N-Methylmesoporphyrin IX (NMM) is a extensively used G-quadruplex DNA-specific fluorescent binding agent and an effective probe for monitoring Aβ fibrillation. N-Methylmesoporphyrin IX is an in situ inhibitor and ex situ monitor of Aβ amyloid production in vitro and intracellularly. N-Methylmesoporphyrin IX is sensitive to G-quadruplex DNA but not to duplex, triplex, and single-stranded forms of DNA. N-Methylmesoporphyrin IX does not fluoresce alone or in the context of monomeric Aβ, but emits strong fluorescence by stacking with Aβ assemblies.

Physicochemical Properties

Molecular Formula	C35H40N4O4
Molecular Weight	580.7165
Exact Mass	580.305
CAS #	142234-85-3
PubChem CID	656404
Appearance	Brown to black solid powder
Density	1.26g/cm3
Index of Refraction	1.642
LogP	4.085
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Heavy Atom Count	43
Complexity	980
Defined Atom Stereocenter Count	0
InChi Key	XODZICXILWCPBD-UHFFFAOYSA-N
InChi Code	InChI=1S/C35H40N4O4/c1-8-22-18(3)26-14-27-19(4)24(10-12-34(40)41)29(36-27)15-30-25(11-13-35(42)43)20(5)28(38-30)16-33-23(9-2)21(6)32(39(33)7)17-31(22)37-26/h14-17,37H,8-13H2,1-7H3,(H,40,41)(H,42,43)
Chemical Name	3-[18-(2-carboxyethyl)-7,12-diethyl-3,8,13,17,22-pentamethyl-23H-porphyrin-2-yl]propanoic 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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

N-methylmesoporphyrin IX (NMM) was introduced into the incubated Aβ40 solution employing NMM as an ectopic probe. The NMM concentration was held constant at 1 μM. 1 μM NMM containing 0.1 μM or 0.5 μM rhodamine B and 10 μM Aβ40 was evaluated in order to investigate the impact of rhodamine B. For seven days at 37°C, NMM (10 μM) was incubated with Aβ40 (50 μM) in investigations where NMM was used as an in situ inhibitor. Before the PL measurement, more NMM was added to maintain a consistent NMM concentration of 1 μM. The excitation wavelength of NMM is 399 nm, and the fluorescence spectrum collection range is 550 to 700 nm[1]. G-quadruplex DNA is the only type of DNA that N-Methyl Mesoporphyrin IX (NMM) is sensitive to; duplex, triplex, and single-stranded DNA are not. Following its attachment to quadruplex DNA, NMM can modify its macrocyclic shape to align with the end face of the G-quadruplex, hence augmenting its fluorescence and facilitating effective π-π stacking [1].

References

[1]. N-Methyl Mesoporphyrin IX as an Effective Probe for Monitoring Alzheimer's Disease β-Amyloid Aggregation in Living Cells. ACS Chem Neurosci. 2017 Jun 21;8(6):1299-1304.

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	1.7220 mL	8.6100 mL	17.2200 mL
	5 mM	0.3444 mL	1.7220 mL	3.4440 mL
	10 mM	0.1722 mL	0.8610 mL	1.7220 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.