 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C92H148O46 |
| Molecular Weight | 1990.13192g/mol |
| Exact Mass | 1988.924 |
| CAS # | 141256-04-4 |
| PubChem CID | 73652135 |
| Appearance | White to light yellow solid powder |
| LogP | -2.4 |
| Hydrogen Bond Donor Count | 23 |
| Hydrogen Bond Acceptor Count | 46 |
| Rotatable Bond Count | 38 |
| Heavy Atom Count | 138 |
| Complexity | 4100 |
| Defined Atom Stereocenter Count | 51 |
| SMILES | CC[C@H](C)[C@H](C[C@@H](CC(=O)O[C@@H](C[C@@H](CC(=O)O[C@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O)O)O)O)OC(=O)[C@]56CCC(C[C@H]5C7=CC[C@@H]8[C@]9(CC[C@@H]([C@@]([C@@H]9CC[C@]8([C@@]7(C[C@H]6O)C)C)(C)C=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)C)(C)C)C)O)[C@@H](C)CC)O)O[C@H]1[C@@H]([C@H]([C@@H](O1)CO)O)O |
| InChi Key | DRHZYJAUECRAJM-DWSYSWFDSA-N |
| InChi Code | InChI=1S/C92H148O46/c1-13-36(3)46(126-54(102)25-41(98)24-47(37(4)14-2)127-80-62(110)58(106)49(30-94)128-80)23-40(97)26-55(103)131-69-39(6)125-82(73(65(69)113)136-79-64(112)60(108)68(38(5)124-79)132-78-67(115)70(45(100)32-122-78)133-84-75(116)91(120,34-96)35-123-84)138-85(119)92-22-21-86(7,8)27-43(92)42-15-16-51-87(9)19-18-53(88(10,33-95)50(87)17-20-89(51,11)90(42,12)28-52(92)101)130-83-74(137-81-63(111)59(107)57(105)48(29-93)129-81)71(66(114)72(135-83)76(117)118)134-77-61(109)56(104)44(99)31-121-77/h15,33,36-41,43-53,56-75,77-84,93-94,96-101,104-116,120H,13-14,16-32,34-35H2,1-12H3,(H,117,118)/t36-,37-,38-,39+,40-,41-,43-,44+,45+,46-,47-,48+,49-,50+,51+,52+,53-,56-,57-,58-,59-,60-,61+,62+,63+,64+,65-,66-,67+,68-,69-,70-,71-,72-,73+,74+,75-,77-,78-,79-,80+,81-,82-,83+,84-,87-,88-,89+,90+,91+,92+/m0/s1 |
| Chemical Name | (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-[(3S,5S,6S)-5-[(3S,5S,6S)-5-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyloctanoyl]oxy-3-hydroxy-6-methyloctanoyl]oxy-4-hydroxy-6-methyloxan-2-yl]oxycarbonyl-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | NLRP3 inflammasome |
| ln Vivo | Research on mouse APCs (DCs and macrophages) identifies QS-21 as an activator of the NLRP3 inflammasome, which in turn triggers the release of the proinflammatory cytokine IL-1β/IL-18 that is dependent on caspase-1 and promotes the maturation of Th 17 cells or INF-γ-mediated Th1 responses [3]. |
| References |
[1]. Development of Improved Vaccine Adjuvants Based on the Saponin Natural Product QS-21 through Chemical Synthesis. Acc Chem Res. 2016;49(9):1741-1756. [2]. Identification of QS-21 as an Inflammasome-activating Molecular Component of Saponin Adjuvants. J Biol Chem. 2016;291(3):1123-1136. [3]. Lacaille-Dubois MA. Updated insights into the mechanism of action and clinical profile of the immunoadjuvant QS-21: A review. Phytomedicine. 2019;60:152905. |
| Additional Infomation |
QS-21 is an investigational adjuvant, which is a substance added to vaccines and other immunotherapies that is designed to enhance the body’s immune response to the antigen contained within the treatment. It is the leading member of the Stimulon family of adjuvants. As a vaccine additive, it is currently being evaluated in clinical trials in a variety of disease areas by Antigenics. Stimulon has been reported in Quillaja saponaria with data available. QS21 is a purified, natural saponin isolated from the soapbark tree Quillaja saponaria Molina with potential immunoadjuvant activity. When co-administered with vaccine peptides, QS21 may increase total antitumoral vaccine-specific antibody responses and cytotoxic T-cell responses. See also: Obi-821 (part of). Drug Indication Investigated for use/treatment in genital herpes, HIV infection, hepatitis (viral, B), influenza, malaria, melanoma, and viral infection. Mechanism of Action QS-21 has the potential ability to increase total vaccine-specific antibody response and T-cell response. In addition, QS-21 appears to increase potency of the vaccine with relatively small quantities of antigen and to exhibit synergy with other adjuvants. Because of the ability of QS-21 to improve the body’s immune response to very low doses of antigen, vaccine antigen may be ‘spared,’ which could significantly decrease the amount of antigen required for a given dose and make vaccine production more economical. |
Solubility Data
| Solubility (In Vitro) |
DMSO: 100 mg/mL (50.25 mM) H2O: 50 mg/mL (25.12 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (1.26 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (1.26 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (1.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 100 mg/mL (50.25 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |