Recent approaches for the synthesis of modified cryptophycins

Weiss C, Sammet B, Sewald N (2013)
Natural Product Reports 30(7): 924-940.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Weiss, Christine; Sammet, BenediktUniBi; Sewald, NorbertUniBi
Einrichtung
Fakultät für Chemie > Organische Chemie III
Abstract / Bemerkung
Cryptophycins are a family of antimitotic depsipeptides with very high cytotoxicity even against multi-drug resistant (MDR) cancer cells. The first representative was isolated from cyanobacteria Nostoc sp. in 1990. Their bioactivity is based on their interaction with the protein tubulin. Cryptophycins were found to induce apoptosis due to inhibition of the microtubule dynamics. Consequently, cryptophycin analogues are considered as potential antitumour agents. Retrosynthetically, cryptophycins can be subdivided into four building blocks, namely units A-D, to be assembled in the total synthesis. Since the discovery of this compound class, numerous synthetic analogues have been designed for structure-activity relationship (SAR) studies. This review gives a critical overview on cryptophycins, while the main focus lies on the synthetic challenges of recently published cryptophycins, together with emerging concepts on cryptophycin bioconjugation and prodrug design.
Erscheinungsjahr
2013
Zeitschriftentitel
Natural Product Reports
Band
30
Ausgabe
7
Seite(n)
924-940
ISSN
0265-0568
eISSN
1460-4752
Page URI
https://pub.uni-bielefeld.de/record/2613107

Zitieren

Weiss C, Sammet B, Sewald N. Recent approaches for the synthesis of modified cryptophycins. Natural Product Reports. 2013;30(7):924-940.
Weiss, C., Sammet, B., & Sewald, N. (2013). Recent approaches for the synthesis of modified cryptophycins. Natural Product Reports, 30(7), 924-940. doi:10.1039/c3np70022d
Weiss, Christine, Sammet, Benedikt, and Sewald, Norbert. 2013. “Recent approaches for the synthesis of modified cryptophycins”. Natural Product Reports 30 (7): 924-940.
Weiss, C., Sammet, B., and Sewald, N. (2013). Recent approaches for the synthesis of modified cryptophycins. Natural Product Reports 30, 924-940.
Weiss, C., Sammet, B., & Sewald, N., 2013. Recent approaches for the synthesis of modified cryptophycins. Natural Product Reports, 30(7), p 924-940.
C. Weiss, B. Sammet, and N. Sewald, “Recent approaches for the synthesis of modified cryptophycins”, Natural Product Reports, vol. 30, 2013, pp. 924-940.
Weiss, C., Sammet, B., Sewald, N.: Recent approaches for the synthesis of modified cryptophycins. Natural Product Reports. 30, 924-940 (2013).
Weiss, Christine, Sammet, Benedikt, and Sewald, Norbert. “Recent approaches for the synthesis of modified cryptophycins”. Natural Product Reports 30.7 (2013): 924-940.

14 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Synthesis and Biological Evaluation of RGD⁻Cryptophycin Conjugates for Targeted Drug Delivery.
Borbély A, Figueras E, Martins A, Esposito S, Auciello G, Monteagudo E, Di Marco A, Summa V, Cordella P, Perego R, Kemker I, Frese M, Gallinari P, Steinkühler C, Sewald N., Pharmaceutics 11(4), 2019
PMID: 30939768
Octreotide Conjugates for Tumor Targeting and Imaging.
Figueras E, Martins A, Borbély A, Le Joncour V, Cordella P, Perego R, Modena D, Pagani P, Esposito S, Auciello G, Frese M, Gallinari P, Laakkonen P, Steinkühler C, Sewald N., Pharmaceutics 11(5), 2019
PMID: 31067748
Conjugates of Cryptophycin and RGD or isoDGR Peptidomimetics for Targeted Drug Delivery.
Borbély A, Figueras E, Martins A, Bodero L, Raposo Moreira Dias A, López Rivas P, Pina A, Arosio D, Gallinari P, Frese M, Steinkühler C, Gennari C, Piarulli U, Sewald N., ChemistryOpen 8(6), 2019
PMID: 31275795
A flavin-dependent halogenase from metagenomic analysis prefers bromination over chlorination.
Neubauer PR, Widmann C, Wibberg D, Schröder L, Frese M, Kottke T, Kalinowski J, Niemann HH, Sewald N., PLoS One 13(5), 2018
PMID: 29746521
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
In Vivo Antitumor Activity of a Novel Acetazolamide-Cryptophycin Conjugate for the Treatment of Renal Cell Carcinomas.
Cazzamalli S, Figueras E, Pethő L, Borbély A, Steinkühler C, Neri D, Sewald N., ACS Omega 3(11), 2018
PMID: 30533574
syn-Selective crotylation of aldehydes using bismuth-crotyl bromide-(1-butyl-3-methylimidazolium bromide) combination: some synthetic applications.
Goswami D, Koli MR, Chatterjee S, Chattopadhyay S, Sharma A., Org Biomol Chem 15(17), 2017
PMID: 28406519
Cryptophycins: cytotoxic cyclodepsipeptides with potential for tumor targeting.
Weiss C, Figueras E, Borbely AN, Sewald N., J Pept Sci 23(7-8), 2017
PMID: 28661555
Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.
Chen H, Lin Z, Arnst KE, Miller DD, Li W., Molecules 22(8), 2017
PMID: 28763044
Cyanobacterial Metabolite Calothrixins: Recent Advances in Synthesis and Biological Evaluation.
Xu S, Nijampatnam B, Dutta S, Velu SE., Mar Drugs 14(1), 2016
PMID: 26771620
Unique marine derived cyanobacterial biosynthetic genes for chemical diversity.
Kleigrewe K, Gerwick L, Sherman DH, Gerwick WH., Nat Prod Rep 33(2), 2016
PMID: 26758451
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
Stabilizing versus destabilizing the microtubules: a double-edge sword for an effective cancer treatment option?
Fanale D, Bronte G, Passiglia F, Calò V, Castiglia M, Di Piazza F, Barraco N, Cangemi A, Catarella MT, Insalaco L, Listì A, Maragliano R, Massihnia D, Perez A, Toia F, Cicero G, Bazan V., Anal Cell Pathol (Amst) 2015(), 2015
PMID: 26484003
The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.
Kalesse M, Cordes M, Symkenberg G, Lu HH., Nat Prod Rep 31(4), 2014
PMID: 24595879

71 References

Daten bereitgestellt von Europe PubMed Central.


Schwartz, J. Ind. Microbiol. Biotechnol. 5(), 1990

Trimurtulu, J. Am. Chem. Soc. 116(), 1994

Kobayashi, Chem. Pharm. Bull. 42(), 1994

Kobayashi, Tetrahedron Lett. 35(), 1994

Tius, Tetrahedron 58(), 2002

Eissler, Synthesis (), 2006

Nahrwold, Chim. Oggi 26(), 2008
Characterization of the interaction of cryptophycin 1 with tubulin: binding in the Vinca domain, competitive inhibition of dolastatin 10 binding, and an unusual aggregation reaction.
Bai R, Schwartz RE, Kepler JA, Pettit GR, Hamel E., Cancer Res. 56(19), 1996
PMID: 8813133
In vitro effect of cryptophycin 52 on microtubule assembly and tubulin: molecular modeling of the mechanism of action of a new antimitotic drug.
Barbier P, Gregoire C, Devred F, Sarrazin M, Peyrot V., Biochemistry 40(45), 2001
PMID: 11695898
Localization of the antimitotic peptide and depsipeptide binding site on beta-tubulin.
Mitra A, Sept D., Biochemistry 43(44), 2004
PMID: 15518544
Dolastatin 10, a powerful cytostatic peptide derived from a marine animal. Inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain.
Bai R, Pettit GR, Hamel E., Biochem. Pharmacol. 39(12), 1990
PMID: 2353935
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

Golakoti, J. Am. Chem. Soc. 117(), 1995
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
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

Raub, Mol. Pharmaceutics 3(), 2006
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
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
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
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
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
The cryptophycins: their synthesis and anticancer activity.
Eggen M, Georg GI., Med Res Rev 22(2), 2002
PMID: 11857635
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
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
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 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
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
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

Norman, J. Org. Chem. 63(), 1998
"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
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
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
Short and efficient synthesis of cryptophycin unit A.
Eissler S, Nahrwold M, Neumann B, Stammler HG, Sewald N., Org. Lett. 9(5), 2007
PMID: 17284043

Wang, Tetrahedron Lett. 33(), 1992

Yadav, Tetrahedron Lett. 52(), 2011
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
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

Barrow, J. Am. Chem. Soc. 117(), 1995
Synthesis and cytotoxicity studies of new cryptophycin analogues.
Liu WL, Zhang JC, Jiang FQ, Fu L., Arch. Pharm. (Weinheim) 342(10), 2009
PMID: 19714674
Enantioselective synthesis of a 3'-dephenylcryptophycin synthon.
Eggen MJ, Georg GI., Bioorg. Med. Chem. Lett. 8(22), 1998
PMID: 9873698

Danner, Eur. J. Org. Chem. 2005(), 2005

Park, Angew. Chem. 114(), 2002

Andrus, Tetrahedron Lett. 50(), 2009
A two step synthesis of a key unit B precursor of cryptophycins by asymmetric hydrogenation.
Sammet B, Brax M, Sewald N., Beilstein J Org Chem 7(), 2011
PMID: 21448253

Drexler, J. Organomet. Chem. 621(), 2001

Schmidt, Synthesis (), 1992
Cyclic sulfamidates as versatile lactam precursors. An evaluation of synthetic strategies towards (-)-aphanorphine.
Bower JF, Szeto P, Gallagher T., Org. Biomol. Chem. 5(1), 2006
PMID: 17164919
Total synthesis of cryptophycin analogues via a scaffold approach.
McCubbin JA, Maddess ML, Lautens M., Org. Lett. 8(14), 2006
PMID: 16805535

Jost, Angew. Chem., Int. Ed. 41(), 2002

White, J. Org. Chem. 64(), 1999
3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors.
Weide T, Arve L, Prinz H, Waldmann H, Kessler H., Bioorg. Med. Chem. Lett. 16(1), 2005
PMID: 16236508
Stereospecific synthesis of cryptophycin 1.
Li LH, Tius MA., Org. Lett. 4(10), 2002
PMID: 12000261

Eißler, Chem.–Eur. J. 15(), 2009

Tripathy, Tetrahedron Lett. 45(), 2004

Mast, Chem.–Eur. J. 11(), 2005
Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain.
Eggen M, Mossman CJ, Buck SB, Nair SK, Bhat L, Ali SM, Reiff EA, Boge TC, Georg GI., J. Org. Chem. 65(23), 2000
PMID: 11073583
Synthesis of cryptophycin 52 using the Shi epoxidation.
Hoard DW, Moher ED, Martinelli MJ, Norman BH., Org. Lett. 4(10), 2002
PMID: 12000306

Fray, Tetrahedron: Asymmetry 9(), 1998
Enantioselective synthesis of (+)-cryptophycin 52 (LY355703), a potent antimitotic antitumor agent.
Ghosh AK, Swanson L., J. Org. Chem. 68(25), 2003
PMID: 14656116
Total Synthesis of Cryptophycins via a Chemoenzymatic Approach.
Salamonczyk GM, Han K, Guo Zw , Sih CJ., J. Org. Chem. 61(20), 1996
PMID: 11667584
Synthesis of cryptophycin 52 using the sharpless asymmetric dihydroxylation: diol to epoxide transformation optimized for a base-sensitive substrate.
Liang J, Moher ED, Moore RE, Hoard DW., J. Org. Chem. 65(10), 2000
PMID: 10814209

Kolb, Tetrahedron 48(), 1992

Sammet, Synlett (), 2009

Bolduc, Chem. Commun. 48(), 2012
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

Stoncius, Synthesis (), 2005
Total synthesis and biological evaluation of fluorinated cryptophycins.
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
Chemoenzymatic synthesis of cryptophycin anticancer agents by an ester bond-forming non-ribosomal peptide synthetase module.
Ding Y, Rath CM, Bolduc KL, Hakansson K, Sherman DH., J. Am. Chem. Soc. 133(37), 2011
PMID: 21823639

Haubner, Angew. Chem., Int. Ed. Engl. 36(), 1997
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

Sammet, Pharm. Pat. Analyst 1(), 2012
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