Synthesis, crystal structure, and cytotoxicity studies of titanacalix[4 and 8]arene complexes

David M. Miller-Shakesby; Shubhanchi Nigam; David L. Hughes; Enrique Lopez-Estelles; Mark R. J. Elsegood; Christopher J. Cawthorne; Stephen J. Archibald; Carl Redshaw

doi:10.1039/c8dt01992d

Synthesis, crystal structure, and cytotoxicity studies of titanacalix[4 and 8]arene complexes

David M. Miller-Shakesby, Shubhanchi Nigam, David L. Hughes, Enrique Lopez-Estelles, Mark R. J. Elsegood, Christopher J. Cawthorne, Stephen J. Archibald, Carl Redshaw

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

8 Citations (Scopus)

Abstract

Reaction of 5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene (L(OH)₂(Opentyl)₂) with [TiCl₄] afforded the dichlorotitanoacalix[4]arene complex [TiCl₂L(O)₂(Opentyl)₂] (1) in good yield. Hydrolysis of 1 led to the isolation of the complex {[TiL(O)₃(Opentyl)]₂(μ-OH)(μ-Cl)} (2). Reaction of 5,11,17,23,29,35,41,47-p-tert-butyl-49,50,51,52,53,54,55,56-octapropoxycalix[8]arene (L′(Opropyl)₈) with [TiCl₄] in refluxing toluene afforded, following work-up, a 35:65 mixture (3) of the complex [Ti(NCMe)Cl]₂[TiCl(μ-O)]₂L′ and the silicone grease derived complex [Ti(NCMe)Cl]₂[Ti(μ-O)]₂[OSi(CH₃)₂OSi(CH₃)₂O]L′ in which the grease replaces two chloride ligands. The molecular structures of 1·2MeCN, 2·7MeCN, and 3·10MeCN have been determined. The complexes were studied using in vitro cell assays and were found to have CC₅₀ values in the range 111-186 μM, i.e. they have low toxicity.

Original language	English
Pages (from-to)	8992-8999
Number of pages	8
Journal	Dalton Transactions
Volume	47
Issue number	27
Early online date	12 Jun 2018
DOIs	https://doi.org/10.1039/c8dt01992d
Publication status	Published - 21 Jul 2018

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https://repository.lboro.ac.uk/articles/Synthesis_crystal_structure_and_cytotoxicity_studies_of_titanacalix_4_and_8_arene_complexes/9393611

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@article{6c996423e0e8477992a8dd5ecdb44fc6,

title = "Synthesis, crystal structure, and cytotoxicity studies of titanacalix[4 and 8]arene complexes",

abstract = "Reaction of 5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene (L(OH)2(Opentyl)2) with [TiCl4] afforded the dichlorotitanoacalix[4]arene complex [TiCl2L(O)2(Opentyl)2] (1) in good yield. Hydrolysis of 1 led to the isolation of the complex {[TiL(O)3(Opentyl)]2(μ-OH)(μ-Cl)} (2). Reaction of 5,11,17,23,29,35,41,47-p-tert-butyl-49,50,51,52,53,54,55,56-octapropoxycalix[8]arene (L′(Opropyl)8) with [TiCl4] in refluxing toluene afforded, following work-up, a 35:65 mixture (3) of the complex [Ti(NCMe)Cl]2[TiCl(μ-O)]2L′ and the silicone grease derived complex [Ti(NCMe)Cl]2[Ti(μ-O)]2[OSi(CH3)2OSi(CH3)2O]L′ in which the grease replaces two chloride ligands. The molecular structures of 1·2MeCN, 2·7MeCN, and 3·10MeCN have been determined. The complexes were studied using in vitro cell assays and were found to have CC50 values in the range 111-186 μM, i.e. they have low toxicity.",

author = "Miller-Shakesby, {David M.} and Shubhanchi Nigam and Hughes, {David L.} and Enrique Lopez-Estelles and Elsegood, {Mark R. J.} and Cawthorne, {Christopher J.} and Archibald, {Stephen J.} and Carl Redshaw",

year = "2018",

month = jul,

day = "21",

doi = "10.1039/c8dt01992d",

language = "English",

volume = "47",

pages = "8992--8999",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "27",

}

TY - JOUR

T1 - Synthesis, crystal structure, and cytotoxicity studies of titanacalix[4 and 8]arene complexes

AU - Miller-Shakesby, David M.

AU - Nigam, Shubhanchi

AU - Hughes, David L.

AU - Lopez-Estelles, Enrique

AU - Elsegood, Mark R. J.

AU - Cawthorne, Christopher J.

AU - Archibald, Stephen J.

AU - Redshaw, Carl

PY - 2018/7/21

Y1 - 2018/7/21

N2 - Reaction of 5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene (L(OH)2(Opentyl)2) with [TiCl4] afforded the dichlorotitanoacalix[4]arene complex [TiCl2L(O)2(Opentyl)2] (1) in good yield. Hydrolysis of 1 led to the isolation of the complex {[TiL(O)3(Opentyl)]2(μ-OH)(μ-Cl)} (2). Reaction of 5,11,17,23,29,35,41,47-p-tert-butyl-49,50,51,52,53,54,55,56-octapropoxycalix[8]arene (L′(Opropyl)8) with [TiCl4] in refluxing toluene afforded, following work-up, a 35:65 mixture (3) of the complex [Ti(NCMe)Cl]2[TiCl(μ-O)]2L′ and the silicone grease derived complex [Ti(NCMe)Cl]2[Ti(μ-O)]2[OSi(CH3)2OSi(CH3)2O]L′ in which the grease replaces two chloride ligands. The molecular structures of 1·2MeCN, 2·7MeCN, and 3·10MeCN have been determined. The complexes were studied using in vitro cell assays and were found to have CC50 values in the range 111-186 μM, i.e. they have low toxicity.

AB - Reaction of 5,11,17,23-tetra-tert-butyl-dihydroxy-26,28-bis(2-pentoxy)calix[4]arene (L(OH)2(Opentyl)2) with [TiCl4] afforded the dichlorotitanoacalix[4]arene complex [TiCl2L(O)2(Opentyl)2] (1) in good yield. Hydrolysis of 1 led to the isolation of the complex {[TiL(O)3(Opentyl)]2(μ-OH)(μ-Cl)} (2). Reaction of 5,11,17,23,29,35,41,47-p-tert-butyl-49,50,51,52,53,54,55,56-octapropoxycalix[8]arene (L′(Opropyl)8) with [TiCl4] in refluxing toluene afforded, following work-up, a 35:65 mixture (3) of the complex [Ti(NCMe)Cl]2[TiCl(μ-O)]2L′ and the silicone grease derived complex [Ti(NCMe)Cl]2[Ti(μ-O)]2[OSi(CH3)2OSi(CH3)2O]L′ in which the grease replaces two chloride ligands. The molecular structures of 1·2MeCN, 2·7MeCN, and 3·10MeCN have been determined. The complexes were studied using in vitro cell assays and were found to have CC50 values in the range 111-186 μM, i.e. they have low toxicity.

UR - http://www.scopus.com/inward/record.url?scp=85049806283&partnerID=8YFLogxK

U2 - 10.1039/c8dt01992d

DO - 10.1039/c8dt01992d

M3 - Article

AN - SCOPUS:85049806283

SN - 1477-9226

VL - 47

SP - 8992

EP - 8999

JO - Dalton Transactions

JF - Dalton Transactions

IS - 27

ER -

Synthesis, crystal structure, and cytotoxicity studies of titanacalix[4 and 8]arene complexes

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