Pyrophosphate sensing by a fluorescent Zn2+ bound triazole linked imino-thiophenyl conjugate of calix[4]arene in HEPES buffer medium: spectroscopy, microscopy, and cellular studies.

An in situ prepared Zn(2+) complex of triazole linked imino-thiophenyl conjugate of calix[4]arene, [ZnL], was demonstrated to be highly fluorescent in HEPES buffer solution. [ZnL] has been used as a chemo-sensing ensemble for the recognition of phosphates in general and pyrophosphates in particular among the eighteen different anions studied. The chemo-sensing behavior of the [ZnL] has been demonstrated through fluorescence, absorption, visual fluorescent color changes, ESI MS, and (1)H NMR titrations. Variations in the microstructural features of L, its zinc complex and the complex upon addition of PPi have been demonstrated through atomic force microscopy and transmission electron microscopy. Such studies have been extended to see the permeability of the conjugate into the HeLa cells by fluorescence microscopy. In accession, a reversible "write-read-erase-read" logic gate property of L has been demonstrated through a feedback loop in the presence of Zn(2+) and PPi.

[1]  Philip A. Gale,et al.  Structural and molecular recognition studies with acyclic anion receptors. , 2006, Accounts of chemical research.

[2]  Pengfei Wang,et al.  New sensing mechanisms for design of fluorescent chemosensors emerging in recent years. , 2011, Chemical Society reviews.

[3]  M. Ronaghi,et al.  Real-time DNA sequencing using detection of pyrophosphate release. , 1996, Analytical biochemistry.

[4]  Z. Tao,et al.  Pyrene-linked triazole-modified homooxacalix[3]arene: a unique C3 symmetry ratiometric fluorescent chemosensor for Pb2+. , 2011, Organic letters.

[5]  D. Churchill,et al.  Labile zinc-assisted biological phosphate chemosensing and related molecular logic gating interpretations. , 2012, Inorganic chemistry.

[6]  Weisheng Liu,et al.  Development and applications of fluorescent indicators for Mg2+ and Zn2+. , 2011, The journal of physical chemistry. A.

[7]  M. Nilsson,et al.  Neurotoxicity of cysteine: interaction with glutamate , 1995, Brain Research.

[8]  B. Creaven,et al.  Coordination chemistry of calix[4]arene derivatives with lower rim functionalisation and their applications , 2009 .

[9]  M. Kumar,et al.  Optical chemosensor for Ag+, Fe3+, and cysteine: information processing at molecular level. , 2011, Organic letters.

[10]  Arjan W. Kleij,et al.  Dimetallic Activation of Dihydrogen Phosphate by Zn(salphen) Chromophores , 2010 .

[11]  M. Licchelli,et al.  The design of luminescent sensors for anions and ionisable analytes , 2000 .

[12]  D. Mccarty,et al.  Measurement of inorganic pyrophosphate in biological fluids. Elevated levels in some patients with osteoarthritis, pseudogout, acromegaly, and uremia. , 1973, The Journal of clinical investigation.

[13]  J. D. Walsh,et al.  Calix[4]arene derivatives containing azine functionality: A Zn(II)-responsive fluorescent sensor , 2011 .

[14]  H. Hatta,et al.  Improvement of functional properties of egg white protein through phosphorylation by dry-heating in the presence of pyrophosphate. , 2004, Journal of agricultural and food chemistry.

[15]  D. Spring,et al.  Fluorescent chemosensors for Zn(2+). , 2010, Chemical Society reviews.

[16]  V. Yam,et al.  A highly selective bifunctional luminescence probe for potassium and fluoride ions. , 2011, Organic letters.

[17]  Su Yeon Lee,et al.  Hyperbranched calixarenes: synthesis and applications as fluorescent probes. , 2009, Chemical communications.

[18]  Joakim Andréasson,et al.  An all-photonic molecular keypad lock. , 2009, Chemistry.

[19]  R. Waring,et al.  Plasma cysteine and sulphate levels in patients with motor neurone, Parkinson's and Alzheimer's disease , 1990, Neuroscience Letters.

[20]  Geoffrey Burnstock,et al.  Purinergic Signalling: ATP Release , 2001, Neurochemical Research.

[21]  Sung-Jin Kim,et al.  Pyrophosphate-selective fluorescent chemosensor at physiological pH: formation of a unique excimer upon addition of pyrophosphate. , 2007, Journal of the American Chemical Society.

[22]  A. Goldman,et al.  Site-specific effects of zinc on the activity of family II pyrophosphatase. , 2004, Biochemistry.

[23]  F. Sansone,et al.  A new chiral rigid cone water soluble peptidocalix[4]arene and its inclusion complexes with α-amino acids and aromatic ammonium cations , 1999 .

[24]  N. Marcotte,et al.  Pyrophosphate detection in water by fluorescence competition assays: inducing selectivity through the choice of the indicator. , 2002, Angewandte Chemie.

[25]  C. P. Rao,et al.  Triazole-linked-thiophene conjugate of calix[4]arene: its selective recognition of Zn2+ and as biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein. , 2011, The Journal of organic chemistry.

[26]  Rajesh Kumar,et al.  Thiacalix[4]arene based reconfigurable molecular switches: set-reset memorized sequential device. , 2011, Organic & biomolecular chemistry.

[27]  J. Sessler,et al.  Artificial receptors for the recognition of phosphorylated molecules. , 2011, Chemical reviews.

[28]  Félix Sancenón,et al.  Fluorogenic and chromogenic chemosensors and reagents for anions. , 2003, Chemical reviews.

[29]  Philip A. Gale,et al.  Anion Recognition and Sensing: The State of the Art and Future Perspectives. , 2001, Angewandte Chemie.

[30]  Yuan Li,et al.  Coordination dynamics of zinc in proteins. , 2009, Chemical reviews.

[31]  Juyoung Yoon,et al.  Imidazolium receptors for the recognition of anions. , 2006, Chemical Society reviews.

[32]  Terence E. Rice,et al.  Signaling Recognition Events with Fluorescent Sensors and Switches. , 1997, Chemical reviews.

[33]  C. P. Rao,et al.  Lower rim 1,3-diderivative of calix[4]arene-appended salicylidene imine (H(2)L): experimental and computational studies of the selective recognition of H(2)L toward Zn(2+) and sensing phosphate and amino acid by [ZnL]. , 2010, The Journal of organic chemistry.

[34]  Y. Urano,et al.  A fluorescent anion sensor that works in neutral aqueous solution for bioanalytical application. , 2002, Journal of the American Chemical Society.

[35]  J. Berg.  Zinc Finger Domains: From Predictions to Design , 1995 .

[36]  K. C. Chang,et al.  A Bifunctional Chromogenic Calix[4]arene Chemosensor for Both Cations and Anions: A Potential Ca2+ and F– Switched INHIBIT Logic Gate with a YES Logic Function , 2010 .

[37]  Guangyan Qing,et al.  Enantioselective Fluorescent Sensors for Chiral Carboxylates Based on Calix[4]arenes Bearing an L‐Tryptophan Unit , 2007 .

[38]  Han Na Lee,et al.  Simple but effective way to sense pyrophosphate and inorganic phosphate by fluorescence changes. , 2007, Organic letters.

[39]  Javier Cervera,et al.  Understanding carbamoyl phosphate synthetase deficiency: impact of clinical mutations on enzyme functionality. , 2005, Journal of molecular biology.

[40]  Ernest Beutler,et al.  Glucose-6-phosphate dehydrogenase deficiency: a historical perspective. , 2008, Blood.

[41]  P. Chakrabarti.  Anion binding sites in protein structures. , 1993, Journal of molecular biology.

[42]  Jong‐In Hong,et al.  An azophenol-based chromogenic pyrophosphate sensor in water. , 2003, Journal of the American Chemical Society.

[43]  A. Prasanna de Silva.  Molecular Logic Gate Arrays , 2011 .

[44]  F. W. Smith,et al.  Zinc deficiency up-regulates expression of high-affinity phosphate transporter genes in both phosphate-sufficient and -deficient barley roots. , 2000, Plant physiology.

[45]  Jennie Weston,et al.  Mode of action of bi- and trinuclear zinc hydrolases and their synthetic analogues. , 2005, Chemical reviews.

[46]  Arjan W. Kleij,et al.  Colorimetric discrimination between important alkaloid nuclei mediated by a bis-salphen chromophore. , 2008, Organic letters.

[47]  Pablo Ballester,et al.  Cover Picture: Inclusion of Cavitands and Calix[4]arenes into a Metallobridged para‐(1H‐Imidazo[4,5‐f][3,8]phenanthrolin‐2‐yl)‐Expanded Calix[4]arene (Angew. Chem. Int. Ed. 1‐2/2007) , 2007 .

[48]  M. Yılmaz,et al.  Synthesis and fluorescence sensing properties of novel pyrene-armed calix[4]arene derivatives , 2011 .

[49]  D. Churchill,et al.  Aqueous fluorometric and colorimetric sensing of phosphate ions by a fluorescent dinuclear zinc complex. , 2009, Inorganic chemistry.

[50]  M. Brown,et al.  Genetic studies of disorders of calcium crystal deposition. , 2002, Rheumatology.

[51]  D. Eide.  Zinc transporters and the cellular trafficking of zinc. , 2006, Biochimica et biophysica acta.

[52]  Jong Seung Kim,et al.  Host-guest sensing by calixarenes on the surfaces. , 2012, Chemical Society reviews.

[53]  C. Redshaw,et al.  Ratiometric fluorescent receptors for both Zn2+ and H2PO4(-) ions based on a pyrenyl-linked triazole-modified homooxacalix[3]arene: a potential molecular traffic signal with an R-S latch logic circuit. , 2011, The Journal of organic chemistry.

[54]  F. Schmidtchen,et al.  Artificial Organic Host Molecules for Anions. , 1997, Chemical reviews.

[55]  Leila Motiei,et al.  Electrically addressable multistate volatile memory with flip-flop and flip-flap-flop logic circuits on a solid support. , 2010, Angewandte Chemie.

[56]  M. Sharratt,et al.  Biological effects of food additives. II.—sodium pyrophosphate† , 1962 .

[57]  Carla G. Taylor.  Zinc, the Pancreas, and Diabetes: Insights from Rodent Studies and Future Directions , 2005, Biometals.

[58]  C. Rao,et al.  Ion and molecular recognition by lower rim 1,3-di-conjugates of calix[4]arene as receptors. , 2011, Chemical reviews.

[59]  E. Ho.  Zinc deficiency, DNA damage and cancer risk. , 2004, The Journal of nutritional biochemistry.

[60]  Juyoung Yoon,et al.  Chemosensors for pyrophosphate. , 2009, Accounts of chemical research.

[61]  M. Stenzel,et al.  Hypophosphatasia – Recent Advances in Diagnosis and Treatment , 2009 .

[62]  Jun Feng Zhang,et al.  Novel 2,2′-bipyridine-modified calix[4]arenes: ratiometric fluorescent chemosensors for Zn2+ ion , 2010 .

[63]  A. Jones,et al.  Association between synovial fluid levels of inorganic pyrophosphate and short term radiographic outcome of knee osteoarthritis. , 1996, Annals of the rheumatic diseases.

[64]  F. Perret,et al.  An ESI/MS study of the formation of ternary 25,27-bis(dihydroxy-phosphoryloxy) calixarene-metal ion-aminoacid complexes , 2002 .

[65]  J. Chinta,et al.  Calix[4]arene-based 1,3-diconjugate of salicylyl imine having dibenzyl amine moiety (L): synthesis, characterization, receptor properties toward Fe2+, Cu2+, and Zn2+, crystal structures of its Zn2+ and Cu2+ complexes, and selective phosphate sensing by the [ZnL]. , 2011, Inorganic chemistry.