Separate PI3K and mTORC1 inhibitors joined by prodrug linker
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Active Metabolite(s)
1381217β-hydroxy Wortmannin 13346Rapamycin
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Wortmannin-Rapamycin Conjugate

Item No. 13671

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(4S,4aR,5R,6aS,7S,9aR,E)-1-(((3-(dimethylamino)propyl)(methyl)amino)methylene)-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetate 8-(7E,15E,17E,19E)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34aS-hexadecahydro-9R,27-dihydroxy-3S-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10R,21S-dimethoxy-6R,8,12R,14S,20,26R-hexamethyl-23S,27R-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone octanedioate
CAS Number
1067892-47-0
Molecular Formula
C88H131N3O23
Formula Weight
1598.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/ml
λmax
256, 267, 277, 289, 318, 411 nm
SMILES
O=C(O[C@H]1[C@H](OC)C[C@H](C[C@@H](C)[C@@](CC([C@H](C)/C=C(C)/[C@@H](O)[C@@H](OC)C([C@H](C)C[C@H](C)/C=C/C=C/C=C(C)/[C@@H](OC)C[C@](O2)([H])CC[C@@H](C)[C@]2(O)C3=O)=O)=O)([H])OC([C@]4([H])CCCCN4C3=O)=O)CC1)CCCCCCC(O[C@H]5CC[C@]6([H])[C@]5(C)C[C@@H](OC(C)=O)C([C@]([C@@H](COC)OC(/C7=C/N(C)CCCN(C)C)=O)(C)C7=C8O)=C6C8=O)=O
InChi Code
InChI=1S/C88H131N3O23/c1-51-28-21-20-22-29-52(2)66(106-15)46-60-35-33-57(7)88(104,114-60)82(100)83(101)91-41-26-25-30-63(91)85(103)111-67(47-64(93)53(3)43-56(6)78(97)81(108-17)77(96)55(5)42-51)54(4)44-59-34-37-65(68(45-59)107-16)110-72(94)31-23-18-19-24-32-73(95)112-70-38-36-62-74-76(69(109-58(8)92)48-86(62,70)9)87(10)71(50-105-14)113-84(102)61(75(87)80(99)79(74)98)49-90(13)40-27-39-89(11)12/h20-22,28-29,43,49,51,53-55,57,59-60,62-63,65-71,78,81,97,99,104H,18-19,23-27,30-42,44-48,50H2,1-17H3/b22-20+,28-21+,52-29+,56-43+,61-49+/t51-,53-,54-,55-,57-,59+,60+,62+,63+,65-,66+,67+,68-,69-,70+,71-,78-,81+,86+,87+,88-/m1/s1
InChi Key
GVMCLKAVNVFURS-UXLLMVCWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Phosphoinositide 3-kinase (PI3K) and mammalian target of rapamycin (mTOR) act synergistically in promoting cancer. Wortmannin is a potent inhibitor of PI3K enzymes, while rapamycin blocks mTOR Complex 1 TORC1.1,2 Wortmannin-rapamycin conjugate consists of analogs of 17-hydroxy wortmannin and rapamycin conjugated via a prodrug linker.3 Hydrolysis of the prodrug linker in vivo releases the inhibitors. The wortmannin-rapamycin conjugate inhibits the growth of HT-29 colon tumors and A498 renal tumors in mice better than rapamycin alone.3 Also, the conjugate, when given in combination with the VEGF-blocker bevacizumab, produces substantial regression of larger A498 tumors. Finally, the wortmannin-rapamycin conjugate is tolerated better than an equivalent mixture of the inhibitors.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fruman, D.A., Meyers, R.E., and Cantley, L.C. Phosphoinositide kinases. Annu. Rev. Biochem. 67, 481-507 (2008).

    2. Carracedo, A., and Pandolfi, P.P. The PTEN-PI3K pathway: Of feedbacks and cross-talks. Oncogene 27(41), 5527-5541 (2008).

    3. Ayral-Kaloustian, S., Gu, J., Lucas, J., et al. Hybrid inhibitors of phosphatidylinositol 3-kinase (PI3K) and the mammalian target of rapamycin (mTOR): Design, synthesis, and superior antitumor activity of novel wortmannin-rapamycin conjugates. J. Med. Chem. 53(1), 452-459 (2010).