Novel crown-ether-methylenediphosphonotetrathioate hybrids as Zn(II) chelators

Diana Meltzer; Hugo E. Gottlieb; Aviran Amir; Linda J.W. Shimon; Bilha Fischer

doi:10.1039/c5dt03935e

Novel crown-ether-methylenediphosphonotetrathioate hybrids as Zn(II) chelators

Diana Meltzer
, Hugo E. Gottlieb
, Aviran Amir
, Linda J.W. Shimon
, Bilha Fischer

Weizmann Institute of Science, Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

Abstract

Hybrids of methylenediphosphonotetrathioate and crown-ether (MDPT-CE) were synthesized forming 7-,8-,9-,10- and 13-membered rings. Both 7- and 13-membered ring-containing compounds were found to be highly stable to air-oxidation for at least four weeks. These hybrids bind Zn(ii) by both MDPT and CE moieties, forming a 2 : 1 L : Zn(ii) complex. Interestingly, the 13-membered ring MDPT-CE showing a high affinity to Zn(ii) (K_a 3 ± 0.5 × 10⁶ mol^-2 L²) does not bind Li(i) or Na(i). The 13-Membered MDPT-CE hybrid is a promising water-soluble, air-stable, high-affinity Zn(ii)-chelator, exhibiting selectivity to Zn(ii) vs. Mg(ii), Na(i), and Li(i).

Original language	English
Pages (from-to)	21073-21080
Number of pages	8
Journal	Dalton Transactions
Volume	44
Issue number	48
DOIs	https://doi.org/10.1039/c5dt03935e
State	Published - 12 Nov 2015

ASJC Scopus subject areas

Inorganic Chemistry

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10.1039/c5dt03935e

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title = "Novel crown-ether-methylenediphosphonotetrathioate hybrids as Zn(II) chelators",

abstract = "Hybrids of methylenediphosphonotetrathioate and crown-ether (MDPT-CE) were synthesized forming 7-,8-,9-,10- and 13-membered rings. Both 7- and 13-membered ring-containing compounds were found to be highly stable to air-oxidation for at least four weeks. These hybrids bind Zn(ii) by both MDPT and CE moieties, forming a 2 : 1 L : Zn(ii) complex. Interestingly, the 13-membered ring MDPT-CE showing a high affinity to Zn(ii) (Ka 3 ± 0.5 {\texttimes} 106 mol-2 L2) does not bind Li(i) or Na(i). The 13-Membered MDPT-CE hybrid is a promising water-soluble, air-stable, high-affinity Zn(ii)-chelator, exhibiting selectivity to Zn(ii) vs. Mg(ii), Na(i), and Li(i).",

author = "Diana Meltzer and Gottlieb, \{Hugo E.\} and Aviran Amir and Shimon, \{Linda J.W.\} and Bilha Fischer",

note = "Publisher Copyright: {\textcopyright} 2015 The Royal Society of Chemistry.",

year = "2015",

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doi = "10.1039/c5dt03935e",

language = "English",

volume = "44",

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publisher = "Royal Society of Chemistry",

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T1 - Novel crown-ether-methylenediphosphonotetrathioate hybrids as Zn(II) chelators

AU - Meltzer, Diana

AU - Gottlieb, Hugo E.

AU - Amir, Aviran

AU - Shimon, Linda J.W.

AU - Fischer, Bilha

PY - 2015/11/12

Y1 - 2015/11/12

N2 - Hybrids of methylenediphosphonotetrathioate and crown-ether (MDPT-CE) were synthesized forming 7-,8-,9-,10- and 13-membered rings. Both 7- and 13-membered ring-containing compounds were found to be highly stable to air-oxidation for at least four weeks. These hybrids bind Zn(ii) by both MDPT and CE moieties, forming a 2 : 1 L : Zn(ii) complex. Interestingly, the 13-membered ring MDPT-CE showing a high affinity to Zn(ii) (Ka 3 ± 0.5 × 106 mol-2 L2) does not bind Li(i) or Na(i). The 13-Membered MDPT-CE hybrid is a promising water-soluble, air-stable, high-affinity Zn(ii)-chelator, exhibiting selectivity to Zn(ii) vs. Mg(ii), Na(i), and Li(i).

AB - Hybrids of methylenediphosphonotetrathioate and crown-ether (MDPT-CE) were synthesized forming 7-,8-,9-,10- and 13-membered rings. Both 7- and 13-membered ring-containing compounds were found to be highly stable to air-oxidation for at least four weeks. These hybrids bind Zn(ii) by both MDPT and CE moieties, forming a 2 : 1 L : Zn(ii) complex. Interestingly, the 13-membered ring MDPT-CE showing a high affinity to Zn(ii) (Ka 3 ± 0.5 × 106 mol-2 L2) does not bind Li(i) or Na(i). The 13-Membered MDPT-CE hybrid is a promising water-soluble, air-stable, high-affinity Zn(ii)-chelator, exhibiting selectivity to Zn(ii) vs. Mg(ii), Na(i), and Li(i).

UR - https://www.scopus.com/pages/publications/84948844515

U2 - 10.1039/c5dt03935e

DO - 10.1039/c5dt03935e

M3 - Article

C2 - 26592926

SN - 1477-9226

VL - 44

SP - 21073

EP - 21080

JO - Dalton Transactions

JF - Dalton Transactions

IS - 48

ER -

Novel crown-ether-methylenediphosphonotetrathioate hybrids as Zn(II) chelators

Abstract

ASJC Scopus subject areas

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