Directing intracellular supramolecular assembly
with N-heteroaromatic quaterthiophene analogues
David Y.W. Ng
, Roman Vill
, Yuzhou Wu
, Kaloian Koynov
, Yu Tokura
, Weina Liu
, Susanne Sihler
, Sandra Ritz
, Holger Barth
, Ulrich Ziener
& Tanja Weil
Self-assembly in situ, where synthetic molecules are programmed to organize in a speciﬁc
and complex environment i.e., within living cells, can be a unique strategy to inﬂuence cellular
functions. Here we present a small series of rationally designed oligothiophene analogues
that speciﬁcally target, locate and dynamically self-report their supramolecular behavior
within the conﬁnement of a cell. Through the recognition of the terminal alkyl substituent and
the amphiphilic pyridine motif, we show that the cell provides different complementary
pathways for self-assembly that can be traced easily with ﬂuorescence microscopy as their
molecular organization emits in distinct ﬂuorescent bands. Importantly, the control and
induction of both forms are achieved by time, temperature and the use of the intracellular
transport inhibitor, baﬁlomycin A1. We showcase the importance of both intrinsic (cell) and
extrinsic (stimulus) factors for self-organization and the potential of such a platform toward
developing synthetic functional components within living cells.
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
Institute of Organic Chemistry III, Ulm University, Albert-Einstein-
Allee 11, 89081 Ulm, Germany.
Institute of Molecular Biology, Ackermannweg 4, 55128 Mainz, Germany.
Institute of Pharmacology and Toxicology, Ulm
University Medical Center, Albert-Einstein-Allee 11, 89081 Ulm, Germany. David Y.W. Ng and Roman Vill contributed equally to this work. Correspondence
and requests for materials should be addressed to D.Y.W.N. (email: firstname.lastname@example.org) or to U.Z. (email: email@example.com)
or to T.W. (email: firstname.lastname@example.org)