Moroidin is a tubulin polymerization inhibitor that potently inhibits purified tubulin polymerization. Moroidin is a bicyclic octapeptide belonging to the cyclotide family Urticariaceae. Moroidin has cytotoxicities on a variety of cancer/tumor cells and can cause apoptosis in A549 human lung cancer/tumor cells.

Physicochemical Properties

Molecular Formula	C47H66N14O10
Molecular Weight	987.11474943161
Exact Mass	986.509
CAS #	104041-75-0
PubChem CID	23247762
Appearance	Typically exists as solid at room temperature
LogP	2.442
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	11
Heavy Atom Count	71
Complexity	2030
Defined Atom Stereocenter Count	8
SMILES	O=C1[C@H]([C@@H](C2C=CC3C4=C(N5C=NC(C[C@@H](C(=O)O)NC(CNC([C@H](CCC/N=C(\N)/N)NC([C@H](C4)NC([C@H](C(C)C)NC([C@H](CC(C)C)N1)=O)=O)=O)=O)=O)=C5)NC=3C=2)C(C)C)NC([C@@H]1CCC(N1)=O)=O
InChi Key	UCSHFBQCLZMAJY-QFMFBHDYSA-N
InChi Code	InChI=1S/C47H66N14O10/c1-21(2)14-31-43(67)59-37(23(5)6)44(68)58-32-17-27-26-10-9-24(36(22(3)4)38(45(69)57-31)60-41(65)29-11-12-34(62)53-29)15-30(26)55-39(27)61-19-25(52-20-61)16-33(46(70)71)54-35(63)18-51-40(64)28(56-42(32)66)8-7-13-50-47(48)49/h9-10,15,19-23,28-29,31-33,36-38,55H,7-8,11-14,16-18H2,1-6H3,(H,51,64)(H,53,62)(H,54,63)(H,56,66)(H,57,69)(H,58,68)(H,59,67)(H,60,65)(H,70,71)(H4,48,49,50)/t28-,29-,31-,32-,33-,36+,37-,38-/m0/s1
Chemical Name	(8R,9S,12S,15S,18S,21S,27S)-21-[3-(diaminomethylideneamino)propyl]-12-(2-methylpropyl)-10,13,16,19,22,25-hexaoxo-9-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-8,15-di(propan-2-yl)-2,11,14,17,20,23,26,30,32-nonazapentacyclo[16.14.2.13,7.129,32.04,33]hexatriaconta-1(33),3,5,7(36),29(35),30-hexaene-27-carboxylic 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

ln Vitro	Moroidin (Compound 1) has cytotoxic effects on cancer cells, with IC50 values of 3.2, 8.3, 9.6, 5.2, and 9.9 μM in A549, H1299, U87, U251, and HCT116 cells. It can be applied for 24, 48, or 72 hours. correspondingly [1]. Moroidin (0.01-100 μM; 24 hours, 48 hours, and 72 hours) inhibits the polymerization of microtubules and lowers the levels of β-tubulin in A549 cells [1]. In A549 cells, moroidin (0–20 μM; 48 hours) causes apoptosis and stops the cell cycle in the G2/M phase [1]. A549 cell migration and invasion are inhibited by motroidin (0.5, 1, 2 μM; 0, 24, 48 h) [1].
Cell Assay	Cell viability assay [1] Cell Types: A549 cell Tested Concentrations: 0.01-100 μM Incubation Duration: 24 h, 48 h, 72 h Experimental Results: The effect of inhibiting tubulin polymerization and proliferation of A549 cells is not as good as colchicine. Western Blot Analysis [1] Cell Types: A549 cells Tested Concentrations: 2.5 μM, 5 μM, 10μM Incubation Duration: Experimental Results: Caused a dose-dependent decrease in tubulin protein levels in A549 cells. Apoptosis analysis [1] Cell Types: A549 Cell Tested Concentrations: 0-20 μM Incubation Duration: 48 h Experimental Results: The percentage of cell apoptosis increased Dramatically. Cytotoxicity assay[1] Cell Types: A549, H1299, U87, U251, HCT116 and MCF-7 Cell Tested Concentrations: 0-80 μM Incubation Duration: 24, 48 or 72 h Experimental Results: Inhibition of cancer cell proliferation in vitro and in A549 Cells exhibit high sensitivity and low IC50 values. Cell cycle analysis [1] Cell Types: A549 cells Tested Concentrations: 0-20 μM Incubation Duration: 48 h Experimental Results: It caused a dose-dependent increase in the proportion of cells in the G2/M phase
References	[1]. Xiaoya Xu, et al. Moroidin, a Cyclopeptide from the Seeds of Celosia cristata That Induces Apoptosis in A549 Human Lung Cancer Cells. J Nat Prod. 2022 Aug 11.

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	1.0131 mL	5.0653 mL	10.1306 mL
	5 mM	0.2026 mL	1.0131 mL	2.0261 mL
	10 mM	0.1013 mL	0.5065 mL	1.0131 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.