Aptamers for pharmaceuticals and their application in environmental analytics

Aptamers are single-stranded DNA or RNA oligonucleotides, which are able to bind with high affinity and specificity to their target. This property is used for a multitude of applications, for instance as molecular recognition elements in biosensors and other assays. Biosensor application of aptamers offers the possibility for fast and easy detection of environmental relevant substances. Pharmaceutical residues, deriving from human or animal medical treatment, are found in surface, ground, and drinking water. At least the whole range of frequently administered drugs can be detected in noticeable concentrations. Biosensors and assays based on aptamers as specific recognition elements are very convenient for this application because aptamer development is possible for toxic targets. Commonly used biological receptors for biosensors like enzymes or antibodies are mostly unavailable for the detection of pharmaceuticals. This review describes the research activities of aptamer and sensor developments for pharmaceutical detection, with focus on environmental applications.

[1]  T. Simonsson,et al.  G-Quadruplex DNA Structures Variations on a Theme , 2001, Biological chemistry.

[2]  A novel separation and enrichment method of 17β-estradiol using aptamer-anchored microbeads , 2011, Bioprocess and biosystems engineering.

[3]  E. Gragoudas,et al.  Pegaptanib for neovascular age-related macular degeneration. , 2004, The New England journal of medicine.

[4]  J. Szostak,et al.  In vitro selection of RNA molecules that bind specific ligands , 1990, Nature.

[5]  H. Sørensen,et al.  Risk of adverse birth outcome and miscarriage in pregnant users of non-steroidal anti-inflammatory drugs: population based observational study and case-control study , 2001, BMJ : British Medical Journal.

[6]  C. Berens,et al.  A tetracycline-binding RNA aptamer. , 2001, Bioorganic & medicinal chemistry.

[7]  G. Tocchini-Valentini,et al.  In vitro selection of dopamine RNA ligands. , 1997, Biochemistry.

[8]  An Allosteric Ribozyme Regulated by Doxycyline. , 2000, Angewandte Chemie.

[9]  S. Steinberg,et al.  Activity of thalidomide in AIDS-related Kaposi's sarcoma. , 2000, Journal of clinical oncology : official journal of the American Society of Clinical Oncology.

[10]  L. Gold,et al.  Systematic evolution of ligands by exponential enrichment: RNA ligands to bacteriophage T4 DNA polymerase. , 1990, Science.

[11]  B. Sullenger,et al.  Generation of species cross-reactive aptamers using "toggle" SELEX. , 2001, Molecular therapy : the journal of the American Society of Gene Therapy.

[12]  Ciara K O'Sullivan,et al.  Reagentless, reusable, ultrasensitive electrochemical molecular beacon aptasensor. , 2006, Journal of the American Chemical Society.

[13]  Kevin W Plaxco,et al.  Reagentless measurement of aminoglycoside antibiotics in blood serum via an electrochemical, ribonucleic acid aptamer-based biosensor. , 2010, Analytical chemistry.

[14]  Su Jin Lee,et al.  The affinity ratio--its pivotal role in gold nanoparticle-based competitive colorimetric aptasensor. , 2011, Biosensors & bioelectronics.

[15]  Ji-Hye Han,et al.  Arsenic removal from Vietnamese groundwater using the arsenic-binding DNA aptamer. , 2009, Environmental science & technology.

[16]  A. Pardi,et al.  High-resolution molecular discrimination by RNA. , 1994, Science.

[17]  R. Green,et al.  Diclofenac poisoning is widespread in declining vulture populations across the Indian subcontinent , 2004, Proceedings of the Royal Society of London. Series B: Biological Sciences.

[18]  P. Doris Central cardiovascular regulation and the role of vasopressin: a review. , 1984, Clinical and experimental hypertension. Part A, Theory and practice.

[19]  Jörn Glökler,et al.  Nonradioactive fluorescence microtiter plate assay monitoring aptamer selections. , 2007, BioTechniques.

[20]  Man Bock Gu,et al.  Electrochemical aptasensor for tetracycline detection , 2010, Bioprocess and biosystems engineering.

[21]  H. Noller Ribosomal RNA and translation. , 1991, Annual review of biochemistry.

[22]  Cherylyn Beckey,et al.  Pegaptanib: A Novel Approach to Ocular Neovascularization , 2006, The Annals of pharmacotherapy.

[23]  Ángel Maquieira,et al.  Review on immunoanalytical determination of tetracycline and sulfonamide residues in edible products , 2009, Analytical and bioanalytical chemistry.

[24]  Frieder W Scheller From biosensor to biochip , 2007, The FEBS journal.

[25]  A. Heeger,et al.  An electronic, aptamer-based small-molecule sensor for the rapid, label-free detection of cocaine in adulterated samples and biological fluids. , 2006, Journal of the American Chemical Society.

[26]  R. Schroeder,et al.  Inhibition of the self-cleavage reaction of the human hepatitis delta virus ribozyme by antibiotics. , 1996, Journal of molecular biology.

[27]  R. Rando,et al.  The binding site of a specific aminoglycoside binding RNA molecule. , 1998, Biochemistry.

[28]  Aleem Ahmed Khan,et al.  Diclofenac residues as the cause of vulture population decline in Pakistan , 2004, Nature.

[29]  Ming Zhou,et al.  Solid-state probe based electrochemical aptasensor for cocaine: a potentially convenient, sensitive, repeatable, and integrated sensing platform for drugs. , 2010, Analytical chemistry.

[30]  S. Moro,et al.  Anthracyclines: recent developments in their separation and quantitation. , 2001, Journal of chromatography. B, Biomedical sciences and applications.

[31]  L. Gold,et al.  RNA aptamers to the peptidyl transferase inhibitor chloramphenicol. , 1997, Chemistry & biology.

[32]  Y. Hashimoto Novel biological response modifiers derived from thalidomide. , 1998, Current medicinal chemistry.

[33]  M. Kwon,et al.  In vitro selection of RNA against kanamycin B. , 2001, Molecules and cells.

[34]  Y Wang,et al.  RNA molecules that specifically and stoichiometrically bind aminoglycoside antibiotics with high affinities. , 1996, Biochemistry.

[35]  A. Ferré-D’Amaré,et al.  Structural basis for specific, high-affinity tetracycline binding by an in vitro evolved aptamer and artificial riboswitch. , 2008, Chemistry & biology.

[36]  A. Ellington,et al.  In vitro selection of RNA lectins: using combinatorial chemistry to interpret ribozyme evolution. , 1995, Chemistry & biology.

[37]  Yan Li,et al.  Electrogenerated chemiluminescence aptamer-based biosensor for the determination of cocaine , 2007 .

[38]  J. Killian,et al.  Minimal RNA constructs that specifically bind aminoglycoside antibiotics with high affinities. , 1998, Biochemistry.

[39]  I. R. Paeng,et al.  Development of direct competitive enzyme-linked aptamer assay for determination of dopamine in serum. , 2011, Analytica chimica acta.

[40]  Lijie Cao,et al.  Cocaine detection via rolling circle amplification of short DNA strand separated by magnetic beads. , 2011, Biosensors & bioelectronics.

[41]  L. Hurley,et al.  G-quadruplex DNA: a potential target for anti-cancer drug design. , 2000, Trends in pharmacological sciences.

[42]  Ming Zhou,et al.  Microfluidic electrochemical aptameric assay integrated on-chip: a potentially convenient sensing platform for the amplified and multiplex analysis of small molecules. , 2011, Analytical chemistry.

[43]  Barbara Kasprzyk-Hordern,et al.  The occurrence of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs in surface water in South Wales, UK. , 2008, Water research.

[44]  R. Roos,et al.  Huntington's disease: a clinical review , 2010, Orphanet journal of rare diseases.

[45]  L. Kiesel Molecular mechanisms of gonadotrophin releasing hormone-stimulated gonadotrophin secretion. , 1993, Human reproduction.

[46]  Juewen Liu,et al.  A simple and sensitive "dipstick" test in serum based on lateral flow separation of aptamer-linked nanostructures. , 2006, Angewandte Chemie.

[47]  M. Djordjevic SELEX experiments: new prospects, applications and data analysis in inferring regulatory pathways. , 2007, Biomolecular engineering.

[48]  Birgit Cech,et al.  A DNA aptamer with high affinity and specificity for therapeutic anthracyclines. , 2008, Analytical biochemistry.

[49]  M. Famulok,et al.  In vitro selection of a viomycin-binding RNA pseudoknot. , 1997, Chemistry & biology.

[50]  Ronny Blust,et al.  Cocaine and metabolites in waste and surface water across Belgium. , 2009, Environmental pollution.

[51]  D. Patel,et al.  Saccharide-RNA recognition in an aminoglycoside antibiotic-RNA aptamer complex. , 1997, Chemistry & biology.

[52]  M Famulok,et al.  Aptamers that bind to the antibiotic moenomycin A. , 2001, Bioorganic & medicinal chemistry.

[53]  R. Stoltenburg,et al.  FluMag-SELEX as an advantageous method for DNA aptamer selection , 2005, Analytical and bioanalytical chemistry.

[54]  P. S. Kim,et al.  Bioactive and nuclease-resistant L-DNA ligand of vasopressin. , 1997, Proceedings of the National Academy of Sciences of the United States of America.

[55]  B. Le Bizec,et al.  Novel analytical methods for the determination of steroid hormones in edible matrices. , 2008, Analytica chimica acta.

[56]  Man Bock Gu,et al.  ssDNA aptamers that selectively bind oxytetracycline. , 2008, Bioorganic & medicinal chemistry.

[57]  R. Condray,et al.  Cognition, dopamine and bioactive lipids in schizophrenia. , 2011, Frontiers in bioscience.

[58]  Adelheid Lempradl,et al.  Monovalent Ion Dependence of Neomycin B Binding to an RNA Aptamer Characterized by Spectroscopic Methods , 2007, Chembiochem : a European journal of chemical biology.

[59]  Chunhai Fan,et al.  A target-responsive electrochemical aptamer switch (TREAS) for reagentless detection of nanomolar ATP. , 2007, Journal of the American Chemical Society.

[60]  Discrimination of recombinant from natural human growth hormone using DNA aptamers. , 2011, Journal of biomolecular techniques : JBT.

[61]  R. Schroeder,et al.  Modulation of RNA function by aminoglycoside antibiotics , 2000, The EMBO journal.

[62]  C. Ban,et al.  Gold nanoparticle-based colorimetric detection of kanamycin using a DNA aptamer. , 2011, Analytical biochemistry.

[63]  J. Szostak,et al.  Selection in vitro of single-stranded DNA molecules that fold into specific ligand-binding structures , 1992, Nature.

[64]  W. Amoaku Pegaptanib in Exudative Age-Related Macular Degeneration , 2005, Drugs.

[65]  Michael Famulok,et al.  All you wanted to know about SELEX , 2004, Molecular Biology Reports.

[66]  M Yarus,et al.  Diversity of oligonucleotide functions. , 1995, Annual review of biochemistry.

[67]  Chang-Hoon Han,et al.  Development of immunoassays for the detection of kanamycin in veterinary fields , 2006, Journal of veterinary science.

[68]  Itamar Willner,et al.  Electronic aptamer-based sensors. , 2007, Angewandte Chemie.

[69]  S. Gill,et al.  Detection and plasma pharmacokinetics of an anti-vascular endothelial growth factor oligonucleotide-aptamer (NX1838) in rhesus monkeys. , 1999, Journal of chromatography. B, Biomedical sciences and applications.

[70]  D. Patel,et al.  Saccharide-RNA recognition in a complex formed between neomycin B and an RNA aptamer. , 1999, Structure.

[71]  Mutational analysis of a signaling aptamer suggests a mechanism for ligand-triggered structure-switching. , 2009, Biochemical and biophysical research communications.

[72]  Man Bock Gu,et al.  Specific detection of oxytetracycline using DNA aptamer-immobilized interdigitated array electrode chip. , 2009, Analytica chimica acta.

[73]  M. Gu,et al.  Isolation and characterization of enantioselective DNA aptamers for ibuprofen. , 2010, Bioorganic & medicinal chemistry.

[74]  Kevin W Plaxco,et al.  A reagentless signal-on architecture for electronic, aptamer-based sensors via target-induced strand displacement. , 2005, Journal of the American Chemical Society.

[75]  Milan N Stojanovic,et al.  Aptamer-based colorimetric probe for cocaine. , 2002, Journal of the American Chemical Society.

[76]  Yi Lu,et al.  Functional-DNA–Based Nanoscale Materials and Devices for Sensing Trace Contaminants in Water , 2008 .

[77]  Su Jin Lee,et al.  Single-stranded DNA aptamers specific for antibiotics tetracyclines. , 2008, Bioorganic & medicinal chemistry.

[78]  Y. Lévi,et al.  Assessment of river contamination by estrogenic compounds in Paris area (France). , 2004, The Science of the total environment.

[79]  C. Niemeyer REVIEW Nanoparticles, Proteins, and Nucleic Acids: Biotechnology Meets Materials Science , 2022 .

[80]  Kevin W Plaxco,et al.  An electrochemical sensor for the detection of protein-small molecule interactions directly in serum and other complex matrices. , 2009, Journal of the American Chemical Society.

[81]  R. Rando,et al.  Specific binding of aminoglycoside antibiotics to RNA. , 1995, Chemistry & biology.

[82]  M. Stojanović,et al.  Aptamer-based folding fluorescent sensor for cocaine. , 2001, Journal of the American Chemical Society.

[83]  María Jesús Lobo-Castañón,et al.  Modified-RNA aptamer-based sensor for competitive impedimetric assay of neomycin B. , 2007, Journal of the American Chemical Society.

[84]  R. Vilar,et al.  Stabilisation of G-quadruplex DNA by small molecules. , 2008, Current topics in medicinal chemistry.

[85]  E. Westhof,et al.  Deciphering RNA recognition: aminoglycoside binding to the hammerhead ribozyme. , 1998, Chemistry & biology.

[86]  A. Hoberman,et al.  Effects of thalidomide on developmental, peri- and postnatal function in female New Zealand white rabbits and offspring. , 2004, Toxicological sciences : an official journal of the Society of Toxicology.

[87]  A. Hüttenhofer,et al.  In vitro selection analysis of neomycin binding RNAs with a mutagenized pool of variants of the 16S rRNA decoding region. , 1996, Biochemistry.

[88]  Peter W. Chen,et al.  Vasopressin: New Uses in Critical Care , 2002, The American journal of the medical sciences.

[89]  N. de-los-Santos-Álvarez,et al.  Impedimetric aptasensor for tobramycin detection in human serum. , 2011, Biosensors & bioelectronics.

[90]  J. Collins,et al.  How antibiotics kill bacteria: from targets to networks , 2010, Nature Reviews Microbiology.

[91]  C. Peterson,et al.  In vitro fertilisation. A review of drug therapy and clinical management. , 1996, Drugs.

[92]  Pinar Calik,et al.  Human growth hormone-specific aptamer identification using improved oligonucleotide ligand evolution method. , 2010, Protein expression and purification.

[93]  M. Cleuvers Mixture toxicity of the anti-inflammatory drugs diclofenac, ibuprofen, naproxen, and acetylsalicylic acid. , 2004, Ecotoxicology and environmental safety.

[94]  Yang Li,et al.  Self-assembly of supramolecular aptamer structures for optical or electrochemical sensing. , 2009, The Analyst.

[95]  Petra Burgstaller,et al.  GnRH binding RNA and DNA Spiegelmers: a novel approach toward GnRH antagonism. , 2002, Chemistry & biology.

[96]  A. Heeger,et al.  Label-free electronic detection of thrombin in blood serum by using an aptamer-based sensor. , 2005, Angewandte Chemie.

[97]  D. Alberts,et al.  The pharmacokinetics of daunomycin in man , 1971, Clinical pharmacology and therapeutics.

[98]  Aniela Wochner,et al.  Semi-automated selection of DNA aptamers using magnetic particle handling. , 2007, BioTechniques.

[99]  M. Famulok,et al.  Fluorescence Correlation Spectroscopy as a New Method for the Investigation of Aptamer/Target Interactions , 2001, Biological chemistry.

[100]  W. Rocca,et al.  When does Parkinson disease start? , 2010, Archives of neurology.

[101]  Su Jin Lee,et al.  ssDNA aptamers that recognize diclofenac and 2-anilinophenylacetic acid. , 2009, Bioorganic & medicinal chemistry.

[102]  M. Famulok,et al.  A novel RNA motif for neomycin recognition. , 1995, Chemistry & biology.

[103]  F. Ventura,et al.  Stimulatory drugs of abuse in surface waters and their removal in a conventional drinking water treatment plant. , 2008, Environmental science & technology.

[104]  K. Ludwig Molecular mechanisms of gonadotrophin releasing hormone-stimulated gonadotrophin secretion , 1993 .

[105]  S. Sigurdsson,et al.  Folding of the cocaine aptamer studied by EPR and fluorescence spectroscopies using the bifunctional spectroscopic probe Ç , 2009, Nucleic Acids Research.

[106]  M. Win,et al.  Codeine-binding RNA aptamers and rapid determination of their binding constants using a direct coupling surface plasmon resonance assay , 2006, Nucleic acids research.

[107]  L. Britt,et al.  The action of vasopressin on the gastrointestinal tract. A review of the literature. , 1972, The American journal of digestive diseases.

[108]  D. Patel,et al.  Encapsulating streptomycin within a small 40-mer RNA. , 2003, Chemistry & biology.

[109]  Itamar Willner,et al.  Integrated nanoparticle-biomolecule hybrid systems: synthesis, properties, and applications. , 2004, Angewandte Chemie.

[110]  Jaehoon Yu,et al.  Elucidation of the RNA target of linezolid by using a linezolid-neomycin B heteroconjugate and genomic SELEX. , 2007, Bioorganic & medicinal chemistry.

[111]  Dinshaw J. Patel,et al.  Solution structure of the tobramycin–RNA aptamer complex , 1998, Nature Structural Biology.

[112]  D. Patel,et al.  Adaptive recognition by nucleic acid aptamers. , 2000, Science.

[113]  Daniel P Morse,et al.  Direct selection of RNA beacon aptamers. , 2007, Biochemical and biophysical research communications.

[114]  Juewen Liu,et al.  Fast colorimetric sensing of adenosine and cocaine based on a general sensor design involving aptamers and nanoparticles. , 2005, Angewandte Chemie.

[115]  V. Erdmann,et al.  Mirror-image RNA that binds D-adenosine , 1996, Nature Biotechnology.

[116]  Sara Tombelli,et al.  Aptamers biosensors for pharmaceutical compounds. , 2010, Combinatorial chemistry & high throughput screening.

[117]  Julia Promisel Cooper,et al.  The telomere protein Taz1 is required to prevent and repair genomic DNA breaks. , 2003, Molecular cell.

[118]  S. Gopinath Methods developed for SELEX , 2006, Analytical and bioanalytical chemistry.

[119]  Ioanis Katakis,et al.  Aptamers: molecular tools for analytical applications , 2008, Analytical and bioanalytical chemistry.

[120]  Arica A Lubin,et al.  Continuous, real-time monitoring of cocaine in undiluted blood serum via a microfluidic, electrochemical aptamer-based sensor. , 2009, Journal of the American Chemical Society.

[121]  Q. Gao,et al.  Double covalent coupling method for the fabrication of highly sensitive and reusable electrogenerated chemiluminescence sensors. , 2010, Analytical chemistry.

[122]  M. Gu,et al.  Electrochemical detection of 17β-estradiol using DNA aptamer immobilized gold electrode chip , 2007 .

[123]  P. Barnes Theophylline: new perspectives for an old drug. , 2003, American journal of respiratory and critical care medicine.

[124]  Kevin W Plaxco,et al.  Structure-switching biosensors: inspired by Nature. , 2010, Current opinion in structural biology.

[125]  Peter Seto,et al.  Distribution of estrogens, 17β-estradiol and estrone, in Canadian municipal wastewater treatment plants , 2005 .

[126]  J. Oehlmann,et al.  Endocrine disruptors in bottled mineral water: total estrogenic burden and migration from plastic bottles , 2009, Environmental science and pollution research international.

[127]  K. Docherty,et al.  A consensus repeat sequence from the human insulin gene linked polymorphic region adopts multiple quadriplex DNA structures in vitro , 1992, FEBS letters.

[128]  J. Schwaiger,et al.  Toxic effects of the non-steroidal anti-inflammatory drug diclofenac. Part I: histopathological alterations and bioaccumulation in rainbow trout. , 2004, Aquatic toxicology.

[129]  M. Ladisch,et al.  Recombinant Human Insulin , 1992, Biotechnology progress.

[130]  David Erickson,et al.  Aptamer based surface enhanced Raman scattering detection of vasopressin using multilayer nanotube arrays. , 2010, Biosensors & bioelectronics.

[131]  C. Mantzoros,et al.  Recombinant human growth hormone: old and novel uses. , 1998, The American journal of medicine.

[132]  Milan N Stojanovic,et al.  Fluorescent Sensors Based on Aptamer Self-Assembly. , 2000, Journal of the American Chemical Society.

[133]  R. Stoltenburg,et al.  SELEX--a (r)evolutionary method to generate high-affinity nucleic acid ligands. , 2007, Biomolecular engineering.

[134]  A. C. Hansen,et al.  Abuse of codeine separated from over-the-counter drugs containing acetylsalicylic acid and codeine , 2005, International Journal of Legal Medicine.

[135]  J. Cowan,et al.  Recognition of a cognate RNA aptamer by neomycin B: quantitative evaluation of hydrogen bonding and electrostatic interactions. , 2000, Nucleic acids research.

[136]  Ryan Walsh,et al.  Retention of function in the DNA homolog of the RNA dopamine aptamer. , 2009, Biochemical and biophysical research communications.

[137]  S. Jørgensen,et al.  Drugs in the environment. , 2000, Chemosphere.

[138]  K. Ikebukuro,et al.  Aptameric enzyme subunit for biosensing based on enzymatic activity measurement. , 2006, Analytical chemistry.

[139]  L. McGown,et al.  Insulin capture by an insulin-linked polymorphic region G-quadruplex DNA oligonucleotide. , 2006, Journal of the American Chemical Society.

[140]  C. O’Sullivan Aptasensors – the future of biosensing? , 2002, Analytical and bioanalytical chemistry.

[141]  Koji Sode,et al.  Selection of DNA aptamers against insulin and construction of an aptameric enzyme subunit for insulin sensing. , 2009, Biosensors & bioelectronics.

[142]  A. Evans Enantioselective pharmacodynamics and pharmacokinetics of chiral non-steroidal anti-inflammatory drugs , 2004, European Journal of Clinical Pharmacology.

[143]  Omowunmi A Sadik,et al.  Status of biomolecular recognition using electrochemical techniques. , 2009, Biosensors & bioelectronics.

[144]  A. Ellington,et al.  Screening chemical libraries for nucleic-acid-binding drugs by in vitro selection: A test case with lividomycin , 2005, Molecular Diversity.

[145]  Ming Zhou,et al.  G-Quadruplex-based DNAzyme for colorimetric detection of cocaine: using magnetic nanoparticles as the separation and amplification element. , 2011, The Analyst.

[146]  Jian-hui Jiang,et al.  A new aptameric biosensor for cocaine based on surface-enhanced Raman scattering spectroscopy. , 2008, Chemistry.

[147]  Andrew D Ellington,et al.  Aptamer therapeutics advance. , 2006, Current opinion in chemical biology.

[148]  Hiroaki Ozaki,et al.  Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity. , 2007, Journal of the American Chemical Society.

[149]  S. Sun Technology evaluation: SELEX, Gilead Sciences Inc. , 2000, Current opinion in molecular therapeutics.

[150]  R. Schroeder,et al.  In vitro selection and characterization of streptomycin-binding RNAs: recognition discrimination between antibiotics. , 1998, RNA.

[151]  Bertold Hock,et al.  VITELLOGENIN : A BIOMARKER FOR ENDOCRINE DISRUPTORS , 1998 .