Anticancer agents from natural products

751 Pages·2012·8.97 MB·English

by  Cragg

Cragg
Kingston
ANTICANCER AGENTS
Newman ANTICANCER
from NATURAL PRODUCTS
AGENTS from
N A
A N
Praise for the First Edition
NATURAL
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“The book brings home to us not only the amazing chemical complexity of the natural
world but also the vast reservoir of potential new healing agents that yet remain to be U I
tapped. This impressive work, which maintains a uniformly high standard throughout, C PRODUCTS
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will be of major benefit to a wide readership.” A
—Chemistry World
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N
“An ideal foundation for scientists engaged in developing new and improved drugs
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based on natural sources.” C Second Edition

—Memoriile Sectiilor Stiintifice P E
R
The approach to drug discovery from natural sources has yielded many important R
new pharmaceuticals inaccessible by other routes. In many cases the isolated natural

product may not be an effective drug for any of several reasons, but it nevertheless O
A
may become a drug through chemical modification or have a novel pharmacophore
for future drug design. In summarizing the status of natural products as cancer D
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chemotherapeutics, Anticancer Agents from Natural Products, Second
U
Edition covers the: E

C N
• History of each covered drug—a discussion of its mechanism on action,
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medicinal chemistry, synthesis, and clinical applications
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• Potential for novel drug discovery through the use of genome mining as
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well as future developments in anticancer drug discovery S
• Important biosynthetic approaches to “unnatural” natural products
f
Anticancer Agents from Natural Products, Second Edition discusses how r
complex target-oriented synthesis—enabled by historic advances in methodology—has o Edited by
enormously expanded the scope of the possible. This book covers the current clinically
m Gordon M. Cragg
used anticancer agents that are either natural products or are clearly derived from
natural product leads. It also reviews drug candidates currently in clinical development
David G.I. Kingston
since many of these will be clinically used drugs in the future.
Second
David J. Newman
K10713 Edition
ISBN: 978-1-4398-1382-9
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ANTICANCER
AGENTS from
NATURAL
PRODUCTS
Second Edition

ANTICANCER
AGENTS from
NATURAL
PRODUCTS
Second Edition
Edited by
Gordon M. Cragg
David G.I. Kingston
David J. Newman
CRC Press
Taylor & Francis Group
6000 Broken Sound Parkway NW, Suite 300
Boca Raton, FL 33487-2742
© 2012 by Taylor & Francis Group, LLC
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No claim to original U.S. Government works
Version Date: 20110427
International Standard Book Number-13: 978-1-4398-1383-6 (eBook - PDF)
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Contents
Preface...............................................................................................................................................ix
Editors................................................................................................................................................xi
Contributors....................................................................................................................................xiii
Chapter 1 Introduction...................................................................................................................1
Gordon M. Cragg, David G. I. Kingston, and David J. Newman
Chapter 2 Camptothecin.and.Its.Analogs......................................................................................5
Nicolas J. Rahier, Craig J. Thomas, and Sidney M. Hecht
Chapter 3 The.Discovery.and.Development.of.the.Combretastatins...........................................27
Kevin G. Pinney, George R. Pettit, Mary Lynn Trawick,
Christopher Jelinek, and David J. Chaplin
Chapter 4 Homoharringtonine.and.Related.Compounds............................................................65
Hideji Itokawa, Yukio Hitotsuyanagi, and Kuo-Hsiung Lee
Chapter 5 Podophyllotoxins.and.Analogs....................................................................................95
Kuo-Hsiung Lee and Zhiyan Xiao
Chapter 6 Taxol.and.Its.Analogs................................................................................................123
David G. I. Kingston
Chapter 7 The.Vinca.Alkaloids.................................................................................................177
Fanny Roussi, Françoise Guéritte, and Jacques Fahy
Chapter 8 The.Bryostatins.........................................................................................................199
David J. Newman
Chapter 9 The.Isolation,.Characterization,.and.Development.of.a.Novel.Class.of.
Potent Antimitotic.Macrocyclic.Depsipeptides:.The.Cryptophycins........................219
Rima S. Al-awar and Chuan Shih
Chapter 10 Chemistry.and.Biology.of.the.Discodermolides,.Potent.Mitotic.Spindle.Poisons.....241
Sarath P. Gunasekera and Amy E. Wright
v
vi Contents
Chapter 11 The.Dolastatins:.Novel.Antitumor.Agents.from.Dolabella auricularia..................263
Erik Flahive and Jayaram Srirangam
Chapter 12 Ecteinascidin-743.(Yondelis®),.Aplidin®,.and.Irvalec®.............................................291
Carmen Cuevas, Andrés Francesch, Carlos M. Galmarini, Pablo Avilés,
and Simon Munt
Chapter 13 Discovery.of.E7389,.A.Fully.Synthetic.Macrocyclic.Ketone.Analog.
of Halichondrin B......................................................................................................317
Melvin J. Yu, Yoshito Kishi, and Bruce A. Littlefield
Chapter 14 HTI-286.(Taltobulin),.A Synthetic.Analog.of.the Antimitotic.Natural.
Product Hemiasterlin.................................................................................................347
Raymond J. Andersen, David E. Williams, Wendy K. Strangman,
and Michel Roberge
Chapter 15 The.Actinomycins.....................................................................................................363
Anthony B. Mauger and Helmut Lackner
Chapter 16 Anthracyclines...........................................................................................................383
Federico-Maria Arcamone
Chapter 17 Ansamitocins.(Maytansinoids).................................................................................407
Tin-Wein Yu, Heinz G. Floss, Gordon M. Cragg, and David J. Newman
Chapter 18 Benzoquinone.Ansamycins.......................................................................................429
Kenneth M. Snader
Chapter 19 Bleomycin.Group.Antitumor.Agents........................................................................451
Sidney M. Hecht
Chapter 20 Biochemical.and.Biological.Evaluation.of.(+)-CC-1065.Analogs.and.
Conjugates with Polyamides.....................................................................................479
Rohtash Kumar and J. William Lown
Chapter 21 Epothilone,.A.Myxobacterial.Metabolite.with.Promising.Antitumor.Activity........513
Gerhard Höfle and Hans Reichenbach
Chapter 22 Enediynes..................................................................................................................575
Philip R. Hamann, Janis Upeslacis, and Donald B. Borders
Contents vii
Chapter 23 The.Mitomycins........................................................................................................623
William A. Remers
Chapter 24 Staurosporines.and.Structurally.Related.Indolocarbazoles.as.
Antitumor.Agents......................................................................................................647
Michelle Prudhomme
Chapter 25 Combinatorial.Biosynthesis.of.Anticancer.Natural.Products...................................671
Steven G. Van Lanen and Ben Shen
Chapter 26 Developments.and.Future.Trends.in.Anticancer.Natural.
Products.Drug.Discovery..........................................................................................699
Gordon M. Cragg and David J. Newman

Preface
Natural.products.continue.to.make.new.contributions.to.cancer.chemotherapy.since.the.first.edition.
of.this.volume.was.published.in.2005..These.developments.include.the.clinical.introductions.of.
cabazitaxel.in.June.2010.(the.first.new.taxane.drug.to.enter.clinical.use.since.docetaxel.was.intro-
duced.in.the.1990s),.of.ixabepilone.(the.first.epothilone.analog.to.enter.clinical.use),.of.the.marine.
natural.product.analog.eribulin.(which.was.approved.by.the.FDA.in.November.2010.for.second.line.
therapy.in.resistant.breast.cancer),.and.of.the.difluorinated.vinca.alkaloid.vinflunine.in.2009..In.
addition,.antibody.drug.conjugates.are.showing.considerable.promise.in.cancer.therapy..While.the.
enediyne.calicheamicin.γI.was.the.first.antibody-targeted.chemotherapeutic.agent.to.be.registered.
1
for.humans,.marketed.as.Mylotarg.(gemtuzumab.ozogamicin),.it.has.recently.been.withdrawn.from.
the.US.market,.but..SMANCS,.a.neocarzinostatin.conjugate,.is.approved.in.Japan.for.patients.with.
liver.cancer.metastases..Of.particular.note.are.antibody-maytansinoid.(DM1.and.DM4).conjugates,.
and.a.biological.licence.application.(BLA,.equivalent.to.the.NDA.application.for.small.molecules).
has.been.submitted.to.the.FDA.by.Genentech.for.marketing.approval.of.one.such.conjugate,.T-DM1.
or.trastuzumab.emtansine,..as.a.treatment.for.Her2+.breast.cancer.
The.chapters.in.this.book.have.all.been.substantially.revised.and.updated.from.those.in.the.first.
edition..In.some.instances.where.the.original.authors.were.unable.to.undertake.the.revision.of.their.
chapters,.updates.by.an.editor.have.been.included..The.editors.hope.that.this.revised.volume.will.
continue.to.provide.examples.and.inspiration.to.natural.product.researchers.as.well.having.real.
value.for.scientists.looking.for.information.on.the.next.generation.of.anticancer.drugs.
Gordon M. Cragg, David G. I. Kingston, and David J. Newman
ix