Monocrotaline
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MedKoo CAT#: 571152

CAS#: 315-22-0

Description: Monocrotaline is a natural ligand that exhibits dose-dependent cytotoxicity as a pyrrolizidine alkaloid and toxic plant constituent; the alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. However, it also has therapeutic potential against hepatocellular carcinoma. It acts against p53, HGF and TREM1 proteins, which play a threatening role in causing hepatocellular carcinoma. It is a novel scaffold for liver cancer with superior efficacy and lesser side effects. A

Chemical Structure

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Monocrotaline
CAS# 315-22-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 571152
Name: Monocrotaline
CAS#: 315-22-0
Chemical Formula: C16H23NO6
Exact Mass: 325.15
Molecular Weight: 325.361
Elemental Analysis: C, 59.07; H, 7.13; N, 4.31; O, 29.50

Price and Availability

Size Price Availability Quantity
100mg USD 240
500mg USD 450
1g USD 790
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Synonym: Monocrotaline; NSC 28693; NSC-28693; NSC28693

IUPAC/Chemical Name: 20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)- (9CI)

InChi Key: QVCMHGGNRFRMAD-XFGHUUIASA-N

InChi Code: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1

SMILES Code: O=C(O[C@]1([H])CCN2[C@]1([H])C(CO3)=CC2)[C@H](C)[C@@](C)(O)[C@@](C)(O)C3=O

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: >2 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: Monocrotaline is an pyrrolizidine alkaloid extracted from the seeds of the Crotalaria pallida plant to induce pulmonary hypertension in rodents.
In vitro activity: The in silico docking study has provided an insight and evidence for the antineoplastic activity of monocrotaline against p53, HGF and TREM1 proteins which play a threatening role in causing hepatocellular carcinoma. The in vitro cytotoxicity of monocrotaline was proved at IC50 24.966 µg/mL and genotoxicity at 2 X IC50 against HepG2 cells. Reference: Anticancer Agents Med Chem. 2014;14(9):1237-48. https://pubmed.ncbi.nlm.nih.gov/25028149/
In vivo activity: In this study, the benefits of induced pluripotent stem cells (iPSCs) and iPSC-conditioned medium (iPSC CM) were explored in monocrotaline (MCT)-induced PAH (pulmonary arterial hypertension) rats. This study demonstrated that both iPSCs and iPSC CM significantly reduced the right ventricular systolic pressure and ameliorated the hypertrophy of the right ventricle in MCT-induced PAH rats in models of both disease prevention and disease reversal. In the prevention of MCT-induced PAH, iPSC-based therapy led to the decreased accumulation of inflammatory cells and down-regulated the expression of the IL-1β, IL-6, IL-12α, IL-12β, IL-23 and IFNγ genes in lung specimens, which implied that iPSC-based therapy may be involved in the regulation of inflammation. Reference: PLoS One. 2016 Feb 3;11(2):e0142476. https://pubmed.ncbi.nlm.nih.gov/26840075/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Chloroform 5.0 15.37
DMF 1.0 3.07
DMSO 30.3 93.23
Water 2.0 6.15

Preparing Stock Solutions

The following data is based on the product molecular weight 325.36 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. Li P, Song J, Du H, Lu Y, Dong S, Zhou S, Guo Z, Wu H, Zhao X, Qin Y, Zhu N. MicroRNA-663 prevents monocrotaline-induced pulmonary arterial hypertension by targeting TGF-β1/smad2/3 signaling. J Mol Cell Cardiol. 2021 Dec;161:9-22. doi: 10.1016/j.yjmcc.2021.07.010. Epub 2021 Jul 31. PMID: 34339758. 2. Kusuma SS, Tanneeru K, Didla S, Devendra BN, Kiranmayi P. Antineoplastic activity of monocrotaline against hepatocellular carcinoma. Anticancer Agents Med Chem. 2014;14(9):1237-48. doi: 10.2174/1871520614666140715085907. PMID: 25028149. 3. Yang L, Tian J, Wang J, Zeng J, Wang T, Lin B, Linneman J, Li L, Niu Y, Gou D, Zhang Y. The protective role of EP300 in monocrotaline-induced pulmonary hypertension. Front Cardiovasc Med. 2023 Feb 22;10:1037217. doi: 10.3389/fcvm.2023.1037217. PMID: 36910531; PMCID: PMC9992637. 4. Huang WC, Ke MW, Cheng CC, Chiou SH, Wann SR, Shu CW, Chiou KR, Tseng CJ, Pan HW, Mar GY, Liu CP. Therapeutic Benefits of Induced Pluripotent Stem Cells in Monocrotaline-Induced Pulmonary Arterial Hypertension. PLoS One. 2016 Feb 3;11(2):e0142476. doi: 10.1371/journal.pone.0142476. PMID: 26840075; PMCID: PMC4740504.
In vitro protocol: 1. Li P, Song J, Du H, Lu Y, Dong S, Zhou S, Guo Z, Wu H, Zhao X, Qin Y, Zhu N. MicroRNA-663 prevents monocrotaline-induced pulmonary arterial hypertension by targeting TGF-β1/smad2/3 signaling. J Mol Cell Cardiol. 2021 Dec;161:9-22. doi: 10.1016/j.yjmcc.2021.07.010. Epub 2021 Jul 31. PMID: 34339758. 2. Kusuma SS, Tanneeru K, Didla S, Devendra BN, Kiranmayi P. Antineoplastic activity of monocrotaline against hepatocellular carcinoma. Anticancer Agents Med Chem. 2014;14(9):1237-48. doi: 10.2174/1871520614666140715085907. PMID: 25028149.
In vivo protocol: 1. Yang L, Tian J, Wang J, Zeng J, Wang T, Lin B, Linneman J, Li L, Niu Y, Gou D, Zhang Y. The protective role of EP300 in monocrotaline-induced pulmonary hypertension. Front Cardiovasc Med. 2023 Feb 22;10:1037217. doi: 10.3389/fcvm.2023.1037217. PMID: 36910531; PMCID: PMC9992637. 2. Huang WC, Ke MW, Cheng CC, Chiou SH, Wann SR, Shu CW, Chiou KR, Tseng CJ, Pan HW, Mar GY, Liu CP. Therapeutic Benefits of Induced Pluripotent Stem Cells in Monocrotaline-Induced Pulmonary Arterial Hypertension. PLoS One. 2016 Feb 3;11(2):e0142476. doi: 10.1371/journal.pone.0142476. PMID: 26840075; PMCID: PMC4740504.

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1: Kusuma SS, Tanneeru K, Didla S, Devendra BN, Kiranmayi P. Antineoplastic activity of monocrotaline against hepatocellular carcinoma. Anticancer Agents Med Chem. 2014;14(9):1237-48. PubMed PMID: 25028149.

2: Nogueira-Ferreira R, Vitorino R, Ferreira R, Henriques-Coelho T. Exploring the monocrotaline animal model for the study of pulmonary arterial hypertension: A network approach. Pulm Pharmacol Ther. 2015 Dec;35:8-16. doi: 10.1016/j.pupt.2015.09.007. Epub 2015 Sep 21. Review. PubMed PMID: 26403584.

3: Polonio IB, Acencio MM, Pazetti R, Almeida FM, Silva BS, Pereira KA, Souza R. Lodenafil treatment in the monocrotaline model of pulmonary hypertension in rats. J Bras Pneumol. 2014 Jul-Aug;40(4):421-4. English, Portuguese. PubMed PMID: 25210965; PubMed Central PMCID: PMC4201173.

4: Fontoura D, Oliveira-Pinto J, Tavares-Silva M, Leite S, Vasques-Nóvoa F, Mendes-Ferreira P, Lourenço AP, Leite-Moreira AF. Myocardial and anti-inflammatory effects of chronic bosentan therapy in monocrotaline-induced pulmonary hypertension. Rev Port Cardiol. 2014 Apr;33(4):213-22. doi: 10.1016/j.repc.2013.09.016. Epub 2014 Apr 26. PubMed PMID: 24780128.

5: Masubuchi S, Komeda K, Takai S, Jin D, Tashiro K, Li ZL, Otsuki Y, Okamura H, Hayashi M, Uchiyama K. Chymase inhibition attenuates monocrotaline-induced sinusoidal obstruction syndrome in hamsters. Curr Med Chem. 2013;20(21):2723-9. Review. PubMed PMID: 23521680.

6: Chaumais MC, Ranchoux B, Montani D, Dorfmüller P, Tu L, Lecerf F, Raymond N, Guignabert C, Price L, Simonneau G, Cohen-Kaminsky S, Humbert M, Perros F. N-acetylcysteine improves established monocrotaline-induced pulmonary hypertension in rats. Respir Res. 2014 Jun 14;15:65. doi: 10.1186/1465-9921-15-65. PubMed PMID: 24929652; PubMed Central PMCID: PMC4065537.

7: Conotte R, Colet JM. A metabonomic evaluation of the monocrotaline-induced sinusoidal obstruction syndrome (SOS) in rats. Toxicol Appl Pharmacol. 2014 Apr 15;276(2):147-56. doi: 10.1016/j.taap.2014.02.008. Epub 2014 Feb 25. PubMed PMID: 24582690.

8: Yamada Y, Maruyama J, Zhang E, Okada A, Yokochi A, Sawada H, Mitani Y, Hayashi T, Suzuki K, Maruyama K. Effect of thrombomodulin on the development of monocrotaline-induced pulmonary hypertension. J Anesth. 2014 Feb;28(1):26-33. doi: 10.1007/s00540-013-1663-z. Epub 2013 Jul 2. PubMed PMID: 23817901.

9: Li XW, Wang XM, Li S, Yang JR. [Effects of rutaecarpine on right ventriclar remodeling in rats with monocrotaline-induced pulmonary hypertension]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2014 Sep;30(5):405-10. Chinese. PubMed PMID: 25571629.

10: Dias-Neto M, Luísa-Neves A, Pinho S, Gonçalves N, Mendes M, Eloy C, Lopes JM, Gonçalves D, Ferreira-Pinto M, Leite-Moreira AF, Henriques-Coelho T. Pathophysiology of infantile pulmonary arterial hypertension induced by monocrotaline. Pediatr Cardiol. 2015 Jun;36(5):1000-13. doi: 10.1007/s00246-015-1111-y. Epub 2015 Jan 22. PubMed PMID: 25608696.

11: Gomez-Arroyo JG, Farkas L, Alhussaini AA, Farkas D, Kraskauskas D, Voelkel NF, Bogaard HJ. The monocrotaline model of pulmonary hypertension in perspective. Am J Physiol Lung Cell Mol Physiol. 2012 Feb 15;302(4):L363-9. doi: 10.1152/ajplung.00212.2011. Epub 2011 Sep 30. Review. PubMed PMID: 21964406.

12: Kazama K, Okada M, Yamawaki H. A novel adipocytokine, omentin, inhibits monocrotaline-induced pulmonary arterial hypertension in rats. Biochem Biophys Res Commun. 2014 Sep 12;452(1):142-6. doi: 10.1016/j.bbrc.2014.08.070. Epub 2014 Aug 21. PubMed PMID: 25152392.

13: Kolli MB, Manne ND, Para R, Nalabotu SK, Nandyala G, Shokuhfar T, He K, Hamlekhan A, Ma JY, Wehner PS, Dornon L, Arvapalli R, Rice KM, Blough ER. Cerium oxide nanoparticles attenuate monocrotaline induced right ventricular hypertrophy following pulmonary arterial hypertension. Biomaterials. 2014 Dec;35(37):9951-62. doi: 10.1016/j.biomaterials.2014.08.037. Epub 2014 Sep 15. PubMed PMID: 25224369; PubMed Central PMCID: PMC4758344.

14: Li W, Wang K, Lin G, Peng Y, Zheng J. Lysine Adduction by Reactive Metabolite(s) of Monocrotaline. Chem Res Toxicol. 2016 Mar 21;29(3):333-41. doi: 10.1021/acs.chemrestox.5b00488. Epub 2016 Feb 8. PubMed PMID: 26812400.

15: Li XW, Guo B, Shen YY, Yang JR. [Effect of chrysin on expression of NOX4 and NF-κB in right ventricle of monocrotaline-induced pulmonary arterial hypertension of rats]. Yao Xue Xue Bao. 2015 Sep;50(9):1128-34. Chinese. PubMed PMID: 26757549.

16: Periasamy S, Chien SP, Liu MY. Therapeutic oral sesame oil is ineffectual against monocrotaline-induced sinusoidal obstruction syndrome in rats. JPEN J Parenter Enteral Nutr. 2013 Jan;37(1):129-33. doi: 10.1177/0148607112445795. Epub 2012 Apr 27. PubMed PMID: 22544841.

17: Wang R, Zhou SJ, Zeng DS, Xu R, Fei LM, Zhu QQ, Zhang Y, Sun GY. Plasmid-based short hairpin RNA against connective tissue growth factor attenuated monocrotaline-induced pulmonary vascular remodeling in rats. Gene Ther. 2014 Nov;21(11):931-7. doi: 10.1038/gt.2014.62. Epub 2014 Jul 31. PubMed PMID: 25077774.

18: Amin KA, Hashem KS, Al-muzafar HM, Taha EM. Oxidative hepatotoxicity effects of monocrotaline and its amelioration by lipoic acid, S-adenosyl methionine and vitamin E. J Complement Integr Med. 2014 Jan 10;11(1):35-41. doi: 10.1515/jcim-2013-0041. PubMed PMID: 24413220.

19: Zhang WH, Qiu MH, Wang XJ, Sun K, Zheng Y, Jing ZC. Up-regulation of hexokinase1 in the right ventricle of monocrotaline induced pulmonary hypertension. Respir Res. 2014 Oct 8;15:119. doi: 10.1186/s12931-014-0119-9. PubMed PMID: 25287584; PubMed Central PMCID: PMC4198683.

20: Yao J, Li CG, Gong LK, Feng CC, Li CZ, Gao M, Luan Y, Qi XM, Ren J. Hepatic cytochrome P450s play a major role in monocrotaline-induced renal toxicity in mice. Acta Pharmacol Sin. 2014 Feb;35(2):292-300. doi: 10.1038/aps.2013.145. Epub 2013 Dec 23. PubMed PMID: 24362331; PubMed Central PMCID: PMC4651220.