Debromoaplysiatoxin | 52423-28-6 | anticancer

MedKoo Cat#: 581646 | Name: Debromoaplysiatoxin

Description:

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

Debromoaplysiatoxin is a toxic agent produced by the blue-green alga Lyngbya majuscula. This alga lives in marine waters and causes seaweed dermatitis. Furthermore, it is a tumor promoter which has an anti-proliferative activity against various cancer cell lines in mice.

Chemical Structure

Debromoaplysiatoxin

CAS#52423-28-6

Theoretical Analysis

MedKoo Cat#: 581646

Name: Debromoaplysiatoxin

CAS#: 52423-28-6

Chemical Formula: C32H48O10

Exact Mass: 592.3247

Molecular Weight: 592.73

Elemental Analysis: C, 64.84; H, 8.16; O, 26.99

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

Debromoaplysiatoxin; Aplysiatoxin, 17-debromo-; G-2408; NSC 271679.

IUPAC/Chemical Name

(1R,4R,13R,14S)-13-hydroxy-9-(1-hydroxyethyl)-3-(5-(3-hydroxyphenyl)-5-methoxypentan-2-yl)-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione

InChi Key

REAZZDPREXHWNV-FNYQTHNFSA-N

InChi Code

InChI=1S/C32H48O10/c1-18(11-12-24(38-7)22-9-8-10-23(34)13-22)29-20(3)26-16-32(41-29)30(5,6)15-19(2)31(37,42-32)17-28(36)39-25(21(4)33)14-27(35)40-26/h8-10,13,18-21,24-26,29,33-34,37H,11-12,14-17H2,1-7H3/t18?,19-,20+,21?,24?,25?,26?,29?,31+,32+/m0/s1

SMILES Code

C[C@H]1CC([C@]23CC([C@H](C(O2)C(C)CCC(c4cccc(c4)O)OC)C)OC(=O)CC(OC(=O)C[C@]1(O3)O)C(C)O)(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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 592.73 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

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PubMed PMID: 29129688. 4: Puschner B, Bautista AC, Wong C. Debromoaplysiatoxin as the Causative Agent of Dermatitis in a Dog after Exposure to Freshwater in California. Front Vet Sci. 2017 Apr 6;4:50. doi: 10.3389/fvets.2017.00050. eCollection 2017. PubMed PMID: 28428958; PubMed Central PMCID: PMC5382154. 5: Kikumori M, Yanagita RC, Tokuda H, Suenaga K, Nagai H, Irie K. Structural optimization of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, as an anticancer lead. Biosci Biotechnol Biochem. 2016;80(2):221-31. doi: 10.1080/09168451.2015.1091718. Epub 2015 Oct 9. PubMed PMID: 26452398. 6: Youssef DT, Shaala LA, Mohamed GA, Ibrahim SR, Banjar ZM, Badr JM, McPhail KL, Risinger AL, Mooberry SL. 2,3-seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens. Nat Prod Res. 2015;29(8):703-9. doi: 10.1080/14786419.2014.982647. Epub 2014 Nov 25. PubMed PMID: 25421266. 7: Gupta DK, Kaur P, Leong ST, Tan LT, Prinsep MR, Chu JJ. Anti-Chikungunya viral activities of aplysiatoxin-related compounds from the marine cyanobacterium Trichodesmium erythraeum. Mar Drugs. 2014 Jan 3;12(1):115-27. doi: 10.3390/md12010115. PubMed PMID: 24394406; PubMed Central PMCID: PMC3917264. 8: Taylor MS, Stahl-Timmins W, Redshaw CH, Osborne NJ. Toxic alkaloids in Lyngbya majuscula and related tropical marine cyanobacteria. Harmful Algae. 2014 Jan;31:1-8. doi: 10.1016/j.hal.2013.09.003. Epub 2013 Oct 2. PubMed PMID: 28040098. 9: Yanagita RC, Kamachi H, Kikumori M, Tokuda H, Suzuki N, Suenaga K, Nagai H, Irie K. Effects of the methoxy group in the side chain of debromoaplysiatoxin on its tumor-promoting and anti-proliferative activities. Bioorg Med Chem Lett. 2013 Aug 1;23(15):4319-23. doi: 10.1016/j.bmcl.2013.05.096. Epub 2013 Jun 7. PubMed PMID: 23803585. 10: Kikumori M, Yanagita RC, Tokuda H, Suzuki N, Nagai H, Suenaga K, Irie K. Structure-activity studies on the spiroketal moiety of a simplified analogue of debromoaplysiatoxin with antiproliferative activity. J Med Chem. 2012 Jun 14;55(11):5614-26. doi: 10.1021/jm300566h. Epub 2012 Jun 6. PubMed PMID: 22625994. 11: Westrick JA, Szlag DC, Southwell BJ, Sinclair J. A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment. Anal Bioanal Chem. 2010 Jul;397(5):1705-14. doi: 10.1007/s00216-010-3709-5. Epub 2010 May 26. Review. PubMed PMID: 20502884. 12: Harr KE, Szabo NJ, Cichra M, Phlips EJ. Debromoaplysiatoxin in Lyngbya-dominated mats on manatees (Trichechus manatus latirostris) in the Florida King's Bay ecosystem. Toxicon. 2008 Aug 1;52(2):385-8. doi: 10.1016/j.toxicon.2008.05.016. Epub 2008 Jun 5. PubMed PMID: 18585400. 13: Capper A, Tibbetts IR, O'Neil JM, Shaw GR. The fate of Lyngbya majuscula toxins in three potential consumers. J Chem Ecol. 2005 Jul;31(7):1595-606. 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Illness associated with eating seaweed, Hawaii, 1994. West J Med. 1998 Nov;169(5):293-5. PubMed PMID: 9830364; PubMed Central PMCID: PMC1305326. 19: Nagai H, Yasumoto T, Hokama Y. Manauealides, some of the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. J Nat Prod. 1997 Sep;60(9):925-8. PubMed PMID: 9322366. 20: Nagai H, Yasumoto T, Hokama Y. Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon. 1996 Jul;34(7):753-61. PubMed PMID: 8843576.