WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H413944
CAS#: 123598-19-6
Description: DT 5461 is a synthetic lipid A analogue with immunomodulatory and antitumour activity.
Hodoodo Cat#: H413944
Name: DT 5461
CAS#: 123598-19-6
Chemical Formula: C76H139N4O22P
Exact Mass: 1,490.96
Molecular Weight: 1,491.930
Elemental Analysis: C, 61.18; H, 9.39; N, 3.76; O, 23.59; P, 2.08
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Synonym: DT 5461; DT5461; DT-5461; DT5461a; DT 5461a; DT-5461a
IUPAC/Chemical Name: 1,3-Dicarboxyisopropyl-2-deoxy-6-O-(2-deoxy-3-O(N-dodecanoylglycyl)-4-O-phosphono-2-tetradecanoylamino-beta-D-glucopyranosyl)-3-O-(N-dodecanoylglycyl)-2-tetradecanoylamino-alpha-D-glucopyranoside
InChi Key: HJIUQQMLRSJYAW-GVSSOHGDSA-N
InChi Code: InChI=1S/C76H139N4O22P/c1-9-13-17-21-25-29-31-35-39-43-47-51-61(84)79-65-67(99-63(86)53-77-59(82)49-45-41-37-33-27-23-19-15-11-3)66(102-103(94,95)96)57(55-81)98-69(65)97-56-58-68(88)75(73(5,6)71(89)90,101-64(87)54-78-60(83)50-46-42-38-34-28-24-20-16-12-4)70(76(93,100-58)74(7,8)72(91)92)80-62(85)52-48-44-40-36-32-30-26-22-18-14-10-2/h57-58,65-70,81,88,93H,9-56H2,1-8H3,(H,77,82)(H,78,83)(H,79,84)(H,80,85)(H,89,90)(H,91,92)(H2,94,95,96)/t57-,58-,65-,66-,67-,68-,69-,70-,75+,76-/m1/s1
SMILES Code: O[C@]1(C(C)(C(O)=O)C)[C@H](NC(CCCCCCCCCCCCC)=O)[C@@]([C@@H]([C@@H](CO[C@H]2[C@H](NC(CCCCCCCCCCCCC)=O)[C@H]([C@@H]([C@@H](CO)O2)OP(O)(O)=O)OC(CNC(CCCCCCCCCCC)=O)=O)O1)O)(C(C)(C(O)=O)C)OC(CNC(CCCCCCCCCCC)=O)=O
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: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 1,491.93 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: | |
In vitro protocol: | |
In vivo protocol: |
1: Sato K, Saiki I, Yoo YC, Igarashi Y, Kiso M, Hasegawa A, Azuma I. DT-5461, a new synthetic lipid A analogue, inhibits lung and liver metastasis of tumor in mice. Jpn J Cancer Res. 1992 Oct;83(10):1081-7. doi: 10.1111/j.1349-7006.1992.tb02725.x. PMID: 1452460; PMCID: PMC5918675.
2: Sato K, Yoo YC, Fukushima A, Saiki I, Takahashi TA, Fujihara M, Tono-Oka S, Azuma I. A novel synthetic lipid A analog with low endotoxicity, DT-5461, prevents lethal endotoxemia. Infect Immun. 1995 Aug;63(8):2859-66. doi: 10.1128/IAI.63.8.2859-2866.1995. PMID: 7622206; PMCID: PMC173388.
3: Sato K, Yoo YC, Mochizuki M, Saiki I, Takahashi TA, Azuma I. Inhibition of tumor-induced angiogenesis by a synthetic lipid A analogue with low endotoxicity, DT-5461. Jpn J Cancer Res. 1995 Apr;86(4):374-82. doi: 10.1111/j.1349-7006.1995.tb03067.x. PMID: 7539783; PMCID: PMC5920831.
4: Onozuka K, Shimada S, Yamasu H, Osada Y, Nakano M. Non-specific resistance induced by a low-toxic lipid A analogue, DT-5461, in murine salmonellosis. Int J Immunopharmacol. 1993 Aug;15(6):657-64. doi: 10.1016/0192-0561(93)90138-o. PMID: 8407050.
5: Kumazawa E, Tohgo A, Soga T, Kusama T, Osada Y. Significant antitumor effect of a synthetic lipid A analogue, DT-5461, on murine syngeneic tumor models. Cancer Immunol Immunother. 1992;35(5):307-14. doi: 10.1007/BF01741143. PMID: 1394335.
6: Kumazawa E, Akimoto T, Kita Y, Jimbo T, Joto N, Tohgo A. Intratumoral production of tumor necrosis factor augmented by endogenous interferons results in potent antitumor effects of DT-5461, a synthetic lipid A analog. J Immunother Emphasis Tumor Immunol. 1995 Apr;17(3):141-50. doi: 10.1097/00002371-199504000-00003. PMID: 7542128.
7: Sato K, Fujihara M, Takahashi TA, Choon Yoo Y, Hata K, Tono-Oka S, Suzuki T, Sekiguchi S, Azuma I. Endotoxin antagonism by a synthetic lipid A analogue, DT-5461, with low endotoxicity in human peripheral blood monocytes. Biochem Biophys Res Commun. 1995 Nov 2;216(1):367-74. doi: 10.1006/bbrc.1995.2633. PMID: 7488114.
8: Sagara-Ishijima N, Furuhama K. Toxic characteristics of the synthetic lipid A derivative DT-5461 in rats and monkeys. Toxicol Sci. 1999 Jun;49(2):324-31. doi: 10.1093/toxsci/49.2.324. PMID: 10416279.
9: Yoshida R, Sato K, Yoo YC, Yoshimatsu K, Tamura M, Ishihara C, Arikawa J, Azuma I. Effect of the synthetic lipid A-related compound, DT-5461, on resistance to Sendai virus infection in mice. Immunopharmacology. 1994 Sep- Oct;28(2):153-61. doi: 10.1016/0162-3109(94)90031-0. PMID: 8002289.
10: Kumazawa E, Jimbo T, Akimoto T, Joto N, Tohgo A. Antitumor effect of DT-5461, a lipid A derivative, against human tumor xenografts is mediated by intratumoral production of tumor necrosis factor and affected by host immunosuppressive factors in nude mice. Cancer Invest. 1997;15(6):522-30. doi: 10.3109/07357909709047593. PMID: 9412657.