JANUARY 2008 Volume 19, Number 1 Copyright 2008 by the American Chemical Society
Editorial: What’s New The Chemistry of Targeting This is the first of twelve issues of Bioconjugate Chemistry for 2008, a doubling of the print frequency. The change is mainly symbolic, but the underlying scientific progress is notable. One aspect of bioconjugate chemistry that has come into focus in recent years, which might be called the chemistry of targeting, has pervasively entered mainstream research in biology and medicine. Papers in this and recent issues of the journal give an idea of how it works in practice. Of course, the chemistry must come before the targeting, and there is plenty of chemistry. For example, synthetic peptides with target-binding properties, discovered by library screening, can be prepared with artificial components for conjugation to proteins (1). Synthetic reagents can be incorporated into natural proteins by ligation (2), and library-selected peptides with interesting new reactivity for conjugation to synthetic reagents can be cloned into proteins (3). Designing a nucleophilic affinity label to replace an electrophilic one can use an expressed protein to advantage and change the parameters of targeting (4), and a new fluorescent conjugate traces the intracellular targets of an electrophilic drug (5). Then, the challenge of making new molecules that work in ViVo begins. How can we add the properties of signal generation or therapeutic activity to a structure that provides affinity for particular cell types, and endow the product with the requisite biological behavior required for specific accumulation in the target? Here is an opportunity for creative thinking, especially when the goal is to deliver a payload to sites in the interior of a cell. The approach depends on the task. Cell-penetrating peptides are developing into reliable tools for intracellular targeting (6). Polymeric assemblies for nonviral gene delivery show promise (7), and quantum dots provide an interesting platform for siRNA (8). Delivery of proteins to cellular targets involves different strategies (9), as does protein-mediated delivery of small molecules (10). Alongside this activity is new work related to vaccines (11), to highly sensitive RNA detection (12), and to the design of lipophilic prodrugs (13). And of course there are nanoparticle bioconjugates beyond those mentioned above, aimed at preparing ordered assemblies of biomolecules (14), liposomes guided by engineered proteins (15), and nanorod bioconjugates for intracellular Raman detection (16). Enzymatic biotinylation of DNA, followed by cross-linking with streptavidin, can lead to the stable formation of complex new synthetic nanostructures (17). These are only a few recent examples of bioconjugate chemistry published in the journal. Space restrictions do not allow a fuller account here; we invite you to see for yourself. As time goes forward, I believe we will see more emphasis on the construction of large, complex, multifunctional particles (18); clever chemistry and biology to specifically fuse biological molecules to nonbiological partners (19); better ways to target drugs and probes in ViVo (20); and no doubt some unexpected developments in this always surprising field.
Thanks to Our Reviewers It is a pleasure to acknowledge the contributions of the reviewers of manuscripts submitted in 2007 for publication in Bioconjugate Chemistry. Their unselfish service has been essential in the shaping of the 18th volume of the journal. The scientific community is fortunate that its members are willing to share their time and specialized knowledge in this way. The reviewers are listed on the following pages. Claude F. Meares Editor-in-Chief 10.1021/bc700467w CCC: $40.75 2008 American Chemical Society Published on Web 01/16/2008
2 Bioconjugate Chem., Vol. 19, No. 1, 2008
LITERATURE CITED (1) Romanini, D., and Francis, M. B. Attachment of peptide building blocks to proteins through tyrosine bioconjugation. Bioconjugate Chem.,[Online early access] DOI: 10.1021/ bc700231v. Published online December 11, 2007. (2) Kalia, J., Abbott, N. L., and Raines, R. T. (2007) General method for site-specific protein immobilization by staudinger ligation. Bioconjugate Chem. 18, 1064–1069. (3) Tanaka, F., Fuller, R., Asawapornmongkol, L., Warsinke, A., Gobuty, S., and Barbas, C. F. (2007) Development of a small peptide tag for covalent labeling of proteins. Bioconjugate Chem. 18, 1318–1324. (4) Miao, Z., McCoy, M. R., Singh, D. D., Barrios, B., Hsu, O. L., Cheal, S. M., and Meares, C. F. Cysteinylated protein as reactive disulfide: an alternative route to affinity labeling. Bioconjugate Chem.,[Online early access] DOI: 10.1021/ bc700330j. Published online December 7, 2007. (5) Barnes, K. R., Blois, J., Smith, A., Yuan, H., Reynolds, F., Weissleder, R., Cantley, L. C., and Josephson, L. Fate of a bioactive fluorescent wortmannin derivative in cells. Bioconjugate Chem.,[Online early access] DOI: 10.1021/bc7002204. Published online November 8, 2007. (6) Myrberg, H., Zhang, L., Mäe, M., and Langel, U. Design of a tumor-homing cell-penetrating peptide. Bioconjugate Chem.,[Online early access] DOI: 10.1021/bc0701139. Published online November 15, 2007. (7) Germershaus, O., Neu, M., Behe, M., and Kissel, T. HER2 targeted polyplexes: the effect of polyplex composition and conjugation chemistry on in vitro and in vivo characteristics. Bioconjugate Chem.,[Online early access] DOI: 10.1021/ bc700311n. Published online November 23, 2007. (8) Derfus, A. M., Chen, A. A., Min, D. H., Ruoslahti, E., and Bhatia, S. N. (2007) Targeted quantum dot conjugates for siRNA delivery. Bioconjugate Chem. 18, 1391–1396. (9) Bell, S. J., Fam, C. M., Chlipala, E. A., Carlson, S. J., Lee, J. I., Rosendahl, M. S., Doherty, D. H., and Cox, G. N. Enhanced circulating half-life and antitumor activity of a site-specific pegylated interferon-R protein therapeutic. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc070131q. Published online November 20, 2007. (10) Hollander, I., Kunz, A., and Hamann, P. R. Selection of reaction additives used in the preparation of monomeric antibodycalicheamicin conjugates. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700321z. Published online November 10, 2007.
(11) Nahas, D. D., Palladino, J. S., Joyce, J. G., and Hepler, R. W. Amino acid analysis of peptide loading ratios in conjugate vaccines: a comparison of direct electrochemical detection and 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate pre-column derivatization methods. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700232z. Published online December 12, 2007. (12) Walls, Z. F., and Gambhir, S. S. BRET-based method for detection of specific RNA species. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700278n. Published online December 12, 2007. (13) Pignatello, R., Pantò, V., Salmaso, S., Bersani, S., Pistarà, V., Kepe, V., Barrio, J. R., and Puglisi, G. Flurbiprofen derivatives in Alzheimer’s disease: synthesis, pharmacokinetic and biological assessment of lipoamino acid prodrugs. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700312y. Published online December 12, 2007. (14) Matsuura, S. I., Itoh, T., Ishii, R., Sakaguchi, K., Tsunoda, T., Hanaoka, T., and Mizukami, F. The ensemble of heteroproteins in inorganic nanochannels. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700340e. Published online November 30, 2007. (15) Messerschmidt, S. K., Kolbe, A., M/uller, D., Knoll, M., Pleiss, J., and Kontermann, zfn > R. E. Novel single-chain Fv′ formats for the generation of immunoliposomes by site-directed coupling. Bioconjugate Chem. [Online early access] DOI: 10.1021/bc700349k. Published online November 8, 2007. (16) Oyelere, A. K., Chen, P. C., Huang, X., El-Sayed, I. H., and El-Sayed, M. A. (2007) Peptide-conjugated gold nanorods for nuclear targeting. Bioconjugate Chem. 18, 1490–1497. (17) Wilkinson, S., Diechtierow, M., Estabrook, R. A., Schmidt, F., Lugowski, M., Weinhold, E., and Reich, N. O. Molecular scale architecture: engineered three- and four-way junctions. Bioconjugate Chem.,[Online early access] DOI: 10.1021/ bc700270k. Published online December 11, 2007. (18) Oba, M., Fukushima, S., Kanayama, N., Aoyagi, K., Nishiyama, N., Koyama, H., and Kataoka, K. (2007) Cyclic RGD peptide-conjugated polyplex micelles as a targetable gene delivery system directed to cells possessing Rvβ3 and Rvβ5 integrins. Bioconjugate Chem. 18, 1415–1423. (19) Parthasarathy, R., Subramanian, S., and Boder, E. T. (2007) Sortase A as a novel molecular “stapler” for sequence-specific protein conjugation. Bioconjugate Chem. 18, 469–476. (20) Wang, D., Miller, S. C., Shlyakhtenko, L. S., Portillo, A. M., Liu, X. M., Papangkorn, K., Kopecková, P., Lyubchenko, Y., Higuchi, W. I., and Kopecek, J. (2007) Osteotropic peptide that differentiates functional domains of the skeleton. Bioconjugate Chem. 18, 1375–1378.
Bioconjugate Chem., Vol. 19, No. 1, 2008 3
Reviewers for 2007 Seetharama Acharya Samuel Achilefu Toshihiro Akaike Takeshi Akasaka Kazunari Akiyoshi Terry Allen Stephen Alley Julio Alvarez Jane Anastassopoulou Daniel Anderson Carolyn Anderson David Andreu Peter Antal Christophe Antczak Ichio Aoki Yasuhiro Aoyama Yasushi Arano Hidetoshi Arima Bruce Armitage Luis Arnaut Ulrich Arnold Erik Arstad Hiroyuki Asanuma Recep Avci You Han Bae Sandor Bajusz James Baker Milan Balaz Suki Bansal Giovanna Barbarella Sailen Barik Philippe Barthelemy Jacqueline Barton Serge Beaucage Craig Beeson Martin Behe Jean-Paul Behr Dennis Benjamin David Benson Sangeeta Bhatia Anna Bielinska Gary Bignami Otto Boerman Alexei Bogdanov Bernard Boitrel Ester Boix Sylvia Bosze Alexandre Boutorine Luisa Bracci Tibor Braun David Brautigan Martin Brechbiel Vladimir Bregadze Kevin Brindle Timothy Bugg Thomas Bugge Kevin Burgess
Patrick Burke Paolo Caliceti Amin Cao Paul Carter Elliott Chaikof Carole Chaix Ken Chang Young-Tae Chang Dominique Charmot A. Charrier Arabinda Chaudhuri Xiaoyuan Chen Yu Chen Jianjun Cheng Kenneth Christensen Bong Hyun Chung Mary Cloninger Wayne Cody Seth Cohen John Collins George Conder Eain Conford Umberto Costantino Patrick Couvreur James Cowan Gabriella Csik Ekaterina Dadachova Johanthan Dattelbaum Mark Davis Philip Dawson Jean-Luc Decout Clemens Decristoforo Marion DeJong Gerard Deleris Antony D’Emanuele Sally DeNardo Maria Derosa Svetlana Doronina Trevor Douglas Francis D’Sousa Adriano Duatti Stefan Dubel Gene Dubowchik Yves Dufrene Pascal Dumy Petar Dvornic Allen Ebens Alex Eberle Philip Elsinga Conan Fee Arthur Felix Gregg Fields David Filpula M. G. Finn Valery Fokin Andreas Frey Wolfgang Fritzsche
Darin Furgeson Tsutomu Furuzono Shiroh Futaki Xiaohu Gao Jean Gariepy Indraneel Ghosh Jose Giner Richard Goodman Kurt Gothelf David Grainger Anna Grandas Kai Griebenow Herman Gruber Gilles Guichard Ajay Gupta Michael Hamblin Robert Haner Atsushi Harada Gilad Haran Hideyoshi Harashima Frederick Haselton Roland Haubner Craig Hawker Frederic Heitz Wim. Hennink Greg Hermanson Kiyotaka Hitomi Donald Hnatowich Mathias Hoehn Timothy Hoffman Daniel Horak Jeanne Haushalter Thomas Holstein Fredrik Hook Jari Hovinen Ferenc Hudecz Rodica-Mariana Ion Marcos Intaglietta T. Ishida Yoshihiro Ito Shinobu Itoh Yasuhiko Iwasaki Hiroo Iwata Bela Ivan Hieronim Jakubowski Lee Josephson Rudolph Juliano Guenther Jung H. Karnes Uray Katalin Kazunori Kataoka Yoshiki Katayama John Katzenellenbogen Hiroyoshi Kawakami Shigeru Kawakami M. Kawashita Christine Keating
Kimberly Kelly David Kessel Horst Kessler Fabian Kiessling Akihiko Kikuchi SungWan Kim William Kinney Kent Kirshenbaum Akio Kishida Eva Kiss Thomas Kissel Alexei Kisselev Rene Kizek Toni Kline Harm-Anton Klok Hisataka Kobayashi Kazukiyo Kobayashi Kazuo Kobayashi Hisashi Koga Kentara Kogure Laszlo Kohidal Robert Kok Makoto Komiyama Akihiko Kondo Kenji Kono Jindrich Kopecek Lajos Kovacs Heinz-Bernhard Kraatz Felix Kratz James Kronauge Glen Kwon Ick Kwon Vinod Labhasetwar Pirjo Laakkonen Kit Lam Robert Langer Jorg Langowski Bernard Lebleu Doo Sung Lee Robert Lee Sang-Bok Lee Yan Lee Polly Leung Raphael Levy Jason Lewis Mike Lewis Yadong Li Karl Linden David Link Shuang Liu Timothy Long Harri Lonnberg Zheng-Rong Lu Robert Lyon Robert Mach Helmut Maecke Hiroshi Maeda
4 Bioconjugate Chem., Vol. 19, No. 1, 2008
Mizuo Maeda Y. Magata Michele Maggini Yoshi Maitani Zsuzsa Majer Giovanna Mancini Chengde Mao Mauro Marastoni Atsushi Maruyama Kazuo Maruyama Ralph Mason Takehisa Matsuda Hiroshi Matsui William McBride Jason McCarthy Charlotte McDonough Thomas Meade Claude Meares Igor Medintz Morten Meldal Oleg Melnyk Christine Menager Fredric Menger Andre Merbach Damon Meyer Geerd Meyer Gabor Mezo Nils Metzler-Nolte Tamara Minko Anna Moore Milan Mrksich Tom Muir Jogeshwar Mukherjee Catherine Murphy William Murphy Igor Nabiev Takeshi Nagasaki Yukio Nagasaki Shinsaku Nakagawa Hiroyuki Nakamura Jun Nakanishi Mamoru Nakanishi Arun Nandi Dario Neri Placido Neri Nasri Nesnas Martin Newcomb Christof Niemeyer Takuro Niidome Yoshihior Nishida Makiya Nishikawa Victoria Nogues Yuichi Ohya Akimitsu Okamoto Nicole Okeley Naoto Oku
Sean O’Malley David Oupicky Daniel Pack Mark Pagel Andre Palmer Francesco Pampaloni Ravindra Pandey Roberto Paolesse Anna Papini Wolfgang Parak In-Kyu Park Jong-sang Park Kinam Park Tae Gwan Park David Parker Anil Patri Carlo Pedone Xiaojun Peng Andrej Petri Lucia Pohl Glenn Prestwich David Putnam Eva Rajnavolgyi T. Ramqvist Tariq Rana Jianghong Rao Ken Raymond Francesca Reig Raymond Reilly Theresa Reineke Jean-Serge Remy Richard Renneberg Alexander Ribbe Kevin Rice Steve Roffler Anthony Romieu Keith Rose Vincent Rotello Jayanta Roy Yasuyuki Sadzuka Ahmad Safavy Cyrus Safinya Hideo Saji Kengo Sakaguchi Shinji Sakuma Bruno Samori Yogesh Sanghvi Xavier Santarelli Angela Sastre Toshinori Sato A. G. Schatzlein David Scheinberg Cara-Lynne Schengrund Roger Schibili Francis Schuber Katarina Schwarzerova
Paolo Scrimin Frank Seela V. Sefton Hans Senn Peter Senter Takeshi Serizawa Doron Shabat Adam Shapiro Frances Sharom Wei-Chiang Shen Dean Sherry Kiyotaka Shiba Injae Shin Sepp Siefert Daniel Silva G. Silva Robert Sharkey Lonnie Shea David Smith Robert Spooner Caroline Springer Patrick Stayton Yasuo Suda Helga Suli-Vargha Mike Sun Shouheng Sun Xue-Long Sun Avadhesha Surolia Ryo Suzuki Sonke Svenson Thomas Swihart Frank Szoka Yasuhiko Tabata Maryam Tabrizian Yoshinobu Takakura Shinji Takeoka Nagasaki Takeshi Toshifumi Takeuchi Eiichi Tamiya Weihong Tan Fujie Tanaka Frederic Taran Jack Taunton Kai Temming Dave Thompson Paolo Ticilla Louis Tiefenauer David Tilley Werner Tjarks Brian Toki Don Tomalia Vladimir Torchilin Alexei Touchkine Pam Trail Roger Tsien Yasuo Tsutsumi
Ching Tung Gerardo Turcatti Karel Ulbrich Hasan Uludag Tadayuki Uno Katalin Uray Vladimir Uversky Hiroshi Uyama Ganesan Vaidynathan Henry van Brocklin Serve Van Callenbergh Gooitzen van Dam Johan Van Lier Henk-Jan van Manen Francesco Veronese Graca Vicente S. V. Vinogradov Michael Vogeser Albrecht von Arnim Ernst Wagner Lai-Xi Wang Qian Wang Colin Watts Adam Wax Ralph Weissleder Michael Welch Theodore Wensel Sytske Welling-Wester Hans-Juergen Wester Shawn Wettig Scott Wilbur Meir Wilchek Lon Wilson Gayle Woloschak Anna Wu Hiroyasu Yamaguchi Masayuki Yamamoto Tetsuji Yamaoka Ichiro Yamashita Hao Yan Victor Yang Chen-Shen Yeh Makoto Yoshimoto Masayuki Yokoyama Hua-Zhong Yu Jaehoon Yu Samuel Zalipsky Arie Zask Marina Zenkova Gang Zheng Qi-Huang Zheng Bing Zu Guy Zuber BC700467W
