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MedKoo Cat#: 523123 | Name: Aphidicolin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus, Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase A,D in eukaryotic cells and in some viruses (vaccinia and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.

Chemical Structure

Aphidicolin
Aphidicolin
CAS#38966-21-1

Theoretical Analysis

MedKoo Cat#: 523123

Name: Aphidicolin

CAS#: 38966-21-1

Chemical Formula: C20H34O4

Exact Mass: 338.2457

Molecular Weight: 338.49

Elemental Analysis: C, 70.97; H, 10.13; O, 18.91

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
ICI 69653; ICI69653; ICI-69653; NSC 234714; NSC234714; NSC-234714; Aphidicolin
IUPAC/Chemical Name
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol
InChi Key
NOFOAYPPHIUXJR-APNQCZIXSA-N
InChi Code
InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
SMILES Code
OC[C@@]1(C)[C@]2([H])CC[C@](C[C@@](C3)([H])[C@](CO)(O)CC4)([H])[C@]43[C@@]2(C)CC[C@H]1O
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, not in water
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

Preparing Stock Solutions

The following data is based on the product molecular weight 338.49 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
1: Groelly FJ, Dagg RA, Petropoulos M, Rossetti GG, Prasad B, Panagopoulos A, Paulsen T, Karamichali A, Jones SE, Ochs F, Dionellis VS, Puig Lombardi E, Miossec MJ, Lockstone H, Legube G, Blackford AN, Altmeyer M, Halazonetis TD, Tarsounas M. Mitotic DNA synthesis is caused by transcription-replication conflicts in BRCA2-deficient cells. Mol Cell. 2022 Sep 15;82(18):3382-3397.e7. doi: 10.1016/j.molcel.2022.07.011. Epub 2022 Aug 23. PMID: 36002001; PMCID: PMC9631240. 2: Niu S, Xia JM, Li Z, Yang LH, Yi ZW, Xie CL, Peng G, Luo ZH, Shao Z, Yang XW. Aphidicolin Chemistry of the Deep-Sea-Derived Fungus Botryotinia fuckeliana MCCC 3A00494. J Nat Prod. 2019 Aug 23;82(8):2307-2331. doi: 10.1021/acs.jnatprod.9b00705. Epub 2019 Aug 12. PMID: 31403790. 3: Navarro-Serna S, Piñeiro-Silva C, Luongo C, Parrington J, Romar R, Gadea J. Effect of Aphidicolin, a Reversible Inhibitor of Eukaryotic Nuclear DNA Replication, on the Production of Genetically Modified Porcine Embryos by CRISPR/Cas9. Int J Mol Sci. 2022 Feb 15;23(4):2135. doi: 10.3390/ijms23042135. PMID: 35216252; PMCID: PMC8880323. 4: Cinatl J, Cinatl J, Mainke M, Weissflog A, Steigmann G, Rabenau H, Doerr HW, Kornhuber B. Aphidicolin selectively kills neuroblastoma cells in vitro. Cancer Lett. 1992 Dec 24;67(2-3):199-206. doi: 10.1016/0304-3835(92)90144-k. PMID: 1483268. 5: Wardlaw CP, Petrini JHJ. ISG15 conjugation to proteins on nascent DNA mitigates DNA replication stress. Nat Commun. 2022 Oct 10;13(1):5971. doi: 10.1038/s41467-022-33535-y. PMID: 36216822; PMCID: PMC9550767. 6: Park JH, Cho DH, Hwang YJ, Choi YM, Lee JY, Jo I. Nuclear localization of endothelial nitric oxide synthase and nitric oxide production attenuates aphidicolin-induced endothelial cell death. Nitric Oxide. 2021 May 1;109-110:12-19. doi: 10.1016/j.niox.2021.02.001. Epub 2021 Feb 13. PMID: 33592314. 7: Marheineke K, Hyrien O. Aphidicolin triggers a block to replication origin firing in Xenopus egg extracts. J Biol Chem. 2001 May 18;276(20):17092-100. doi: 10.1074/jbc.M100271200. Epub 2001 Mar 6. PMID: 11279043. 8: Ban A, Tanaka M, Fujii R, Minami A, Oikawa H, Shintani T, Gomi K. Subcellular localization of aphidicolin biosynthetic enzymes heterologously expressed in Aspergillus oryzae. Biosci Biotechnol Biochem. 2018 Jan;82(1):139-147. doi: 10.1080/09168451.2017.1399789. Epub 2017 Dec 1. PMID: 29191129. 9: Sargent JM, Elgie AW, Williamson CJ, Taylor CG. Aphidicolin markedly increases the platinum sensitivity of cells from primary ovarian tumours. Br J Cancer. 1996 Dec;74(11):1730-3. doi: 10.1038/bjc.1996.622. PMID: 8956785; PMCID: PMC2077213. 10: Lin J, Niu S, Ding Z, Wang R, Dai Q, Wei W, Luo R, Liu L. Isolation and Characterization of Aphidicolin Derivatives from Tolypocladium inflatum. Molecules. 2017 Jul 12;22(7):1168. doi: 10.3390/molecules22071168. PMID: 28704971; PMCID: PMC6152040. 11: Santos GB, Krogh R, Magalhaes LG, Andricopulo AD, Pupo MT, Emery FS. Semisynthesis of new aphidicolin derivatives with high activity against Trypanosoma cruzi. Bioorg Med Chem Lett. 2016 Feb 15;26(4):1205-8. doi: 10.1016/j.bmcl.2016.01.033. Epub 2016 Jan 14. PMID: 26810263. 12: Starczewska E, Beyaert M, Michaux L, Vekemans MC, Saussoy P, Bol V, Arana Echarri A, Smal C, Van Den Neste E, Bontemps F. Targeting DNA repair with aphidicolin sensitizes primary chronic lymphocytic leukemia cells to purine analogs. Oncotarget. 2016 Jun 21;7(25):38367-38379. doi: 10.18632/oncotarget.9525. PMID: 27223263; PMCID: PMC5122396. 13: Vande Loock K, Decordier I, Ciardelli R, Haumont D, Kirsch-Volders M. An aphidicolin-block nucleotide excision repair assay measuring DNA incision and repair capacity. Mutagenesis. 2010 Jan;25(1):25-32. doi: 10.1093/mutage/gep039. Epub 2009 Oct 20. PMID: 19843590. 14: Michaelis M, Zimmer A, Handjou N, Cinatl J, Cinatl J Jr. Increased systemic efficacy of aphidicolin encapsulated in liposomes. Oncol Rep. 2005 Jan;13(1):157-60. PMID: 15583818. 15: Kuwakado K, Kubota M, Hirota H, Adachi S, Matsubara K, Kasai Y, Akiyama Y, Mikawa H. Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines. Biochem Pharmacol. 1993 Dec 3;46(11):1909-16. doi: 10.1016/0006-2952(93)90631-6. PMID: 8267640. 16: Wang L, Paradee W, Mullins C, Shridhar R, Rosati R, Wilke CM, Glover TW, Smith DI. Aphidicolin-induced FRA3B breakpoints cluster in two distinct regions. Genomics. 1997 May 1;41(3):485-8. doi: 10.1006/geno.1997.4690. PMID: 9169152. 17: Fukuda M, Ohashi M. Aphidicolin inhibits cell growth by accumulation of G2 cells. Cell Biol Int Rep. 1983 Aug;7(8):579-85. doi: 10.1016/0309-1651(83)90111-x. PMID: 6413078. 18: Yu EY, Zhao RY, Wang DS. Inhibitory effect of Aphidicolin - a tetracyclic diterpene - on the proliferation and apoptotic induction in human cervical cancer (HeLa) cells. J BUON. 2015 Nov-Dec;20(6):1480-6. Retraction in: J BUON. 2021 Jan-Feb;26(1):291. PMID: 26854444. 19: Cinatl J Jr, Cinatl J, Kotchetkov R, Driever PH, Bertels S, Siems K, Jas G, Bindseil K, Rabenau HF, Pouckova P, Doerr HW, Schwabe D. Aphidicolin glycinate inhibits human neuroblastoma cell growth in vivo. Oncol Rep. 1999 May- Jun;6(3):563-8. doi: 10.3892/or.6.3.563. PMID: 10203592. 20: Baranovskiy AG, Babayeva ND, Suwa Y, Gu J, Pavlov YI, Tahirov TH. Structural basis for inhibition of DNA replication by aphidicolin. Nucleic Acids Res. 2014 Dec 16;42(22):14013-21. doi: 10.1093/nar/gku1209. Epub 2014 Nov 27. PMID: 25429975; PMCID: PMC4267640.