 mL | 6.0064 mL | |
| 5 mM | 0.1201 mL | 0.6006 mL | 1.2013 mL | |
| 10 mM | 0.0601 mL | 0.3003 mL | 0.6006 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT06293664 | Recruiting | Other: α-MSH infusion Other: Placebo solutions |
Type 2 Diabetes Mellitus | Dasman Diabetes Institute | March 4, 2024 | Not Applicable |
| NCT06153134 | Recruiting | Drug: 2% Kojic Acid | Melasma | Universitas Padjadjaran | December 22, 2023 | Early Phase 1 |
| NCT01717079 | Terminated | Anorexia Nervosa | Procedure: Sham rTMS Procedure: rTMS |
University Hospital, Rouen | May 2013 | Not Applicable |
| NCT05709444 | Recruiting | Drug: Bremelanotide Drug: RAAS inhibition therapy |
Kidney Disease | Palatin Technologies, Inc | December 26, 2022 | Phase 2 |
| NCT05600985 | Recruiting | Procedure: FS-LASIK | Dry Eye | Peking University Third Hospital |
October 29, 2022 |
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