FLUORESCENT LOCK - Chemical & Engineering News Archive (ACS

Jan 31, 2005 - Imaging probes fluoresce only when unmasked by trimethyl lock ... They found the tool in a reaction used in drug delivery: the trimethy...
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NEWS OF THE WEEK BUSINESS

CHEMICAL EARNINGS Higher prices and volumes continue to drive improvement in results that have published their results have shown at least double-digit growth over the same period in 2003. The largest percentage gain was at Monsanto, which, after taking out a number of unusual charges, managed to inFOURTH QUARTER crease its earningsfromconEarnings jump at chemical companies tinuing operations to $35.0 million, 236.5% above the SALES EARNINGS3 CHANGE FROM 2003 PROFIT MARGIN1 fourth-quarter-2003 level. ($ MILLIONS) SALES EARNINGS 2004 2003 Air Products $1,991.0 $166.8 18.2% 26.6% Sales at the company were 8.4% 7.8% Cabot 495.0 35.0 16.7 7.1 6.7 11.0 up just 6.8% to $1.10 billion. Cytec Industries 450.6 28.0 24.5 91.8 6.2 4.0 C E O Hugh Grant says, Dow Chemical 10,936.0 823.0 31.3 73.3 7.5 5.7 "The value of our seeds and [biotech] traits business is DuPont 6,000.0 371.0 -7.4 25.3 6.2 4.6 growing globally" He adds Monsanto 1,098.0 35.0 6.8 236.5 3.2 1.0 that the company saw good PPG Industries 2,411.0 186.0 10.9 43.1 7.7 6.0 early performance in the Praxair 1,786.0 181.0 22.2 16.8 10.1 10.6 quarter not only in the U.S., a After-tax earnings from continuing operations, excluding significant extraordinary but also in Brazil, Europe, and nonrecurring items, b After-tax earnings as a percentage of sales. and Australia.

E

ARLY RESULTS FROM CHEM-

ical companies indicate that the fourth quarter of 2004 continued the industry's streak of sales and earnings improvement. All eight chemical firms

BIOIMAGING

FLUORESCENT LOCK Imaging probes fluoresce only when unmasked by trimethyl lock reaction STRAINED When an esterase cleaves the O-R bond, the phenoxide, made more nucleophilic by strain from methyl crowding, attacks the amide carbon and frees fluorescent rhodamine 110.

W

HEN RONALD T. RAINES

at the University of Wisconsin, Madison, wanted to track peptides that traveled from the outside into mammalian cells, the biochemist found himself at a loss. He and coworkers needed a new tool—a molecule they could attach to the peptide that would fluoresce only inside

H9N

= Rhodamine 110

10

C & E N / J A N U A R Y 31 , 2005

the cell. They found the tool in a reaction used in drug delivery: the trimethyl lock. Drug delivery strategists know that the crowding of three methyl groups in an 0-hydroxycinnamic acid derivative causes strain that is relieved by cyclization—or locking—into a lactone. If a leaving group, such as an acetyl, is attached to the phenolic oxygen and a drug is placed at the carboxyl end through an amide bond, for example, cleavage of the leaving group (usually by an enzyme) leads to rapid cyclization and drug release. In place of a drug, Raines and coworkers Sunil S. Chandran and

Industry leader Dow Chemical had the largest dollar earnings growth among the companies— $348.0 million, or 73.3%, to $823.0 million. Sales were up 31.3% to $10.9 billion. CEO Andrew N . Liveris explains: "In part, the margin expansion was driven by the improvement we saw in industry fundamentals. But price/volume management and our ongoing commitment to controlling costs were equally important contributors." N u m b e r two D u P o n t saw earnings increase 25.3% to $371.0 million. While sales at the company declined 7.4% to $6.0 billion, when the company's divested textile and interiors business is excluded from fourth-quarter 2003, total comparable segment sales were up 14%. The company notes that all of its segments showed growth in pretax income. Another big gainer during the quarter was Cytec Industries, where earnings almost doubled, rising 91.8% to $28.0 million, and sales increased 24.5% to $450.6 million.—WILLIAM ST0RCK

KimberlyA. Dickson use fluorescent rhodamine 110. When rhodamine 110 is so bound, it doesn't fluoresce; when the trimethyl lock releases rhodamine 110, it fluoresces brightly [J. Am. Chem. Soc, published onlineJan. 20, http://dx. doi.org/10.1021/ja043736v]. The new molecule is an especially good biological imaging tool, Raines says, because it is stable and not fluorescent in biological media until triggered. Inside the cell, esterases cleave the O-linked acetyl group and free the bright fluorophore. The molecule can be conjugated to almost any protein. It can also be tailored to respond to "an enzyme of the user's choice," Raines says. Versions that fluoresce when a molecule moves into different cellular compartments—mitochondria, the Golgi apparatus, or the nucleus—are conceivable, he adds.—LOUISA DALTON HTTP://WWW.CEN-ONLINE.ORG