Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting

Weiss C, Figueras Agustí E, Borbély AN, Sewald N (2017)
Journal of Peptide Science 23(7-8): 514-531.

Download
OA 5.73 MB
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Volltext vorhanden für diesen Nachweis
Abstract / Bemerkung
Cryptophycins are a class of 16-membered highly cytotoxic macrocyclic depsipeptides isolated from cyanobacteria. The biological activity is based on their ability to interact with tubulin. They interfere with microtubule dynamics and prevent microtubules from forming correct mitotic spindles, which causes cell-cycle arrest and apoptosis. Their strong antiproliferative activities with 100-fold to 1000-fold potency compared with those of paclitaxel and vinblastine have been observed. Cryptophycins are highly promising drug candidates, as their biological activity is not negatively affected by P-glycoprotein, a drug efflux system commonly found in multidrug-resistant cancer cell lines and solid tumors. Cryptophycin-52 had been investigated in phase II clinical trials but failed because of its high neurotoxicity. Recently, cryptophycin conjugates with peptides and antibodies have been developed for targeted delivery in tumor therapy. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.
Erscheinungsjahr
Zeitschriftentitel
Journal of Peptide Science
Band
23
Zeitschriftennummer
7-8
Seite
514-531
Konferenz
Conference on Rokko Mountain
Konferenzort
Kobe, JAPAN
ISSN
eISSN
PUB-ID

Zitieren

Weiss C, Figueras Agustí E, Borbély AN, Sewald N. Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. Journal of Peptide Science. 2017;23(7-8):514-531.
Weiss, C., Figueras Agustí, E., Borbély, A. N., & Sewald, N. (2017). Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. Journal of Peptide Science, 23(7-8), 514-531. doi:10.1002/psc.3015
Weiss, C., Figueras Agustí, E., Borbély, A. N., and Sewald, N. (2017). Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. Journal of Peptide Science 23, 514-531.
Weiss, C., et al., 2017. Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. Journal of Peptide Science, 23(7-8), p 514-531.
C. Weiss, et al., “Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting”, Journal of Peptide Science, vol. 23, 2017, pp. 514-531.
Weiss, C., Figueras Agustí, E., Borbély, A.N., Sewald, N.: Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting. Journal of Peptide Science. 23, 514-531 (2017).
Weiss, Christine, Figueras Agustí, Eduard, Borbély, Adina Noémi, and Sewald, Norbert. “Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting”. Journal of Peptide Science 23.7-8 (2017): 514-531.
Alle Dateien verfügbar unter der/den folgenden Lizenz(en):
Copyright Statement:
This Item is protected by copyright and/or related rights. [...]
Volltext(e)
Access Level
OA Open Access
Zuletzt Hochgeladen
2018-01-29T15:05:06Z

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Novel unit B cryptophycin analogues as payloads for targeted therapy.
Figueras E, Borbély A, Ismail M, Frese M, Sewald N., Beilstein J Org Chem 14(), 2018
PMID: 29977395
Cyanopeptolins with Trypsin and Chymotrypsin Inhibitory Activity from the Cyanobacterium Nostoc edaphicum CCNP1411.
Mazur-Marzec H, Fidor A, Cegłowska M, Wieczerzak E, Kropidłowska M, Goua M, Macaskill J, Edwards C., Mar Drugs 16(7), 2018
PMID: 29949853
Reviving old protecting group chemistry for site-selective peptide-protein conjugation.
Gunnoo SB, Iyer A, Vannecke W, Decoene KW, Hebbrecht T, Gettemans J, Laga M, Loverix S, Lasters I, Madder A., Chem Commun (Camb) 54(84), 2018
PMID: 30285017

125 References

Daten bereitgestellt von Europe PubMed Central.

Eradication of large colon tumor xenografts by targeted delivery of maytansinoids.
Liu C, Tadayoni BM, Bourret LA, Mattocks KM, Derr SM, Widdison WC, Kedersha NL, Ariniello PD, Goldmacher VS, Lambert JM, Blattler WA, Chari RV., Proc. Natl. Acad. Sci. U.S.A. 93(16), 1996
PMID: 8710920
Antibody-drug conjugates in tumor therapy.
Sammet B, Steinkuhler C, Sewald N., Pharm Pat Anal 1(1), 2012
PMID: 24236714

Sewald, 2015
Antibody-drug conjugates: an emerging concept in cancer therapy.
Chari RV, Miller ML, Widdison WC., Angew. Chem. Int. Ed. Engl. 53(15), 2014
PMID: 24677743
Antibody drug conjugates.
Bakhtiar R., Biotechnol. Lett. 38(10), 2016
PMID: 27334710
Hyaluronic acid as drug delivery for sodium butyrate: improvement of the anti-proliferative activity on a breast-cancer cell line.
Coradini D, Pellizzaro C, Miglierini G, Daidone MG, Perbellini A., Int. J. Cancer 81(3), 1999
PMID: 10209956
Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate.
Luo Y, Prestwich GD., Bioconjug. Chem. 10(5), 1999
PMID: 10502340
A hyaluronic acid-taxol antitumor bioconjugate targeted to cancer cells.
Luo Y, Ziebell MR, Prestwich GD., Biomacromolecules 1(2), 2000
PMID: 11710102
Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates.
Luo Y, Bernshaw NJ, Lu ZR, Kopecek J, Prestwich GD., Pharm. Res. 19(4), 2002
PMID: 12033370
Small Molecules for Active Targeting in Cancer.
Kue CS, Kamkaew A, Burgess K, Kiew LV, Chung LY, Lee HB., Med Res Rev 36(3), 2016
PMID: 26992114
Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates.
Gabizon A, Shmeeda H, Horowitz AT, Zalipsky S., Adv. Drug Deliv. Rev. 56(8), 2004
PMID: 15094214
Drug delivery and release systems for targeted tumor therapy.
Bohme D, Beck-Sickinger AG., J. Pept. Sci. 21(3), 2015
PMID: 25703117
Synthesis and biological evaluation of RGD peptidomimetic-paclitaxel conjugates bearing lysosomally cleavable linkers.
Dal Corso A, Caruso M, Belvisi L, Arosio D, Piarulli U, Albanese C, Gasparri F, Marsiglio A, Sola F, Troiani S, Valsasina B, Pignataro L, Donati D, Gennari C., Chemistry 21(18), 2015
PMID: 25784522
Dual-drug RGD conjugates provide enhanced cytotoxicity to melanoma and non-small lung cancer cells.
Gilad Y, Noy E, Senderowitz H, Albeck A, Firer MA, Gellerman G., Biopolymers 106(2), 2016
PMID: 26715008
Synthesis, biological studies and molecular dynamics of new anticancer RGD-based peptide conjugates for targeted drug delivery.
Gilad Y, Noy E, Senderowitz H, Albeck A, Firer MA, Gellerman G., Bioorg. Med. Chem. 24(2), 2015
PMID: 26719208
Recent advances in tumor-targeting anticancer drug conjugates.
Jaracz S, Chen J, Kuznetsova LV, Ojima I., Bioorg. Med. Chem. 13(17), 2005
PMID: 15955702
Taxol and other microtubule-interacting agents
Fojo, Curr. Opin. Oncol. Endocr. Metab. Investig. Drugs 2(), 2000
Microtubule-interacting drugs for cancer treatment.
Checchi PM, Nettles JH, Zhou J, Snyder JP, Joshi HC., Trends Pharmacol. Sci. 24(7), 2003
PMID: 12871669
Stabilizing versus destabilizing the microtubules: a double-edge sword for an effective cancer treatment option?
Fanale D, Bronte G, Passiglia F, Calo V, Castiglia M, Di Piazza F, Barraco N, Cangemi A, Catarella MT, Insalaco L, Listi A, Maragliano R, Massihnia D, Perez A, Toia F, Cicero G, Bazan V., Anal Cell Pathol (Amst) 2015(), 2015
PMID: 26484003
Arrangement of subunits in flagellar microtubules.
Amos L, Klug A., J. Cell. Sci. 14(3), 1974
PMID: 4830832
Chromosome-microtubule interactions during mitosis.
McIntosh JR, Grishchuk EL, West RR., Annu. Rev. Cell Dev. Biol. 18(), 2002
PMID: 12142285
Microtubule polymerization dynamics.
Desai A, Mitchison TJ., Annu. Rev. Cell Dev. Biol. 13(), 1997
PMID: 9442869
Tubulin rings: which way do they curve?
Nogales E, Wang HW, Niederstrasser H., Curr. Opin. Struct. Biol. 13(2), 2003
PMID: 12727521
Microtubules as a target for anticancer drugs.
Jordan MA, Wilson L., Nat. Rev. Cancer 4(4), 2004
PMID: 15057285
Taxol stabilizes microtubules in mouse fibroblast cells.
Schiff PB, Horwitz SB., Proc. Natl. Acad. Sci. U.S.A. 77(3), 1980
PMID: 6103535
Mechanism of mitotic block and inhibition of cell proliferation by taxol at low concentrations.
Jordan MA, Toso RJ, Thrower D, Wilson L., Proc. Natl. Acad. Sci. U.S.A. 90(20), 1993
PMID: 8105478
Substoichiometric binding of taxol suppresses microtubule dynamics.
Derry WB, Wilson L, Jordan MA., Biochemistry 34(7), 1995
PMID: 7857932
Taxol suppresses dynamics of individual microtubules in living human tumor cells.
Yvon AM, Wadsworth P, Jordan MA., Mol. Biol. Cell 10(4), 1999
PMID: 10198049
Pharmaceuticals from cultured algae
Schwartz, J. Ind. Microbiol. 5(), 1990
Biosynthetic characterization and chemoenzymatic assembly of the cryptophycins. Potent anticancer agents from cyanobionts.
Magarvey NA, Beck ZQ, Golakoti T, Ding Y, Huber U, Hemscheidt TK, Abelson D, Moore RE, Sherman DH., ACS Chem. Biol. 1(12), 2006
PMID: 17240975
Structure determination, conformational analysis, chemical stability studies, and antitumor evaluation of the cryptophycins. Isolation of 18 new analogs from Nostoc sp. strain GSV 224
Golakoti, J. Am. Chem. Soc. 117(), 1995
Secondary metabolites from cyanobacteria: complex structures and powerful bioactivities
Gademann, Curr Org. Chem. 12(), 2008
Marine cyanobacteria - a prolific source of natural products
Burja, Tetrahedron 57(), 2001

AUTHOR UNKNOWN, 0
Evaluation of Nostoc strain ATCC 53789 as a potential source of natural pesticides.
Biondi N, Piccardi R, Margheri MC, Rodolfi L, Smith GD, Tredici MR., Appl. Environ. Microbiol. 70(6), 2004
PMID: 15184126
Total structures of cryptophycins, potent antitumor depsipeptides from the blue-green alga Nostoc sp. strain GSV 224
Trimurtulu, J. Am. Chem. Soc. 116(), 1994
The absolute stereostructure of arenastatin A, a potent cytotoxic depsipeptide from the Okinawan marine sponge Dysidea arenaria
Kobayashi, Chem. Pharm. Bull. 42(), 1994
Arenastatin A, a potent cytotoxic depsipeptide from the Okinawan marine sponge Dysidea arenaria
Kobayashi, Tetrahedron Lett. 35(), 1994
Three new cryptophycins from Nostoc sp. GSV 224.
Subbaraju GV, Golakoti T, Patterson GM, Moore RE., J. Nat. Prod. 60(3), 1997
PMID: 9090872
Isolation and structure determination of cryptophycins 38, 326, and 327 from the terrestrial cyanobacterium Nostoc sp. GSV 224.
Chaganty S, Golakoti T, Heltzel C, Moore RE, Yoshida WY., J. Nat. Prod. 67(8), 2004
PMID: 15332864
The synthesis of cryptophycins
Eißler, Synthesis (), 2006
Recent approaches for the synthesis of modified cryptophycins.
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Interaction of cryptophycin 1 with tubulin and microtubules.
Kerksiek K, Mejillano MR, Schwartz RE, Georg GI, Himes RH., FEBS Lett. 377(1), 1995
PMID: 8543019
Interaction of the antitumor compound cryptophycin-52 with tubulin.
Panda D, Ananthnarayan V, Larson G, Shih C, Jordan MA, Wilson L., Biochemistry 39(46), 2000
PMID: 11087360
Mechanism of action of the unusually potent microtubule inhibitor cryptophycin 1.
Panda D, Himes RH, Moore RE, Wilson L, Jordan MA., Biochemistry 36(42), 1997
PMID: 9335554
Antiproliferative mechanism of action of cryptophycin-52: kinetic stabilization of microtubule dynamics by high-affinity binding to microtubule ends.
Panda D, DeLuca K, Williams D, Jordan MA, Wilson L., Proc. Natl. Acad. Sci. U.S.A. 95(16), 1998
PMID: 9689077
The cryptophycin-tubulin ring structure indicates two points of curvature in the tubulin dimer.
Watts NR, Cheng N, West W, Steven AC, Sackett DL., Biochemistry 41(42), 2002
PMID: 12379108
Induction of apoptosis by cryptophycin 1, a new antimicrotubule agent.
Mooberry SL, Busquets L, Tien G., Int. J. Cancer 73(3), 1997
PMID: 9359493
Cryptophycin: a new antimicrotubule agent active against drug-resistant cells.
Smith CD, Zhang X, Mooberry SL, Patterson GM, Moore RE., Cancer Res. 54(14), 1994
PMID: 7913408
Cryptophycin-induced hyperphosphorylation of Bcl-2, cell cycle arrest and growth inhibition in human H460 NSCLC cells.
Lu K, Dempsey J, Schultz RM, Shih C, Teicher BA., Cancer Chemother. Pharmacol. 47(2), 2001
PMID: 11269744
Cryptophycins: a novel class of potent antimitotic antitumor depsipeptides.
Shih C, Teicher BA., Curr. Pharm. Des. 7(13), 2001
PMID: 11472266
Strategies to overcome or circumvent P-glycoprotein mediated multidrug resistance.
Yuan H, Li X, Wu J, Li J, Qu X, Xu W, Tang W., Curr. Med. Chem. 15(5), 2008
PMID: 18289002
Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding.
Aller SG, Yu J, Ward A, Weng Y, Chittaboina S, Zhuo R, Harrell PM, Trinh YT, Zhang Q, Urbatsch IL, Chang G., Science 323(5922), 2009
PMID: 19325113
Cryptophycin 1 cellular levels and effects in vitro using L1210 cells.
Foster BJ, Fortuna M, Media J, Wiegand RA, Valeriote FA., Invest New Drugs 16(3), 1998
PMID: 10360599
Antitumor activity of cryptophycins: effect of infusion time and combination studies.
Menon K, Alvarez E, Forler P, Phares V, Amsrud T, Shih C, Al-Awar R, Teicher BA., Cancer Chemother. Pharmacol. 46(2), 2000
PMID: 10972484
Phase I trial of the cryptophycin analogue LY355703 administered as an intravenous infusion on a day 1 and 8 schedule every 21 days.
Stevenson JP, Sun W, Gallagher M, Johnson R, Vaughn D, Schuchter L, Algazy K, Hahn S, Enas N, Ellis D, Thornton D, O'Dwyer PJ., Clin. Cancer Res. 8(8), 2002
PMID: 12171879
Phase I and pharmacological studies of the cryptophycin analogue LY355703 administered on a single intermittent or weekly schedule.
Sessa C, Weigang-Kohler K, Pagani O, Greim G, Mora O, De Pas T, Burgess M, Weimer I, Johnson R., Eur. J. Cancer 38(18), 2002
PMID: 12460783
A multicenter phase II study of the cryptophycin analog LY355703 in patients with platinum-resistant ovarian cancer.
D'Agostino G, del Campo J, Mellado B, Izquierdo MA, Minarik T, Cirri L, Marini L, Perez-Gracia JL, Scambia G., Int. J. Gynecol. Cancer 16(1), 2006
PMID: 16445613
Pharmacokinetics and tissue distribution of cryptophycin 52 (C-52) epoxide and cryptophycin 55 (C-55) chlorohydrin in mice with subcutaneous tumors.
Boinpally RR, Polin L, Zhou SL, Jasti BR, Wiegand RA, White K, Kushner J, Horwitz JP, Corbett TH, Parchment RE., Cancer Chemother. Pharmacol. 52(1), 2003
PMID: 12739061
The search for new antitumor drugs from blue-green algae
Moore, Curr. Pharm. Des. 2(), 1996
Cryptophycins-309, 249 and other cryptophycin analogs: preclinical efficacy studies with mouse and human tumors.
Liang J, Moore RE, Moher ED, Munroe JE, Al-awar RS, Hay DA, Varie DL, Zhang TY, Aikins JA, Martinelli MJ, Shih C, Ray JE, Gibson LL, Vasudevan V, Polin L, White K, Kushner J, Simpson C, Pugh S, Corbett TH., Invest New Drugs 23(3), 2005
PMID: 15868377
Improved total synthesis and structure-activity relationship of arenastatin A, a potent cytotoxic spongean depsipeptide.
Kobayashi M, Wang W, Ohyabu N, Kurosu M, Kitagawa I., Chem. Pharm. Bull. 43(9), 1995
PMID: 7586087
Synthesis and in vitro cytotoxicity of cryptophycins and related analogs
Muys, Bioorg. Med. Chem. Lett. 6(), 1996

AUTHOR UNKNOWN, 0
Novel cryptophycin antitumor agents: synthesis and cytotoxicity of fragment "B" analogues.
Patel VF, Andis SL, Kennedy JH, Ray JE, Schultz RM., J. Med. Chem. 42(14), 1999
PMID: 10411479
Halohydrin analogues of cryptophycin 1: synthesis and biological activity.
Georg GI, Ali SM, Stella VJ, Waugh WN, Himes RH., Bioorg. Med. Chem. Lett. 8(15), 1998
PMID: 9873466
Biological evaluation of cryptophycin 52 fragment A analogues: effect of the multidrug resistance ATP binding cassette transporters on antitumor activity.
Al-Awar RS, Corbett TH, Ray JE, Polin L, Kennedy JH, Wagner MM, Williams DC., Mol. Cancer Ther. 3(9), 2004
PMID: 15367700

AUTHOR UNKNOWN, 0
Design and synthesis of a new class of cryptophycins based tubulin inhibitors.
Kumar A, Kumar M, Sharma S, Guru SK, Bhushan S, Shah BA., Eur J Med Chem 93(), 2015
PMID: 25647428
A convergent approach to cryptophycin 52 analogues: synthesis and biological evaluation of a novel series of fragment a epoxides and chlorohydrins.
Al-Awar RS, Ray JE, Schultz RM, Andis SL, Kennedy JH, Moore RE, Liang J, Golakoti T, Subbaraju GV, Corbett TH., J. Med. Chem. 46(14), 2003
PMID: 12825938
Efficient synthesis of cryptophycin-52 and novel para-alkoxymethyl unit A analogues.
Eissler S, Bogner T, Nahrwold M, Sewald N., Chemistry 15(42), 2009
PMID: 19760734
The remarkable transport mechanism of P-glycoprotein: a multidrug transporter.
Al-Shawi MK, Omote H., J. Bioenerg. Biomembr. 37(6), 2005
PMID: 16691488
Total synthesis and antitubulin activity of c10 analogues of cryptophycin-24.
Buck SB, Huff JK, Himes RH, Georg GI., J. Med. Chem. 47(3), 2004
PMID: 14736249
Synthesis and cytotoxicity studies of new cryptophycin analogues.
Liu WL, Zhang JC, Jiang FQ, Fu L., Arch. Pharm. (Weinheim) 342(10), 2009
PMID: 19714674
The growing impact of click chemistry on drug discovery.
Kolb HC, Sharpless KB., Drug Discov. Today 8(24), 2003
PMID: 14678739
Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions.
Angell YL, Burgess K., Chem Soc Rev 36(10), 2007
PMID: 17721589
Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation.
Mesenzani O, Massarotti A, Giustiniano M, Pirali T, Bevilacqua V, Caldarelli A, Canonico P, Sorba G, Novellino E, Genazzani AA, Tron GC., Bioorg. Med. Chem. Lett. 21(2), 2010
PMID: 21167709
Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors.
Brik A, Muldoon J, Lin YC, Elder JH, Goodsell DS, Olson AJ, Fokin VV, Sharpless KB, Wong CH., Chembiochem 4(11), 2003
PMID: 14613121
1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.
Bock VD, Speijer D, Hiemstra H, van Maarseveen JH., Org. Biomol. Chem. 5(6), 2007
PMID: 17340013
Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues.
Beierle JM, Horne WS, van Maarseveen JH, Waser B, Reubi JC, Ghadiri MR., Angew. Chem. Int. Ed. Engl. 48(26), 2009
PMID: 19266506
"Clicktophycin-52": a bioactive cryptophycin-52 triazole analogue.
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N., Org. Lett. 12(5), 2010
PMID: 20131817
Interaction of arenastatin A with porcine brain tubulin.
Morita K, Koiso Y, Hashimoto Y, Kobayashi M, Wang W, Ohyabu N, Iwasaki S., Biol. Pharm. Bull. 20(2), 1997
PMID: 9057981
Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region).
Varie DL, Shih C, Hay DA, Andis SL, Corbett TH, Gossett LS, Janisse SK, Martinelli MJ, Moher ED, Schultz RM, Toth JE., Bioorg. Med. Chem. Lett. 9(3), 1999
PMID: 10091686
Synthesis and biological evaluation of novel cryptophycin analogs with modification in the beta-alanine region.
Shih C, Gossett LS, Gruber JM, Grossman CS, Andis SL, Schultz RM, Worzalla JF, Corbett TH, Metz JT., Bioorg. Med. Chem. Lett. 9(1), 1999
PMID: 9990459
Conjugates of modified cryptophycins and RGD-peptides enter target cells by endocytosis.
Nahrwold M, Weiß C, Bogner T, Mertink F, Conradi J, Sammet B, Palmisano R, Royo Gracia S, Preuße T, Sewald N., J. Med. Chem. 56(5), 2013
PMID: 23387527
Total synthesis and anti-tubulin activity of epi-c3 analogues of cryptophycin-24.
Buck SB, Huff JK, Himes RH, Georg GI., J. Med. Chem. 47(14), 2004
PMID: 15214797
Synthesis of stable analogs in blood and conformational analysis of arenastatin A, a potent cytotoxic spongean depsipeptide
Murakami, Tetrahedron 57(), 2001
Approaches for the synthesis of functionalized cryptophycins.
Sammet B, Bogner T, Nahrwold M, Weiss C, Sewald N., J. Org. Chem. 75(20), 2010
PMID: 20857920
Total synthesis of cryptophycin analogues. Isosteric replacement of the C-D ester
Norman, J. Org. Chem. 63(), 1998
Synthesis of amide analogs of arenastatin A
Murakami, Tetrahedron 56(), 2000
Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide.
Kotoku N, Kato T, Narumi F, Ohtani E, Kamada S, Aoki S, Okada N, Nakagawa S, Kobayashi M., Bioorg. Med. Chem. 14(22), 2006
PMID: 16877000
Fluorine in pharmaceuticals: looking beyond intuition.
Muller K, Faeh C, Diederich F., Science 317(5846), 2007
PMID: 17901324
Fluorine in medicinal chemistry: a review of anti-cancer agents
Isanbor, J. Fluor. Chem. 127(), 2006
Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
Bégué, J. Fluor. Chem. 127(), 2006
Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules
Kirk, J. Fluor. Chem. 127(), 2006

Kirsch, 2004
Odor-structure relationships using fluorine as a probe
Michel, Tetrahedron 56(), 2000

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
Total synthesis and biological evaluation of fluorinated cryptophycins.
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: isolation, crystal structure, and conformation in solution
Höfle, Angew. Chem. Int. Ed. 35(), 1996
Synthesis of cryptothilone 1, the first cryptophycin-epothilone hybrid.
White JD, Smits H, Hamel E., Org. Lett. 8(18), 2006
PMID: 16928045

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
The cryptophycins as potent payloads for antibody drug conjugates.
Verma VA, Pillow TH, DePalatis L, Li G, Phillips GL, Polson AG, Raab HE, Spencer S, Zheng B., Bioorg. Med. Chem. Lett. 25(4), 2015
PMID: 25613677

AUTHOR UNKNOWN, 0

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 28661555
PubMed | Europe PMC

Suchen in

Google Scholar