MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 585003 | Name: Calotropin

Description:

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

Calotropin, or Calotoxin, is a a cardenolide from calotropis gigantea that inhibits Wnt signaling by increasing casein kinase 1α in colon cancer cells.

Chemical Structure

Calotropin
Calotropin
CAS#1986-70-5

Theoretical Analysis

MedKoo Cat#: 585003

Name: Calotropin

CAS#: 1986-70-5

Chemical Formula: C29H40O9

Exact Mass: 532.2672

Molecular Weight: 532.63

Elemental Analysis: C, 65.40; H, 7.57; O, 27.03

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Calotropin; Cardenolide; Calotoxin
IUPAC/Chemical Name
Card-20(22)-enolide, 14-hydroxy-19-oxo-3,2-((tetrahydro-3,4-dihydroxy-6-methyl-2H-pyran-2,3-diyl)bis(oxy))-, (2alpha(2S,4S,6R),3beta,5alpha)-
InChi Key
OWPWFVVPBYFKBG-GHFYYFPWSA-N
InChi Code
InChI=1S/C29H40O9/c1-15-9-23(31)29(34)25(36-15)37-21-11-17-3-4-20-19(27(17,14-30)12-22(21)38-29)5-7-26(2)18(6-8-28(20,26)33)16-10-24(32)35-13-16/h10,14-15,17-23,25,31,33-34H,3-9,11-13H2,1-2H3/t15?,17-,18+,19-,20+,21-,22-,23?,25?,26+,27+,28-,29?/m0/s1
SMILES Code
O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@@]5([H])C[C@@](OC6C(O)(O7)C(O)CC(C)O6)([H])[C@]7([H])C[C@]5(C=O)[C@@]4([H])CC[C@]23C)=C1
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 532.63 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
1: Tian L, Xie XH, Zhu ZH. Calotropin regulates the apoptosis of non small cell cancer by regulating the cytotoxic T lymphocyte associated antigen 4 mediated TGF β/ERK signaling pathway. Mol Med Rep. 2018 Jun;17(6):7683-7691. doi: 10.3892/mmr.2018.8853. Epub 2018 Apr 5. PubMed PMID: 29620207; PubMed Central PMCID: PMC5983968. 2: Mo EP, Zhang RR, Xu J, Zhang H, Wang XX, Tan QT, Liu FL, Jiang RW, Cai SH. Calotropin from Asclepias curasavica induces cell cycle arrest and apoptosis in cisplatin-resistant lung cancer cells. Biochem Biophys Res Commun. 2016 Sep 16;478(2):710-5. doi: 10.1016/j.bbrc.2016.08.011. Epub 2016 Aug 4. PubMed PMID: 27498029. 3: Park HY, Toume K, Arai MA, Sadhu SK, Ahmed F, Ishibashi M. Calotropin: a cardenolide from calotropis gigantea that inhibits Wnt signaling by increasing casein kinase 1α in colon cancer cells. Chembiochem. 2014 Apr 14;15(6):872-8. doi: 10.1002/cbic.201300786. Epub 2014 Mar 18. PubMed PMID: 24644251. 4: Wang SC, Lu MC, Chen HL, Tseng HI, Ke YY, Wu YC, Yang PY. Cytotoxicity of calotropin is through caspase activation and downregulation of anti-apoptotic proteins in K562 cells. Cell Biol Int. 2009 Dec;33(12):1230-6. doi: 10.1016/j.cellbi.2009.08.013. Epub 2009 Sep 2. PubMed PMID: 19732845. 5: Zhou L, Cai L, Guo Y, Zhang H, Wang P, Yi G, Huang Y. Calotropin activates YAP through downregulation of LATS1 in colorectal cancer cells. Onco Targets Ther. 2019 May 23;12:4047-4054. doi: 10.2147/OTT.S200873. eCollection 2019. PubMed PMID: 31190898; PubMed Central PMCID: PMC6536122. 6: Heinemann U, Pal GP, Hilgenfeld R, Saenger W. Crystal and molecular structure of the sulfhydryl protease calotropin DI at 3.2 A resolution. J Mol Biol. 1982 Nov 15;161(4):591-606. PubMed PMID: 6759664. 7: Gupta RS, Sharma N, Dixit VP. Calotropin - a novel compound for fertility control. Anc Sci Life. 1990 Apr;9(4):224-30. PubMed PMID: 22557704; PubMed Central PMCID: PMC3331333. 8: El-Layeh RA, Youness RA, Askary H, Abdelmotaal A, Assal RA. 36PStructural diversity of the cardenolide calotropin renders it as a targeted therapy for harnessing TNBC progression through tuning nitric oxide (NO) levels. Ann Oncol. 2019 Feb 1;30(Supplement_1). pii: mdz026.007. doi: 10.1093/annonc/mdz026.007. PubMed PMID: 30810184. 9: KUPCHAN SM, KNOX JR, KELSEY JE, SAENZRENAULD JA. CALOTROPIN, A CYTOTOXIC PRINCIPLE ISOLATED FROM ASCLEPIAS CURASSAVICA L. Science. 1964 Dec 25;146(3652):1685-6. PubMed PMID: 14224519. 10: Liu J, Bai LP, Yang F, Yao X, Lei K, Kei Lam CW, Wu Q, Zhuang Y, Xiao R, Liao K, Kuok H, Li T, Liu L. Potent Antagonists of RORγt, Cardenolides from Calotropis gigantea, Exhibit Discrepant Effects on the Differentiation of T Lymphocyte Subsets. Mol Pharm. 2019 Feb 4;16(2):798-807. doi: 10.1021/acs.molpharmaceut.8b01063. Epub 2019 Jan 22. PubMed PMID: 30592425. 11: Sarma K, Roychoudhury S, Bora SS, Dehury B, Parida P, Das S, Das R, Dohutia C, Nath S, Deb B, Modi MK. Molecular Modeling and Dynamics Simulation Analysis of KATNAL1 for Identification of Novel Inhibitor of Sperm Maturation. Comb Chem High Throughput Screen. 2017;20(1):82-92. doi: 10.2174/1386207320666170116120104. PubMed PMID: 28093975. 12: Mebs D, Wunder C, Toennes SW. Poor sequestration of toxic host plant cardenolides and their rapid loss in the milkweed butterfly Danaus chrysippus (Lepidoptera: Nymphalidae: Danainae: Danaini). Toxicon. 2017 Jun 1;131:1-5. doi: 10.1016/j.toxicon.2017.03.006. Epub 2017 Mar 9. PubMed PMID: 28284846. 13: Sengupta A, Bhattacharya D, Pal G, Sinha NK. Comparative studies on calotropins DI and DII from the latex of Calotropis gigantea. Arch Biochem Biophys. 1984 Jul;232(1):17-25. PubMed PMID: 6430236. 14: Koh CH, Wu J, Chung YY, Liu Z, Zhang RR, Chong K, Korzh V, Ting S, Oh S, Shim W, Tian HY, Wei H. Identification of Na+/K+-ATPase inhibition-independent proarrhythmic ionic mechanisms of cardiac glycosides. Sci Rep. 2017 May 26;7(1):2465. doi: 10.1038/s41598-017-02496-4. Erratum in: Sci Rep. 2017 Sep 13;7(1):11498. PubMed PMID: 28550304; PubMed Central PMCID: PMC5446409. 15: Rascón-Valenzuela LA, Velázquez C, Garibay-Escobar A, Vilegas W, Medina-Juárez LA, Gámez-Meza N, Robles-Zepeda RE. Apoptotic activities of cardenolide glycosides from Asclepias subulata. J Ethnopharmacol. 2016 Dec 4;193:303-311. doi: 10.1016/j.jep.2016.08.022. Epub 2016 Aug 18. PubMed PMID: 27545974. 16: Gurung AB, Ali MA, Bhattacharjee A, AbulFarah M, Al-Hemaid F, Abou-Tarboush FM, Al-Anazi KM, Al-Anazi FS, Lee J. Molecular docking of the anticancer bioactive compound proceraside with macromolecules involved in the cell cycle and DNA replication. Genet Mol Res. 2016 May 9;15(2). doi: 10.4238/gmr.15027829. PubMed PMID: 27173346. 17: Rascón-Valenzuela L, Velázquez C, Garibay-Escobar A, Medina-Juárez LA, Vilegas W, Robles-Zepeda RE. Antiproliferative activity of cardenolide glycosides from Asclepias subulata. J Ethnopharmacol. 2015 Aug 2;171:280-6. doi: 10.1016/j.jep.2015.05.057. Epub 2015 Jun 9. PubMed PMID: 26068432. 18: Ibrahim SR, Mohamed GA, Shaala LA, Moreno L, Banuls Y, Kiss R, Youssef DT. Proceraside A, a new cardiac glycoside from the root barks of Calotropis procera with in vitro anticancer effects. Nat Prod Res. 2014;28(17):1322-7. doi: 10.1080/14786419.2014.901323. Epub 2014 Mar 31. PubMed PMID: 24678783. 19: Kadiyala M, Ponnusankar S, Elango K. Calotropis gigantiea (L.) R. Br (Apocynaceae): a phytochemical and pharmacological review. J Ethnopharmacol. 2013 Oct 28;150(1):32-50. doi: 10.1016/j.jep.2013.08.045. Epub 2013 Sep 6. Review. PubMed PMID: 24012528. 20: Verma SK, Jha E, Panda PK, Thirumurugan A, Patro S, Parashar SKS, Suar M. Molecular insights to alkaline based bio-fabrication of silver nanoparticles for inverse cytotoxicity and enhanced antibacterial activity. Mater Sci Eng C Mater Biol Appl. 2018 Nov 1;92:807-818. doi: 10.1016/j.msec.2018.07.037. Epub 2018 Jul 17. PubMed PMID: 30184810.

View History

Camicinal HCl

Camicinal HCl