Fiacitabine - CAS 69123-90-6
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Not Intended for Therapeutic Use. For research use only.
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Fiacitabine is a selective inhibitior of DNA replication of herpes simplex virus(HSV). It was active at much lower concentrations than arabinosylcytosine, iododeoxyuridine, and arabinosyladenine. It was slightly more active against herpes simplex virus type 1 than acycloquanosine and slightly more toxic to normal cells.
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NSC 382097; FIAC; FOAC
1.Recognition and treatment of shingles.
Nikkels AF1, Piérard GE. Drugs. 1994 Oct;48(4):528-48.
Varicella zoster virus (VZV) is responsible for a primary infection (varicella) followed by a latency, eventually resulting in herpes zoster (shingles). The replication cycle of VZV is normally interrupted after varicella. Consequently, VZV remains dormant in the organism. Reactivation occurs after viraemia, and the development of tissue alterations (skin and viscera) depends on the immunological status of the patient. Diagnosis of herpes zoster relies on clinical recognition and cytological and histological evaluations combined with immunohistochemistry and molecular biology techniques. Treatment of herpes zoster primarily relies upon antiviral drugs and incidentally on immunomodulating agents, specific immunoglobulins, antimicrobial agents, antiviral enzymes and corticosteroids. Drugs with a clinically relevant activity against varicella zoster virus infections include aciclovir, adenosine monophosphate, bromodeoxyuridine, desciclovir, fiacitabine, idoxuridine, interferon-alpha and vidarabine.
2.Particular characteristics of the anti-human cytomegalovirus activity of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in vitro.
Neyts J1, Snoeck R, Balzarini J, De Clercq E. Antiviral Res. 1991 Jul;16(1):41-52.
The acyclic nucleoside phosphonate analogue (S)-1-[3-hydroxy-2-phosphonylmethoxypropyl]cytosine (HPMPC) is a potent and selective inhibitor of human cytomegalovirus (HCMV) replication and DNA synthesis. Unlike 9-(1,3-dihydroxy-2-propoxymethyl)guanine (DHPG), HPMPC inhibits HCMV replication in cell cultures which have been treated with the compound before infection. Upon short-pulse treatment of HCMV-infected cells with HPMPC, a long-lasting antiviral response is obtained. The antiviral activity of HPMPC, unlike the antiviral activity of other cytosine derivatives (i.e. Ara-C, FIAC), is not readily reversed by 2'-deoxycytidine or cytidine. Neutral and alkaline sucrose gradient analysis of HCMV DNA isolated from HPMPC-treated HCMV-infected cell cultures revealed that HPMPC does not cause (detectable) single- or double-strand breakage of HCMV DNA.
3.Radiosynthesis of F-18 labeled cytidine analog 2'-fluoro-5-iodo-l-beta-d-arabinofuranosylcytosine ([(18)F]FIAC).
Wu CY1, Chan PC, Chang WT, Liu RS, Alauddin MM, Wang HE. Appl Radiat Isot. 2009 Jul-Aug;67(7-8):1362-5. doi: 10.1016/j.apradiso.2009.02.083. Epub 2009 Feb 28.
We reported the synthesis of 2'-deoxy-2'-[(18)F]fluoro-5-iodo-1-beta-d-arabinofuranosyl-5-iodo-cytosine ([(18)F]FIAC) with 15-20% radiochemical yield (decay corrected) in 3.5h. 2-deoxy-2-[(18)F]fluoro-1,3,5-tri-O-benzoyl-alpha-d-arabinofuranose was prepared following literature procedures with some modifications (yield>70%). The (18)F-fluorosugar was converted to 1-bromo-(18)F-fluorosugar, and then coupled with 5-iodocytocine silyl ether. A mixture of acetonitrile (ACN) and 1,2-dichloroethane (DCE) were employed to achieve optimum radiochemical yield and acceptable beta-anomer selectivity (alpha/beta=1/3). After hydrolyzed with sodium methoxide, the crude product was purified using HPLC to afford the beta-[(18)F]FIAC with high radiochemical purity (>or=98%).
4.Therapeutic gene expression in transduced mesenchymal stem cells can be monitored using a reporter gene.
Zhang G1, Lan X, Yen TC, Chen Q, Pei Z, Qin C, Zhang Y. Nucl Med Biol. 2012 Nov;39(8):1243-50. doi: 10.1016/j.nucmedbio.2012.06.010. Epub 2012 Jul 15.
AIM: We constructed a recombinant adenovirus construct Ad5-sr39tk-IRES-VEGF(165) (Ad5-SIV) that contained a mutant herpes viral thymidine kinase reporter gene (HSV1-sr39tk) and the human vascular endothelial growth factor 165 (VEGF(165)) gene for noninvasive imaging of gene expression. The recombinant adenovirus Ad5-SIV was transfected into rat bone marrow-derived mesenchymal stem cells (MSCs), and we measured the expression of HSV1-sr39tk and VEGF(165) to evaluate the feasibility of monitoring VEGF(165) expression using reporter gene expression.
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