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MedKoo Cat#: 592231 | Name: Senecionine
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Description:

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

Senecionine is an antineoplastic agent.

Chemical Structure

Senecionine
CAS#130-01-8

Theoretical Analysis

MedKoo Cat#: 592231

Name: Senecionine

CAS#: 130-01-8

Chemical Formula: C18H35NO5

Exact Mass: 335.1733

Molecular Weight: 335.40

Elemental Analysis: C, 64.46; H, 7.51; N, 4.18; O, 23.85

Price and Availability

Size Price Availability Quantity
1mg USD 410.00
5mg USD 1,020.00
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Related CAS #
No Data
Synonym
Senecionine; NSC 89935; NSC-89935; NSC89935
IUPAC/Chemical Name
(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
InChi Key
HKODIGSRFALUTA-JTLQZVBZSA-N
InChi Code
InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1
SMILES Code
O=C(O[C@]1([H])CCN2[C@]1([H])C(COC([C@](C)(O)[C@H](C)C/3)=O)=CC2)C3=C/C
Appearance
Solid powder
Purity
>98% (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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Senecionine decreases the activities of glutathione S-transferase, aminopyrine demethylase and arylhydrocarbon hydroxylase (AHH).
In vitro activity:
In vitro experiments with senecionine, a pyrrolizidine alkaloid (PA), were conducted using primary mouse hepatocytes and liver sinusoidal endothelial cells (LSECs). However, upon metabolic activation by primary mouse hepatocytes, senecionine exhibited cytotoxicity to cultivated LSECs with an EC50 of approximately 22 µM. The study confirmed the cytochrome P450 (CYP)-dependency of senecionine bioactivation, revealing that toxic metabolites are generated by hepatic CYPs. Reference: Arch Toxicol. 2020 Jan;94(1):219-229. https://pubmed.ncbi.nlm.nih.gov/31606820/
In vivo activity:
This study investigated the metabolism, bioactivation, detoxication, and toxicity variations among senecionine, adonifoline, and other pyrrolizidine alkaloids. Significant pharmacokinetic differences were observed between intravenous and oral administrations of senecionine and adonifoline, with fast absorption, lower bioavailability, and rapid metabolism to PA N-oxides and hydroxylation products. The higher N-oxygenation activity and pronounced toxicity of senecionine, compared to adonifoline, in rats raised questions about the potential relationship between SEN's elevated metabolic rate and its potent toxicity in vivo. Reference: Anal Bioanal Chem. 2011 Jul;401(1):275-87. https://pubmed.ncbi.nlm.nih.gov/21573843/
Solvent mg/mL mM comments
Solubility
DMSO 1.4 4.26
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 335.40 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. Hessel-Pras S, Braeuning A, Guenther G, Adawy A, Enge AM, Ebmeyer J, Henderson CJ, Hengstler JG, Lampen A, Reif R. The pyrrolizidine alkaloid senecionine induces CYP-dependent destruction of sinusoidal endothelial cells and cholestasis in mice. Arch Toxicol. 2020 Jan;94(1):219-229. doi: 10.1007/s00204-019-02582-8. Epub 2019 Oct 12. PMID: 31606820. 2. Yang X, Wang H, Ni HM, Xiong A, Wang Z, Sesaki H, Ding WX, Yang L. Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice. Redox Biol. 2017 Aug;12:264-273. doi: 10.1016/j.redox.2017.02.020. Epub 2017 Mar 2. PMID: 28282614; PMCID: PMC5344326. 3. Chen Y, Tang Y, Liu P, Wang J, Wang W, Wang C, Ding L, Xiong A, Yang L, Wang Z. Species difference in toxicokinetics and safety assessment of senecionine N-oxide in a UDP-glucuronosyltransferase 1A4 humanized mouse model. Chem Biol Interact. 2023 Aug 1;380:110505. doi: 10.1016/j.cbi.2023.110505. Epub 2023 Apr 18. PMID: 37080376. 4. Wang C, Li Y, Gao J, He Y, Xiong A, Yang L, Cheng X, Ma Y, Wang Z. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Anal Bioanal Chem. 2011 Jul;401(1):275-87. doi: 10.1007/s00216-011-5075-3. Epub 2011 May 15. PMID: 21573843.
In vitro protocol:
1. Hessel-Pras S, Braeuning A, Guenther G, Adawy A, Enge AM, Ebmeyer J, Henderson CJ, Hengstler JG, Lampen A, Reif R. The pyrrolizidine alkaloid senecionine induces CYP-dependent destruction of sinusoidal endothelial cells and cholestasis in mice. Arch Toxicol. 2020 Jan;94(1):219-229. doi: 10.1007/s00204-019-02582-8. Epub 2019 Oct 12. PMID: 31606820. 2. Yang X, Wang H, Ni HM, Xiong A, Wang Z, Sesaki H, Ding WX, Yang L. Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice. Redox Biol. 2017 Aug;12:264-273. doi: 10.1016/j.redox.2017.02.020. Epub 2017 Mar 2. PMID: 28282614; PMCID: PMC5344326.
In vivo protocol:
1. Chen Y, Tang Y, Liu P, Wang J, Wang W, Wang C, Ding L, Xiong A, Yang L, Wang Z. Species difference in toxicokinetics and safety assessment of senecionine N-oxide in a UDP-glucuronosyltransferase 1A4 humanized mouse model. Chem Biol Interact. 2023 Aug 1;380:110505. doi: 10.1016/j.cbi.2023.110505. Epub 2023 Apr 18. PMID: 37080376. 2. Wang C, Li Y, Gao J, He Y, Xiong A, Yang L, Cheng X, Ma Y, Wang Z. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Anal Bioanal Chem. 2011 Jul;401(1):275-87. doi: 10.1007/s00216-011-5075-3. Epub 2011 May 15. PMID: 21573843.

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PF-0419789

PF-0419789