Bufalin | CAS#465-21-4 | SRC-3 inhibitor

MedKoo Cat#: 563504 | Name: Bufalin

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Description:

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

Bufalin is an inhibitor of steroid receptor coactivator 3 (SRC-3). It acts by inducing cell death through the ROS-mediated RIP1/RIP3/PARP-1 pathways.

Chemical Structure

Bufalin

CAS#465-21-4

Theoretical Analysis

MedKoo Cat#: 563504

Name: Bufalin

CAS#: 465-21-4

Chemical Formula: C24H34O4

Exact Mass: 386.2457

Molecular Weight: 386.53

Elemental Analysis: C, 74.58; H, 8.87; O, 16.56

Price and Availability

Size	Price	Availability
5mg	USD 250.00	2 Weeks
10mg	USD 450.00	2 Weeks
25mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Bufalin; NSC 89595; NSC89595; NSC-89595

IUPAC/Chemical Name

5-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one

InChi Key

QEEBRPGZBVVINN-BMPKRDENSA-N

InChi Code

InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1

SMILES Code

O=C1C=CC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]23C)=CO1

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:

Bufalin acts as a potent Na+/K+-ATPase inhibitor, binds to the subunit α1, α2 and α3, with Kd of 42.5, 45 and 40 nM, respectively.

In vitro activity:

Bufalin targeted the SRC-3 protein to reduce MIF release in chemoresistant cells in order to regulate the polarization of M2 macrophages. Reference: Cancer Lett. 2021 Aug 10;513:63-74. https://pubmed.ncbi.nlm.nih.gov/34000344/

In vivo activity:

In addition, bufalin restrained the tumor growth and development in vivo in mice via enhancing the expression of circ_0046264. Reference: Biotechnol Lett. 2021 Jun;43(6):1229-1240. https://pubmed.ncbi.nlm.nih.gov/33534015/

	Solvent	mg/mL	mM
Solubility
	DMSO	36.0	93.14
	DMF	25.0	64.68
	Ethanol	27.5	71.15
	Ethanol:PBS (pH 7.2) (1:2)	0.3	0.78

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 386.53 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.

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. Chen J, Wang H, Jia L, He J, Li Y, Liu H, Wu R, Qiu Y, Zhan Y, Yuan Z, Cao Y, Li W, Xu K, Yin P. Bufalin targets the SRC-3/MIF pathway in chemoresistant cells to regulate M2 macrophage polarization in colorectal cancer. Cancer Lett. 2021 Aug 10;513:63-74. doi: 10.1016/j.canlet.2021.05.008. Epub 2021 May 14. PMID: 34000344. 2. Pan L, Nie L, Yao S, Bi A, Ye Y, Wu Y, Tan Z, Wu Z. Bufalin exerts antitumor effects in neuroblastoma via the induction of reactive oxygen species‑mediated apoptosis by targeting the electron transport chain. Int J Mol Med. 2020 Dec;46(6):2137-2149. doi: 10.3892/ijmm.2020.4745. Epub 2020 Oct 6. PMID: 33125107; PMCID: PMC7595673. 3. Zou D, Song J, Deng M, Ma Y, Yang C, Liu J, Wang S, Wen Z, Tang Y, Qu X, Zhang Y. Bufalin inhibits peritoneal dissemination of gastric cancer through endothelial nitric oxide synthase-mitogen-activated protein kinases signaling pathway. FASEB J. 2021 May;35(5):e21601. doi: 10.1096/fj.202002780R. PMID: 33913201. 4. Jin J, Yao Z, Qin H, Wang K, Xin X. Bufalin inhibits the malignant development of non-small cell lung cancer by mediating the circ_0046264/miR-522-3p axis. Biotechnol Lett. 2021 Jun;43(6):1229-1240. doi: 10.1007/s10529-021-03081-6. Epub 2021 Feb 3. PMID: 33534015.

In vitro protocol:

In vivo protocol:

1. Zou D, Song J, Deng M, Ma Y, Yang C, Liu J, Wang S, Wen Z, Tang Y, Qu X, Zhang Y. Bufalin inhibits peritoneal dissemination of gastric cancer through endothelial nitric oxide synthase-mitogen-activated protein kinases signaling pathway. FASEB J. 2021 May;35(5):e21601. doi: 10.1096/fj.202002780R. PMID: 33913201. 2. Jin J, Yao Z, Qin H, Wang K, Xin X. Bufalin inhibits the malignant development of non-small cell lung cancer by mediating the circ_0046264/miR-522-3p axis. Biotechnol Lett. 2021 Jun;43(6):1229-1240. doi: 10.1007/s10529-021-03081-6. Epub 2021 Feb 3. PMID: 33534015.

1: Soumoy L, Ghanem GE, Saussez S, Journe F. Bufalin for an innovative therapeutic approach against cancer. Pharmacol Res. 2022 Oct;184:106442. doi: 10.1016/j.phrs.2022.106442. Epub 2022 Sep 9. PMID: 36096424. 2: Yu Z, Li Y, Li Y, Zhang J, Li M, Ji L, Tang Y, Zheng Y, Sheng J, Han Q, Li F, Guo J, Wang L, Sun X, Gao Y, Feng H. Bufalin stimulates antitumor immune response by driving tumor-infiltrating macrophage toward M1 phenotype in hepatocellular carcinoma. J Immunother Cancer. 2022 May;10(5):e004297. doi: 10.1136/jitc-2021-004297. PMID: 35618286; PMCID: PMC9125767. 3: Dou L, Zou D, Song F, Jin Y, Li Y, Zhang Y. Bufalin suppresses ovarian cancer cell proliferation via EGFR pathway. Chin Med J (Engl). 2021 Dec 22;135(4):456-461. doi: 10.1097/CM9.0000000000001879. PMID: 34935692; PMCID: PMC8869555. 4: Fang K, Zhan Y, Zhu R, Wang Y, Wu C, Sun M, Qiu Y, Yuan Z, Liang X, Yin P, Xu K. Bufalin suppresses tumour microenvironment-mediated angiogenesis by inhibiting the STAT3 signalling pathway. J Transl Med. 2021 Sep 8;19(1):383. doi: 10.1186/s12967-021-03058-z. PMID: 34496870; PMCID: PMC8424978. 5: Yang L, Zhou F, Zhuang Y, Liu Y, Xu L, Zhao H, Xiang Y, Dai X, Liu Z, Huang X, Wang L, Zhao C. Acetyl-bufalin shows potent efficacy against non-small-cell lung cancer by targeting the CDK9/STAT3 signalling pathway. Br J Cancer. 2021 Feb;124(3):645-657. doi: 10.1038/s41416-020-01135-6. Epub 2020 Oct 30. PMID: 33122847; PMCID: PMC7851395. 6: Jiang HY, Zheng HM, Xia C, Li X, Wang G, Zhao T, Cui XN, Wang RY, Liu Y. The Research Progress of Bufalin in the Treatment of Hepatocellular Carcinoma. Onco Targets Ther. 2022 Mar 22;15:291-298. doi: 10.2147/OTT.S333233. PMID: 35345394; PMCID: PMC8957335. 7: Farooqi AA, Rakhmetova VS, Kapanova G, Tashenova G, Tulebayeva A, Akhenbekova A, Ibekenov O, Turgambayeva A, Xu B. Bufalin-Mediated Regulation of Cell Signaling Pathways in Different Cancers: Spotlight on JAK/STAT, Wnt/β-Catenin, mTOR, TRAIL/TRAIL-R, and Non-Coding RNAs. Molecules. 2023 Feb 27;28(5):2231. doi: 10.3390/molecules28052231. PMID: 36903477; PMCID: PMC10004807. 8: Wang J, Xia Y, Zuo Q, Chen T. Molecular mechanisms underlying the antimetastatic activity of bufalin. Mol Clin Oncol. 2018 May;8(5):631-636. doi: 10.3892/mco.2018.1591. Epub 2018 Mar 21. PMID: 29732152; PMCID: PMC5921222. 9: Lan YL, Lou JC, Jiang XW, Wang X, Xing JS, Li S, Zhang B. A research update on the anticancer effects of bufalin and its derivatives. Oncol Lett. 2019 Apr;17(4):3635-3640. doi: 10.3892/ol.2019.10062. Epub 2019 Feb 21. PMID: 30915168; PMCID: PMC6430489. 10: Su S, Dou H, Wang Z, Zhang Q. Bufalin inhibits ovarian carcinoma via targeting mTOR/HIF-α pathway. Basic Clin Pharmacol Toxicol. 2021 Feb;128(2):224-233. doi: 10.1111/bcpt.13487. Epub 2020 Oct 2. PMID: 32905663. 11: Li M, Wang XJ, Zhao Q, Wang JX, Xing HY, Zhang YZ, Zhang XX, Zhi YY, Li H, Ma J. Bufalin-induced cardiotoxicity: new findings into mechanisms. Chin J Nat Med. 2020 Jul;18(7):550-560. doi: 10.1016/S1875-5364(20)30065-0. PMID: 32616195. 12: Ding L, Yang Y, Lu Q, Qu D, Chandrakesan P, Feng H, Chen H, Chen X, Liao Z, Du J, Cao Z, Weygant N. Bufalin Inhibits Tumorigenesis, Stemness, and Epithelial-Mesenchymal Transition in Colorectal Cancer through a C-Kit/Slug Signaling Axis. Int J Mol Sci. 2022 Nov 1;23(21):13354. doi: 10.3390/ijms232113354. PMID: 36362141; PMCID: PMC9656328. 13: Sampath V, Horesh N, Sasi B, Zannadeh H, Pogodin I, Singh SV, Deutsch J, Lichtstein D. Synthesis and Biological Evaluation of Novel Bufalin Derivatives. Int J Mol Sci. 2022 Apr 4;23(7):4007. doi: 10.3390/ijms23074007. PMID: 35409366; PMCID: PMC8999407. 14: Liu XD, Song CY, Kong CC, Tian X. Bufalin Induces Programmed Necroptosis in Triple-Negative Breast Cancer Drug-Resistant Cell Lines through RIP1/ROS- Mediated Pathway. Chin J Integr Med. 2022 Oct;28(10):900-908. doi: 10.1007/s11655-021-3458-7. Epub 2021 Nov 26. PMID: 34826043. 15: LingHu HR, Luo H, Gang L. Bufalin Induces Glioma Cell Death by Apoptosis or Necroptosis. Onco Targets Ther. 2020 May 27;13:4767-4778. doi: 10.2147/OTT.S242567. PMID: 32581545; PMCID: PMC7274536. 16: Zheng YD, He Z, Su ZC, Wang H, Jiang XH, Fang X, Lu SL, Li Y. Bufalin induces apoptosis and autophagy via the Ca2+/CaMKKβ/AMPK/Beclin1 signaling pathway in osteosarcoma cells. Cell Biol Int. 2023 Aug;47(8):1344-1353. doi: 10.1002/cbin.12021. Epub 2023 Mar 29. PMID: 36987947. 17: Long L, Zhong W, Guo L, Ji J, Nie H. Effect of Bufalin-PLGA Microspheres in the Alleviation of Neuropathic Pain via the CCI Model. Front Pharmacol. 2022 Jun 13;13:910885. doi: 10.3389/fphar.2022.910885. PMID: 35770074; PMCID: PMC9234216. 18: Yuan Z, Liu C, Sun Y, Li Y, Wu H, Ma S, Shang J, Zhan Y, Yin P, Gao F. Bufalin exacerbates Photodynamic therapy of colorectal cancer by targeting SRC-3/HIF-1α pathway. Int J Pharm. 2022 Aug 25;624:122018. doi: 10.1016/j.ijpharm.2022.122018. Epub 2022 Jul 14. PMID: 35839982. 19: Ju Q, Shi Q, Liu C, Fu G, Shi H. Bufalin suppresses esophageal squamous cell carcinoma progression by activating the PIAS3/STAT3 signaling pathway. J Thorac Dis. 2023 Apr 28;15(4):2141-2160. doi: 10.21037/jtd-23-486. Epub 2023 Apr 25. PMID: 37197494; PMCID: PMC10183519. 20: Miao L, Liu Y, Ali NM, Dong Y, Zhang B, Cui X. Bufalin serves as a pharmaceutic that mitigates drug resistance. Drug Metab Rev. 2023 Apr 27:1-10. doi: 10.1080/03602532.2023.2206065. Epub ahead of print. PMID: 37114332.