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MedKoo Cat#: 585163 | Name: Crotonoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Crotonoside is a nucleoside analog derived from Croton tiglium with reported antitumor and immunosuppressive properties. It interferes with DNA and RNA synthesis by mimicking natural nucleosides, thereby inhibiting nucleic acid replication and cell proliferation. Crotonoside has shown cytotoxic activity in various cancer cell lines and has been investigated for its potential in chemotherapy and immune modulation.

Chemical Structure

Crotonoside
Crotonoside
CAS#1818-71-9

Theoretical Analysis

MedKoo Cat#: 585163

Name: Crotonoside

CAS#: 1818-71-9

Chemical Formula: C10H13N5O5

Exact Mass: 283.0917

Molecular Weight: 283.24

Elemental Analysis: C, 42.41; H, 4.63; N, 24.73; O, 28.24

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Crotonoside; Isoguanine riboside; Isoguanosine; 2-Hydroxyadenosine; Crotonosid; NSC 12161; NSC12161; NSC-12161;
IUPAC/Chemical Name
2,3-dihydro-2-oxo-adenosine
InChi Key
MIKUYHXYGGJMLM-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC(C(N)=N3)=C2NC3=O)O1)O)O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Crotonoside inhibits FLT3 and HDAC3/6, exhibits selective inhibition in acute myeloid leukemia (AML) cells.
In vitro activity:
Compared to the DMSO mock control, the percentages of CD11c+ cells were dose-dependently and significantly reduced upon the addition of crotonoside (Figure 6), suggesting that crotonoside constrained DC differentiation. Reference: Plants (Basel). 2020 Nov; 9(11): 1535. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7698099/
In vivo activity:
The in vivo antitumor activity of crotonoside was evaluated in the subcutaneous tumor xenograft model of NOD-SCID mice. The animals were treated with different doses of crotonoside at 70 mg/kg/day (i.p.), 35 mg/kg/day (i.p.) and 70 mg/kg (qod, i.v.) or with vehicle (i.p.) alone. Treatment of cells for 24 h with crotonoside induced a significant antitumor activity and inhibited xenograft tumor progress as compared to treatment with vehicle. Reference: Oncotarget. 2017 Nov 28; 8(61): 103087–103099. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5732713/
Solvent mg/mL mM
Solubility
DMSO 41.0 144.75
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 283.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lin SC, Lin CC, Li S, Lin WY, Lehman CW, Bracci NR, Tsai SW. Alleviation of Collagen-Induced Arthritis by Crotonoside through Modulation of Dendritic Cell Differentiation and Activation. Plants (Basel). 2020 Nov 10;9(11):1535. doi: 10.3390/plants9111535. PMID: 33182776; PMCID: PMC7698099. 2. Li YZ, Yu S, Yan PA, Gong DY, Wu FL, He Z, Yuan YY, Zhao AY, Tang X, Zhang RQ, Peng C, Cao ZX. Crotonoside exhibits selective post-inhibition effect in AML cells via inhibition of FLT3 and HDAC3/6. Oncotarget. 2017 Sep 8;8(61):103087-103099. doi: 10.18632/oncotarget.20710. PMID: 29262547; PMCID: PMC5732713. 3. Lin SC, Lin CC, Li S, Lin WY, Lehman CW, Bracci NR, Tsai SW. Alleviation of Collagen-Induced Arthritis by Crotonoside through Modulation of Dendritic Cell Differentiation and Activation. Plants (Basel). 2020 Nov 10;9(11):1535. doi: 10.3390/plants9111535. PMID: 33182776; PMCID: PMC7698099. 4. Liu Z, Jia Y, Song L, Tian Y, Zhang P, Zhang P, Cao Z, Ma J. Antiarrhythmic effect of crotonoside by regulating sodium and calcium channels in rabbit ventricular myocytes. Life Sci. 2020 Mar 1;244:117333. doi: 10.1016/j.lfs.2020.117333. Epub 2020 Jan 18. PMID: 31962132.
In vitro protocol:
1. Lin SC, Lin CC, Li S, Lin WY, Lehman CW, Bracci NR, Tsai SW. Alleviation of Collagen-Induced Arthritis by Crotonoside through Modulation of Dendritic Cell Differentiation and Activation. Plants (Basel). 2020 Nov 10;9(11):1535. doi: 10.3390/plants9111535. PMID: 33182776; PMCID: PMC7698099. 2. Li YZ, Yu S, Yan PA, Gong DY, Wu FL, He Z, Yuan YY, Zhao AY, Tang X, Zhang RQ, Peng C, Cao ZX. Crotonoside exhibits selective post-inhibition effect in AML cells via inhibition of FLT3 and HDAC3/6. Oncotarget. 2017 Sep 8;8(61):103087-103099. doi: 10.18632/oncotarget.20710. PMID: 29262547; PMCID: PMC5732713.
In vivo protocol:
1. Lin SC, Lin CC, Li S, Lin WY, Lehman CW, Bracci NR, Tsai SW. Alleviation of Collagen-Induced Arthritis by Crotonoside through Modulation of Dendritic Cell Differentiation and Activation. Plants (Basel). 2020 Nov 10;9(11):1535. doi: 10.3390/plants9111535. PMID: 33182776; PMCID: PMC7698099. 2. Liu Z, Jia Y, Song L, Tian Y, Zhang P, Zhang P, Cao Z, Ma J. Antiarrhythmic effect of crotonoside by regulating sodium and calcium channels in rabbit ventricular myocytes. Life Sci. 2020 Mar 1;244:117333. doi: 10.1016/j.lfs.2020.117333. Epub 2020 Jan 18. PMID: 31962132.
1: Gate G, Szabla R, Haggmark MR, Šponer J, Sobolewski AL, de Vries MS. Photodynamics of alternative DNA base isoguanine. Phys Chem Chem Phys. 2019 Jun 26;21(25):13474-13485. doi: 10.1039/c9cp01622h. PubMed PMID: 31204732. 2: Li YZ, Yu S, Yan PA, Gong DY, Wu FL, He Z, Yuan YY, Zhao AY, Tang X, Zhang RQ, Peng C, Cao ZX. Crotonoside exhibits selective post-inhibition effect in AML cells via inhibition of FLT3 and HDAC3/6. Oncotarget. 2017 Sep 8;8(61):103087-103099. doi: 10.18632/oncotarget.20710. eCollection 2017 Nov 28. PubMed PMID: 29262547; PubMed Central PMCID: PMC5732713. 3: Yan P, Zhang L, Peng C, Zhang R. Pharmacokinetics and tissue distribution of crotonoside. Xenobiotica. 2018 Jan;48(1):28-36. doi: 10.1080/00498254.2016.1276311. Epub 2017 Jan 19. PubMed PMID: 28100102.