Synonym
TZL; Tonantzitlolone; Tonantzitlolone A;
IUPAC/Chemical Name
(1R,2S,3R,6S,10S,12R,14R,15R,Z)-1,2-dihydroxy-3,7,7,10,14-pentamethyl-11-oxo-16,17-dioxatricyclo[10.3.1.13,6]heptadec-8-en-15-yl (E)-3-methylpent-2-enoate
InChi Key
YMEAIOHYSIGDJY-VDLZEVDKSA-N
InChi Code
InChI=1S/C26H40O7/c1-8-15(2)13-20(27)31-22-17(4)14-18-21(28)16(3)9-11-24(5,6)19-10-12-25(7,33-19)23(29)26(22,30)32-18/h9,11,13,16-19,22-23,29-30H,8,10,12,14H2,1-7H3/b11-9-,15-13+/t16-,17+,18+,19-,22+,23-,25+,26-/m0/s1
SMILES Code
CC/C(C)=C/C(O[C@@H]([C@@](O1)(O)[C@@H](O)[C@@]2(C)CC[C@@](O2)([H])C(C)(C)/C=C\[C@@H]3C)[C@H](C)C[C@]1([H])C3=O)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
464.60
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 |
1: Rubaiy HN. Treasure troves of pharmacological tools to study transient
receptor potential canonical 1/4/5 channels. Br J Pharmacol. 2019
Apr;176(7):832-846. doi: 10.1111/bph.14578. Epub 2019 Mar 6. Review. PubMed PMID:
30656647; PubMed Central PMCID: PMC6433652.
2: Rubaiy HN, Ludlow MJ, Siems K, Norman K, Foster R, Wolf D, Beutler JA, Beech
DJ. Tonantzitlolone is a nanomolar potency activator of transient receptor
potential canonical 1/4/5 channels. Br J Pharmacol. 2018 Aug;175(16):3361-3368.
doi: 10.1111/bph.14379. Epub 2018 Jun 28. PubMed PMID: 29859013; PubMed Central
PMCID: PMC6057908.
3: Busch T, Dräger G, Kunst E, Benson H, Sasse F, Siems K, Kirschning A.
Synthesis and antiproliferative activity of new tonantzitlolone-derived diterpene
derivatives. Org Biomol Chem. 2016 Oct 14;14(38):9040-5. doi: 10.1039/c6ob01697a.
Epub 2016 Sep 7. PubMed PMID: 27604289.
4: Pfeffer TJ, Sasse F, Schmidt CF, Lakämper S, Kirschning A, Scholz T. The
natural diterpene tonantzitlolone A and its synthetic enantiomer inhibit cell
proliferation and kinesin-5 function. Eur J Med Chem. 2016 Apr 13;112:164-170.
doi: 10.1016/j.ejmech.2016.02.022. Epub 2016 Feb 8. PubMed PMID: 26896705.
5: Sourbier C, Scroggins BT, Mannes PZ, Liao PJ, Siems K, Wolf D, Beutler JA,
Linehan WM, Neckers L. Tonantzitlolone cytotoxicity toward renal cancer cells is
PKCθ- and HSF1-dependent. Oncotarget. 2015 Oct 6;6(30):29963-74. doi:
10.18632/oncotarget.4676. PubMed PMID: 26298773; PubMed Central PMCID:
PMC4745775.
6: Olivon F, Palenzuela H, Girard-Valenciennes E, Neyts J, Pannecouque C, Roussi
F, Grondin I, Leyssen P, Litaudon M. Antiviral Activity of Flexibilane and
Tigliane Diterpenoids from Stillingia lineata. J Nat Prod. 2015 May
22;78(5):1119-28. doi: 10.1021/acs.jnatprod.5b00116. Epub 2015 May 6. PubMed
PMID: 25946116.
7: Busch T, Kirschning A. Recent advances in the total synthesis of
pharmaceutically relevant diterpenes. Nat Prod Rep. 2008 Apr;25(2):318-41. doi:
10.1039/b705652b. Epub 2008 Feb 11. Review. PubMed PMID: 18389140.
8: Jasper C, Adibekian A, Busch T, Quitschalle M, Wittenberg R, Kirschning A.
Total synthesis of cyclic diterpene tonantzitlolone based on a highly
stereoselective substrate-controlled aldol reaction and ring-closing metathesis.
Chemistry. 2006 Nov 24;12(34):8719-34. PubMed PMID: 16955524.
9: Jasper C, Wittenberg R, Quitschalle M, Jakupovic J, Kirschning A. Total
synthesis and elucidation of the absolute configuration of the diterpene
tonantzitlolone. Org Lett. 2005 Feb 3;7(3):479-82. Erratum in: Org Lett. 2005 Apr
28;7(9):1885. PubMed PMID: 15673269.
