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Meta-Topolin

Cat No.:V29417 Purity: ≥98%
Meta-Topolin (m-Topolin) is a highly active aromatic cytokinin.
Meta-Topolin
Meta-Topolin Chemical Structure CAS No.: 75737-38-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Meta-Topolin (m-Topolin) is a highly active aromatic cytokinin.
Meta-Topolin (CAS# 75737-38-1), also known as m-topolin or 6-(3-hydroxybenzylamino)purine, is an aromatic adenine-based cytokinin that was first isolated from poplar leaves. It has a molecular weight of 241.25 and a molecular formula of C₁₂H₁₁N₅O. This compound exhibits potent cytokinin activity, promoting cell division and differentiation in plants. It is particularly effective in stimulating shoot proliferation and inducing adventitious root formation. Meta-Topolin is widely used in plant tissue culture, agriculture, and horticulture applications.
Biological Activity I Assay Protocols (From Reference)
Targets
Meta-Topolin targets cytokinin receptors in plants, which are histidine kinases involved in signal transduction pathways regulating cell division, differentiation, and development. As a cytokinin, it mimics the action of natural cytokinins such as zeatin and is more active than 6-benzylaminopurine (6-BA) in certain applications. It can also undergo ribosylation at the 9-position, forming 9-β-D-ribofuranosyl and 9-β-D-glucopyranosyl derivatives.
ln Vitro
Poplar leaves were initially used to extract meta-topolin. In plant tissues, meta-topolin and its derivatives 9-β-D-ribofuranosyl and 9-β-v-glucopyranosyl are found naturally. When it comes to encouraging shoot production in plant tissue culture, meta-topolin outperforms zeatin and benzyladenine [1]. Shoot production in Spathiphyllum is remarkably similar in media that contain both meta-topolin and BAP [2].
In vitro, Meta-Topolin exhibits potent cytokinin activity, promoting cell division and differentiation in plant cells. It is particularly effective in stimulating shoot proliferation and inducing adventitious root formation in plant tissue culture. It generally causes less root inhibition than 6-benzylaminopurine (6-BA), making it a preferred cytokinin for certain plant propagation applications. Its activity is comparable to or greater than that of zeatin and BAP in various plant species.
ln Vivo
In vivo, Meta-Topolin is used in plant tissue culture, agriculture, and horticulture to enhance plant growth, improve crop yield, and aid in plant propagation. It is effective in stimulating shoot proliferation and inducing adventitious root formation in whole plants. Its high activity and low root inhibition make it a valuable tool for micropropagation and plant breeding programs.
Enzyme Assay
In vitro assays for Meta-Topolin are conducted in plant tissue culture systems. Cytokinin activity is assessed by measuring the promotion of cell division in plant cells, such as tobacco callus or soybean cotyledonary node cultures. Shoot proliferation and adventitious root formation are evaluated by culturing plant explants (e.g., shoot tips, nodal segments) on media containing varying concentrations of the compound (typically 0.1-10 µM) and measuring the number of shoots or roots produced.
Cell Assay
Meta-Topolin is used in plant cell culture assays to study cytokinin signaling and plant development. Plant cells or tissues are cultured on media containing Meta-Topolin at concentrations ranging from 0.1 to 10 µM. Morphological changes, shoot proliferation, root formation, and biomass accumulation are assessed. Gene expression analysis may be performed to study cytokinin-responsive genes.
Animal Protocol
In vivo animal studies are not applicable for Meta-Topolin, as it is a plant growth regulator and not used in animal models. Meta-Topolin is a plant growth regulator and does not have pharmacokinetic properties in animals. It is not administered systemically to animals.
Toxicity/Toxicokinetics
Toxicological data for Meta-Topolin are limited, as it is used as a plant growth regulator and not intended for human consumption. Standard laboratory safety precautions apply. It may cause skin and eye irritation.
References
[1]. Strnad M, et al. Meta-topolin, a highly active aromatic cytokinin from poplar leaves (Populus × canadensis Moench., cv. Robusta). Phytochemistry 45(2):213-218.
[2]. Werbrouck S, et al. Meta-topolin, an alternative to benzyladenine in tissue culture? 1996. 98 (2):291-297.
Additional Infomation
Meta-Topolin is an aromatic adenine-based cytokinin that promotes plant cell division and differentiation. It is used in plant tissue culture, agriculture, and horticulture. It has a molecular weight of 241.25 and formula C₁₂H₁₁N₅O. It is not a drug and has no clinical approval.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H11N5O
Molecular Weight
241.253
Exact Mass
241.096
CAS #
75737-38-1
PubChem CID
11557770
Appearance
White to off-white solid powder
Density
1.5±0.1 g/cm3
Boiling Point
611.9±45.0 °C at 760 mmHg
Melting Point
284-286ºC
Flash Point
323.9±28.7 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.805
LogP
1.3
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Heavy Atom Count
18
Complexity
277
Defined Atom Stereocenter Count
0
SMILES
OC1=CC=CC(CNC2=C3N=CNC3=NC=N2)=C1
InChi Key
BUDWTFCZGZYQHZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H11N5O/c18-9-3-1-2-8(4-9)5-13-11-10-12(15-6-14-10)17-7-16-11/h1-4,6-7,18H,5H2,(H2,13,14,15,16,17)
Chemical Name
3-[(7H-purin-6-ylamino)methyl]phenol
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~518.13 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.62 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (8.62 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (8.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.1451 mL 20.7254 mL 41.4508 mL
5 mM 0.8290 mL 4.1451 mL 8.2902 mL
10 mM 0.4145 mL 2.0725 mL 4.1451 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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

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