Hexamethylenetetramine carboxyborane: synthesis, structural characterization and CO releasing properties

被引：18

作者：

Ayudhya, T. I. ^{[1
]}

Raymond, C. C. ^{[2
]}

Dingra, N. N. ^{[1
]}

机构：

[1] Florida Southwestern State Coll, Sch Pure & Appl Sci, Ft Myers, FL 33919 USA

[2] SUNY Coll Oswego, Dept Chem, Oswego, NY 13126 USA

来源：

DALTON TRANSACTIONS | 2017年 / 46卷 / 03期

关键词：

CARBON-MONOXIDE RELEASE; AMINE-CARBOXYBORANES; BORON ANALOGS; HEME OXYGENASE-1; MOLECULES; COMPLEXES; ACIDS; DERIVATIVES; METAL; BORANOCARBONATE;

D O I：

10.1039/c6dt03856e

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Carbon monoxide, although widely known as a toxic gas, has received great attention in the past few decades due to its promising role as a medical gas. Several classes of carbon monoxide releasing molecules (CORMs) have been synthesised with many of them having pharmacological activities under physiological conditions. Herein, we report the synthesis and structural characterization of the first example of amine carboxyborane that releases CO under physiological conditions without the aid of inducers. A representative compound hexamethylenetetramine carboxyborane (HMTA-CB) described here has a half-life of 2.7 days and gradually releases CO with the rate constant of 3.0 x 10(-6) s(-1). Its ability to promote cell growth shows the beneficial effect of slow CO release to supplement CO in small amounts over time.

引用

页码：882 / 889

页数：8

共 45 条

[1] Chemistry and biological activities of CO-releasing molecules (CORMs) and transition metal complexes [J].

Alberto, Roger ;

Motterlini, Roberto .

DALTON TRANSACTIONS, 2007, (17) :1651-1660

[2] An artificial CO-releasing metalloprotein built by histidine-selective metallation [J].

Albuquerque, Ines S. ;

Jeremias, Helia F. ;

Chaves-Ferreira, Miguel ;

Matak-Vinkovic, Dijana ;

Boutureira, Omar ;

Romao, Carlos C. ;

Bernardes, Gonalo J. L. .

CHEMICAL COMMUNICATIONS, 2015, 51 (19) :3993-3996

[3] Modification of the deoxy-myoglobin/carbonmonoxy-myoglobin UV-vis assay for reliable determination of CO-release rates from organometallic carbonyl complexes [J].

Atkin, Anthony J. ;

Lynam, Jason M. ;

Moulton, Benjamin E. ;

Sawle, Philip ;

Motterlini, Roberto ;

Boyle, Nicola M. ;

Pryce, Mary T. ;

Fairlamb, Ian J. S. .

DALTON TRANSACTIONS, 2011, 40 (21) :5755-5761

[4] Light-triggered CO release from nanoporous non-wovens [J].

Bohlender, Carmen ;

Glaeser, Steve ;

Klein, Moritz ;

Weisser, Juergen ;

Thein, Susanne ;

Neugebauer, Ute ;

Popp, Juergen ;

Wyrwa, Ralf ;

Schiller, Alexander .

JOURNAL OF MATERIALS CHEMISTRY B, 2014, 2 (11) :1454-1463

[5] Synthesis and pharmacological activities of amine-boranes [J].

Burnham, BS .

CURRENT MEDICINAL CHEMISTRY, 2005, 12 (17) :1995-2010

[6] Recent advances in the medicinal chemistry of α-aminoboronic acids, amine-carboxyboranes and their derivatives [J].

Dembitsky, VM ;

Quntar, AA ;

Srebnik, M .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2004, 4 (09) :1001-1018

[7] Intracellular CO Release from Composite of Ferritin and Ruthenium Carbonyl Complexes [J].

Fujita, Kenta ;

Tanaka, Yuya ;

Sho, Takeya ;

Ozeki, Shuichi ;

Abe, Satoshi ;

Hikage, Tatsuo ;

Kuchimaru, Takahiro ;

Kizaka-Kondoh, Shinae ;

Ueno, Takafumi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (48) :16902-16908

[8] Designed Iron Carbonyls as Carbon Monoxide (CO) Releasing Molecules: Rapid CO Release and Delivery to Myoglobin in Aqueous Buffer, and Vasorelaxation of Mouse Aorta [J].

Gonzalez, Margarita A. ;

Fry, Nicole L. ;

Burt, Richard ;

Davda, Riddhi ;

Hobbs, Adrian ;

Mascharak, Pradip K. .

INORGANIC CHEMISTRY, 2011, 50 (07) :3127-3134

[9] Synthesis, characterization, and photoinduced CO-release reactivity of a Pb(II) flavonolate complex: Comparisons to Group 12 analogs [J].

Grubel, Katarzyna ;

Saraf, Sushma L. ;

Anderson, Stacey N. ;

Laughlin, Brynna J. ;

Smith, Rhett C. ;

Arif, Atta M. ;

Berreau, Lisa M. .

INORGANICA CHIMICA ACTA, 2013, 407 :91-97

[10] Synthesis, characterization, and bromine substitution of diamine complexes of carboxyborane and methoxycarbonylborane. Diazabora rings containing B-carboxyl and B-carboxylato groups [J].

Gyori, B ;

Berente, Z ;

Kovacs, Z .

INORGANIC CHEMISTRY, 1998, 37 (20) :5131-5141

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