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143839-74-1-L 685818 L 685818

L 685818

For research use only. Not for therapeutic Use.

  • CAT Number: I030330
  • CAS Number: 143839-74-1
  • Molecular Formula: C43H69NO13
  • Molecular Weight: 808.01
  • Purity: 98%
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Related Small Molecules: Phenmedipham     EACC     Thalidomide-4-O-C10-NH2 hydrochloride    

L 685818 is the C18-hydroxy, C21-ethyl analog of FK-506; binds to FKBP-12; antagonizes FK-506 and rapamycin.


Catalog Number I030330
CAS Number 143839-74-1
Synonyms

L 685818; L-685818; L685818; L-685,818; L 685,818; L685,818;

Molecular Formula C43H69NO13
Purity 98%
Target Fungal
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,11,19-trihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,11R*,12S*,14R*,15S*,16R*,18S*,19S*,26aR*))-
InChI InChI=1S/C43H69NO13/c1-10-29-18-23(2)37(48)24(3)19-35(54-8)39-36(55-9)20-26(5)43(52,57-39)40(49)41(50)44-16-12-11-13-30(44)42(51)56-38(27(6)32(46)22-33(29)47)25(4)17-28-14-15-31(45)34(21-28)53-7/h17-18,24,26-32,34-39,45-46,48,52H,10-16,19-22H2,1-9H3/b23-18+,25-17+/t24-,26-,27-,28+,29-,30+,31?,32+,34?,35+,36+,37-,38-,39-,43-/m1/s1
InChIKey NOQNPBXNHMZMTC-KIJDSWADSA-N
SMILES O=C([C@@](CCCC1)([H])N1C(C([C@@]2(O)[C@H](C)C[C@H](OC)[C@@](O2)([H])[C@@H](OC)C[C@@H](C)[C@H](O)/C(C)=C/[C@H]3CC)=O)=O)O[C@H](/C(C)=C/[C@H]4CC(OC)C(O)CC4)[C@H](C)[C@@H](O)CC3=O
Reference

1: Onyewu C, Blankenship JR, Del Poeta M, Heitman J. Ergosterol biosynthesis inhibitors become fungicidal when combined with calcineurin inhibitors against Candida albicans, Candida glabrata, and Candida krusei. Antimicrob Agents Chemother. 2003 Mar;47(3):956-64. PubMed PMID: 12604527; PubMed Central PMCID: PMC149324.
2: Kontoyiannis DP, Lewis RE, Osherov N, Albert ND, May GS. Combination of caspofungin with inhibitors of the calcineurin pathway attenuates growth in vitro in Aspergillus species. J Antimicrob Chemother. 2003 Feb;51(2):313-6. PubMed PMID: 12562696.
3: Oz HS, Hughes WT, Thomas EK, McClain CJ. Effects of immunomodulators on acute Trypanosoma Cruzi infection in mice. Med Sci Monit. 2002 Jun;8(6):BR208-11. PubMed PMID: 12070425.
4: Guo X, Dawson VL, Dawson TM. Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons. Eur J Neurosci. 2001 May;13(9):1683-93. PubMed PMID: 11359520.
5: Del Poeta M, Cruz MC, Cardenas ME, Perfect JR, Heitman J. Synergistic antifungal activities of bafilomycin A(1), fluconazole, and the pneumocandin MK-0991/caspofungin acetate (L-743,873) with calcineurin inhibitors FK506 and L-685,818 against Cryptococcus neoformans. Antimicrob Agents Chemother. 2000 Mar;44(3):739-46. PubMed PMID: 10681348; PubMed Central PMCID: PMC89756.
6: Allen C, Yu Y, Maysinger D, Eisenberg A. Polycaprolactone-b-poly(ethylene oxide) block copolymer micelles as a novel drug delivery vehicle for neurotrophic agents FK506 and L-685,818. Bioconjug Chem. 1998 Sep-Oct;9(5):564-72. PubMed PMID: 9736490.
7: Salowe SP, Hermes JD. Competitive and slow-binding inhibition of calcineurin by drug x immunophilin complexes. Arch Biochem Biophys. 1998 Jul 15;355(2):165-74. PubMed PMID: 9675023.
8: Bassing CH, Shou W, Muir S, Heitman J, Matzuk MM, Wang XF. FKBP12 is not required for the modulation of transforming growth factor beta receptor I signaling activity in embryonic fibroblasts and thymocytes. Cell Growth Differ. 1998 Mar;9(3):223-8. PubMed PMID: 9543388.
9: Wiederrecht G, Siekierka JJ. Yeast immunophilins: purification and assay of yeast FKBP12. Methods Enzymol. 1998;290:74-84. PubMed PMID: 9534152.
10: Steiner JP, Connolly MA, Valentine HL, Hamilton GS, Dawson TM, Hester L, Snyder SH. Neurotrophic actions of nonimmunosuppressive analogues of immunosuppressive drugs FK506, rapamycin and cyclosporin A. Nat Med. 1997 Apr;3(4):421-8. PubMed PMID: 9095176.
11: Odom A, Del Poeta M, Perfect J, Heitman J. The immunosuppressant FK506 and its nonimmunosuppressive analog L-685,818 are toxic to Cryptococcus neoformans by inhibition of a common target protein. Antimicrob Agents Chemother. 1997 Jan;41(1):156-61. PubMed PMID: 8980772; PubMed Central PMCID: PMC163677.
12: Dumont FJ, Fischer P, Sirotina A. Increased LFA-1-mediated homotypic cell adhesion is associated with the G1 growth arrest induced by rapamycin in a T cell lymphoma. Exp Cell Res. 1995 Jul;219(1):146-58. PubMed PMID: 7543051.
13: Teutsch M, Higer M, Wang D, Wortis HW. Induction of CD5 on B and T cells is suppressed by cyclosporin A, FK-520 and rapamycin. Int Immunol. 1995 Mar;7(3):381-92. PubMed PMID: 7540861.
14: Becker JW, Rotonda J, McKeever BM, Chan HK, Marcy AI, Wiederrecht G, Hermes JD, Springer JP. FK-506-binding protein: three-dimensional structure of the complex with the antagonist L-685,818. J Biol Chem. 1993 May 25;268(15):11335-9. PubMed PMID: 7684380.
15: Dumont FJ, Staruch MJ, Koprak SL, Siekierka JJ, Lin CS, Harrison R, Sewell T, Kindt VM, Beattie TR, Wyvratt M, et al. The immunosuppressive and toxic effects of FK-506 are mechanistically related: pharmacology of a novel antagonist of FK-506 and rapamycin. J Exp Med. 1992 Sep 1;176(3):751-60. PubMed PMID: 1380976; PubMed Central PMCID: PMC2119351.

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