selenate selenite sensor

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    Graphical Abstract

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    Abstract

    +urcumin - is sudied for is binding affini o/ards differen anions such as %P0 "2, %"P0

    2,

    0Ac2, 32, +l2, Br2, 42, N0(2, )0

    "2, As0(2, As0"

    (2, )e0("2and )e0

    "2b 5626is and fluorescence

    specroscop in 1&7 v5v a!ueous mehanol mainained a p% 1&.'. 5626is sudies of curcumin

    sho/ed seleci$e raiomeric response A"89:A&, upon comple#aion of selenae or selenie ions.

    3luorescence iraions of curcumin sho/ed and (." fold fluorescence enhancemen in emission

    a 9'& nm, /ih 1 e!ui$. of selenae and selenie ions, respeci$el. ;he seleci$e fluorescence

    enhancemen is aribued o significan loss of e#cied sae hdrogen:proon ransfer process

    and a significan proon donaion b he mehanol, upon comple#aion of selenae:selenie ion b

    curcumin. ;he Job"

    anion>curcumin. ;he limi of deecion for selenae and selenie /ere deermined o be 1& and

    1" nM, respeci$el.

    !"#$r%s& )elenium, curcumin, fluorescence, absorbance, ?%P;:?)P;

    '( I)tr$%*cti$)

    )elenium is an essenial micronurien a lo/ concenraions in $arious life forms including

    humans, bu sho/ o#ici a ele$aed concenraions Reill, "&&8@ 3leming, 1'&. 4 has found

    applicaion in commodiies used in dail life lie $ulcani=ing addii$e for rubber 0nan, 1',

    phooelecric de$ices Manase$i e al., 18, baeries, glasses colorans, insecicides:ani2

    dandruff Monerio e al., "&&@ )al$ador e al. "&&&3, sin disease reamen +han e al.,

    1', phoosensii$e drums and caals in urea:urehane snhesis Mi=una e al., "&&&. C1,"D.

    )elenium is /idel dispersed in igneous rocs KolEonen, 1F( and hdrohermal deposis of

    Au, )b, %g and Ag ;amari e al., 1&. Apar from his, i finds is /a ino our en$ironmen

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    from anhropogenic sources lie sulphuric acid plans, ore processing /ase, hermal plans, oil

    refineries and agriculural drainage Mason e al., "&&&@ Rosenfeld Beah, "&1( C9,8D.

    )elenium e#iss in four o#idaion saes such as elemenal )e &, selenide )e"H, selenie )e0("H,

    )e46 and selenae )e0"H, )e64 C)indee$a, 18, 'D. %o/e$er in a!ueous en$ironmen,

    selenie and selenae ions are he mos abundan forms of selenium, /hereb )e46 is more

    o#ic han )e64 CGraham, 11, D. A high dail inae of selenium in he human die is

    direcl associaed /ih dermaiis, faigue, chronic gasroinesinal disease, irriaion of sin and

    ees and losing hair nails C"D. +hronic e#posure is also associaed /ih li$er, pancreas, hear,

    idne problems and increased ris of cancer C1D. ;hus, Iorld %ealh 0rgani=aion I%0 and

    5nied )ae ?n$ironmenal Proecion Agenc 5)?PA ha$e prescribed ma#imum permissible

    limi of 1& g:- C1&D and 9& g:- C11D, in poable /aer, respeci$el.

    6arious echni!ues are a$ailable for selenium analsis in /aer including %dride Generaor

    %G coupled /ih aomic fluorescence Ref., Aomic absorpion and 4nduci$e +oupled Plasma

    mass specromer Ref., gas chromaograph G+ Ref. and %P-+:ion chromaograph

    Ref., Neuron Aci$aion analsis and cahodic sripping $olammer +)6 Ko

    Namiesni, "&&&@ Bednar e al., "&&@ +ooe Bruland, 1'FC21&D. ;hese mehods are ime

    consuming, cosl, cumbersome, re!uire rained manpo/er and lac real2ime monioring for

    operaion ref. Alernai$el, fluorescence mehods are one of he seleci$e, sensii$e, cos and

    ime efficien mehod for analsis in real2ime monioring used in en$ironmen, medicines and

    in*vitro : in*vivomonioring emcheno, "&&'@ )ahana et al, "&11. 0ne of he mehods for

    seleci$e analsis of selenium is based on he dosimeric fluorogenic sensing using 1,"2

    diaminonaphalene AN and is deri$ai$es Marine=, "&1(. Apar from his hos2gues

    comple#aion induced fluorogenic sensing of selenium has been repored recenl Ref..

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    %o/e$er, his sensing beha$ior is aribued o he binding of selenium as eiher as a caion or

    anion is no clearl undersood.

    %os2gues recogniion based e!uilibrium approach ha$e been recenl e#plored o sho/

    fluorogenic sensing of selenium /ih -0 upo 2222 C)ong, +airui, @ 3eng, GuodongD. ;he oher

    approach for selenium sensing in$ol$es he anion recogniion?$ans, Nicholas % and he basic

    design of he anion recepor comprise of eiher a posii$el charged recepors carring

    ammoniumCrefD, imida=oliumCoon, J.@ Kim, ). K.@ )ingh, N. J.@ Kim, K. ). +hem. )oc. Re$.

    "&&8, (9, (99 )ensors and Acuaors B "&1(, 1'9, 1''21D, pridiniumCrefD and guanidinium

    CrefD funcional groups and hdrogen bond donor moieies lie amideC)pecrochimica Aca, Par

    A> Molecular and Biomolecular )pecroscop "&1, 1"1, 88"288 +hem. )oc. Re$. " "&1(,

    189"21888 ;erahedron -eers "&1", 9(, '12'"(, +hem. )oc. Re$ie/ "&1(, "&, Amide

    based recepors for anionsD, urea:hiourea C+oordinaion +hemisr Re$ie/s "&19, "9, '&2

    1", ;erahedron -eers "&1, 99(, '1&2'1(, refD, Ben=imida=ole )ingh, N., Jang, .

    0. "&&F. Ben=imida=ole2based ripodal recepor> highl seleci$e fluorescen chemosensor for

    iodide in a!ueous soluion. 6rganic letters, /1&, 1121. Journal of 0rganomeallic

    +hemisr "&1, FF&, '92(.@ prrole C)ensors and Acuaors, B> +hemical "&18, ""9, "'2

    (9, ;erahedron "&1(, 88, 1F"921F(.refD and phenol C)pecrochimica Aca, Par A>

    Molecular and Biomolecular )pecroscop "&1, 1"1, (&82(1".D. Naurall rosine is an

    essenial funcional moie for binding of anion chloride in he chloride channels and

    halorhodopsin CC11D R. u=ler, ?.B. +ampbell, R. MacKinnon, )cience (&& "&&( 1&'L11".

    C1"D R. u=ler, ?. +ampbell, M. +adene, B. +hai, R. MacKinnon, Naure 19 "&&" "'FL".

    C1(D M. Kolbe, %. Besir, -.0. ?ssen, . 0eserhel, )cience "'' "&&& 1(&L1(8. C1D M.;.

    3accioi, 6.). +heung, +.). -unde, ). Rouhani, N.). Baliga, R.M. Glaeser, Biochemisr (

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    "&& (L(D. ;hus, phenols pla a $ial role in anion recogniion and $arious chromogenic

    recepors are repored in proic as /ell as aproic sol$ensC)pecrochimica Aca, Par A>

    Molecular and Biomolecular )pecroscop "&19, 19&, '12'"& Journal of Molecular )rucure

    "&19, 1&, 1'218&, ?uropean Journal of 0rganic +hemisr "&1, "&1"", F92F88D.

    0ne of presen auhors sudied he chromogenic anion sensing beha$ior of a=ophenol deri$ai$e

    of hiacali#CDarene, /hereb an unusual comple#aion induced e#ended conEugaion /as

    obser$ed upon comple#aion of fluoride, hdrogenphosphae and aceae ion Kumar, ManoE, J.

    Nagendra Babu, and 6andana Bhalla. A=ophenol appended hia cali# CD arenes for

    colorimeric sensing of anions> A comple#aion induced e#ended conEugaion. Talanta'1, no. 1

    "&1&> 21.. A/ual e al. "&19 sudied a colorimeric phenol sensor cum adsorben based on

    %,%2di(2carbo#saliclidene2(,2diamino292hdro#pra=ole immobili=ed mesoporous silica

    monolihforsensing:adsorpion of selenie ion /ih a limi of deecion 1.1Og-21ref.

    Sch!+! '& Keo2enol auomerism of curcumin

    Polphenolic naural produc, +urcumin L, /as sudied for seleci$e colorimeric and

    fluorogenic sensing of fluoride ion as erabulammonium sal ;BA in non2a!ueous sol$en

    o$er oher anions such as Ac02, %"P02and +l2 ionIu et al, "&&. +urcumin L consiss of

    /o meho#phenols aached smmericall hrough 7, 82unsauraed82dieone liner, /hich

    leads o eoLenol auomerismCJNP, "&&F, 1(218D Sch!+! '. ue o his characerisic

    phenomenon, i e#hibis ineresing phoophsical and phoochemical properies CJPP+PR, "&&,

    1&, '129D and meal comple#ing abili Ianninger, )., -oren=, 6., )ubhan, A., ?delmann, 3.

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    ;. "&19. Meal comple#es of curcumin 2 snheic sraegies, srucures and medicinal

    applicaions. Chemical Society Revie9s, 1119, '829&&". doi> 1&.1&(:+9+)&&&''B. ;he

    presen sud in$esigaes he use of curcumin in buffered a!ueous condiions for he seleci$e

    fluorogenic sensing of selenae and selenie ions.

    ,( E-p!ri+!)tal

    ,(' Mat!rial

    +urcumin, "2Aminophenol, )odium monohdrogen phosphae Na"%P0, sodium dihdrogen

    phosphae Na%"P0, )odium niraeNaN0(, )odium arsenae Na"As0, )odium arsenie

    NaAs0", )odium selenae Na")e0, )odium selenie Na")e0(, )odium aceae

    +%(+00Na, )odium fluoride Na3, )odium chloride Na+l, )odium bromide NaBr,

    )odium iodide Na4, )odium sulphae Na")0, Mehanol +%(0% /ere of analical or

    gra$imeric reagen grade. )oluions /ere prepared in laboraor using disilled /aer 1'OQ

    conduci$i R40N) 4N4A R0 ssem Model No. Basic (8& series.

    ,(, Sp!ctr$sc$pic +!as*r!+!)ts

    Absorbance sudies /ere done on P+ based 5621'&& )himad=u specrophoomeer using 1 ml

    !uar= cu$ees !uar=, /ih he help of 56 probe ".( sof/are in he specrum mode.

    3lorescence sudies /ere carried ou on a P+ based )nerg %1 Microplae reader /ih he help

    of Gen 9 sof/are using bioe biocell plae and 1m- !uar= cu$ees because of is high

    sensii$i and narro/er specrum in he fluorescence /a$elengh range (&&2F&&nm. ;he

    samples /ere e#cied a heir respeci$e absorpion ma#ima.

    ,(. /r!parati$) $0 a)al"tical sa+pl!

    1&OM soluion of he anion recepor /as prepared in 1&&ml mehanol b dissol$ing .9mg of

    he anion recepor. )imilarl soluions of he anion recepor /ere prepared in aceonirile,

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    M)0, 1&7 $:$ of /aer in mehanol, 1&7 $:$ of /aer in aceonirile and 1&7 $:$ of /aer in

    ;%3.

    ,(1 /r!parati$) $0 a)i$) s$l*ti$)s

    &.&1M soluions of he anion soluions /ere prepared in disilled /aer using sodium sals of

    mono hdrogen phosphae, dihdrogen phosphae, arsenae, arsenie, selenae, selenie, aceae,

    flouride, chloride, bromide, iodide, sulphae. 3rom he soc soluions, 1ml of he 1&&OM

    /oring soluions of he anions /ere prepared and used for fluorescence and absorbance sudies.

    ".9 5626isible ;iraions

    ".8 3luorescence ;iraions

    .( R!s*lts a)% %isc*ssi$)

    .(' UV2Vis St*%i!s

    +urcumin L is a phenolic bioaci$e componen of urmeric Curcuma longa, a perennial plan

    of he ginger famil ingiberaceae, nai$e o ropical )ouh Asia. ;o e$aluae he binding

    abili of curcumin o/ards differen anions, 56L6is e#perimens /ere carried ou in

    %"0>+%(0% >1, $:$ /ih p% mainained a "21" using $arious buffers. ;he 5626isible

    absorpion specra of curcumin a differen p% is sho/n in 3ig. 1. ;he absorpion specrum of

    curcumin is characeri=ed b he presence of absorpion ma#imum pea a (F and ( nm a p%

    ", /hich corresponds o he elecronic dipole allo/ed S2S* and inramolecular charge ransfer

    ransiion, respeci$el Ref. J. 3luorescence "&1&, "&, '(2'9&, sila, e al. Biochem Biphs.

    Res +ommunicaion "&&(, FF82F'". ;he obser$ed pea a (9 nm is characeri=ed b a small

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    blue shif from "9 nm in /aer b 1& nm, accouned o he presence of mehanol in polar

    en$ironmen of he mi#ed sol$en C)pecrochimica Aca A "&&, 8&, 1&12FD.

    Fig*r! '&?ffec of p% "21" on he characerisic 5626is absorpion beha$ior of +urcumin in

    1&7 $:$ a!ueous mehanol.

    A p% ', a ne/ absorpion pea a "89 nm is obser$ed characerisic of curcumin in basic media.

    %o/e$er, he inense absorpion band obser$ed a (9 nm sho/ed a hperchromic red shif o

    & nm a p% 1" /ih significan broadening. ;he decrease in absorpion a (89 nm upon

    increase in p% of he soluion, is accouned o proon dri$en inramolecular charge ransfer.

    Ihereas, he blue shif in he absorpion band a "9 nm upon increase in he p% of he soluion

    could be accouned o he sep/ise deproonaion of curcumin 3igure ". ;he deproonaion of

    curcumin leads o he liberaion of curuminae, /hich is characeri=ed b inense charge ransfer

    specra a & nm Chao e al. NP+ "&&', ""2"("D. ;he ne/ absorpion band a "89 nm in basic

    p% is characerisic of he phenolic moie of curcumin CNe/ J +hem "&1, (', 1((821(9D. ;he

    absorpion band due o he phenolic moie is obser$ed o decrease furher upon increasing he

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    p% upo 1" due o he formaion phenolae ions, /hich suppors he blue shif in curcumin charge

    ransfer specra upo & nm.

    Sch!+! ,& Proopropic e!uilibria of +urcumin Priadarshini. "&&

    +urcumin soluions 1 T 1&H8M in 1&7v5v a!ueous mehanol mainained a p% 1&.', /ere

    added 1 e!ui$. of represenai$e anions lie arsenae, arsenie, fluoride, chloride, bromide,

    iodide, aceae, selenae, selenie, nirae, monohdrogenphosphae, dihdrogenphosphae and

    sulphae as heir sodium sals. 4n he absence of hese anions, he absorpion specrum of

    curcumin /as characeri=ed b he presence of one absorpion ma#imum pea a & nm 3ig.

    ". ;he 56L$is absorpion band a & nm sho/ed a significan decrease in he absorpion

    inensi upon addiion of 1 e!ui$alen of selenae:selenie ion. +urcumin sho/ed no change in

    5626is specra upon addiion of fluoride, chloride, bromide, iodide, aceae,

    dihdrogenphosphae, nirae and hdrogensulphae. %o/e$er, in presence of 1 e!ui$. of arsenie

    and arsenae here /as a decrease in he 5626is absorpion band a nm. ;hus, a seleci$e

    ineracion be/een curcumin and selenie:selenie ions is e$iden a p% 1&.'.

    3igure >

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    Fig*r! ,&Absorpion specra of curcumin 1#1&28M in Me0%> %"0 1> v5v a p% 1&.' uponabsorbance iraions /ih a selenae b selenie. 4nse sho/ing he raiomeric response a "89

    nm and & nm as a funcion of )elenae concenraion.

    .(, Fl*$r!sc!)c! St*%"

    +urcumin e#hibied a characerisic /ee emission a 9'& nm upon e#ciaion a "& nm in 1&7

    $:$ a!ueous mehanol mainained a p% 1&.'. ;his emission a 9'& nm is aribued o locall

    e#cied lo/es * sae in 1&7 $:$ a!ueous mehanol soluion a p% 1&.' C/atra %(3

    bara4at3 ,5''3 sp!ctr$ch!+ acta part a 673 '5.12'51'D. ;he emission is characeri=ed b a

    large soes shif, as repored b L e al. for curcumin in proic sol$ens, /hereb inermolecular

    hdrogen bonding be/een he curcuminae ions, ma induce change in he conformaions and

    hereb increasing he ou of plane $ibraionsIu et al., "&&. ;he /ea fluorescence of

    curcumin in 1&7 $:$ a!ueous mehanol mainained a p% 1&.', is aribued eiher o he

    formaion of non2fluorescen and sable charge2ransfer comple# of he pe curcumin (2 %"0U

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    Bong P.%. Bull. Kor. +hem. )oc. "&&&, "1, '12'8 or o he presence of ?#cied )ae proon

    ransfer ?)P; mechanism e#ising be/een he curcuminae ion and he binar sol$en

    /aer:mehanol Journal of Phsical +hemisr A "&1", 118, "&(2"&'.

    Fig*r! 1&?mission specra of curcumin 1OM in presence of $arious anions in Me0%>% "0 >1

    $:$ under buffer condiions g Na"%P0:Na0% buffer p% 1&.'1 h Na"%P0:Na0% buffer p%11.(.

    5pon addiion of 1 e!ui$alen of )elenae:selenie ions o he a!ueous mehanolic soluion of

    curcumin mainained a p% 1&.', a significan fluorescence enhancemen /as obser$ed 3ig. ".

    5nder he same condiions as abo$e no significan fluorescence changes 3ig. " /ere obser$ed

    in presence of oher anions 32, +l2, Br2, 42, N0(2, 0Ac2, 22222 and )0

    2. %o/e$er a significan

    enhancemen /as obser$ed in he presence of arsenae, arsenie and %"P02 ions. ;hese

    obser$aions indicae ha curcumin has seleci$i for )elenae:selenie o$er oher ions 3ig. (.

    ;he addiion of $arious anions o curcumin 1#1& 28M in a!ueous mehanol mainained a p%

    from 8.8211.(, /ere also carried ou. 4 /as obser$ed ha he ineracion of he anions /ih

    curcumin /as no e$iden in he p% range 8.8121&.9&, ho/e$er in case of p% 11.(&, a

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    fluorescence enhancemen a emission of 9'& nm /as obser$ed in presence of all he anions.

    ;hus, i is inferred ha curcumin seleci$el ineracs /ih selenae and selenie ions in 1&7

    a!ueous mehanol mainained a p% 1&.'.

    3luorescence iraion of curcumin /ih selenae:selenie /ere carried ou in a!ueous mehanolic

    soluion mainained a p% 1&.'. 5pon addiion of selenae ions &21 e!ui$. o he /eal

    fluorescen a!ueous mehanol soluion of curcumin mainained a p% 1&.', a significan

    enhancemen in he fluorescence inensi a 9'& nm /as obser$ed. 5pon addiion of 1 e!ui$. of

    selenae ion, 2fold increase in he fluorescence inensi /as obser$ed a 9'& nm3ig. . ;he

    limi of deecion for selenae using he fluorescence iraion daa /as found o be 1& nM.

    )imilarl, upon addiion of 1 e!ui$. of selenie here is a significan increase in he emission of

    curcumin upo (." fold /as obser$ed.

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    Fig*r! 8&?mission specra of curcumin 1OM in Me0%>%"0 >1 $:$ a p% 1&.'1 upon

    fluorescence iraions /ih selenae and selenie

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    ;he comple#aion as obser$ed from he fluorescence sudies is 1>" )e64:46>+urcumin

    comple#, /hich indicaes /o molecules of curcumin are in$ol$ed in he comple#aion of

    selenie and selenae ions. Based on he specroscopic e$idences, he proposed comple#aion

    mechanism of anion b curcumin is as gi$en belo/ in he 3igure F.

    Fig*r! 9> +omple#aion of curcumin /ih selenae and selenie b hdrogen bonding /ih he

    phenolic 0% group

    ;he anion induced fluorescence enhancemen of curcumin in a!ueous mehanol soluion is

    aribued o he disrupion of he ?)P; phenomenon in curcumin upon binding of anion. A p%

    1&.', he anions are in compleel ioni=ed as )e0"2 or )e0(

    "2CAlas of ?h2p% diagrams

    inercomparison of hermodnamic daabases Geological )ur$e of Japan 0pen 3ile Repor

    No.1 "&&9 hp>::///.eosremediaion.com:do/nload:+hemisr:+hemical

    7"&Properies:?hVp%Viagrams.pdfD and curcumin is compleel deproonaed a p% abo$e

    1&.9 C)pecrochim Aca A 8&, "&&, 1&121&FD. %o/e$er, i is e$iden ha curcumin undergoes

    a ?#cied )ae 4nramolecular %drogen ;ransfer, ?)4%; or ?)4P; in mehanolic soluions

    CAdhiar e al. J. Phs. +hemisr B "&&, 11(, 9"99 Adhiar e al. "&1&, 11, "F@

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    Journal of Phsical +hemisr B "&1&, 11, 1"1"21"1(D. ;his ?)P; induced !uenching of

    fluorescence is more pronounced under basic condiions due o he ground sae proon ransfer

    in conEuncion /ih ?)P; phenomenon of curcuminae ions Journal of Phsical +hemisr A

    "&1", 118, "&(2"&'. ;hus, i is !uie e$iden ha mehanol has a significan role o pla in he

    selenae:selenie ion binding b curcuminae ion. ;hus, he proposed mechanism in$ol$es a

    proon ransfer in he ground sae from mehanol o he comple# during curcuminae

    comple#aion of )elenae:selenie ions. ;his binding mechanism is furher suppored b he 562

    6is absorpion band due o he phenol group of curcumin being e$iden in presence of selenae

    and selenie ion. 3urher, binding of selenae o curcumin /as sudied in a!ueous aceonirile

    soluion mainained a p% 1&.'. No changes /ere obser$ed in he fluorescence and absorbance

    characerisics of he curcuminae generaed in he aproic sol$en in /aer. ;his furher pro$es

    ha /aer does no inerfere /ih he binding of selenae and selenie ions b curcuminae ion in

    a!ueous aceonirile soluion mainained a p% 1&.'.

    C$)cl*si$)&

    4n his sud, curcumin has been in$esigaed for is seleci$e fluorogenic deecion of selenae

    and selenie ions in a!ueous soluion. ;he proon ransfer be/een mehanol and curcuminae

    during he comple#aion of anion, resuls in he pronounced radiai$e deca due o disrupion of

    he non2radiai$e ?)P; of curcumin in presence of proic sol$en. ;hus, in coninuaion of his

    phenomenon $arious ?)P; based sensors can be de$iced for real2ime anion sensing in a!ueous

    mari#.

    Ac4)$#l!%g!+!)ts

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    ;his /or /as suppored in erms of funds, fello/ship and +enral 4nsrumenaion 3acili b

    +enral 5ni$ersi of PunEab, Bahinda for M Phil2Ph /or of Mr. Rabindra Kumar. J.

    Nagendra Babu is hanful o );, Ne/ elhi for pro$iding funds hrough ); 3as ;rac

    oung )cienis as ProEec Ref. No. "&:"&1& for research suppor.

    R!0!r!)c!

    A. J. Bednar, R. A. Kirgan, I. ;. Jones, +omparison of sandard and reacion cell induci$el

    coupled plasma mass specromer in he deerminaion of chromium and selenium

    species b %P-+L4+PLM), Anal. +him. Aca 8(" "&& "F2(.

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