5-Azidomethyl-uridine is a reagent for click chemistry bearing an azide (N3) moiety. 5-Azidomethyl-uridine may be used as an alternative to BrU (5-bromouridine) or copper catalysts requiring 5-EU (5-ethyluridine) for measuring nascent RNA synthesis in proliferating cells. 5-AmU is cell permeable (penetrable) and may bind to nascent RNA rather than its natural analog uridine. This hypothesis is based on the previously demonstrated suitability of 5-AmdU (5-azidomethyl-2'-deoxyuridine) for monitoring DNA synthesis, and 5-AmUTP (5-azidomethyl-utp) for RNA Suitability for synthetic monitoring. 5-Azidomethyl-uridine is a click chemical reagent. It has an azide (N3) moiety and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an alkyne group. SPAAC (Strain-promoted alkyne-azide cycloaddition) may also happen with compounds bearing a BCN or DBCO group.

Physicochemical Properties

Molecular Formula	C10H13N5O6
Molecular Weight	299.24
Exact Mass	299.086
CAS #	24751-67-5
PubChem CID	121487445
Appearance	White to off-white solid powder
LogP	-1.07
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Heavy Atom Count	21
Complexity	530
Defined Atom Stereocenter Count	4
SMILES	C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)CN=[N+]=[N-]
InChi Key	ZAFBFGDCEFQDFD-JXOAFFINSA-N
InChi Code	InChI=1S/C10H13N5O6/c11-14-12-1-4-2-15(10(20)13-8(4)19)9-7(18)6(17)5(3-16)21-9/h2,5-7,9,16-18H,1,3H2,(H,13,19,20)/t5-,6-,7-,9-/m1/s1
Chemical Name	5-(azidomethyl)-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
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

References

[1]. Recent applications of click chemistry in drug discovery. Expert Opin Drug Discov. 2019 Aug;14(8):779-789.

Solubility Data

Solubility (In Vitro)

DMSO: 125 mg/mL (417.72 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (6.95 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 (6.95 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (6.95 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	3.3418 mL	16.7090 mL	33.4180 mL
	5 mM	0.6684 mL	3.3418 mL	6.6836 mL
	10 mM	0.3342 mL	1.6709 mL	3.3418 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.