Adaphostin
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MedKoo CAT#: 527877

CAS#: 241127-58-2

Description: Adaphostin is a novel activator of Fas-mediated death pathway in Bcr/Abl-positive leukaemia. Upregulation of HO-1 is a novel molecular marker of adaphostin's action.

Chemical Structure

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Adaphostin
CAS# 241127-58-2
Instruction

Theoretical Analysis

MedKoo Cat#: 527877
Name: Adaphostin
CAS#: 241127-58-2
Chemical Formula: C24H27NO4
Exact Mass: 393.19
Molecular Weight: 393.483
Elemental Analysis: C, 73.26; H, 6.92; N, 3.56; O, 16.26

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 weeks
25mg USD 650 2 weeks
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Synonym: Adaphostin

IUPAC/Chemical Name: 1-Adamantyl 4-((2,5-dihydroxybenzyl)amino)benzoate

InChi Key: YJZSUCFGHXQWDM-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H27NO4/c26-21-5-6-22(27)19(10-21)14-25-20-3-1-18(2-4-20)23(28)29-24-11-15-7-16(12-24)9-17(8-15)13-24/h1-6,10,15-17,25-27H,7-9,11-14H2

SMILES Code: O=C(OC12CC3CC(C2)CC(C3)C1)C4=CC=C(NCC5=CC(O)=CC=C5O)C=C4

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: Soluble in DMSO

Shelf Life: >2 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 393.48 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.

Recalculate based on batch purity %
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:

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1: Rivera-Del Valle N, Cheng T, Irwin ME, Donnella H, Singh MM, Chandra J. Combinatorial effects of histone deacetylase inhibitors (HDACi), vorinostat and entinostat, and adaphostin are characterized by distinct redox alterations. Cancer Chemother Pharmacol. 2018 Mar;81(3):483-495. doi: 10.1007/s00280-017-3509-0. Epub 2018 Jan 8. PubMed PMID: 29313067; PubMed Central PMCID: PMC5837827.

2: Fan F, Tonon G, Bashari MH, Vallet S, Antonini E, Goldschmidt H, Schulze-Bergkamen H, Opferman JT, Sattler M, Anderson KC, Jäger D, Podar K. Targeting Mcl-1 for multiple myeloma (MM) therapy: drug-induced generation of Mcl-1 fragment Mcl-1(128-350) triggers MM cell death via c-Jun upregulation. Cancer Lett. 2014 Feb 28;343(2):286-94. doi: 10.1016/j.canlet.2013.09.042. Epub 2013 Oct 8. PubMed PMID: 24120758.

3: Aguiló JI, Iturralde M, Monleón I, Iñarrea P, Pardo J, Martínez-Lorenzo MJ, Anel A, Alava MA. Cytotoxicity of quinone drugs on highly proliferative human leukemia T cells: reactive oxygen species generation and inactive shortened SOD1 isoform implications. Chem Biol Interact. 2012 Jun 25;198(1-3):18-28. doi: 10.1016/j.cbi.2012.05.001. Epub 2012 May 16. PubMed PMID: 22609468.

4: Chen YJ, Wang JJ, Chang LS. Naja nigricollis CMS-9 enhances the mitochondria-mediated death pathway in adaphostin-treated human leukaemia U937 cells. Clin Exp Pharmacol Physiol. 2011 Nov;38(11):755-63. doi: 10.1111/j.1440-1681.2011.05585.x. PubMed PMID: 21824174.

5: Liu WH, Chang LS. Adaphostin promotes caffeine-evoked autocrine Fas-mediated death pathway activation in Bcr/Abl-positive leukaemia cells. Biochem J. 2011 Nov 1;439(3):453-67. doi: 10.1042/BJ20110725. PubMed PMID: 21745187.

6: Fer ND, Shoemaker RH, Monks A. Adaphostin toxicity in a sensitive non-small cell lung cancer model is mediated through Nrf2 signaling and heme oxygenase 1. J Exp Clin Cancer Res. 2010 Jul 9;29:91. doi: 10.1186/1756-9966-29-91. PubMed PMID: 20618971; PubMed Central PMCID: PMC2909968.

7: Sánchez Y, Calle C, de Blas E, Aller P. Modulation of arsenic trioxide-induced apoptosis by genistein and functionally related agents in U937 human leukaemia cells. Regulation by ROS and mitogen-activated protein kinases. Chem Biol Interact. 2009 Nov 10;182(1):37-44. doi: 10.1016/j.cbi.2009.08.015. Epub 2009 Aug 29. PubMed PMID: 19720055.

8: Zhang J, Sattler M, Tonon G, Grabher C, Lababidi S, Zimmerhackl A, Raab MS, Vallet S, Zhou Y, Cartron MA, Hideshima T, Tai YT, Chauhan D, Anderson KC, Podar K. Targeting angiogenesis via a c-Myc/hypoxia-inducible factor-1alpha-dependent pathway in multiple myeloma. Cancer Res. 2009 Jun 15;69(12):5082-90. doi: 10.1158/0008-5472.CAN-08-4603. Epub 2009 Jun 9. PubMed PMID: 19509231.

9: Verrax J, Pedrosa RC, Beck R, Dejeans N, Taper H, Calderon PB. In situ modulation of oxidative stress: a novel and efficient strategy to kill cancer cells. Curr Med Chem. 2009;16(15):1821-30. Review. PubMed PMID: 19442148.

10: Howard AN, Bridges KA, Meyn RE, Chandra J. ABT-737, a BH3 mimetic, induces glutathione depletion and oxidative stress. Cancer Chemother Pharmacol. 2009 Dec;65(1):41-54. doi: 10.1007/s00280-009-1001-1. Epub 2009 Apr 29. PubMed PMID: 19404643.

11: Chandra J. Oxidative stress by targeted agents promotes cytotoxicity in hematologic malignancies. Antioxid Redox Signal. 2009 May;11(5):1123-37. doi: 10.1089/ARS.2008.2302. Review. PubMed PMID: 19018667; PubMed Central PMCID: PMC2842131.

12: Stockwin LH, Bumke MA, Yu SX, Webb SP, Collins JR, Hollingshead MG, Newton DL. Proteomic analysis identifies oxidative stress induction by adaphostin. Clin Cancer Res. 2007 Jun 15;13(12):3667-81. PubMed PMID: 17575232.

13: Podar K, Raab MS, Tonon G, Sattler M, Barilà D, Zhang J, Tai YT, Yasui H, Raje N, DePinho RA, Hideshima T, Chauhan D, Anderson KC. Up-regulation of c-Jun inhibits proliferation and induces apoptosis via caspase-triggered c-Abl cleavage in human multiple myeloma. Cancer Res. 2007 Feb 15;67(4):1680-8. PubMed PMID: 17308109.

14: Barnes DJ, De S, van Hensbergen P, Moravcsik E, Melo JV. Different target range and cytotoxic specificity of adaphostin and 17-allylamino-17-demethoxygeldanamycin in imatinib-resistant and sensitive cell lines. Leukemia. 2007 Mar;21(3):421-6. Epub 2007 Jan 25. PubMed PMID: 17252018.

15: Le SB, Hailer MK, Buhrow S, Wang Q, Flatten K, Pediaditakis P, Bible KC, Lewis LD, Sausville EA, Pang YP, Ames MM, Lemasters JJ, Holmuhamedov EL, Kaufmann SH. Inhibition of mitochondrial respiration as a source of adaphostin-induced reactive oxygen species and cytotoxicity. J Biol Chem. 2007 Mar 23;282(12):8860-72. Epub 2007 Jan 9. PubMed PMID: 17213201.

16: Mukhopadhyay I, Sausville EA, Doroshow JH, Roy KK. Molecular mechanism of adaphostin-mediated G1 arrest in prostate cancer (PC-3) cells: signaling events mediated by hepatocyte growth factor receptor, c-Met, and p38 MAPK pathways. J Biol Chem. 2006 Dec 8;281(49):37330-44. Epub 2006 Sep 6. PubMed PMID: 16956884.

17: Long J, Manchandia T, Ban K, Gao S, Miller C, Chandra J. Adaphostin cytoxicity in glioblastoma cells is ROS-dependent and is accompanied by upregulation of heme oxygenase-1. Cancer Chemother Pharmacol. 2007 Mar;59(4):527-35. Epub 2006 Aug 19. PubMed PMID: 16924499.

18: Orsolic N, Golemovic M, Quintás-Cardama A, Scappini B, Manshouri T, Chandra J, Basic I, Giles F, Kantarjian H, Verstovsek S. Adaphostin has significant and selective activity against chronic and acute myeloid leukemia cells. Cancer Sci. 2006 Sep;97(9):952-60. Epub 2006 Jul 4. PubMed PMID: 16822295.

19: Dasmahapatra G, Nguyen TK, Dent P, Grant S. Adaphostin and bortezomib induce oxidative injury and apoptosis in imatinib mesylate-resistant hematopoietic cells expressing mutant forms of Bcr/Abl. Leuk Res. 2006 Oct;30(10):1263-72. Epub 2006 Feb 14. PubMed PMID: 16481037.

20: Li M, Wang H, Hill DL, Stinson S, Veley K, Grossi I, Peggins J, Covey JM, Zhang R. Preclinical pharmacology of the novel antitumor agent adaphostin, a tyrphostin analog that inhibits bcr/abl. Cancer Chemother Pharmacol. 2006 May;57(5):607-14. Epub 2005 Dec 6. PubMed PMID: 16331493.