Bufothionine

Bufothionine
Names
	IUPAC name 5,5-Dimethyl-6-(sulfinooxy)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-5-ium
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	4474818;
PubChem CID	5315536;
	InChI InChI=1S/C12H14N2O3S/c1-14(2)6-5-8-7-13-9-3-4-10(17-18(15)16)12(14)11(8)9/h3-4,7,13H,5-6H2,1-2H3/p+1;
	SMILES O=S(O)Oc1ccc2c3c1[N+](CCc3c[nH]2)(C)C;
Properties
Chemical formula	C12H15N2O3S+
Molar mass	267.32 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Bufothionine is a sulfur-containing compound which is present in the bufotoxins secreted by the parotoid gland of certain toads of the genera Bufo and Chaunus. This specific compound can be found in the skin of certain species of toad such as the Asiatic Toad,[1][2] Chaunus arunco, Chaunus crucifer, Chaunus spinulosus, and Chaunus arenarum.[3]

Bufothionine's Medicinal Prospects in Oncology Practices

Bufothionine has been shown to suppress growth of cancerous liver cells in vitro. Experiments were conducted in which cultured cancer cells were shown to have an increase in G2-M damage checkpoint, ensuring that growth of the cell will not continue until the damage to the DNA is corrected while also showing a drop in the G0 and G1 activity, which pertains to phase where there is cell growth and RNA production[4]. Similarly, Buifothionine has also been shown to increase the chances of cell death and decrease cell growth of gastric cancer related cells by inhibiting the PIM3 gene, which, in cancerous cells, increases the resistance of chemotherapeutic treatments[5].

Notes

Dai, L. P.; Gao, H. M.; Wang, Z. M.; Wang, W. H. (2007). "Isolation and structure identification of chemical constituents from the skin of Bufo bufo gargarizans". Yao xue xue bao = Acta pharmaceutica Sinica. 42 (8): 858–861. PMID 17944235.
Dai, L. P.; Wang, Z. M.; Gao, H. M.; Jiang, X.; Ding, G. Z. (2007). "Determination of bufothionine in skin of Bufo bufo gargarizans and Huachansu injection". Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 32 (3): 224–226. PMID 17432144.
V Deulofeu; Enrique Duprat (February 10, 1944). "The Basic Constituents of the Venom of some South American Toads" (PDF). Journal of Biological Chemistry. American Society for Biochemistry and Molecular Biology. 153: 459–463.
Xie, Rui-Fang; Li, Zhi-Cheng; Gao, Bo; Shi, Zhi-Na; Zhou, Xin (2012-06-01). "Bufothionine, a possible effective component in cinobufocini injection for hepatocellular carcinoma". Journal of Ethnopharmacology. Modernization of Traditional Chinese Medicine. 141 (2): 692–700. doi:10.1016/j.jep.2011.12.018. ISSN 0378-8741.
Wang, Guojun; Liu, Guanghui; Ye, Yanwei; Fu, Yang; Zhang, Xiefu (2019-09-01). "Bufothionine exerts anti-cancer activities in gastric cancer through Pim3". Life Sciences. 232: 116615. doi:10.1016/j.lfs.2019.116615. ISSN 0024-3205.

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[1] Dai, L. P.; Gao, H. M.; Wang, Z. M.; Wang, W. H. (2007). "Isolation and structure identification of chemical constituents from the skin of Bufo bufo gargarizans". Yao xue xue bao = Acta pharmaceutica Sinica. 42 (8): 858–861. PMID 17944235.

[2] Dai, L. P.; Wang, Z. M.; Gao, H. M.; Jiang, X.; Ding, G. Z. (2007). "Determination of bufothionine in skin of Bufo bufo gargarizans and Huachansu injection". Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 32 (3): 224–226. PMID 17432144.

[JBC_-_10_Feb_1994_-_Deulofeu_and_Duprat_-_The_Basic_Constituents_of_the_Venom_of_some_South_American_Toads-3] V Deulofeu; Enrique Duprat (February 10, 1944). "The Basic Constituents of the Venom of some South American Toads" (PDF). Journal of Biological Chemistry. American Society for Biochemistry and Molecular Biology. 153: 459–463.

[4] Xie, Rui-Fang; Li, Zhi-Cheng; Gao, Bo; Shi, Zhi-Na; Zhou, Xin (2012-06-01). "Bufothionine, a possible effective component in cinobufocini injection for hepatocellular carcinoma". Journal of Ethnopharmacology. Modernization of Traditional Chinese Medicine. 141 (2): 692–700. doi:10.1016/j.jep.2011.12.018. ISSN 0378-8741.

[5] Wang, Guojun; Liu, Guanghui; Ye, Yanwei; Fu, Yang; Zhang, Xiefu (2019-09-01). "Bufothionine exerts anti-cancer activities in gastric cancer through Pim3". Life Sciences. 232: 116615. doi:10.1016/j.lfs.2019.116615. ISSN 0024-3205.